dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-111c3c38c2084791aebe57e394f1900a | CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCC(N)=O>>NC(=O)CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C(NCCN(C)C)=O)C=C1.NCC(=O)N>>C(N)(=O)CNC(=O)C=1C=C(C(=CC1)C1=CC=C(C=C1)Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CN(C)CCN[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][c:23]3[cH:24][c:25](-[c:26]4[n:27][c:28]5[cH:29][c:30]([C:31](=[O:32])[OH:33])[cH:34][cH:35][c:36]5[n:37]4[CH:38]4[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]4)[cH:44][cH:45][c:46]3[n:47]2)[cH:4... | CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCC(N)=O | NC(=O)CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | Acylation | OtherReaction | 1f65584d811005ce14184af76efdc3ec878b3e465d13ed08b308dc607a0589b2 | 03a81fa1546c38bfa4e40f8ce9e6dc6167e96678946fcdc6826a1cac3ec22183 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-C-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[C:9]-[NH2;D1;+0:10]>>[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 491, except glycine-amide was used instead of N1,N1-dimethyl-ethane-1,2-diamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine.Tertiary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCC(N)=O>>NC(=O)CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99c6a1e8c6c7464bab7e2cd7672dc794 | CN.CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C(NCCN(C)C)=O)C=C1.CN>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C(NC)=O)C=C1 | [CH3:1][NH2:2].CN(C)CCN[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][c:20]3[cH:21][c:22](-[c:23]4[n:24][c:25]5[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][c:33]5[n:34]4[CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)[cH:41][cH:42][c:43]3[... | CN.CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | Acylation | OtherReaction | 1f65584d811005ce14184af76efdc3ec878b3e465d13ed08b308dc607a0589b2 | 03a81fa1546c38bfa4e40f8ce9e6dc6167e96678946fcdc6826a1cac3ec22183 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-C-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 491, except methyl amine was used instead of N1,N1-dimethyl-ethane-1,2-diamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine.Tertiary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CN.CN(C)CCNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>CNC(=O)c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bc369d38810466ab18eca61c30d4b9c | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C>>Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N | O.CCN(C(C)C)C(C)C.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC(=C(C=C2)N)N | CC[O:13][C:11]([c:10]1[cH:9][c:8]([NH2:7])[c:16]([NH:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:15][cH:14]1)=[O:12].CN(C)[C:6](O[n:1]1n[n:26][c:25]2[c:2]1[cH:3][cH:4][cH:5][cH:24]2)=[N+](C)C>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]3[n:17]2[... | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C | Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N | null | null | CCO.CN(C)C=O | C-C Coupling | OtherReaction | d39ae955bfa4ef5891d52b381ea2e0e1ca27cefff268c209f2c6b3d4e1830bd5 | 9c4acf9207ee3ded4a6acb3ac7c7bac8cb4fb0acc2fea04aa290e99ed7cf07f9 | c1ccc(-c2nc3ccccc3n2C2CCCCC2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8](-[NH;D2;+0:9]-[C:10](-[C:11])-[C:12]):[c:13].C-N(-C)-[C;H0;D3;+0:14](-O-[n;H0;D3;+0:15]1:n:[n;H0;D2;+0:16]:[c:17]2:[c:18]:[cH;D2;+0:19]:[c:20]:[c:21]:[c:22]:2:1)=[N+](-C)-C>>[C:11]-[C:10](-[n;H0;D3;+0:9]1:[c:8](:[c:13]):[c:6](:[c:5]:[c:4]-[C... | 95.5 | [{"value": 95.5, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC(=C(C=C2)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1 g (2.84 mmol) of the product of the previous step, 0.91 g (2.84 mmol) of TBTU and 0.73 g (5.68 mmol) of DIEA in 10 mL anhydrous DMF was allowed to stand at room temperature for 15 min. To this solution was added 0.90 g (3.41 mmol) of Compound 11, and the solution was allowed to stand at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Ester.Primary amine.Secondary amine | Carboxylic acid.Primary amine.Primary amine | c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccccc1.c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | CCO.CN(C)C=O | null | 0.25 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C>CCO.CN(C)C=O>Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afe93530b68c4c44afbddeeb0e91daec | Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N.O=C(C(=O)c1ccccc1)c1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC(=C(C=C2)N)N.C1(=CC=CC=C1)C(=O)C(=O)C1=CC=CC=C1>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:12]1[cH:13][cH:14][c:15]([NH2:16])[c:32]([NH2:31])[cH:33]1)[n:34]2[CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1.O=[C:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:24](=O)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[O:1]=[C:2]([OH:3])[c:... | Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N.O=C(C(=O)c1ccccc1)c1ccccc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 80ad7d4b359f2683f57c053570cf5c6857c4f32e8ec9869e4f38f79c70cafc8c | d53d864708a4cd37c2fe33ca368498c017ca81ee7d694ff92f9c935efef6bc9e | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18]>>[c:15]:[c:14]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5... | null | [] | null | null | null | null | A solution of 100 mg (0.29 mmol) of Compound 406b and 74 mg (0.35 mmol) of benzil was stirred at room temperature overnight. The solvent was evaporated and the residue was purified on preparative HPLC yielding 10 mg.
Conditions: See reaction.notes.procedure_details.
Workup: The solvent was evaporated; the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2nccnc2c1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | Nc1ccc(-c2nc3cc(C(=O)O)ccc3n2C2CCCCC2)cc1N.O=C(C(=O)c1ccccc1)c1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ebb6a21559541998650aed95637c609 | O=C(C(=O)c1ccc(Br)cc1)c1ccc(Br)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Br)cc4)c(-c4ccc(Br)cc4)nc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2.BrC1=CC=C(C=C1)C(=O)C(=O)C1=CC=C(C=C1)Br>>BrC1=CC=C(C=C1)C1=NC2=CC=C(C=C2N=C1C1=CC=C(C=C1)Br)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | O=C(C(=O)c1cc[c:21]([Br:22])[cH:20][cH:19]1)c1ccc([Br:30])cc1.c1c[c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:36]4[CH:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[cH:35][c:34]3[n:33][c:25]2-[c:26]2[cH:27][cH:28][cH:29][cH:31][cH:32]2)[cH:2... | O=C(C(=O)c1ccc(Br)cc1)c1ccc(Br)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Br)cc4)c(-c4ccc(Br)cc4)nc3c1)n2C1CCCCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 98c5779329f45f09a0843f1bf721d339deed59a6f832812172b8f93f23ccaf08 | 59f867651ee848cc4c1fb1fe036b1f8eb00c88c7ac0bcbe7091b43bab11dfa25 | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=C(-C(=O)-c1:c:c:c(-[Br;H0;D1;+0:1]):c:c:1)-c1:[cH;D2;+0:2]:[c:3]:[c;H0;D3;+0:4](-[Br;D1;H0:5]):c:c:1.[#7;a:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10](-[c:11]2:[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]:2):[c:17]:1-[c;H0;D3;+0:18]1:[c:19]:[cH;D2;+0:20]:c:c:c:1>>[Br;D1;H0:5]-[c;H0;D3;+0:4]1:[c:3]:[cH;D2;+0:2]:[c;H0;D3;+0:18](-[c:1... | null | [] | null | null | null | null | Prepared as described for Compound 406 using 4,4′-dibromobenzil in place of benzil.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Ketone | Aromatic halide.Aromatic halide | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(C(=O)c1ccc(Br)cc1)c1ccc(Br)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Br)cc4)c(-c4ccc(Br)cc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5ab237a4e2847d4b2dfa35bd3ca34f0 | Cc1ccc(C(=O)C(=O)c2ccc(C)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>Cc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(C)cc2)cc1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2.CC1=CC=C(C=C1)C(=O)C(=O)C1=CC=C(C=C1)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=C(C=C2)C)C2=CC=C(C=C2)C | O=C(C(=O)c1[cH:4][cH:3][c:2]([CH3:1])[cH:42][cH:41]1)c1[cH:35][cH:36][c:37]([CH3:38])[cH:39][cH:40]1.c1cc[c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][c:11](-[c:12]4[n:13][c:14]5[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]5[n:23]4[CH:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[cH:30][c:31]3[n:32][c:33]2-[c:34]2... | Cc1ccc(C(=O)C(=O)c2ccc(C)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | Cc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(C)cc2)cc1 | null | null | null | Miscellaneous | OtherReaction | 1080d35fbc20debb247878370c355dffb0943784f68c8ccbb2f515015cf67436 | 04b105348625c11d88400601d6084fcf4ec5b44daa0c1f8954a37a3ab783d9c2 | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=C(-C(=O)-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1)-c1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1.[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15](-[c;H0;D3;+0:16]2:c:c:c:c:c:2):[c:17]:1-[c;H0;D3;+0:18]1:c:c:c:c:c:1>>[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15](-[c;H0;D3;+0:16]2:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2... | null | [] | null | null | null | null | Prepared as described for Compound 406 using 4,4′-dimethylbenzil in place of benzil.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2nccnc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1.c1ccccc1 | HO- | null | null | null | Cc1ccc(C(=O)C(=O)c2ccc(C)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>Cc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62f9c186bdfe4c8fa50217e496f9f459 | O=C(C(=O)c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(F)cc4)c(-c4ccc(F)cc4)nc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2.FC1=CC=C(C=C1)C(=O)C(=O)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C1=NC2=CC=C(C=C2N=C1C1=CC=C(C=C1)F)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | O=C(C(=O)c1cc[c:21]([F:22])[cH:20][cH:19]1)c1cc[c:29]([F:30])[cH:28]c1.c1c[c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:36]4[CH:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[cH:35][c:34]3[n:33][c:25]2-[c:26]2[cH:27]cc[cH:31][cH:32]2)[cH:24][... | O=C(C(=O)c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(F)cc4)c(-c4ccc(F)cc4)nc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | b5ff1b757421adc68e8cc3a1c1e937d4ca45b2b3b7a71e8daf44d408f820e81f | b09cc8aea5fe7202f020f87a8357f25a62cf266759134ef33fd12748362eb2c8 | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=C(-C(=O)-c1:c:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[F;D1;H0:3]):c:c:1)-c1:[cH;D2;+0:4]:[c:5]:[c;H0;D3;+0:6](-[F;D1;H0:7]):c:c:1.[#7;a:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12](-[c:13]2:[c:14]:[cH;D2;+0:15]:c:c:[cH;D2;+0:16]:2):[c:17]:1-[c;H0;D3;+0:18]1:[c:19]:[cH;D2;+0:20]:c:c:c:1>>[F;D1;H0:7]-[c;H0;D3;+0:6]1:[c:5]:[cH;D2;+0:4]:[c;H... | null | [] | null | null | null | null | Prepared as described for Compound 406 using 4,4′-difluorobenzil in place of benzil.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Ketone | Aromatic halide.Aromatic halide | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(C(=O)c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(F)cc4)c(-c4ccc(F)cc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1fc82499d874ad5a57215b2516ffb39 | COc1cccc(C(=O)C(=O)c2cccc(OC)c2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>COc1cccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2cccc(OC)c2)c1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2.COC=1C=C(C=CC1)C(=O)C(=O)C1=CC(=CC=C1)OC>>COC=1C=C(C=CC1)C1=NC2=CC=C(C=C2N=C1C1=CC(=CC=C1)OC)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | O=C(C(=O)[c:36]1[cH:37][cH:38][cH:39][c:40]([O:41][CH3:42])[cH:43]1)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]1.c1ccc(-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13](-[c:14]4[n:15][c:16]5[cH:17][c:18]([C:19](=[O:20])[OH:21])[cH:22][cH:23][c:24]5[n:25]4[CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)[cH:32][c:33]3[n:3... | COc1cccc(C(=O)C(=O)c2cccc(OC)c2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | COc1cccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2cccc(OC)c2)c1 | null | null | null | C-C Coupling | OtherReaction | 2585b5e7fc7fd47b3598fef6a2f3603251109daf26aba6843a50175402531759 | 99def8b73cb571e88df07b5a7104de2d97f258f18cfc88f7c0d26bf53483ceb8 | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=C(-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c;H0;D3;+0:15](-c2:c:c:c:c:c:2):[c;H0;D3;+0:16]:1-c1:c:c:c:c:c:1>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:16]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c;H0;D3;+0:15]:1-[c;H0;D3;+0:1](:[c:2]:[c:3... | null | [] | null | null | null | null | Prepared as described for Compound 406 using 3,3′-dimethoxybenzil in place of benzil.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2nccnc2c1.c1ccccc1 | c1ccccc1.c1ccc2nccnc2c1.c1ccccc1 | c1ccccc1.c1ccc2nccnc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1.c1ccccc1 | HO- | null | null | null | COc1cccc(C(=O)C(=O)c2cccc(OC)c2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>COc1cccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83f7de4a108e48e1bf8dcf3c67b92b2e | COc1ccc(C(=O)C(=O)c2ccc(OC)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>COc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(OC)cc2)cc1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C(=NC1=CC2)C2=CC=CC=C2)C2=CC=CC=C2.COC1=CC=C(C=C1)C(=O)C(=O)C1=CC=C(C=C1)OC>>COC1=CC=C(C=C1)C1=NC2=CC=C(C=C2N=C1C1=CC=C(C=C1)OC)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | O=C(C(=O)[c:35]1[cH:36][cH:37][c:38]([O:39][CH3:40])[cH:41][cH:42]1)c1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][cH:43]1.c1ccc(-[c:34]2[c:7](-[c:6]3ccccc3)[n:8][c:9]3[cH:10][cH:11][c:12](-[c:13]4[n:14][c:15]5[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23]5[n:24]4[CH:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)[... | COc1ccc(C(=O)C(=O)c2ccc(OC)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1 | COc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(OC)cc2)cc1 | null | null | null | C-C Coupling | OtherReaction | 2585b5e7fc7fd47b3598fef6a2f3603251109daf26aba6843a50175402531759 | 99def8b73cb571e88df07b5a7104de2d97f258f18cfc88f7c0d26bf53483ceb8 | c1ccc(-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3nc2-c2ccccc2)cc1 | O=C(-C(=O)-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15](-[c;H0;D3;+0:16]2:c:c:c:c:c:2):[c;H0;D3;+0:17]:1-c1:c:c:c:c:c:1>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:17]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1-[c;H0;D3;+0:16]1:[cH;D... | null | [] | null | null | null | null | Prepared as described for Compound 406 using 4,4′-dimethoxybenzil in place of benzil.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2nccnc2c1 | c1ccccc1.c1ccc2nccnc2c1.c1ccccc1 | c1ccccc1.c1ccc2nccnc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1.c1ccccc1 | HO- | null | null | null | COc1ccc(C(=O)C(=O)c2ccc(OC)cc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)c(-c4ccccc4)nc3c1)n2C1CCCCC1>>COc1ccc(-c2nc3ccc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)cc3nc2-c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a95e450f826d44a79035dcf9ee69447b | COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1OC.O=[N+]([O-])c1ccc(B(O)O)cc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc([N+](=O)[O-])cc4)ccc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=C(C=C2)OC)OC)C(=O)N2CCCC2.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)[N+](=O)[O-])C(=O)N2CCCC2 | COc1cc[c:31](-[c:30]2[c:18](-[c:17]3[n:16][c:15]4[cH:14][cH:13][c:12](-[c:11]5[n:10][c:8]6[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]6)[n:44]5[CH:45]5[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]5)[cH:43][c:42]4[cH:41][cH:40]3)[cH:19][c:20]([C:21](=[O:22])[N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29]2)cc1OC... | COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1OC.O=[N+]([O-])c1ccc(B(O)O)cc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc([N+](=O)[O-])cc4)ccc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | e7016461b6a49ddcd965abff2980136a10dc812f0b18d6cf61eecb08e136094b | 87db1303acea5973f03a377de30076eddd78bf401fd841439ee11d6ebfb23f8b | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | C-O-c1:c:c:[c;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]):c:c:1-O-C.O-B(-O)-c1:[cH;D2;+0:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[c:3]:[c:2](-[c;H0;D3;+0:1]1:[cH;D2;+0:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1):[c:4] | null | [] | null | null | null | null | The title compound (5.2 mg yield) was prepared as described for Compound 419 using 4-nitrophenylboronic acid in place of 3,4-dimethoxyphenylboronic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HO-.B | null | null | null | COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1OC.O=[N+]([O-])c1ccc(B(O)O)cc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc([N+](=O)[O-])cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a2b9777bb2f40ab8aa7be56f19d678a | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)OCC)C=2C=C1C=CC(=NC1=CC2)C(=O)O.[OH-].[Na+]>>C(=O)(O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(=O)O)C2CCCCC2)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:12]1[cH:13][cH:14][c:15]3[n:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23]3[cH:24]1)[n:25]2[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:12]1[cH:13][cH:14][c:1... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A solution of 90 mg (0.2 mmol) of Compound 402a and 1 mL 2 N aq. NaOH in 4 mL MeOH was heated overnight at 55° C. The solvent was evaporated, the residue was dissolved in H2O and neutralized. The precipitate was filtered, washed with H2O and dried. The product was purified by HPLC to yield 34 mg.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.C1CCCCC1 | Other | CO | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1>CO>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef9a621588f5428ca617a34cf18decac | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.C[C@H](N)C(N)=O>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1 | CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)OCC)C=2C=C1C=CC(=NC1=CC2)C(=O)O.N[C@@H](C)C(=O)N.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1 | O[C:20]([c:19]1[n:18][c:17]2[cH:16][cH:15][c:14](-[c:13]3[n:12][c:10]4[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]4)[n:32]3[CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:31][c:30]2[cH:29][cH:28]1)=[O:21].[NH2:22][C@@H:23]([CH3:24])[C:25]([NH2:26])=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.C[C@H](N)C(N)=O | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[C@H;D3;+0:8](-[NH2;D1;+0:9])-[C:10](-[N;D1;H2:11])=[O;D1;H0:12]>>[C;D1;H3:7]-[CH;D3;+0:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:10](-[N;D1;H2:11])=[O;D1;H0:12] | 42.3 | [{"value": 42.3, "product": "C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 100 mg (0.23 mmol) of Compound 402a, 86 mg (0.69 mmol) of L-alaninamide, 322 mg (0.69 mmol) of PyBroP, 84 mg (0.69 mmol) DMAP and 89 mg (0.69 mmol) DIEA in 5 mL anhydrous CH2Cl2 was stirred at room temperature for 24 h. To this solution was added 214 mg (0.92 mmol) of CSA. The solution was stirred for ano... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.C1CCCCC1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 24 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.C[C@H](N)C(N)=O>CN(C)C=1C=CN=CC1.C(Cl)Cl>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-325e96fcb26e4bd99c7218c85a49fa0c | CC(C)[C@H](N)C(N)=O.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1>>CC(C)C(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1.N[C@@H](C(C)C)C(=O)N.C(N)(=O)C(C)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O>>C(N)(=O)C(C(C)C)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | NC(=O)[C@@H](N)[CH:2]([CH3:1])[CH3:3].CC[O:21][C:19]([c:18]1[cH:17][c:16]2[n:15][c:14](-[c:13]3[cH:12][c:11]4[cH:10][cH:9][c:8]([C:6]([NH:5][CH:4](C)[C:36]([NH2:37])=[O:38])=[O:7])[n:35][c:34]4[cH:33][cH:32]3)[n:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[c:24]2[cH:23][cH:22]1)=[O:20]>>[CH3:1][CH:2]([CH3:3])... | CC(C)[C@H](N)C(N)=O.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1 | CC(C)C(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O | null | null | null | C-C Coupling | OtherReaction | 071c3b4b41af2985190b2d71847b92cd1df6399508b7de3ff4e79668678a14ff | 18b0ca9d4623aa7b1f5ac4c47828d437c9d9d5901ab32e97d4b5aa357afc07ba | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[CH;D3;+0:5](-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[#7;a:10])-[C:11](-[N;D1;H2:12])=[O;D1;H0:13].N-C(=O)-[C@@H](-N)-[CH;D3;+0:14](-[C;D1;H3:15])-[C;D1;H3:16]>>[#7;a:10]:[c:9]-[C:7](=[O;D1;H0:8])-[#7:6]-[CH;D3;+0:5](-[C:11](-[N;D1;H2:12])=[O;D1;H0:13])-[CH;D3;+0:14](-[C;D1;H3:1... | null | [] | null | null | null | null | The title compound (5 mg yield) was prepared as described for Compound 497a using L-valinamide in place of L-alaninamide, and hydrolyzed as described for Compound 497.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amide.Primary amine | Carboxylic acid | null | null | c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | null | null | null | CC(C)[C@H](N)C(N)=O.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1>>CC(C)C(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5461eb862a184c4eb8708425c0f39fb1 | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1c[nH]cn1>>NC(=O)C(Cc1ncc[nH]1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1.N[C@@H](CC1=CNC=N1)C(=O)N.C(N)(=O)C(C)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O>>C(N)(=O)C(CC=1NC=CN1)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | [NH2:1][C:2](=[O:3])[CH:4]([CH3:5])[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[n:21][c:22]4[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29][c:30]4[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[n:41]1.NC(=O)[C@@H](N)C[c:6]1[n:7][cH:8][nH:10][cH:9]1>>[NH2:1]... | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1c[nH]cn1 | NC(=O)C(Cc1ncc[nH]1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | null | C-C Coupling | OtherReaction | ed8571bde74ccaf30384e39acb413fdaeeeeafa1a6ef5fae77a2a4b0bdef3321 | 81758d3c7ce7424f80d9452cdaded113984934370422cdecceaeafd777340c3b | O=C(NCCc1ncc[nH]1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | N-C(=O)-[C@@H](-N)-C-[c;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[nH;D2;+0:4]:[cH;D2;+0:5]:1.[CH3;D1;+0:6]-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]>>[N;D1;H2:12]-[C:11](=[O;D1;H0:13])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[CH2;D2;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[cH;D2;+0:5]:[nH;D2;+0:4]:1 | null | [] | null | null | null | null | The title compound (8 mg yield) was prepared as described for Compound 497a using L-histidinamide in place of L-alaninamide and hydrolyzed as described for Compound 497.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | null | null | null | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1c[nH]cn1>>NC(=O)C(Cc1ncc[nH]1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e94738fce59f4a0a8f2a34c090dfa959 | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)CO>>NC(=O)C(CO)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1.N[C@@H](CO)C(=O)N.C(N)(=O)C(C)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O>>C(N)(=O)C(CO)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | C[CH:4]([C:2]([NH2:1])=[O:3])[NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]4[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[n:37]1.NC(=O)[C@@H](N)[CH2:5][OH:6]>>[NH2:1][C:2](=[O:3])[CH:4]([CH2:5][... | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)CO | NC(=O)C(CO)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | null | C-C Coupling | OtherReaction | 16e3eb214afab89471a8ad9638384fe82f9cab3b7c6b51c1bd1dce3fca169e66 | 6a8e7848616d1b73cc1c93873f769d63755d34e8c82bb0761cae921db7d11456 | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | C-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6])-[C:7](-[N;D1;H2:8])=[O;D1;H0:9].N-C(=O)-[C@@H](-N)-[CH2;D2;+0:10]-[O;D1;H1:11]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#7:2]-[CH;D3;+0:1](-[CH2;D2;+0:10]-[O;D1;H1:11])-[C:7](-[N;D1;H2:8])=[O;D1;H0:9] | null | [] | null | null | null | null | The title compound (5 mg yield) was prepared as described for Compound 497a using L-serinamide in place of L-alaninamide and hydrolyzed as described for Compound 497.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary alcohol.Primary amine | Primary alcohol | null | null | c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | null | null | null | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)CO>>NC(=O)C(CO)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f65a74023abf49d7bf98eb90d732f5aa | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1ccccc1>>NC(=O)C(Cc1ccccc1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1.N[C@@H](CC1=CC=CC=C1)C(=O)N.C(N)(=O)C(C)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O>>C(N)(=O)C(CC1=CC=CC=C1)NC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(N[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20](-[c:21]3[n:22][c:23]4[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]4[n:32]3[CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:39][cH:40][c:41]2[n:42]1)C(N)=O.[NH2:1][C:2](=[O:3])[C@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH2:12]>>[N... | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1ccccc1 | NC(=O)C(Cc1ccccc1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | null | Acylation | OtherReaction | f4c2f638e60318948ac90dfa9c03d3444d08f75e7747dac6cdda352858bbba9d | 32a49b43181b22bb62827dc53d8257f7b05464280b1d25a887c02a1434554159 | O=C(NCCc1ccccc1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | C-C(-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-C(-N)=O.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[C@@H;D3;+0:10](-[NH2;D1;+0:11])-[C:12]-[c:13]>>[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:12]-[c:13])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | The title compound (5 mg yield) was prepared as described for Compound 497a using L-phenylalaninamide in place of L-alaninamide and hydrolyzed as described for Compound 497.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | null | null | null | CC(NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1)C(N)=O.NC(=O)[C@@H](N)Cc1ccccc1>>NC(=O)C(Cc1ccccc1)NC(=O)c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7621ebc89f2442885f3f2fb8659b267 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1.Nc1ccc(Cl)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)Nc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC(C)C(N)=O)=O)C2CCCCC2)C=C1.ClC1=CC=C(N)C=C1>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NC2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1 | CC(N[C:20]([c:19]1[n:18][c:17]2[cH:16][cH:15][c:14](-[c:13]3[n:12][c:10]4[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]4)[n:34]3[CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[cH:33][c:32]2[cH:31][cH:30]1)=[O:21])C(N)=O.[NH2:22][c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1.Nc1ccc(Cl)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)Nc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | null | Acylation | OtherReaction | f4c2f638e60318948ac90dfa9c03d3444d08f75e7747dac6cdda352858bbba9d | 32a49b43181b22bb62827dc53d8257f7b05464280b1d25a887c02a1434554159 | O=C(Nc1ccccc1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | C-C(-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-C(-N)=O.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | The title compound was prepared as described for Compound 497a using 4-chloroaniline in place of L-alaninamide yielding 91 mg yellow solid. MS: 553.23 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide.Primary amine | Secondary amide | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NC(C)C(N)=O)ccc3c1)n2C1CCCCC1.Nc1ccc(Cl)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)Nc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2610541fefbf4ea1800dbbcae7606982 | COC(=O)c1ccc(N)c(C=O)c1.Cc1cc(Br)ccc1[N+](=O)[O-]>>Nc1ccc(Br)cc1C=O | COC(C1=CC(=C(C=C1)N)C=O)=O.BrC=1C=CC(=C(C1)C)[N+](=O)[O-]>>NC1=C(C=O)C=C(C=C1)Br | COC(=O)c1ccc(N)c(C=[O:10])c1.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[CH3:9]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[CH:9]=[O:10] | COC(=O)c1ccc(N)c(C=O)c1.Cc1cc(Br)ccc1[N+](=O)[O-] | Nc1ccc(Br)cc1C=O | null | null | null | Functional Group Interconversion | OtherReaction | 042e2a520cc0a3baccb3b60d9fbdcea907b8d1ba199d2456815b2bfb5d0e80b1 | 30708cab4f6652df3674dd025998f44e75ccf959034240412389cee4d338a191 | c1ccccc1 | C-O-C(=O)-c1:c:c:c(-N):c(-C=[O;H0;D1;+0:1]):c:1.O=[N+;H0;D3:2](-[O-])-[c:3](:[c:4]):[c:5](-[CH3;D1;+0:6]):[c:7]>>[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:1]):[c:7] | null | [] | null | null | null | null | The title intermediate was synthesized as described for Compound 7 in five steps starting from 5-bromo-2-nitrotoluene instead of 3-methyl-4-nitrobenazoic acid methyl ester. MS: 199.97 & 201.97 (M+H+); H1-NMR (CDCl3): δ (ppm) 9.75 (s, 1H), 7.71 (s, 1H), 7.39 (d, 1H, J=9.3 Hz), 7.22 (s, 2H), 6.72 (d, 1H, J=9.3 Hz);
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Nitro group.Primary amine | Aldehyde.Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | COC(=O)c1ccc(N)c(C=O)c1.Cc1cc(Br)ccc1[N+](=O)[O-]>>Nc1ccc(Br)cc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-996865c270684c3fb0cde1f265a144da | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | CC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].CO>>COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-] | COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 99 | [{"value": 99.0, "product": "COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-Methyl-3-nitro benzoic acid (12.5 g, 69 mmol) was dissolved in anhydrous methanol (500 mL) in a 1 L flask. HCl gas was then bubbled through the solution until saturation (3 h). The HCl source was then removed, and the reaction was stirred at room temperature overnight. The reaction was then concentrated to dryness an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | 8 | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51e6b8b87432486790abfede31b72046 | O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1>>O=C(O)c1ccc2cc(-c3ccccc3)cnc2c1 | C1(=CC=CC=C1)C1=NC2=CC(=CC=C2C=C1)C(=O)O.COC(C1=CC(=C(C=C1)C=O)N)=O.C1(=CC=CC=C1)CC=O>>C1(=CC=CC=C1)C=1C=NC2=CC(=CC=C2C1)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][c:16](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:17][c:18]2[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][n:17][c:18]2[cH:19]1 | O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1 | O=C(O)c1ccc2cc(-c3ccccc3)cnc2c1 | null | null | null | Miscellaneous | OtherReaction | f6f691826e88d07057a5cbcf7d3e652d23ee5c4f22ff42f1e6c791dc9f00b283 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2cnc3ccccc3c2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1):[c:10]:[c:11]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[#7;a:5]:[cH;D2;+0:4]:1):[c:10]:[c:11] | 87 | [{"value": 87.0, "product": "C1(=CC=CC=C1)C=1C=NC2=CC(=CC=C2C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the same reaction procedure and workup for Compound 405f, 500 mg (2.8 mmol) of Compound 53 was reacted with 340 mg (2.8 mmol) phenylacetaldehyde to produce 603 mg (87% yield) of the title intermediate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | null | null | null | null | O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1>>O=C(O)c1ccc2cc(-c3ccccc3)cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b5b89fcdf564fe386e02f5424db8de5 | O=C(O)c1ccc2c(c1)nc(-c1ccc3ccc(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3cc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [OH-].[Na+].C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC=C1C=CC(=NC1=C2)C2=CC=CC=C2.C(C)(=O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC=C1C=C(C=NC1=C2)C2=CC=CC=C2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:12]1[cH:13][cH:14][c:15]3[cH:16][cH:17][c:24](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[n:25][c:26]3[cH:27]1)[n:28]2[CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:1... | O=C(O)c1ccc2c(c1)nc(-c1ccc3ccc(-c4ccccc4)nc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3cc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | CCO | Miscellaneous | OtherReaction | f6f691826e88d07057a5cbcf7d3e652d23ee5c4f22ff42f1e6c791dc9f00b283 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3c2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1):[c:10]:[c:11]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[#7;a:5]:[cH;D2;+0:4]:1):[c:10]:[c:11] | 17 | [{"value": 17.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C2=CC=C1C=C(C=NC1=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the same reaction procedure and workup as for Compound 405, 450 mg (0.9 mmol) of the product from the previous step was cyclized with 40 mL acetic acid and saponified with 35 mL EtOH and 7 mL 1M NaOH to produce 70 mg (17% yield) of the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | null | CCO | null | null | O=C(O)c1ccc2c(c1)nc(-c1ccc3ccc(-c4ccccc4)nc3c1)n2C1CCCCC1>CCO>O=C(O)c1ccc2c(c1)nc(-c1ccc3cc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f19e1d607e984d218444c87191fc51c7 | Nc1cccc2ccc(O)cc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(Nc1cccc2ccc(O)cc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | N1(CCOCC1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.NC=1C=CC=C2C=CC(=CC12)O>>OC1=CC=C2C=CC=C(C2=C1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]12.C1CN(N[C:2](=[O:1])[c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[n:21][c:22](-[c:23]2[cH:24][cH:25][c:26]4[n:27][c:28](-[c:29]5[cH:30][cH:31][cH:32][cH:33][cH:34]5)[cH:35][n:36][c:37]4[cH:38]2)[n:39]3[CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44]... | Nc1cccc2ccc(O)cc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(Nc1cccc2ccc(O)cc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Acylation | OtherReaction | 4f548ec504fff937628077160178b3c9fed85cfac0828da72bbcc9b51360aa57 | 8f23d7ecda4d84b4383fd8be386f02db6f882d0b1474d7b6f40bedcbb175410a | O=C(Nc1cccc2ccccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-N-N1-C-C-O-C-C-1):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7] | 20 | [{"value": 20.0, "product": "OC1=CC=C2C=CC=C(C2=C1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 574 was used with 8-amino-naphthalen-2-ol (15.9 mg), producing 5 mg of the title compound (20% yield). MS: 590.25 (M+H+) HPLC Procedure A, retention time=15.31 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Primary amine | Secondary amide | C1COCCN1 | null | c1ccc2ccccc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | Nc1cccc2ccc(O)cc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(Nc1cccc2ccc(O)cc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d15d8fd54c041dc9ea09e3f50429660 | Nc1cccc2c(O)cccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(Nc1cccc2c(O)cccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | N1(CCOCC1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.NC1=C2C=CC=C(C2=CC=C1)O>>OC1=C2C=CC=C(C2=CC=C1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]([OH:10])[cH:11][cH:12][cH:13][c:14]12.C1CN(N[C:2](=[O:1])[c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[n:21][c:22](-[c:23]2[cH:24][cH:25][c:26]4[n:27][c:28](-[c:29]5[cH:30][cH:31][cH:32][cH:33][cH:34]5)[cH:35][n:36][c:37]4[cH:38]2)[n:39]3[CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44]... | Nc1cccc2c(O)cccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(Nc1cccc2c(O)cccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Acylation | OtherReaction | 4f548ec504fff937628077160178b3c9fed85cfac0828da72bbcc9b51360aa57 | 8f23d7ecda4d84b4383fd8be386f02db6f882d0b1474d7b6f40bedcbb175410a | O=C(Nc1cccc2ccccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-N-N1-C-C-O-C-C-1):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7] | 25 | [{"value": 25.0, "product": "OC1=C2C=CC=C(C2=CC=C1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 574 was used with 5-amino-naphthalen-1-ol (15.9 mg), producing 7 mg of the title compound (25% yield). MS: 590.24 (M+H+) HPLC Procedure A, retention time=15.26 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Primary amine | Secondary amide | C1COCCN1 | null | c1ccc2ccccc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | Nc1cccc2c(O)cccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(Nc1cccc2c(O)cccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f90156ac52c440d7a7ecf69af9d377f2 | Nc1ccc2cc(C(=O)O)ccc2c1.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(O)c1ccc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc2c1 | N1(CCOCC1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.NC=1C=C2C=CC(=CC2=CC1)C(=O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC=2C=C1C=CC(=CC1=CC2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:44][cH:45][c:46]2[cH:47]1.C1CN(N[C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]4[n:25][c:26](-[c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[cH:33][n:34][c:35]4[cH:36]2)[n:37]3[CH:38]2[CH2:39][CH2:40][... | Nc1ccc2cc(C(=O)O)ccc2c1.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(O)c1ccc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc2c1 | null | null | null | Acylation | OtherReaction | 4f548ec504fff937628077160178b3c9fed85cfac0828da72bbcc9b51360aa57 | 8f23d7ecda4d84b4383fd8be386f02db6f882d0b1474d7b6f40bedcbb175410a | O=C(Nc1ccc2ccccc2c1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-N-N1-C-C-O-C-C-1):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7] | 53 | [{"value": 53.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC=2C=C1C=CC(=CC1=CC2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 574 was used with 6-amino-naphthalene-2-carboxylic acid (18.7 mg), producing 15 mg of the title compound (53% yield). MS: 618.30 (M+H+) HPLC Procedure A, retention time=16.24 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Primary amine | Secondary amide | C1COCCN1 | null | c1ccc2ccccc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | Nc1ccc2cc(C(=O)O)ccc2c1.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(O)c1ccc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fd734490f3241b4926853d768dbdc08 | Cc1cc(=O)oc2cc(N)ccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>Cc1cc(=O)oc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc12 | N1(CCOCC1)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.NC1=CC=C2C(=CC(OC2=C1)=O)C>>CC1=CC(OC2=CC(=CC=C12)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1)=O | [CH3:1][c:2]1[cH:3][c:4](=[O:5])[o:6][c:7]2[cH:8][c:9]([NH2:10])[cH:44][cH:45][c:46]12.C1CN(N[C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]4[n:25][c:26](-[c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[cH:33][n:34][c:35]4[cH:36]2)[n:37]3[CH:38]2[CH2:39][CH2:40][CH2:41]... | Cc1cc(=O)oc2cc(N)ccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | Cc1cc(=O)oc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc12 | null | null | null | Acylation | OtherReaction | 4f548ec504fff937628077160178b3c9fed85cfac0828da72bbcc9b51360aa57 | 8f23d7ecda4d84b4383fd8be386f02db6f882d0b1474d7b6f40bedcbb175410a | O=C(Nc1ccc2ccc(=O)oc2c1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-N-N1-C-C-O-C-C-1):[c:7].[#8;a:8]:[c:9]:[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:12]-[c:11](:[c:13]):[c:10]:[c:9]:[#8;a:8]):[c:7] | 27 | [{"value": 27.0, "product": "CC1=CC(OC2=CC(=CC=C12)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 574 was used with 7-Amino-4-methyl-chromen-2-one (17.5 mg), producing 8 mg of the title compound (27% yield). MS: 606.29 (M+H+) HPLC Procedure A, retention time=19.22 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Primary amine | Secondary amide | C1COCCN1 | null | c1ccc2cccoc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | Cc1cc(=O)oc2cc(N)ccc12.O=C(NN1CCOCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>Cc1cc(=O)oc2cc(NC(=O)c3ccc4c(c3)nc(-c3ccc5nc(-c6ccccc6)cnc5c3)n4C3CCCCC3)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69d0562ddf334b968cb7cf8b9f8bccaf | CO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3c(c1)CCC(c1ccccc1)N3)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2.CO>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1CCC(NC1=CC2)C2=CC=CC=C2 | O[CH3:18].n1[c:16]2[c:15]([cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:17]2)[n:27][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:1... | CO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3c(c1)CCC(c1ccccc1)N3)n2C1CCCCC1 | null | [Pt]=O | null | C-C Coupling | OtherReaction | 8ccad5df995a0e3ae8425227ec1de04f50da0fb9dd9e80ad7109b42b2b8b7108 | d80e9c8f1cb73de4407c680a89390fbbfe9dc0b798896329454cba59f37c6e63 | c1ccc(C2CCc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3N2)cc1 | O-[CH3;D1;+0:1].[c:2]:[c:3]:[c;H0;D3;+0:4]1:n:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[c:13]:1:[c:14]>>[c:2]:[c:3]:[c;H0;D3;+0:4]1:[c:13](:[c:14])-[NH;D2;+0:12]-[CH;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-[CH2;D2;+0:5]-[CH2;D2;+0:1]-1 | 37 | [{"value": 37.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1CCC(NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of Compound 203 (100 mg, 0.23 mmol) and platinum oxide (12 mg, 0.048 mmol) in methanol (5 mL) was hydrogenated at 40 psi for 3 h. The reaction was evaporated to dryness, and purified via HPLC. The resulting compound was then converted to the HCl salt using the standard method, yielding 40 mg (37% yield) of t... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Secondary amine | c1ccc2nccnc2c1 | c1ccc2c(c1)CCCN2 | c1ccc2nc[nH]c2c1.c1ccc2c(c1)CCCN2.c1ccccc1.C1CCCCC1 | Other | [Pt]=O | null | null | CO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>[Pt]=O>O=C(O)c1ccc2c(c1)nc(-c1ccc3c(c1)CCC(c1ccccc1)N3)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6407c5c47c5d40179ff0ffbe2a0ddb91 | O=Cc1ccccc1Br>>OC(Cc1ccccc1)c1ccccc1Br | BrC1=C(C=O)C=CC=C1>>BrC1=C(C=CC=C1)C(CC1=CC=CC=C1)O | [O:1]=[CH:2][c:10]1[cH:11][cH:3][cH:13][cH:14][c:15]1[Br:16]>>[OH:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Br:16] | O=Cc1ccccc1Br | OC(Cc1ccccc1)c1ccccc1Br | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | e0491bf6f518a9ce005e928ff9be06918efd8060222a74d00b75b1e53a66a5b1 | 6318a0e9fb1d756c97d86db7e28e5f6266d7a157dcbb02a5dab947d71eb6de40 | c1ccc(CCc2ccccc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1>>[OH;D1;+0:1]-[CH;D3;+0:2](-[CH2;D2;+0:7]-[c:9](:[c:10]):[c:11])-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:12]:[cH;D2;+0:8]:1 | 69.5 | [{"value": 33.0, "product": "BrC1=C(C=CC=C1)C(CC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "BrC1=C(C=CC=C1)C(CC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | A mixture of 2-bromobenzaldehyde (1 mL, 5.4 mmol) in diethylether (2 mL) was added to a flame dried flask, and flushed with argon. The temperature was reduced to −10° C. and benzylmagnesium chloride was slowly added to the flask via syringe. The reaction was stirred at −10° C. for 1 hour and then stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(C)OCC | -10 | 1 | O=Cc1ccccc1Br>C(C)OCC>OC(Cc1ccccc1)c1ccccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac96ea8dd609482fadcaf9874f73ccec | O=C(Cc1ccccc1)c1ccccc1Br.O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1>>O=C(O)c1ccc2nc(-c3ccccc3)c(-c3ccccc3Br)cc2c1 | [OH-].[K+].BrC1=C(C=CC=C1)C(CC1=CC=CC=C1)=O.C1(=CC=CC=C1)C1=NC2=CC(=CC=C2C=C1)C(=O)O.COC(C1=CC(=C(C=C1)C=O)N)=O>>BrC1=C(C=CC=C1)C=1C(=NC2=CC=C(C=C2C1)C(=O)O)C1=CC=CC=C1 | O=[C:16]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Br:23].c1ccc(-c2c[cH:24][c:25]3[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:26][c:7]3[n:8]2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16](-[c:17]3[cH:18][c... | O=C(Cc1ccccc1)c1ccccc1Br.O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1 | O=C(O)c1ccc2nc(-c3ccccc3)c(-c3ccccc3Br)cc2c1 | null | null | C(C)O | Miscellaneous | OtherReaction | ae62b681ea84868d1d2f7aa4b1dc673955b875637d3380e3d8040d09295c977f | 9db0f73aed071f5fa7238b261fc87a241efa69e871d2f239452605149d0c954e | c1ccc(-c2cc3ccccc3nc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[Br;D1;H0:12]):[c:13].[O;D1;H0:14]=[C:15](-[O;D1;H1:16])-[c:17]1:[c:18]:[cH;D2;+0:19]:[c;H0;D3;+0:20]2:[cH;D2;+0:21]:c:c(-c3:c:c:c:c:c:3):[n;H0;D2;+0:22]:[c;H0;D3;+0:23]:2:[cH;D2;+0:24]:1>>[Br;D1;H0:12]-[c:11... | 40 | [{"value": 40.0, "product": "BrC1=C(C=CC=C1)C=1C(=NC2=CC=C(C=C2C1)C(=O)O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the same reaction procedure and workup as for Compound 405f (235 mg, 1.31 mmol) of Compound 53 was reacted with the product of the previous reaction, Compound 424b (360 mg, 1.31 mmol), in ethanol (12 mL) using 10% w/v KOH in ethanol (1.1 mL) to produce the title compound (210 mg, 40% yield).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | O=C(Cc1ccccc1)c1ccccc1Br.O=C(O)c1ccc2ccc(-c3ccccc3)nc2c1>C(C)O>O=C(O)c1ccc2nc(-c3ccccc3)c(-c3ccccc3Br)cc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0877fc4f7d040d7b6c35f3309892e7a | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)c(-c4ccccc4)cc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)c(-c4ccccc4)cc3c1)n2C1CCCCC1 | BrC1=C(C=CC=C1)C1=NC2=CC=C(C=C2C=C1C1=CC=CC=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O.ClC1=CC=C(C=C1)B(O)O.[F-].[Cs+].C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1>>ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2C2=CC=CC=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C=C1 | Br[c:23]1[c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:41]4[CH:42]4[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]4)[cH:40][c:39]3[cH:38][c:31]2-[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[cH:19][cH:20][cH:21][cH:22]1.OB(O)[c:24]1[cH:25][cH:26][c:2... | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)c(-c4ccccc4)cc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)c(-c4ccccc4)cc3c1)n2C1CCCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2-c2nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3cc2-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 10 | [{"value": 10.0, "product": "ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2C2=CC=CC=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.6, "product": "ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2C2=CC=CC=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C=C1", "details": "CALCULATEDP... | null | null | null | null | Compound 424 (50 mg, 0.083 mmol), 4-chlorophenylboronic acid (20 mg, 0.125 mmol), and CsF (143 mg, 0.94 mmol) were added to degassed dioxane (6 mL). A solution of 2-(dicyclohexylphosphino)biphenyl (5 mg, 0.0125 mmol) and palladium acetate (2 mg, 0.0083 mmol) in degassed dioxane (3 mL) was added to the reaction solution... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCOCC1 | null | null | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)c(-c4ccccc4)cc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCOCC1>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)c(-c4ccccc4)cc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8bed7191e06c456c8c8827c4bb81f6b9 | CC(=O)c1sc(C)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1nc(C)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)s1 | [OH-].[K+].CC=1SC(=C(N1)C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(N=C(S2)C)C | CC(=O)[c:6]1[c:4]([CH3:5])[n:3][c:2]([CH3:1])[s:35]1.Oc1ccc(Br)cc1-[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12](-[c:13]3[n:14][c:15]4[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23]4[n:24]3[CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[n:34]1>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6](-[c:7]2[cH... | CC(=O)c1sc(C)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1nc(C)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)s1 | null | null | C(C)O | C-C Coupling | OtherReaction | 1d5c6f5b005ed70236ee338e17825f9573e4b8d5662849fd033a7cd4739092e7 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4cncs4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8](-[C;D1;H3:9]):[#7;a:10]:[c:11]:1-[C;D1;H3:12]>>[C;D1;H3:9]-[c:8]1:[#16;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11](-[C;D1;H3:12]):[#7;a:10]:1 | 12 | [{"value": 12.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(N=C(S2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2,4-dimethyl-thiazol-5-yl)-ethanone (40 mg, 0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (14 mg, 12% yield).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cscn1.c1ccccc1.c1ccc2ncccc2c1 | c1cscn1.c1ccc2ncccc2c1 | c1cscn1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1sc(C)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1nc(C)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3596edbd2f384c0d836cf126775eadf5 | CC(=O)c1cnccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnccn4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1=C(C=NC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=NC=CN=C2 | CC(=O)[c:18]1[cH:19][n:20][cH:21][cH:22][n:23]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:27][c:26]2[cH:25][cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)... | CC(=O)c1cnccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnccn4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 8d7f7f838313f3fa8ed1d397054cedde74cba805c43cafbd7c0fcc30f04297af | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4cnccn4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1):[c:4]:[c:5] | 10 | [{"value": 10.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=NC=CN=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-pyrazin-2-yl-ethanone (32 mg, 0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (15 mg, 10% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cnccn1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cnccn1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cnccn1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cnccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnccn4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-561575b8e7704ae387f663ecc1da3ca6 | CC(=O)c1cc(C)sc1-c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(-c2ccccc2)s1 | [OH-].[K+].CC1=CC(=C(S1)C1=CC=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(SC(=C2)C)C2=CC=CC=C2 | CC(=O)[c:4]1[cH:3][c:2]([CH3:1])[s:40][c:33]1-[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.Oc1ccc(Br)cc1-[c:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20][c:21]4[n:22]3[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[n:32]1>>[CH3:1][c:2]1... | CC(=O)c1cc(C)sc1-c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(-c2ccccc2)s1 | null | null | C(C)O | C-C Coupling | OtherReaction | 720f87d7df89fae5bee313ea8aae90dd7d141265b6e283e34e49e8dc216a5da5 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2sccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c:8](-[C;D1;H3:9]):[#16;a:10]:[c:11]:1-[c:12]>>[C;D1;H3:9]-[c:8]1:[#16;a:10]:[c:11](-[c:12]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:1 | 6 | [{"value": 6.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(SC(=C2)C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(5-methyl-2-phenyl-thiophen-3-yl)-ethanone (56 mg, 0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (8 mg, 6% yield). MS: 544.27 (M+H+) HPLC Procedure A,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccsc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccsc1.c1ccc2ncccc2c1 | c1ccsc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1.c1ccccc1 | HBr | C(C)O | null | null | CC(=O)c1cc(C)sc1-c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(-c2ccccc2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0314f5eca9248e8bebd8db872902711 | CC(=O)c1cccnc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccnc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1=CC(=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=NC=CC2 | CC(=O)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:27][c:26]2[cH:25][cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1... | CC(=O)c1cccnc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccnc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | d5534b6176d25a1cb3e85eefaaaa0dc1ef5ab28f7e223e08a461bb05612a5757 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1cncc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1):[c:4]:[c:5] | 17 | [{"value": 17.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-pyridin-3-yl-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (19 mg, 17% yield). MS: 449.21 (M+H+) HPLC Procedure A, retention time=7.96 min.
... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccncc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccncc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccncc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cccnc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccnc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6683c72d96d44e91a5ddb2d6855abedd | CC(=O)Nc1ccc(C(C)=O)cc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Br | [OH-].[K+].C(C)(=O)C1=CC(=C(C=C1)NC(C)=O)Br.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>NC1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)Br | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5](C(C)=O)[cH:34][c:35]1[Br:36].Oc1ccc(Br)cc1-[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[n:13][c:14]4[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]4[n:23]3[CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[cH:30][cH:31][c:32]2[n:33]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]... | CC(=O)Nc1ccc(C(C)=O)cc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Br | null | null | C(C)O | C-C Coupling | OtherReaction | b0109585fb62adf21b170d8a9b3adf76273dcbc10a034897a2b5300b11ff5c59 | 5ca2dbb86b1d71648651aa5e8bd2a294710e9b63655fd94318bc1399c5ea000e | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[c;H0;D3;+0:10](-C(-C)=O):[c:11]:[c:12]:1>>[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11]:[c:12]:1 | 15 | [{"value": 15.0, "product": "NC1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with N-(4-acetyl-2-bromo-phenyl)-acetamide (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (16 mg, 15% yield).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Secondary amide.Aromatic alcohol | Primary amine | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)Nc1ccc(C(C)=O)cc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96ce9955b25e4e4398cc1e634f7c3ab1 | CC(=O)c1sc(N)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1nc(N)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].NC=1SC(=C(N1)C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>NC=1SC(=C(N1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:7]1[c:2]([CH3:1])[n:3][c:4]([NH2:5])[s:6]1.Oc1ccc(Br)cc1-[c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[n:15][c:16]4[cH:17][c:18]([C:19](=[O:20])[OH:21])[cH:22][cH:23][c:24]4[n:25]3[CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33][c:34]2[n:35]1>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:6][c:7]1-[c:8... | CC(=O)c1sc(N)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1nc(N)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 1d5c6f5b005ed70236ee338e17825f9573e4b8d5662849fd033a7cd4739092e7 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4cncs4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8](-[N;D1;H2:9]):[#7;a:10]:[c:11]:1-[C;D1;H3:12]>>[C;D1;H3:12]-[c:11]1:[#7;a:10]:[c:8](-[N;D1;H2:9]):[#16;a:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 9 | [{"value": 9.0, "product": "NC=1SC(=C(N1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2-amino-4-methyl-thiazol-5-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (8 mg, 9% yield). MS: 484.19 (M+H+); HPLC Procedure A, retenti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cscn1.c1ccccc1.c1ccc2ncccc2c1 | c1cscn1.c1ccc2ncccc2c1 | c1cscn1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1sc(N)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1nc(N)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cb1bd4899fc45fe94e854b6f97a9f52 | CC(=O)c1cc2cccc(O)c2o1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5cccc(O)c5o4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].OC1=CC=CC=2C=C(OC21)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2OC1=C(C2)C=CC=C1O | CC(=O)[c:18]1[cH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([OH:25])[c:26]2[o:27]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:32]3[CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:31][c:30]2[cH:29][cH:28]1>>[O:1]=[C:2]([OH:3])[c:4]1[c... | CC(=O)c1cc2cccc(O)c2o1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5cccc(O)c5o4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 6652b3d332750b9521edc9f82282db3de6903bc89164acd6b71bb882c727b5c6 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2oc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#8;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#8;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 20 | [{"value": 20.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2OC1=C(C2)C=CC=C1O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(7-hydroxy-benzofuran-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (19 mg, 20% yield). MS: 504.22 (M+H+); HPLC Procedure A, retention... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2occc2c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2occc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccc2occc2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc2cccc(O)c2o1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5cccc(O)c5o4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c01ec35257e41d6b0e9098be9038ce2 | CC(=O)c1ccccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccn4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1=C(C=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=NC=CC=C2 | CC(=O)[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:27][c:26]2[cH:25][cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1... | CC(=O)c1ccccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccn4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | d5534b6176d25a1cb3e85eefaaaa0dc1ef5ab28f7e223e08a461bb05612a5757 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)nc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 61 | [{"value": 61.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=NC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-pyridin-2-yl-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (66 mg, 61% yield). MS: 449.19 (M+H+); HPLC Procedure A, retention time=9.85 min.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccncc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccncc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccncc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccn4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a729877e4fcc43ea942f71b55ecab342 | CC(=O)c1ccncc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccncc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=NC=C2 | CC(=O)[c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:27][c:26]2[cH:25][cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1... | CC(=O)c1ccncc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccncc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | d5534b6176d25a1cb3e85eefaaaa0dc1ef5ab28f7e223e08a461bb05612a5757 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccncc4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1):[c:4]:[c:5] | 62 | [{"value": 62.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=NC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-pyridin-4-yl-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (68 mg, 62% yield). MS: 449.19 (M+H+); HPLC Procedure A, retention time=7.98 min.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccncc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccncc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccncc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccncc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccncc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a60b87d9e7242568651ab3ec98cd8ec | CC(=O)c1ccc2c(c1)CCCC2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCCC5)ccc3c1)n2C1CCCCC1 | [OH-].[K+].C1=C(C=CC=2CCCCC12)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=1CCCCC1C=C2 | CC(=O)[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[CH2:24][CH2:25][CH2:26][CH2:27]2.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:32]3[CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:31][c:30]2[cH:29][cH:28]1>>[O:1]=[C:2]([OH:3])[c... | CC(=O)c1ccc2c(c1)CCCC2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCCC5)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 078f91edee6b5c6d7b7edf432944d3142beda02044934488d4cffac72c411ca2 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCCC5)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 60 | [{"value": 60.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=1CCCCC1C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (65 mg, 60% yield).
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2c(c1)CCCC2 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccc2c(c1)CCCC2.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc2c(c1)CCCC2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCCC5)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf096c975d6f49ce992b5d9c9a8dca70 | CC(=O)c1ccc(-n2ccnc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(-n5ccnc5)cc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1(C=NC=C1)C1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2C=NC=C2 | CC(=O)[c:18]1[cH:19][cH:20][c:21](-[n:22]2[cH:23][cH:24][n:25][cH:26]2)[cH:27][cH:28]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:33]3[CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[cH:32][c:31]2[cH:30][cH:29]1>>[O:1]=[C:2]([OH:3]... | CC(=O)c1ccc(-n2ccnc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(-n5ccnc5)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(-n5ccnc5)cc4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 59 | [{"value": 59.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2C=NC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-imidazol-1-yl-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (75 mg, 59% yield). MS: 514.23 (M+H+); HPLC Procedure A, retention ti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1c[nH]cn1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(-n2ccnc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(-n5ccnc5)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a67946a7234243fc9a807d1bcb5858dc | CC(=O)c1ccc2c(c1)OCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)OCO5)ccc3c1)n2C1CCCCC1 | [OH-].[K+].O1COC2=C1C=CC(=C2)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>O1COC2=C1C=CC(=C2)C2=NC1=CC=C(C=C1C=C2)C2=NC1=C(N2C2CCCCC2)C=CC(=C1)C(=O)O | CC(=O)[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:30][c:29]2[cH:28][cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c... | CC(=O)c1ccc2c(c1)OCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)OCO5)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 9be81f0fe3669a9a52d6d38cfbe45d9e257f62642d0dc37167152cef6460bdb7 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)OCO5)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]-[#8:11]>>[#8:11]-[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 24 | [{"value": 24.0, "product": "O1COC2=C1C=CC(=C2)C2=NC1=CC=C(C=C1C=C2)C2=NC1=C(N2C2CCCCC2)C=CC(=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-benzo[1,3]dioxol-5-yl-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (30 mg, 24% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2c(c1)OCO2.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2c(c1)OCO2 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccc2c(c1)OCO2.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc2c(c1)OCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)OCO5)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74d401b8ec4242da885bcb02ec2dc6e1 | CC(=O)c1ccc(Oc2ccccc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccccc5)cc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].O(C1=CC=CC=C1)C1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)OC2=CC=CC=C2 | CC(=O)[c:18]1[cH:19][cH:20][c:21]([O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:35]3[CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[cH:34][c:33]2[cH:32][cH:31]1>>[O:1]... | CC(=O)c1ccc(Oc2ccccc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccccc5)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(Oc2ccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 31 | [{"value": 31.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)OC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-phenoxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (42 mg, 31% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(Oc2ccccc2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccccc5)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ba75bfd167246c3be98eb0925ef2372 | CC(=O)c1ccc(N2CCNCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCNCC5)cc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1(CCNCC1)C1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2CCNCC2 | CC(=O)[c:18]1[cH:19][cH:20][c:21]([N:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[cH:28][cH:29]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:34]3[CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[cH:33][c:32]2[cH:31][cH:30]1>>[O:1]=[... | CC(=O)c1ccc(N2CCNCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCNCC5)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCNCC5)cc4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 91 | [{"value": 91.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2CCNCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-piperazin-1-yl-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (120 mg, 91% yield). MS: 532.21 (M+H+); HPLC Procedure A, retention ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1C[NH]CCN1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(N2CCNCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCNCC5)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85a15cee2a5e499393429284ebf976d1 | CC(=O)Nc1ccc(C(C)=O)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>CC(=O)Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | [OH-].[K+].C(C)(=O)C1=CC=C(C=C1)NC(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C(C)(=O)NC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:38][cH:37]1.Oc1ccc(Br)cc1-[c:9]1[cH:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[n:16][c:17]4[cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24][c:25]4[n:26]3[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:33][cH:34][c:35]2[n:36]1>>[CH3:1][C:2](=[O:3])[NH:4]... | CC(=O)Nc1ccc(C(C)=O)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | CC(=O)Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | 15 | [{"value": 15.0, "product": "C(C)(=O)NC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with N-(4-acetyl-phenyl)-acetamide (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (19 mg, 15% yield). MS: 505.26 (M+H+); HPLC Procedure A, retention time=9.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)Nc1ccc(C(C)=O)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>CC(=O)Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-172f2be876094ff0ae6346fa773a22d3 | CC(=O)c1ccc(N)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | [OH-].[K+].NC1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>NC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)c1c[cH:3][c:2]([NH2:1])[cH:35][cH:34]1.Oc1ccc(Br)[cH:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[n:13][c:14]4[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]4[n:23]3[CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[cH:30][cH:31][c:32]2[n:33]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:... | CC(=O)c1ccc(N)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | d719b5773425a1262e3c8365a5fe3595c74e53585547b38c08bc2408e1828872 | 5d663a6f3250645b78580d7f1b46d37e7983f21b5145184e88099bc5e394410f | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):c(-O):c:c:1.C-C(=O)-c1:[cH;D2;+0:7]:[c:8]:[c:9](-[N;D1;H2:10]):[cH;D2;+0:11]:c:1>>[N;D1;H2:10]-[c:9]1:[c:8]:[cH;D2;+0:7]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):[cH;D2;+0:1]:[cH;D2;+0:11]:1 | 10 | [{"value": 10.0, "product": "NC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-amino-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (14 mg, 10% yield). MS: 463.23 (M+H+); HPLC Procedure A, retention time=8.62 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(N)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Nc1ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8474d7d175943d79dbc7974c9e6d8b8 | CC(=O)c1ccc(O)c(C(N)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>NC(=O)c1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)ccc1O | [OH-].[K+].C(C)(=O)C=1C=CC(=C(C(=O)N)C1)O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C(N)(=O)C=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)c1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:37]([OH:38])[cH:36][cH:35]1.Oc1ccc(Br)c[c:6]1-[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12](-[c:13]3[n:14][c:15]4[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23]4[n:24]3[CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[n:34]1>>[NH2:1][C:2](=[O:3])[c:4]... | CC(=O)c1ccc(O)c(C(N)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | NC(=O)c1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)ccc1O | null | null | C(C)O | Miscellaneous | OtherReaction | d719b5773425a1262e3c8365a5fe3595c74e53585547b38c08bc2408e1828872 | 5d663a6f3250645b78580d7f1b46d37e7983f21b5145184e88099bc5e394410f | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):c:1.C-C(=O)-c1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9](-[C:10](-[N;D1;H2:11])=[O;D1;H0:12]):[cH;D2;+0:13]:1>>[N;D1;H2:11]-[C:10](=[O;D1;H0:12])-[c:9]1:[c:8]:[c:7]:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):[cH;D2;+0:13]:1 | 10 | [{"value": 10.0, "product": "C(N)(=O)C=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 5-acetyl-2-hydroxy-benzamide (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (13 mg, 10% yield). MS: 507.24 (M+H+); HPLC Procedure A, retention time=10.3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(O)c(C(N)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>NC(=O)c1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d01a71d18ef842d18ec04cd6910db6df | CC(=O)CCCO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCCO)ccc3c1)n2C1CCCCC1 | [OH-].[K+].OCCCC(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CCCO | CC(=O)[CH2:18][CH2:19][CH2:20][OH:21].Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:26]3[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:25][c:24]2[cH:23][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:1... | CC(=O)CCCO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCCO)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 34d51f83d7f890fb6f9dfb3778fa6ac322c2fffc538848b96a4366ff4d298284 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[CH2;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH2;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 90 | [{"value": 90.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 5-hydroxy-pentan-2-one (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (96 mg, 90% yield). MS: 430.23 (M+H+); HPLC Procedure A, retention time=6.84 min, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)CCCO.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCCO)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c59f3b6cd3754c419fc2134e1bdefb94 | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCOCC5)cc4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1(CCOCC1)C1=CC=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2CCOCC2 | CC(=O)[c:18]1[cH:19][cH:20][c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[cH:28][cH:29]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:34]3[CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[cH:33][c:32]2[cH:31][cH:30]1>>[O:1]=[C... | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCOCC5)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCOCC5)cc4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 30 | [{"value": 30.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=C(C=C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-morpholin-4-yl-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (37 mg, 30% yield). MS: 533.28 (M+H+); HPLC Procedure A, retention t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1COCC[NH]1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(N5CCOCC5)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5c7f22729a94281b64769d245a1673a | CC(=O)c1ccccc1[N+](=O)[O-].O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2[nH]c(C3(c4ccccc4[N+](=O)[O-])C=Cc4ncccc4C3)nc2c1 | [OH-].[K+].[N+](=O)([O-])C1=C(C=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>[N+](=O)([O-])C1=C(C=CC=C1)C1(CC=2C=CC=NC2C=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)O | C[C:10](=O)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19].Oc1ccc(Br)cc1-[c:24]1[n:23][c:22]2[cH:21][cH:20]c(-[c:9]3[n:8](C4CCCCC4)[c:7]4[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:31][c:30]4[n:29]3)[cH:28][c:27]2[cH:26][cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]([C:10]3([c:11]4[cH:... | CC(=O)c1ccccc1[N+](=O)[O-].O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2[nH]c(C3(c4ccccc4[N+](=O)[O-])C=Cc4ncccc4C3)nc2c1 | null | null | C(C)O | C-C Coupling | OtherReaction | c629e1407087f3538759c24058fac17e10e3a113a6a18de8478b6567833ad370 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | C1=CC(c2ccccc2)(c2nc3ccccc3[nH]2)Cc2cccnc21 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]3:[cH;D2;+0:4]:[cH;D2;+0:5]:c(-[c;H0;D3;+0:6]4:[#7;a:7]:[c:8](:[c:9]):[c:10](:[c:11]):[n;H0;D3;+0:12]:4-C4-C-C-C-C-C-4):[cH;D2;+0:13]:[c:14]:3:[c:15]:[c:16]:2):c:1.C-[C;H0;D3;+0:17](=O)-[c:18](:[c:19]):[c:20]>>[c:19]:[c:18](-[C;H0;D4;+0:17]1(-[c;H0;D3;+0:6]2:[#7;a:7]:[c:... | 10 | [{"value": 10.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)C1(CC=2C=CC=NC2C=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2-nitro-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (11 mg, 10% yield). MS: 493.21 (M+H+); HPLC Procedure A, retention time=12.72... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccc2ncccc2c1.C1CCCCC1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.C1=Cc2ncccc2CC1 | c1ccc2[nH]cnc2c1.c1ccccc1.C1=Cc2ncccc2CC1 | HBr | C(C)O | null | null | CC(=O)c1ccccc1[N+](=O)[O-].O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2[nH]c(C3(c4ccccc4[N+](=O)[O-])C=Cc4ncccc4C3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51db0a9a57474c7c8a17668faefa5361 | CC(=O)c1ccc(OCc2ccccc2)c(C)c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1c(OCc2ccccc2)ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1O | [OH-].[K+].C(C1=CC=CC=C1)OC1=C(C(=C(C=C1)C(C)=O)O)C.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C(C1=CC=CC=C1)OC1=C(C(=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O)C | CC(=O)[c:14]1[cH:13][cH:12][c:3]([O:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:2]([CH3:1])[c:43]1[OH:44].Oc1ccc(Br)cc1-[c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20](-[c:21]3[n:22][c:23]4[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]4[n:32]3[CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:39][cH:40]... | CC(=O)c1ccc(OCc2ccccc2)c(C)c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1c(OCc2ccccc2)ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1O | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(COc2ccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[O;D1;H1:10]):[c:11]>>[O;D1;H1:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 10 | [{"value": 10.0, "product": "C(C1=CC=CC=C1)OC1=C(C(=C(C=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-benzyloxy-2-hydroxy-3-methyl-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (73 mg, 10% yield). MS: 584.29 (M+H+); HPLC Procedure ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(OCc2ccccc2)c(C)c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1c(OCc2ccccc2)ccc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd4bee7afe7d442a83a108fc3240271f | CC(=O)CCn1cccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCn4cccn4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1(N=CC=C1)CCC(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CCN2N=CC=C2 | CC(=O)[CH2:18][CH2:19][n:20]1[cH:21][cH:22][cH:23][n:24]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:29]3[CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[cH:28][c:27]2[cH:26][cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8... | CC(=O)CCn1cccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCn4cccn4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 34d51f83d7f890fb6f9dfb3778fa6ac322c2fffc538848b96a4366ff4d298284 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(CCn4cccn4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[CH2;D2;+0:6]-[C:7]-[#7;a:8]>>[#7;a:8]-[C:7]-[CH2;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 50 | [{"value": 50.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CCN2N=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 4-pyrazol-1-yl-butan-2-one (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (14 mg, 50% yield). MS: 466.27 (M+H+); HPLC Procedure A, retention time=8.41 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cn[nH]c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)CCn1cccn1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(CCn4cccn4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a816d7855224c32910f87aadd2f86cc | CCCN(CCC)CC(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>CCCN(CCC)Cc1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].C(CC)N(CC(C)=O)CCC.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CN(CCC)CCC | CC(=O)[CH2:8][N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7].Oc1ccc(Br)cc1-[c:9]1[cH:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[n:16][c:17]4[cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24][c:25]4[n:26]3[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:33][cH:34][c:35]2[n:36]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][C... | CCCN(CCC)CC(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | CCCN(CCC)Cc1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 34d51f83d7f890fb6f9dfb3778fa6ac322c2fffc538848b96a4366ff4d298284 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1cnc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc2c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[CH2;D2;+0:6]-[#7:7](-[C:8])-[C:9]>>[C:8]-[#7:7](-[C:9])-[CH2;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 58 | [{"value": 58.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)CN(CCC)CCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-dipropylamino-propan-2-one (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (70 mg, 58% yield). MS: 485.34 (M+H+); HPLC Procedure A, retention time=9.20... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CCCN(CCC)CC(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>CCCN(CCC)Cc1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e80f58ddc4ce449f857fd2bc8077933f | CC(=O)C1CC(CC(=O)O)C1(C)C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>CC1(C)C(CC(=O)O)CC1c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].C(C)(=O)C1C(C(C1)CC(=O)O)(C)C.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C(=O)(O)CC1C(C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)(C)C | CC(=O)[CH:10]1[C:2]([CH3:1])([CH3:3])[CH:4]([CH2:5][C:6](=[O:7])[OH:8])[CH2:9]1.Oc1ccc(Br)cc1-[c:11]1[cH:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[n:18][c:19]4[cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26][c:27]4[n:28]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:35][cH:36][c:37]2[n:38]1>>[CH3:1][C:2]1([CH3... | CC(=O)C1CC(CC(=O)O)C1(C)C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | CC1(C)C(CC(=O)O)CC1c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | b9a481f72a28ac7b25e12538b523667d411e0d7cc54c6ec4a4e21063acb325e9 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(C4CCC4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[C:8]-[C:7]-[CH;D3;+0:6]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 16 | [{"value": 16.0, "product": "C(=O)(O)CC1C(C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e 100 mg, 0.256 mmol) was reacted with (3-acetyl-2,2-dimethyl-cyclobutyl)-acetic acid (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (21 mg, 16% yield). MS: 512.31 (M+H+); HPLC Procedure A, re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | C1CCC1.c1ccccc1.c1ccc2ncccc2c1 | C1CCC1.c1ccc2ncccc2c1 | C1CCC1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)C1CC(CC(=O)O)C1(C)C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>CC1(C)C(CC(=O)O)CC1c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-daddd1a164d64e08853823a139fc8a8c | COc1cc(Br)c2oc(C(C)=O)cc2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1cc(Br)c2oc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2c1 | [OH-].[K+].BrC1=CC(=CC=2C=C(OC21)C(C)=O)OC.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>BrC1=CC(=CC=2C=C(OC21)C2=NC1=CC=C(C=C1C=C2)C2=NC1=C(N2C2CCCCC2)C=CC(=C1)C(=O)O)OC | CC(=O)[c:9]1[o:8][c:7]2[c:5]([Br:6])[cH:4][c:3]([O:2][CH3:1])[cH:40][c:39]2[cH:38]1.Oc1ccc(Br)cc1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]4[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[n:37]1>>[CH3:1][O:2][c... | COc1cc(Br)c2oc(C(C)=O)cc2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1cc(Br)c2oc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2c1 | null | null | C(C)O | C-C Coupling | OtherReaction | 6652b3d332750b9521edc9f82282db3de6903bc89164acd6b71bb882c727b5c6 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2oc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#8;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#8;a:7]:[c:8]:[c:9]:[c:10]:1):[#7;a:2]:[c:3] | 17 | [{"value": 17.0, "product": "BrC1=CC(=CC=2C=C(OC21)C2=NC1=CC=C(C=C1C=C2)C2=NC1=C(N2C2CCCCC2)C=CC(=C1)C(=O)O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(7-bromo-5-methoxy-benzofuran-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound, 17% yield).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2occc2c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2occc2c1.c1ccc2ncccc2c1 | c1ccc2occc2c1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | COc1cc(Br)c2oc(C(C)=O)cc2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1cc(Br)c2oc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61f6d499bfb541ab9f870eff861e92d7 | CC(=O)c1cn(-c2cccnc2Cl)c(=O)[nH]c1=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cn(-c5cccnc5Cl)c(=O)[nH]c4=O)ccc3c1)n2C1CCCCC1 | [OH-].[K+].C(C)(=O)C=1C(NC(N(C1)C=1C(=NC=CC1)Cl)=O)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC1=NC=CC=C1N1C(NC(C(=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)=O)=O | CC(=O)[c:18]1[cH:19][n:20](-[c:21]2[cH:22][cH:23][cH:24][n:25][c:26]2[Cl:27])[c:28](=[O:29])[nH:30][c:31]1=[O:32].Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:37]3[CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)[cH:36][c:35]2[cH:34][... | CC(=O)c1cn(-c2cccnc2Cl)c(=O)[nH]c1=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cn(-c5cccnc5Cl)c(=O)[nH]c4=O)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | d74850c02e111b96eecc8999c56e0c6b62ebedb77fd1307314c936eb4f7f10de | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | O=c1[nH]c(=O)n(-c2cccnc2)cc1-c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8](-[c:9]:[c:10]:[#7;a:11]):[c:12]:[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[#7;a:11]:[c:10]:[c:9]-[#7;a:8]1:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:14](=[O;D1;H0:15]):[#7;a:13]:[c:12]:1 | 31 | [{"value": 31.0, "product": "ClC1=NC=CC=C1N1C(NC(C(=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 5-acetyl-1-(2-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound 45 mg, 31% yield). MS: 593.17 (M+H+); HPLC Pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cncnc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cncnc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cncnc1.c1ccncc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cn(-c2cccnc2Cl)c(=O)[nH]c1=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cn(-c5cccnc5Cl)c(=O)[nH]c4=O)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ab4352dcc90475294b7e409811e18dd | CC(=O)c1c(C)oc2ccc(OCc3ccccc3)cc12.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1oc2ccc(OCc3ccccc3)cc2c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].C(C1=CC=CC=C1)OC=1C=CC2=C(C(=C(O2)C)C(C)=O)C1.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C(C1=CC=CC=C1)OC=1C=CC2=C(C(=C(O2)C)C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C1 | CC(=O)c1[c:2]([CH3:1])[o:3][c:4]2[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][c:17]12.Oc1ccc(Br)c[c:18]1-[c:19]1[cH:20][cH:21][c:22]2[cH:23][c:24](-[c:25]3[n:26][c:27]4[cH:28][c:29]([C:30](=[O:31])[OH:32])[cH:33][cH:34][c:35]4[n:36]3[CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)... | CC(=O)c1c(C)oc2ccc(OCc3ccccc3)cc12.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1oc2ccc(OCc3ccccc3)cc2c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | Miscellaneous | OtherReaction | f9053fce08ec002275338459f38665d646e016556869f4887fb8b643aa6892eb | 5d663a6f3250645b78580d7f1b46d37e7983f21b5145184e88099bc5e394410f | c1ccc(COc2ccc3occ(-c4ccc5cc(-c6nc7ccccc7n6C6CCCCC6)ccc5n4)c3c2)cc1 | Br-c1:c:c:c(-O):[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):c:1.C-C(=O)-c1:[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#8;a:11]:[c;H0;D3;+0:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c;H0;D3;+0:12]1:[#8;a:11]:[c:9](:[c:10]):[c;H0;D3;+0:6](:[c:7]:[c:8]):[c;H0;D3;+0:1]:1-[c:2](:[c:3]):[#7;a:4]:[c:5] | 49 | [{"value": 49.0, "product": "C(C1=CC=CC=C1)OC=1C=CC2=C(C(=C(O2)C)C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(5-benzyloxy-2-methyl-benzofuran-3-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (75 mg, 49% yield). MS: 608.25 (M+H+); HPLC Procedure A... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2occc2c1.c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1c(C)oc2ccc(OCc3ccccc3)cc12.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1oc2ccc(OCc3ccccc3)cc2c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2755454004b444ccb71769aff67be485 | CC(=O)c1ccc2c(c1)c1cc(Cl)ccc1n2C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cn1c2ccc(Cl)cc2c2cc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)ccc21 | [OH-].[K+].ClC=1C=C2C=3C=C(C=CC3N(C2=CC1)C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC=1C=C2C=3C=C(C=CC3N(C2=CC1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:12]1[cH:11][c:10]2[c:9]3[c:3]([n:2]([CH3:1])[c:43]2[cH:42][cH:41]1)[cH:4][cH:5][c:6]([Cl:7])[cH:8]3.Oc1ccc(Br)cc1-[c:13]1[cH:14][cH:15][c:16]2[cH:17][c:18](-[c:19]3[n:20][c:21]4[cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28][c:29]4[n:30]3[CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:37][cH:38][c:39... | CC(=O)c1ccc2c(c1)c1cc(Cl)ccc1n2C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cn1c2ccc(Cl)cc2c2cc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)ccc21 | null | null | C(C)O | C-C Coupling | OtherReaction | 725aef6ab8a30aa618ea5fc003b083d121adb959096e2e66fd47f40fc571d1f6 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5[nH]c6ccccc6c5c4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11]:[c:12]:1>>[#7;a:10]:[c:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c:11]:1 | 12 | [{"value": 12.0, "product": "ClC=1C=C2C=3C=C(C=CC3N(C2=CC1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(6-chloro-9-methyl-9H-carbazol-3-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (18 mg, 12% yield). MS: 585.21 (M+H+); HPLC Procedure A, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2[nH]c3ccccc3c2c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2[nH]c3ccccc3c2c1.c1ccc2ncccc2c1 | c1ccc2[nH]c3ccccc3c2c1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc2c(c1)c1cc(Cl)ccc1n2C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cn1c2ccc(Cl)cc2c2cc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5680b1d7af76442bab13c56201b4a54d | CC(=O)c1ccc2c(c1)CCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCO5)ccc3c1)n2C1CCCCC1 | [OH-].[K+].O1CCC2=C1C=CC(=C2)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=CC1=C(CCO1)C2 | CC(=O)[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[CH2:24][CH2:25][O:26]2.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:30][c:29]2[cH:28][cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5]... | CC(=O)c1ccc2c(c1)CCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCO5)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 2639e0145b47c7d851c30d3552031cd498be6de220ab3c05a72216e261182280 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCO5)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 28 | [{"value": 28.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=CC1=C(CCO1)C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2,3-dihydro-benzofuran-5-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (34 mg, 28% yield). MS: 490.19 (M+H+); HPLC Procedure A, retenti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2c(c1)CCO2.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2c(c1)CCO2 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccc2c(c1)CCO2.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc2c(c1)CCO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc5c(c4)CCO5)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-978bee0078004e92a05619578dbbf7d6 | CC(=O)c1cnn(-c2ccccc2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnn(-c5ccccc5)c4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].C1(=CC=CC=C1)N1N=CC(=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=NN(C2)C2=CC=CC=C2 | CC(=O)[c:18]1[cH:19][n:20][n:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:33]3[CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[cH:32][c:31]2[cH:30][cH:29]1>>[O:1]=[C:2]([OH:3]... | CC(=O)c1cnn(-c2ccccc2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnn(-c5ccccc5)c4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | cc95b929fb804627d249ddb623f43c45e4fbdb1d580c792b60e158754e15fe1e | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-n2cc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cn2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[#7;a:9](-[c:10]):[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[#7;a:9](-[c:10]):[c:11]:1):[c:4]:[c:5] | 51 | [{"value": 51.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=NN(C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(1-phenyl-1H-pyrazol-4-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (69 mg, 51% yield). MS: 514.23 (M+H+); HPLC Procedure B, retention ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cn[nH]c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cn[nH]c1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cnn(-c2ccccc2)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cnn(-c5ccccc5)c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1c097dd2cd146e196d6b9a369c8f4a5 | CC(=O)c1c(C)nn(-c2ccccc2)c1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1nn(-c2ccccc2)c(C)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].CC1=NN(C(=C1C(C)=O)C)C1=CC=CC=C1.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C(=NN(C2C)C2=CC=CC=C2)C | CC(=O)[c:13]1[c:2]([CH3:1])[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]1[CH3:12].Oc1ccc(Br)cc1-[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[n:21][c:22]4[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29][c:30]4[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[n:41]1>>[CH3... | CC(=O)c1c(C)nn(-c2ccccc2)c1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1nn(-c2ccccc2)c(C)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | cc95b929fb804627d249ddb623f43c45e4fbdb1d580c792b60e158754e15fe1e | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-n2cc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cn2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7](-[C;D1;H3:8]):[#7;a:9](-[c:10]):[#7;a:11]:[c:12]:1-[C;D1;H3:13]>>[C;D1;H3:8]-[c:7]1:[#7;a:9](-[c:10]):[#7;a:11]:[c:12](-[C;D1;H3:13]):[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 37 | [{"value": 37.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C(=NN(C2C)C2=CC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (47 mg, 37% yield).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncccc2c1 | c1cn[nH]c1.c1ccc2ncccc2c1 | c1cn[nH]c1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1c(C)nn(-c2ccccc2)c1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1nn(-c2ccccc2)c(C)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-670b118e4ab741148e6a2752f946a6b4 | CC(=O)c1cc(-c2ccc(Cl)c(Cl)c2)no1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(-c5ccc(Cl)c(Cl)c5)no4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].ClC=1C=C(C=CC1Cl)C1=NOC(=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=NO2)C2=CC(=C(C=C2)Cl)Cl | CC(=O)[c:18]1[cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[c:26]([Cl:27])[cH:28]2)[n:29][o:30]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:35]3[CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[cH:34][c:33]2[cH:32][cH:31]1>>[O:... | CC(=O)c1cc(-c2ccc(Cl)c(Cl)c2)no1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(-c5ccc(Cl)c(Cl)c5)no4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 8b4b388453e9a0dc2e42ac24c2b3525cda3f10f82da404e7d5a83f0d31758d59 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2cc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)on2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#8;a:7]:[#7;a:8]:[c:9](-[c:10]):[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#8;a:7]:[#7;a:8]:[c:9](-[c:10]):[c:11]:1):[c:4]:[c:5] | 15 | [{"value": 15.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=NO2)C2=CC(=C(C=C2)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-[3-(3,4-dichloro-phenyl)-isoxazol-5-yl]-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (21 mg, 15% yield). MS: 583.16 (M+H+); HPLC Procedure ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cnoc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cnoc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cnoc1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc(-c2ccc(Cl)c(Cl)c2)no1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(-c5ccc(Cl)c(Cl)c5)no4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a5ab8982e364511ad1f2a069c8b9e89 | CC(=O)c1ccc(Oc2ccc(Cl)cc2)cc1Cl.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccc(Cl)cc5)cc4Cl)ccc3c1)n2C1CCCCC1 | [OH-].[K+].ClC1=C(C=CC(=C1)OC1=CC=C(C=C1)Cl)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC1=C(C=CC(=C1)OC1=CC=C(C=C1)Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:18]1[cH:19][cH:20][c:21]([O:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[cH:30][c:31]1[Cl:32].Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:37]3[CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)[cH:36][c:35]2[cH:34][... | CC(=O)c1ccc(Oc2ccc(Cl)cc2)cc1Cl.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccc(Cl)cc5)cc4Cl)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(Oc2ccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 49 | [{"value": 49.0, "product": "ClC1=C(C=CC(=C1)OC1=CC=C(C=C1)Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (75 mg, 49% yield). MS: 608.17 (M+H+); HPLC Procedure B... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(Oc2ccc(Cl)cc2)cc1Cl.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Oc5ccc(Cl)cc5)cc4Cl)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ffb76ab3ccf49a4b063199ff614b595 | CC(=O)c1cc(-c2ccc(Cl)cc2)oc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1oc(-c2ccc(Cl)cc2)cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].ClC1=CC=C(C=C1)C1=CC(=C(O1)C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC1=CC=C(C=C1)C1=CC(=C(O1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)c1c[c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[o:3][c:2]1[CH3:1].Oc1ccc(Br)[cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[n:21][c:22]4[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29][c:30]4[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[n:41]1>>[CH3:... | CC(=O)c1cc(-c2ccc(Cl)cc2)oc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1oc(-c2ccc(Cl)cc2)cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | Miscellaneous | OtherReaction | ff754d3c410dca834a2b7e1901e9aab845ad13b3e4145cab6f4a8111a1c7e45d | 5d663a6f3250645b78580d7f1b46d37e7983f21b5145184e88099bc5e394410f | c1ccc(-c2cc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)co2)cc1 | Br-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):c(-O):c:c:1.C-C(=O)-c1:c:[c;H0;D3;+0:7](-[c:8](:[c:9]):[c:10]):[#8;a:11]:[c;H0;D3;+0:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c;H0;D3;+0:12]1:[#8;a:11]:[c;H0;D3;+0:7](-[c:8](:[c:9]):[c:10]):[cH;D2;+0:1]:[c;H0;D3;+0:2]:1-[c:3](:[c:4]):[#7;a:5]:[c:6] | 59 | [{"value": 59.0, "product": "ClC1=CC=C(C=C1)C1=CC(=C(O1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-[5-(4-chloro-phenyl)-2-methyl-furan-3-yl]-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (83 mg, 59% yield). MS: 562.21 (M+H+); HPLC Procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccoc1.c1ccccc1 | c1ccoc1 | c1ccoc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc(-c2ccc(Cl)cc2)oc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1oc(-c2ccc(Cl)cc2)cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7146818e4f0f44559a9ad70a49071ce0 | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].ClC1=CC=C(C=C1)C1=NOC(=C1C(C)=O)C.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC1=CC=C(C=C1)C1=NOC(=C1C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C | CC(=O)[c:13]1[c:2]([CH3:1])[o:3][n:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.Oc1ccc(Br)cc1-[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[n:21][c:22]4[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29][c:30]4[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[n:41]1>>[CH3:1... | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 8b4b388453e9a0dc2e42ac24c2b3525cda3f10f82da404e7d5a83f0d31758d59 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2nocc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7](-[C;D1;H3:8]):[#8;a:9]:[#7;a:10]:[c:11]:1-[c:12]>>[C;D1;H3:8]-[c:7]1:[#8;a:9]:[#7;a:10]:[c:11](-[c:12]):[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 12 | [{"value": 12.0, "product": "ClC1=CC=C(C=C1)C1=NOC(=C1C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-yl]-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (16 mg, 12% yield).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cnoc1.c1ccccc1.c1ccc2ncccc2c1 | c1cnoc1.c1ccc2ncccc2c1 | c1cnoc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6b83a0383664f9789a0c05c0c33737e | CC(=O)c1sc(-c2ccc(Cl)cc2)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1nc(-c2ccc(Cl)cc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].ClC1=CC=C(C=C1)C=1SC(=C(N1)C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>ClC1=CC=C(C=C1)C=1SC(=C(N1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:13]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[s:12]1.Oc1ccc(Br)cc1-[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[n:21][c:22]4[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29][c:30]4[n:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[n:41]1>>[CH3... | CC(=O)c1sc(-c2ccc(Cl)cc2)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1nc(-c2ccc(Cl)cc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 1d5c6f5b005ed70236ee338e17825f9573e4b8d5662849fd033a7cd4739092e7 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ncc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)s2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8](-[c:9]):[#7;a:10]:[c:11]:1-[C;D1;H3:12]>>[C;D1;H3:12]-[c:11]1:[#7;a:10]:[c:8](-[c:9]):[#16;a:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 19 | [{"value": 19.0, "product": "ClC1=CC=C(C=C1)C=1SC(=C(N1)C)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-[2-(4-chloro-phenyl)-4-methyl-thiazol-5-yl]-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (27 mg, 19% yield). MS: 580.19 (M+H+); HPLC Proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cscn1.c1ccccc1.c1ccc2ncccc2c1 | c1cscn1.c1ccc2ncccc2c1 | c1cscn1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1sc(-c2ccc(Cl)cc2)nc1C.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1nc(-c2ccc(Cl)cc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-863e45df0a9b457da6839281c85ec600 | CC(=O)c1cc[nH]c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc[nH]c4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1C=C(C=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CNC=C2 | CC(=O)[c:18]1[cH:19][cH:20][nH:21][cH:22]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:26][c:25]2[cH:24][cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10... | CC(=O)c1cc[nH]c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc[nH]c4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 816e79feefe89602d7b2d905a921147b8cdf4b403c7ebb1cb51fc0135c0731fc | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4cc[nH]c4)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:1):[c:4]:[c:5] | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CNC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(1H-pyrrol-3-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (10 mg, 8% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cc[nH]c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cc[nH]c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc[nH]c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc[nH]c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b8e0398f2774bbfb78cf923a33e6319 | CC(=O)c1ccc[nH]1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc[nH]4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].N1C(=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2NC=CC2 | CC(=O)[c:18]1[cH:19][cH:20][cH:21][nH:22]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:26][c:25]2[cH:24][cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10... | CC(=O)c1ccc[nH]1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc[nH]4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | 816e79feefe89602d7b2d905a921147b8cdf4b403c7ebb1cb51fc0135c0731fc | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1c[nH]c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 9 | [{"value": 9.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2NC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(1H-pyrrol-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (11 mg, 9% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1cc[nH]c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1cc[nH]c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc[nH]1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc[nH]4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae0e10489fd54c2eb3daf138afefde83 | CC(=O)c1ccc2c(c1)NC(=O)CO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C1COc2ccc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2N1 | [OH-].[K+].C(C)(=O)C=1C=CC2=C(NC(CO2)=O)C1.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=CC1=C(NC(CO1)=O)C2 | CC(=O)c1ccc2c(c1)[NH:39][C:2](=[O:1])[CH2:3][O:4]2.O[c:5]1[cH:6][cH:7][c:8](Br)[cH:37][c:38]1-[c:9]1[cH:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[n:16][c:17]4[cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24][c:25]4[n:26]3[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:33][cH:34][c:35]2[n:36]1>>[O:1]=[C:2]1[CH2:3]... | CC(=O)c1ccc2c(c1)NC(=O)CO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C1COc2ccc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2N1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 63267276b3feef59673eef8934ab934a3b106549020267a8b09ac43f43b98b96 | fd9d01a3b72789dff10bb12c1092cbb5e4930ebb8892040ac09c3bdfbbddb82b | O=C1COc2ccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)cc2N1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]):[c:7]:[c:8]):[c;H0;D3;+0:9](-O):[c:10]:[c:11]:1.C-C(=O)-c1:c:c:c2:c(:c:1)-[NH;D2;+0:12]-[C:13](=[O;D1;H0:14])-[C:15]-[O;H0;D2;+0:16]-2>>[O;D1;H0:14]=[C:13]1-[C:15]-[O;H0;D2;+0:16]-[c;H0;D3;+0:9]2:[c:10]:[c:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[#7;a... | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C=2C=CC1=C(NC(CO1)=O)C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 6-acetyl-4H-benzo[1,4]oxazin-3-one (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (11 mg, 8% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ether.Secondary amide.Aromatic alcohol | Ether.Secondary amide | c1ccc2c(c1)NCCO2.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2c(c1)NCCO2.c1ccc2ncccc2c1 | c1ccc2c(c1)NCCO2.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc2c(c1)NC(=O)CO2.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C1COc2ccc(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)cc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7aa1f1d49e348c096c6385ebccb7dcd | CC(=O)c1sc(-c2ccccc2)cc1N.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Nc1cc(-c2ccccc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].NC1=C(SC(=C1)C1=CC=CC=C1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>NC1=C(SC(=C1)C1=CC=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:12]1[c:2]([NH2:1])[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[s:11]1.Oc1ccc(Br)cc1-[c:13]1[cH:14][cH:15][c:16]2[cH:17][c:18](-[c:19]3[n:20][c:21]4[cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28][c:29]4[n:30]3[CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:37][cH:38][c:39]2[n:40]1>>[NH2:1][c:2... | CC(=O)c1sc(-c2ccccc2)cc1N.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Nc1cc(-c2ccccc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 720f87d7df89fae5bee313ea8aae90dd7d141265b6e283e34e49e8dc216a5da5 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)s2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1-[N;D1;H2:11]>>[N;D1;H2:11]-[c:10]1:[c:9]:[c:8]:[#16;a:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 14 | [{"value": 14.0, "product": "NC1=C(SC(=C1)C1=CC=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3-amino-5-phenyl-thiophen-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (19 mg, 14% yield). MS: 545.24 (M+H+); HPLC Procedure B, rete... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccsc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccsc1.c1ccc2ncccc2c1 | c1ccsc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1sc(-c2ccccc2)cc1N.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Nc1cc(-c2ccccc2)sc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-22597246d1ff47819738715bf4c1607b | COc1ccc2occ(C(C)=O)c2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1ccc2occ(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)c2c1 | [OH-].[K+].COC=1C=CC2=C(C(=CO2)C(C)=O)C1.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=COC1=C2C=C(C=C1)OC | CC(=O)[c:9]1[cH:8][o:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:39][c:38]21.Oc1ccc(Br)cc1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]4[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[n:37]1>>[CH3:1][O:2][c:3]1[cH:... | COc1ccc2occ(C(C)=O)c2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1ccc2occ(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)c2c1 | null | null | C(C)O | C-C Coupling | OtherReaction | 6652b3d332750b9521edc9f82282db3de6903bc89164acd6b71bb882c727b5c6 | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc2c(c1)nc(-c1ccc3nc(-c4coc5ccccc45)ccc3c1)n2C1CCCCC1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[#8;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#8;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12]):[#7;a:2]:[c:3] | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=COC1=C2C=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(5-methoxy-benzofuran-3-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (10 mg, 8% yield). MS: 518.24 (M+H+); HPLC Procedure B, retention ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccc2occc2c1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2occc2c1.c1ccc2ncccc2c1 | c1ccc2occc2c1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | COc1ccc2occ(C(C)=O)c2c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1ccc2occ(-c3ccc4cc(-c5nc6cc(C(=O)O)ccc6n5C5CCCCC5)ccc4n3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38b97266a3fd4f0495c8c608fcb0193f | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@@H]1CCCC[C@H]1O>>CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c([N+](=O)[O-])c1 | CO.C(C)OC(C1=CC(=C(C=C1)Cl)[N+](=O)[O-])=O.C(C)N(CC)CC.Cl.N[C@H]1[C@@H](CCCC1)O>>C(C)OC(C1=CC(=C(C=C1)N[C@H]1[C@@H](CCCC1)O)[N+](=O)[O-])=O | Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22][c:18]1[N+:19](=[O:20])[O-:21].[NH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[OH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C@@H:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]2[OH:17])[c:18]([N+:19](=[O:20])[O-:21])[c... | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@@H]1CCCC[C@H]1O | CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c([N+](=O)[O-])c1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound 9 (689 mg, 3 mmol) was suspended in acetonitrile (5 mL) and then triethylamine was added (1.3 mL, 9 mmol). trans-2-aminocyclohexanol hydrochloride (682 mg, 4.5 mmol) was then added and the reaction refluxed for 12 hours, 2 mL methanol was then added and the reaction further refluxed for another 24 hours. Water... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HCl | O.C(C)#N | null | null | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@@H]1CCCC[C@H]1O>O.C(C)#N>CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-339bd8a048074752ac0329b6027b2e43 | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CCCC[C@H]1O | C(C)OC(C1=CC(=C(C=C1)N[C@H]1[C@@H](CCCC1)O)N)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>O[C@H]1[C@@H](CCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | CC(C)N(C(C)C)[CH2:23][CH3:22].[O:1]=[C:2]([O:3][CH2:19][CH3:20])[c:4]1[cH:5][cH:6][c:7]([NH:28][C@@H:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]2[OH:35])[c:8]([NH2:10])[cH:9]1.C[N+](C)=[C:17](O[n:25]1n[n:16][c:15]2[cH:14][cH:13][cH:12][cH:27][c:26]21)N([CH3:21])[CH3:24].CN([CH:11]=O)[CH3:18]>>[O:1]=[C:2]([OH:3])[c:4]1... | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CCCC[C@H]1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d5224d3e39b5ea5e36ea115d5bbd42cdeb988ae706ebd58627c54fe64a28c596 | 477f657131ca4589b743a8a28b6796d63976298e2013be05ff0fa3589cec1ea5 | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C(-C)-N(-[CH2;D2;+0:1]-[CH3;D1;+0:2])-C(-C)-C.C-N(-[CH3;D1;+0:3])-[CH;D2;+0:4]=O.C-[N+](-C)=[C;H0;D3;+0:5](-O-[n;H0;D3;+0:6]1:n:[n;H0;D2;+0:7]:[c:8]2:[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]:2:1)-N(-[CH3;D1;+0:14])-[CH3;D1;+0:15].[C:16]-[C:17](-[NH;D2;+0:18]-[c:19](:[c:20]):[c:21](-[NH2;D1;+0:22]):[c:23]:[c:24]-[C:25... | null | [] | null | null | 20 | HOUR | Compound 36A Y=Phenyl, (200 mg, 0.8 mmol) was activated in 8 mL DMF with TBTU (282 mg, 0.88 mmol) and DIEA (0.285 mL, 1.6 mmol) for 30 minutes at room temperature. This solution was then added to Compound 578b (230 mg, 0.83 mmol) and stirred at ambient temperature for 20 hours. The reaction was concentrated to a residu... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Ester.Tertiary amide.Primary amine.Secondary amine.Tertiary amine | Carboxylic acid | c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | 20 | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CCCC[C@H]2O)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CCCC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c192dfdc6f54692b3f47d7b75654ab5 | CC(=O)c1cc(Cl)c(N)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Nc1c(Cl)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Cl | [OH-].[K+].NC1=C(C=C(C=C1Cl)C(C)=O)Cl.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>NC1=C(C=C(C=C1Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)Cl | CC(=O)c1c[c:3]([Cl:4])[c:2]([NH2:1])[c:36]([Cl:37])[cH:35]1.Oc1ccc(Br)[cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12](-[c:13]3[n:14][c:15]4[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23]4[n:24]3[CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[n:34]1>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5]... | CC(=O)c1cc(Cl)c(N)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Nc1c(Cl)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 6a309f5dd455d49d540fdde9d256250a05afc877ae1689368497529377020a76 | a5f50b0757a934668f3fe20d1b59a66d0719baeb97c5ffdb5dc3bf9ea135698a | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):c(-O):c:c:1.C-C(=O)-c1:[cH;D2;+0:7]:[c:8](-[Cl;D1;H0:9]):[c:10](-[N;D1;H2:11]):[c;H0;D3;+0:12](-[Cl;D1;H0:13]):c:1>>[Cl;D1;H0:9]-[c:8]1:[cH;D2;+0:7]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):[cH;D2;+0:1]:[c;H0;D3;+0:12](-[Cl;D1;H0:13]):[c:10]:1-[N;D1;... | 25 | [{"value": 25.0, "product": "NC1=C(C=C(C=C1Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(4-amino-3,5-dichloro-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (31 mg, 25% yield).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Aromatic alcohol | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc(Cl)c(N)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Nc1c(Cl)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-820f8c9b27db46b497cd74a95f2eba26 | CC(=O)c1cccc(Br)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].BrC=1C=C(C=CC1)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>BrC=1C=C(C=CC1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(=O)[c:18]1[cH:19][cH:20][cH:21][c:22]([Br:23])[cH:24]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:29]3[CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[cH:28][c:27]2[cH:26][cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8... | CC(=O)c1cccc(Br)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 12 | [{"value": 12.0, "product": "BrC=1C=C(C=CC1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3-bromo-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (15 mg, 12% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cccc(Br)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-215d7167ecab45e682b9ec273e8cbd0a | COc1cc(OC)cc(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1cc(OC)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | [OH-].[K+].COC=1C=C(C=C(C1)OC)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC(=C2)OC)OC | CC(=O)c1c[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[cH:8]1.Oc1ccc(Br)[cH:38][c:9]1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]4[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[n:37]1>>[CH3:1][O:2][c:3]1[cH:4][c:... | COc1cc(OC)cc(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1cc(OC)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | C(C)O | Miscellaneous | OtherReaction | d2d0a69fbf4e3bd9ee03a6f0fc5f5013ffe449e61086d15d67619284d201f6ab | 713eb02386e817c2cede100961151654d67d2b2ae5918ce33e70a9716d144b1b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):c(-O):c:c:1.C-C(=O)-c1:[cH;D2;+0:7]:[c:8](-[#8:9]):[c:10]:[c;H0;D3;+0:11](-[#8:12]-[C;D1;H3:13]):c:1>>[#8:9]-[c:8]1:[c:10]:[c;H0;D3;+0:11](-[#8:12]-[C;D1;H3:13]):[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):[cH;D2;+0:7]:1 | 35 | [{"value": 35.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3,5-dimethoxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (44 mg, 35% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ether.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | COc1cc(OC)cc(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1cc(OC)cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15024a8393a3454f9146b84f9c03c218 | CC(=O)c1ccc(Cl)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Cl)c(Cl)c4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].ClC=1C=C(C=CC1Cl)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=C(C=C2)Cl)Cl | CC(=O)[c:18]1[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]1.Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:30]3[CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:29][c:28]2[cH:27][cH:26]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c... | CC(=O)c1ccc(Cl)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Cl)c(Cl)c4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 10 | [{"value": 10.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=C(C=C2)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3,4-dichloro-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (12 mg, 10% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(Cl)c(Cl)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(Cl)c(Cl)c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dacedd5040d4e699fc668470c3a21b4 | CC(=O)c1ccc(O)cc1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(O)cc4O)ccc3c1)n2C1CCCCC1 | [OH-].[K+].OC1=C(C=CC(=C1)O)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=C(C=C2)O)O | CC(=O)[c:18]1[cH:19][cH:20][c:21]([OH:22])[cH:23][c:24]1[OH:25].Oc1ccc(Br)cc1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:30]3[CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:29][c:28]2[cH:27][cH:26]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7... | CC(=O)c1ccc(O)cc1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(O)cc4O)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[O;D1;H1:10]):[c:11]>>[O;D1;H1:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=C(C=C2)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2,4-dihydroxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (9.5 mg, 8% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1ccc(O)cc1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccc(O)cc4O)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44615d37ce7345c4b5763a10d4aceb2f | CC(=O)c1cc(O)cc(O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)cc(O)c4)ccc3c1)n2C1CCCCC1 | [OH-].[K+].OC=1C=C(C=C(C1)O)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC(=C2)O)O | CC(=O)c1c[c:20]([OH:21])[cH:22][c:23]([OH:24])[cH:25]1.Oc1ccc(Br)[cH:19][c:18]1-[c:17]1[n:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[n:10][c:8]4[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]4)[n:30]3[CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:29][c:28]2[cH:27][cH:26]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c... | CC(=O)c1cc(O)cc(O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)cc(O)c4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Miscellaneous | OtherReaction | 13d17d3ba2aab432715ff8895dcc7f34b9986951e91088a4bd02b1fd1fc5dcfe | 826d5ed588669e06fdf43ab0d54c49b68fe5f7db98488b3f4628cb32a365c71c | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):c(-O):c:c:1.C-C(=O)-c1:[cH;D2;+0:7]:[c:8](-[O;D1;H1:9]):[c:10]:[c;H0;D3;+0:11](-[O;D1;H1:12]):c:1>>[O;D1;H1:12]-[c;H0;D3;+0:11]1:[c:10]:[c:8](-[O;D1;H1:9]):[cH;D2;+0:7]:[c;H0;D3;+0:2](-[c:3](:[c:4]):[#7;a:5]:[c:6]):[cH;D2;+0:1]:1 | 18 | [{"value": 18.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC(=C2)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3,5-dihydroxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (22 mg, 18% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol.Aromatic alcohol | Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc(O)cc(O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)cc(O)c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb25cede22a5439ebe3be42255bb5afb | CC(=O)c1cc(C)cc([N+](=O)[O-])c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(O)c([N+](=O)[O-])c1 | [OH-].[K+].OC1=C(C=C(C=C1[N+](=O)[O-])C)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C(=CC(=C2)C)[N+](=O)[O-])O | CC(=O)c1[cH:3][c:2]([CH3:1])[cH:39][c:35]([N+:36](=[O:37])[O-:38])[c:33]1[OH:34].Oc1ccc(Br)c[c:4]1-[c:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20][c:21]4[n:22]3[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[cH:29][cH:30][c:31]2[n:32]1>>[CH3:1][c:2]1[cH:3... | CC(=O)c1cc(C)cc([N+](=O)[O-])c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(O)c([N+](=O)[O-])c1 | null | null | C(C)O | Miscellaneous | OtherReaction | 13d17d3ba2aab432715ff8895dcc7f34b9986951e91088a4bd02b1fd1fc5dcfe | 826d5ed588669e06fdf43ab0d54c49b68fe5f7db98488b3f4628cb32a365c71c | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):c:1.C-C(=O)-c1:[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9]:[c:10](-[#7;+:11]):[c;H0;D3;+0:12]:1-[O;D1;H1:13]>>[#7;+:11]-[c:10]1:[c:9]:[c:7](-[C;D1;H3:8]):[cH;D2;+0:6]:[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):[c;H0;D3;+0:12]:1-[O;D1;H1:13] | 31 | [{"value": 31.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C(=CC(=C2)C)[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2-hydroxy-5-methyl-3-nitro-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (40 mg, 31% yield).
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol.Aromatic alcohol | Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | CC(=O)c1cc(C)cc([N+](=O)[O-])c1O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>Cc1cc(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e22d17874ae84b2abaf5e64916ebecb4 | COc1cccc(O)c1C(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1cccc(O)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | [OH-].[K+].OC1=C(C(=CC=C1)OC)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2OC)O | CC(=O)[c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[OH:8].Oc1ccc(Br)cc1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]4[n:27]3[CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[n:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6]... | COc1cccc(O)c1C(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1cccc(O)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):c(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):c:1.C-C(=O)-[c;H0;D3;+0:6](:[c:7](-[#8:8]):[c:9]):[c:10](-[O;D1;H1:11]):[c:12]>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:10](-[O;D1;H1:11]):[c:12] | 69 | [{"value": 69.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(2-hydroxy-6-methoxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (75 mg, 69% yield).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | COc1cccc(O)c1C(C)=O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1cccc(O)c1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bac94a5e2eea431691431af4792ad2f9 | COc1cc(O)c(C(C)=O)c(OC)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1cc(O)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(OC)c1 | [OH-].[K+].OC1=C(C(=CC(=C1)OC)OC)C(C)=O.BrC=1C=CC(=C(C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=C(C=C2OC)OC)O | CC(=O)c1[c:5]([OH:6])[cH:4][c:3]([O:2][CH3:1])[cH:39][c:36]1[O:37][CH3:38].Oc1ccc(Br)c[c:7]1-[c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[n:15][c:16]4[cH:17][c:18]([C:19](=[O:20])[OH:21])[cH:22][cH:23][c:24]4[n:25]3[CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33][c:34]2[n:35]1>>[CH3:1][O:2][c:3]1[cH... | COc1cc(O)c(C(C)=O)c(OC)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1cc(O)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(OC)c1 | null | null | C(C)O | Miscellaneous | OtherReaction | f299fb44097350fa320651d0983e8ebd82ff762908ce3d8478bae97b0f2da916 | 0afcb6b3902647a00fcff3b908d1976f5faf335b657dea68fe2faec85b1ae7cc | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O):[c;H0;D3;+0:1](-[c:2](:[c:3]):[#7;a:4]:[c:5]):c:1.C-C(=O)-c1:[c;H0;D3;+0:6](-[#8:7]-[C;D1;H3:8]):[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12]:1-[O;D1;H1:13]>>[C;D1;H3:8]-[#8:7]-[c;H0;D3;+0:6]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12](-[O;D1;H1:13]):[c;H0;D3;+0:1]:1-[c:2](:[c:3]):[#7;a:4]:[c:5] | 65 | [{"value": 65.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=C(C=C2OC)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with -(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (85 mg, 65% yield).
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ether.Aromatic alcohol.Aromatic alcohol | Ether.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | C(C)O | null | null | COc1cc(O)c(C(C)=O)c(OC)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1cc(O)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b66773aa0bf407c865d37bd2c2576a1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(-c5ccc(Cl)cc5)c4)ccc3c1)n2C1CCCCC1 | BrC=1C=C(C=CC1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O.ClC1=CC=C(C=C1)B(O)O.C([O-])(O)=O.[Na+]>>ClC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | Br[c:22]1[cH:21][cH:20][cH:19][c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:35]4[CH:36]4[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]4)[cH:34][c:33]3[cH:32][cH:31]2)[cH:30]1.OB(O)[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[O:1]=[C:2]([OH... | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(-c5ccc(Cl)cc5)c4)ccc3c1)n2C1CCCCC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C.CO | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 42.2 | [{"value": 42.0, "product": "ClC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.2, "product": "ClC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is... | 90 | CELSIUS | 16 | HOUR | In dried vial with a Teflon lined screw cap, a solution of Compound 482 (156 mg, 0.31 mmol), 4-chlorophenylboronic acid (73 mg, 0.465 mmol), and Palladium Tetrakis (37 mg, 0.031 mmol) in toluene (9 mL), methanol (2 mL), and saturated sodium bicarbonate in water (900 μL) was degassed, flushed with argon, and sealed. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.CO | 90 | 16 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(Br)c4)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.CO>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(-c5ccc(Cl)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-147c10f1b8ef4deabab477614815e219 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(C(N)=O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | [OH-].[K+].COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.C([O-])(O)=O.[Na+].O>>C(N)(=O)C1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=C1 | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45][c:16]1-[c:17]1[cH:18][cH:19][c:20]2[cH:21][c:22](-[c:23]3[n:12][c:25]4[cH:26][c:27]([C:28](=[O:29])[O:30][CH3:7])[cH:31][cH:32][c:33]4[n:34]3[CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[cH:41][cH:42][c:43]2[n:44]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1 | COc1ccc(-c2ccc(C(N)=O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | 3f7edad97709d4bd5d44566bb7179d840b74c5299eb1373f73c2ff159ea5009c | faa5f70adcaec17880da4b509384bb36ded18d7fda4ad0119b5c36e3e1980dbc | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-[CH3;D1;+0:18]):[n;H0;D2;+0:19]:[c;H0;D3;+0:20]:1-[c:21](:[c:22]):[c:23]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:18]1:[c:24]:[c:25]:[c:26](-... | null | [] | 90 | CELSIUS | 16 | HOUR | In a flame dried vial with a Teflon lined screw cap, a solution of Compound 365b (100 mg, 0.175 mmol), 4-amidophenylboronic acid (31 mg, 0.2625 mmol), and Palladium Tetrakis (20 mg, 0.0175 mmol) in toluene (6.5 mL), methanol (1.6 mL), and saturated sodium bicarbonate in water (800 ul) was degassed, flushed with argon, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Carboxylic acid.Primary amide | c1ccccc1.c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO | 90 | 16 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO>COc1ccc(-c2ccc(C(N)=O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7ff849513b44655869091b850785528 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)c(Cl)c1>>COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | [OH-].[K+].COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.FC1=C(C=C(C=C1)B(O)O)Cl.C([O-])(O)=O.[Na+]>>ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F | C[O:29][C:27]([c:26]1[cH:25][c:24]2[n:23][c:22](-[c:21]3[cH:20][c:19]4[cH:18][cH:17][c:16](-[c:15]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]5)[n:43][c:42]4[cH:41][cH:40]3)[n:33]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[c:32]2[cH:31][cH:30]1)=[O:28].OB(O)[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([Cl:13])[cH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)c(Cl)c1 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C.CO | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 7 | [{"value": 7.0, "product": "ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.6, "product": "ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F", "details": "CALCULATEDPERCENTYIELD",... | 90 | CELSIUS | 16 | HOUR | In dried vial with a Teflon lined screw cap, a solution of Compound 365b (100 mg, 0.175 mmol), 4-fluoro-3-chlorophenylboronic acid (61 mg, 0.2625 mmol), and Palladium Tetrakis (20 mg, 0.0175 mmol) in toluene (6.5 mL), methanol (1.6 mL), and saturated sodium bicarbonate in water (800 ul) was degassed, flushed with argon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.CO | 90 | 16 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)c(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.CO>COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a90125c0ee144210b3381874be655e30 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1ccc(B(O)O)cc1>>COc1ccc(-c2ccc([N+](=O)[O-])cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)[N+](=O)[O-])OC | Fc1ccc(-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45][c:16]2-[c:17]2[cH:18][cH:19][c:20]3[cH:21][c:22](-[c:23]4[n:24][c:25]5[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][c:33]5[n:34]4[CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)[cH:41][cH:42][c:43]3[n:44]2)cc1Cl.OB(O)[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[... | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1ccc(B(O)O)cc1 | COc1ccc(-c2ccc([N+](=O)[O-])cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 32c6d9e04f426e2be7276d51def4545d9be5d98cffa0b1b76a196565e6617362 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Cl-c1:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:c:1-F.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 14.3 | [{"value": 14.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)[N+](=O)[O-])OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.3, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)[N+](=O)[O-])OC", "details": "... | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-nitrophenylboronic acid (62 mg, 0.2625 mmol) to produce the title compound (15 mg, 14% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.B | null | null | null | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1ccc(B(O)O)cc1>>COc1ccc(-c2ccc([N+](=O)[O-])cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1825744e8a6c407a8e7b798d3a65e5fe | CN(C)c1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(N(C)C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.CN(C1=CC=C(C=C1)B(O)O)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)N(C)C)OC | OB(O)[c:7]1[cH:8][cH:9][c:10]([N:11]([CH3:12])[CH3:13])[cH:14][cH:15]1.C[O:30][C:28]([c:27]1[cH:26][c:25]2[n:24][c:23](-[c:22]3[cH:21][c:20]4[cH:19][cH:18][c:17](-[c:16]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45]5)[n:44][c:43]4[cH:42][cH:41]3)[n:34]([CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[c:33]2[cH:32][... | CN(C)c1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1 | COc1ccc(-c2ccc(N(C)C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 26 | [{"value": 26.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)N(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-dimethylaminophenylboronic acid (44 mg, 0.2625 mmol) to produce the title compound (27 mg, 26% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | CN(C)c1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(N(C)C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5cbc77d5254481ca690a470d7a938e0 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1cccc(B(O)O)c1>>COc1ccc(-c2cccc([N+](=O)[O-])c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=CC=C2)[N+](=O)[O-])OC | Fc1ccc(-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45][c:16]2-[c:17]2[cH:18][cH:19][c:20]3[cH:21][c:22](-[c:23]4[n:24][c:25]5[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][c:33]5[n:34]4[CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)[cH:41][cH:42][c:43]3[n:44]2)cc1Cl.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[... | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1cccc(B(O)O)c1 | COc1ccc(-c2cccc([N+](=O)[O-])c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 32c6d9e04f426e2be7276d51def4545d9be5d98cffa0b1b76a196565e6617362 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Cl-c1:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:c:1-F.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 7 | [{"value": 7.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=CC=C2)[N+](=O)[O-])OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 3-nitrophenylboronic acid (44 mg, 0.2625 mmol) to produce the title compound (7 mg, 7% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.B | null | null | null | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=[N+]([O-])c1cccc(B(O)O)c1>>COc1ccc(-c2cccc([N+](=O)[O-])c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae30255c8e3b42fa867c623833b9b378 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(C(F)(F)F)cc1>>COc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.FC(C1=CC=C(C=C1)B(O)O)(F)F>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)C(F)(F)F)OC | C[O:31][C:29]([c:28]1[cH:27][c:26]2[n:25][c:24](-[c:23]3[cH:22][c:21]4[cH:20][cH:19][c:18](-[c:17]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:46]5)[n:45][c:44]4[cH:43][cH:42]3)[n:35]([CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[c:34]2[cH:33][cH:32]1)=[O:30].OB(O)[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(C(F)(F)F)cc1 | COc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 12 | [{"value": 12.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)C(F)(F)F)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-trifluoromethylphenylboronic acid (50 mg, 0.2625 mmol) to produce the title compound (14 mg, 12% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(C(F)(F)F)cc1>>COc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d51ab9a3caea428780a298ad2cc96de6 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1ccco1>>COc1ccc(-c2ccco2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.O1C(=CC=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2OC=CC2 | Fc1ccc(-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41][c:12]2-[c:13]2[cH:14][cH:15][c:16]3[cH:17][c:18](-[c:19]4[n:20][c:21]5[cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28][c:29]5[n:30]4[CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)[cH:37][cH:38][c:39]3[n:40]2)cc1Cl.OB(O)[c:7]1[cH:8][cH:9][cH:10][o:11]1>>[CH3:1][... | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1ccco1 | COc1ccc(-c2ccco2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 0e0253b66decd7d74d1a1f97a0c8fe92b35f6d02bfe7317498d3b5459234f4f4 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1coc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1 | Cl-c1:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:c:1-F.O-B(-O)-[c;H0;D3;+0:8]1:[#8;a:9]:[c:10]:[c:11]:[c:12]:1>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#8;a:9]:[c:10]:[c:11]:[c:12]:1):[c:2]:[c:3] | 5 | [{"value": 5.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 2-furanboronic acid (30 mg, 0.2625 mmol) to produce the title compound (5 mg, 5% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccoc1 | c1ccccc1.c1ccoc1 | c1ccccc1.c1ccoc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.B | null | null | null | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1ccco1>>COc1ccc(-c2ccco2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b1343f3b8d943b2a98e378b1d72deef | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.COC1=CC=C(C=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)OC)OC | C[O:28][C:26]([c:25]1[cH:24][c:23]2[n:22][c:21](-[c:20]3[cH:19][c:18]4[cH:17][cH:16][c:15](-[c:14]5[c:7](Br)[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13]5)[n:42][c:41]4[cH:40][cH:39]3)[n:32]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[c:31]2[cH:30][cH:29]1)=[O:27].OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][cH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1 | COc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 15 | [{"value": 15.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-methoxyphenylboronic acid (40 mg, 0.2625 mmol) to produce the title compound (15 mg, 15% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2723f4bee31647beb62e1df971549d8e | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>COc1ccc(-c2cccc(C(=O)O)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1>>C(=O)(O)C=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1 | COc1ccc(Br)c(-c2ccc3cc(-c4nc5c(n4C4CCCCC4)[cH:9][cH:10][c:11]([C:12](=[O:13])[O:14]C)[cH:15]5)ccc3n2)c1.Fc1c[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45][c:16]2-[c:17]2[cH:18][cH:19][c:20]3[cH:21][c:22](-[c:23]4[n:24][c:25]5[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][c:33]5[n:34]4[CH:35]4[CH2:36][CH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | COc1ccc(-c2cccc(C(=O)O)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | Miscellaneous | OtherReaction | 7b44631509d7b2c3d68f050efb14ee329debb5a841ec6fdcf1402f4d0a7dce09 | f35c9d72ec193f2e381c4d42cb243062a5caa8c3ad0413d2a6200b6b5dd7eec3 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-O-C):c:c:1-c1:c:c:c2:c:c(-c3:n:c4:[cH;D2;+0:1]:[c:2](-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C):[c:6]:[cH;D2;+0:7]:c:4:n:3-C3-C-C-C-C-C-3):c:c:c:2:n:1.Cl-c1:c:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):[cH;D2;+0:12]:c:c:1-F>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[c:2]1:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:12]:[c;H0;D3;+0:8](-[... | 23 | [{"value": 23.0, "product": "C(=O)(O)C=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with ethyl 3-boronic acid benzoate (51 mg, 0.2625 mmol) to produce the title compound (26 mg, 23% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Ether | Carboxylic acid | c1ccccc1.c1ccc2ncccc2c1.C1CCCCC1.c1ccc2nc[nH]c2c1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.Br- | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>COc1ccc(-c2cccc(C(=O)O)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf988f9c625644d7a04b04f9cdfba449 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>COc1ccc(-c2ccc(O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)O)OC | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc([O:11]C)ccc4Br)ccc3c1)n2C1CCCCC1.F[c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43][c:14]2-[c:15]2[cH:16][cH:17][c:18]3[cH:19][c:20](-[c:21]4[n:22][c:23]5[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]5[n:32]4[CH:33]4[CH2:34][CH2:35][CH2:36][CH2:37][CH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | COc1ccc(-c2ccc(O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f30117c431a2592965204599aa4c028643efc650df21031e46a71a6eff6364c2 | 96757a10f94e51057570c37db8198b2450e6ebfdc9332f472ca09eb028b6aa59 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c(-[O;H0;D2;+0:1]-C):c:c:1-c1:c:c:c2:c:c(-c3:n:c4:c:c(-C(=O)-O-C):c:c:c:4:n:3-C3-C-C-C-C-C-3):c:c:c:2:n:1.Cl-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-F>>[OH;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[cH;D2;+0:2]:1 | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-phenolboronic acid (36 mg, 0.2625 mmol) to produce the title compound (10 mg, 8% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Ether | Aromatic alcohol | c1ccc2[nH]cnc2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.Br- | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>COc1ccc(-c2ccc(O)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a6328dcf0164138af0f9e9fe1e9d067 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)c(Cl)c1>>COc1ccc(-c2ccc(Cl)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.ClC=1C=C(C=CC1Cl)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=C(C=C2)Cl)Cl)OC | C[O:29][C:27]([c:26]1[cH:25][c:24]2[n:23][c:22](-[c:21]3[cH:20][c:19]4[cH:18][cH:17][c:16](-[c:15]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]5)[n:43][c:42]4[cH:41][cH:40]3)[n:33]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[c:32]2[cH:31][cH:30]1)=[O:28].OB(O)[c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([Cl:13])[c... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)c(Cl)c1 | COc1ccc(-c2ccc(Cl)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 4 | [{"value": 4.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=C(C=C2)Cl)Cl)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 3,4-dichlorophenylboronic acid (50 mg, 0.2625 mmol) to produce the title compound (5 mg, 4% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(Cl)c(Cl)c1>>COc1ccc(-c2ccc(Cl)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac7b8470b97e4ed69ebcda8897d794e2 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1cccc(Cl)c1>>COc1ccc(-c2cccc(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.ClC=1C=C(C=CC1)B(O)O>>ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1 | C[O:28][C:26]([c:25]1[cH:24][c:23]2[n:22][c:21](-[c:20]3[cH:19][c:18]4[cH:17][cH:16][c:15](-[c:14]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43]5)[n:42][c:41]4[cH:40][cH:39]3)[n:32]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[c:31]2[cH:30][cH:29]1)=[O:27].OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1cccc(Cl)c1 | COc1ccc(-c2cccc(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 17 | [{"value": 17.0, "product": "ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 3-chlorophenylboronic acid (41 mg, 0.2625 mmol) to produce the title compound (20 mg, 17% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1cccc(Cl)c1>>COc1ccc(-c2cccc(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cee28962f824527a7804f82b1d870e9 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.B(C=1C=CC(=CC1)C)(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)C)OC | C[O:28][C:26]([c:25]1[cH:24][c:23]2[n:22][c:21](-[c:20]3[cH:19][c:18]4[cH:17][cH:16][c:15](-[c:14]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43]5)[n:42][c:41]4[cH:40][cH:39]3)[n:32]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[c:31]2[cH:30][cH:29]1)=[O:27].OB(O)[c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]1>... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1ccc(B(O)O)cc1 | COc1ccc(-c2ccc(C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 12 | [{"value": 12.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with p-tolylboronic acid (36 mg, 0.2625 mmol) to produce the title compound (12 mg, 12% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(C)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fa46e71435c4562962a37bc739e725a | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1cccc(B(O)O)c1>>COc1ccc(-c2cccc(C)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.C1(=CC(=CC=C1)B(O)O)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=CC=C2)C)OC | C[O:28][C:26]([c:25]1[cH:24][c:23]2[n:22][c:21](-[c:20]3[cH:19][c:18]4[cH:17][cH:16][c:15](-[c:14]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43]5)[n:42][c:41]4[cH:40][cH:39]3)[n:32]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[c:31]2[cH:30][cH:29]1)=[O:27].OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([CH3:12])[cH:13]1>... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1cccc(B(O)O)c1 | COc1ccc(-c2cccc(C)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 27 | [{"value": 27.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC(=CC=C2)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with m-tolylboronic acid (36 mg, 0.2625 mmol) to produce the title compound (27 mg, 27% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.Cc1cccc(B(O)O)c1>>COc1ccc(-c2cccc(C)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8350caabb43a419a964d0c03037cf9b0 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(CN)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.NCC1=CC=C(C=C1)B(O)O>>NCC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=C1 | Fc1ccc(-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][c:15]2-[c:16]2[cH:17][cH:18][c:19]3[cH:20][c:21](-[c:22]4[n:23][c:24]5[cH:25][c:26]([C:27](=[O:28])[OH:29])[cH:30][cH:31][c:32]5[n:33]4[CH:34]4[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]4)[cH:40][cH:41][c:42]3[n:43]2)cc1Cl.OB(O)[c:7]1[cH:8][cH:9][c:10]([CH2:11][NH2:12])... | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCc1ccc(B(O)O)cc1 | COc1ccc(-c2ccc(CN)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 32c6d9e04f426e2be7276d51def4545d9be5d98cffa0b1b76a196565e6617362 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Cl-c1:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:c:1-F.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 46 | [{"value": 46.0, "product": "NCC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-aminomethylphenylboronic acid (49 mg, 0.2625 mmol) to produce the title compound (48 mg, 46% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.B | null | null | null | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.NCc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc(CN)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-addf8a4775ce43b588fd76124ba7beb4 | CCOc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>CCOc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.C(C)OC1=CC=C(C=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)OCC)OC | OB(O)[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:45][cH:44]1.C[O:29][C:27]([c:26]1[cH:25][c:24]2[n:23][c:22](-[c:21]3[cH:20][c:19]4[cH:18][cH:17][c:16](-[c:15]5[c:8](Br)[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]5)[n:43][c:42]4[cH:41][cH:40]3)[n:33]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[c:32]2[cH:31][cH... | CCOc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1 | CCOc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:11] | 16 | [{"value": 16.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)OCC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 4-ethoxyphenylboronic acid (44 mg, 0.2625 mmol) to produce the title compound (17 mg, 16% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | CCOc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>CCOc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69cce5cf2758402fa1fa9ae09f52f727 | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1cccs1>>COc1ccc(-c2cccs2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.S1C(=CC=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2SC=CC2 | Fc1ccc(-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41][c:12]2-[c:13]2[cH:14][cH:15][c:16]3[cH:17][c:18](-[c:19]4[n:20][c:21]5[cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28][c:29]5[n:30]4[CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)[cH:37][cH:38][c:39]3[n:40]2)cc1Cl.OB(O)[c:7]1[cH:8][cH:9][cH:10][s:11]1>>[CH3:1][... | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1cccs1 | COc1ccc(-c2cccs2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 43c61b81957e5d103120d30884b9edaab0a7a61161f36389d85bcd0a6cb56cf7 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1csc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1 | Cl-c1:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:c:1-F.O-B(-O)-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1):[c:2]:[c:3] | 27 | [{"value": 27.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 2-thiopheneboronic acid (34 mg, 0.2625 mmol) to produce the title compound (26 mg, 27% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF.B | null | null | null | COc1ccc(-c2ccc(F)c(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.OB(O)c1cccs1>>COc1ccc(-c2cccs2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39fad7e43001435c9baa4847ee94145c | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ncc(B(O)O)c(OC)n1>>COc1ccc(-c2cnc(OC)nc2OC)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC=1C=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=CC1F.COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)OC)Br)C2CCCCC2)C=C1.COC1=NC=C(C(=N1)OC)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2C(=NC(=NC2)OC)OC | C[O:31][C:29]([c:28]1[cH:27][c:26]2[n:25][c:24](-[c:23]3[cH:22][c:21]4[cH:20][cH:19][c:18](-[c:17]5[c:6](Br)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:46]5)[n:45][c:44]4[cH:43][cH:42]3)[n:35]([CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[c:34]2[cH:33][cH:32]1)=[O:30].OB(O)[c:7]1[cH:8][n:9][c:10]([O:11][CH3:12])[n:13][c:14... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ncc(B(O)O)c(OC)n1 | COc1ccc(-c2cnc(OC)nc2OC)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | e4889be329320133de905898c8e49409b08273a08be014191d1c84d85b74afc8 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11].O-B(-O)-[c;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:1-[#8:18]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:1-[#8:18]):[c:2]:[c:3].[O;D1;H0:10... | 7 | [{"value": 7.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C=2C(=NC(=NC2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 2,4-dimethoxypyrimidine-5-boronic acid (34 mg, 0.2625 mmol) to produce the title compound (8 mg, 7% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr.B | null | null | null | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.COc1ncc(B(O)O)c(OC)n1>>COc1ccc(-c2cnc(OC)nc2OC)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
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