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-f2bc132c6e9a4ccaa92b2c3e67d2293f | O=C(O)c1ccc(O)nc1.O=[N+]([O-])O>>O=C(O)c1cnc(O)c([N+](=O)[O-])c1 | OC1=NC=C(C(=O)O)C=C1.[N+](=O)(O)[O-]>>OC1=NC=C(C(=O)O)C=C1[N+](=O)[O-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]([OH:8])[cH:9][cH:13]1.O[N+:10](=[O:11])[O-:12]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]([OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | O=C(O)c1ccc(O)nc1.O=[N+]([O-])O | O=C(O)c1cnc(O)c([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | cb3ba0bb7f4ff246f608a5c967bfb512792a47826af0eb60d49c2f2aea6e8ead | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccncc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[c:7]1:[c:8]:[cH;D2;+0:9]:[c:10](-[O;D1;H1:11]):[#7;a:12]:[c:13]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:9]1:[c:8]:[c:7](-[C:5](=[O;D1;H0:4])-[O;D1;H1:6]):[c:13]:[#7;a:12]:[c:10]:1-[O;D1;H1:11] | null | [] | null | null | null | null | A solution of 6-hydroxynicotinic acid (10 g, 71.89 mmol) in fuming nitric acid (100 mL) was stirred at 50° C. for 4 h. After evaporation of extra nitric acid, the solid was obtained and it was directly used in the next step reaction. MS: 185.02 (M+H+).
Conditions: See reaction.notes.procedure_details.
Workup: After eva... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | null | null | null | O=C(O)c1ccc(O)nc1.O=[N+]([O-])O>>O=C(O)c1cnc(O)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-406fc899bd3d4b099f369f4a79c20782 | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1>>O=C(O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C=1C=C2C(=NC1)N(C(=N2)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2)Br)C2CCCCC2.[OH-].[Na+].Cl>>BrC1=C(C=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC=2C(=NC=C(C2)C(=O)O)N1C1CCCCC1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n: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]4[cH:19][cH:20][cH:21][cH:22][c:23]4[Br:24])[cH:25][cH:26][c:27]3[cH:28]1)[n:29]2[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](... | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 | O=C(O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc3cc(-c4nc5cccnc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "BrC1=C(C=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC=2C(=NC=C(C2)C(=O)O)N1C1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 2 | HOUR | Compound 477d (0.139 g, 0.25 mmol) was dissolved in MeOH (3 mL) and 2 N aqueous NaOH (1.5 mL) was added. The mixture was stirred at 55° C. for 2 h and then neutralized with 5 N HCl to pH 3 at 0° C. The precipitates formed was collected by filtration and purified by RP HPLC (15% of buffer B to 95% of buffer B) to give t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | Other | CO | 55 | 2 | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1>CO>O=C(O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64def31f788d42a4ab02b00dbb8098c9 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1I.OB(O)c1ccc(Cl)cc1>>CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1 | IC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O.ClC1=CC=C(C=C1)B(O)O>>ClC1=CC=C(C2=CC=C(C=C2C(C)=O)C(=O)N2CCCC2)C=C1 | I[c:16]1[c:4]([C:2]([CH3:1])=[O:3])[cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1.OB(O)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][c:20]([Cl:2... | CC(=O)c1cc(C(=O)N2CCCC2)ccc1I.OB(O)c1ccc(Cl)cc1 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1 | 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.C(=O)(O)[O-].[Na+] | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)cc1)N1CCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | 96 | [{"value": 96.0, "product": "ClC1=CC=C(C2=CC=C(C=C2C(C)=O)C(=O)N2CCCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "ClC1=CC=C(C2=CC=C(C=C2C(C)=O)C(=O)N2CCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 16 | HOUR | A mixture of Compound 419c (0.29 g, 0.845 mmol), 4-chlorobenzeneboronic acid (0.159 g, 1.02 mmol)) and Pd(PPh3)4 (97 mg) in toluene (25 mL), MeOH (6 mL) and saturated NaHCO3 (2.5 mL) was stirred under Ar at 70° C. for 16 h. After evaporation of solvent, the residue was dissolved in CHCl3 (30 mL) and filtered. The filtr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HI.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.C1(=CC=CC=C1)C.CO.C(=O)(O)[O-].[Na+] | 70 | 16 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1I.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.C1(=CC=CC=C1)C.CO.C(=O)(O)[O-].[Na+]>CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc0595cebb4e4adfa1177ca50db6b467 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1.COC(=O)c1ccc(N)c(C=O)c1>>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | [OH-].[K+].Cl.ClC1=CC=C(C2=CC=C(C=C2C(C)=O)C(=O)N2CCCC2)C=C1.COC(C1=CC(=C(C=C1)N)C=O)=O>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1 | O=[C:9]([c:10]1[cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20][cH:21][c:22]1-[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1)[CH3:30].C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:32]([CH:31]=O)[cH:33]1>>[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][c:12... | CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1.COC(=O)c1ccc(N)c(C=O)c1 | O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | null | null | O1CCOCC1.CCO | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3ccccc3n2)c1)N1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[CH;D2;+0:7]=O):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]-[C:16](-[#7:17])=[O;D1;H0:18]):[c:19](-[c:20]):[c:21]>>[#7:17]-[C:16](=[O;D1;H0:18])-[c:15]:[c:14]:[c;H0;D3;+0:13](-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[cH;D2... | null | [] | 75 | CELSIUS | 16 | HOUR | To a mixture of Compound 259a (0.388 g, 1.184 mmol) and Compound 7 (0.223 g, 1.243 mmol) was added a solution of KOH (0.234 g, 3.55 mmol) in EtOH (18 mL). The reaction mixture was stirred under Ar at 75° C. for 16 h. EtOH (10 mL) was added to make a clean solution, which was neutralized by adding 4 N HCl in dioxane (ab... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | O1CCOCC1.CCO | 75 | 16 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1-c1ccc(Cl)cc1.COC(=O)c1ccc(N)c(C=O)c1>O1CCOCC1.CCO>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-888263f4fc154cd191ba199a1d5df0a7 | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>>O=C(c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(-c6nnn[nH]6)ccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | C(C)OC(=O)C=1C=C2C(=NC1)N(C(=N2)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2)Br)C2CCCCC2.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CC(=O)O>>ClC1=CC=C(C=C1)C1=C(C=C(C=C1)C(=O)N1CCCC1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C2=NN=NN2 | CCO[C:26](=O)[c:25]1c[n:30][c:33]2[c:23]([n:22][c:21](-[c:20]3[cH:19][c:18]4[cH:17][cH:16][c:15](-c5ccccc5Br)[n:44][c:43]4[cH:42][cH:41]3)[n:34]2[CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[cH:24]1.CN(C)C(O[n:27]1c2ccccc2[n:29][n:28]1)=[N+](C)C.O=C(O)c1cc2ccc(-[c:14]3[c:6](-[c:7]4[cH:8][cH:9][c:10]([Cl:11])[cH:12... | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | O=C(c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(-c6nnn[nH]6)ccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | 8d86ba4e8767800c3bcd291ca7893857a67e165ff4d51e0952dee7f395f1a402 | a171dd1cb583866dd4fad5604bb3a789b82f3e28beacbe8ddbd07427267747b8 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5cc(-c6nnn[nH]6)ccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | Br-c1:c:c:c:c:c:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].C-C-O-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]2:[#7;a:10]:[c:11](-[c:12]):[#7;a:13](-[C:14]):[c;H0;D3;+0:15]:2:[n;H0;D2;+0:16]:c:1.C-N(-C)-C(-O-[n;H0;D3;+0:17]1:[#7;a:18]:[n;H0;D2;+0:19]:c2:c:c:c:c:c:1:2)=[N+](-C)-C.O-C(=O)-c1:[cH;D2;+0:20]:[cH;D2;+0:2... | 23 | [{"value": 23.0, "product": "ClC1=CC=C(C=C1)C1=C(C=C(C=C1)C(=O)N1CCCC1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C2=NN=NN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The amine was reacted with Compound 259e (0.125 g, 0.274 mmol) in the presence of HBTU (0.114 g, 0.30 mmol), followed cyclization in AcOH according to procedures described for the preparation of Compound 477d. Separation by RP HPLC (from 10% of buffer B to 85% of buffer B) gave the title compound (42 mg, 23%).
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Amidinium.Carboxylic acid.Ester | null | c1cnc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccc2[nH]nnc2c1.c1ccc2ncccc2c1.c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.c1nnn[nH]1.C1CCCCC1.C1CC[NH]C1 | HBr | null | null | null | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>>O=C(c1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(-c6nnn[nH]6)ccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cc70d6dc4db4e4f9f8dc74e63e90d69 | COC(=O)c1ccc(N)c(C=O)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1.COC(C1=CC(=C(C=C1)N)C=O)=O.[OH-].[K+]>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)OC)C=C1 | Nc1ccc(C(=O)[O:2][CH3:1])cc1C=O.O=C(N1CCCC1)[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:24][cH:25][c:26]3[n:27]2)[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[c:1... | COC(=O)c1ccc(N)c(C=O)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 04098378d630e1525077c45496f507935e4a890d731505bb2b49bf8b2c8324d6 | 8ec0d893b2bbd1d8ee7a0446c89acf538dc35e7e5dd91f757952b5249dbccca7 | c1ccc(-c2ccccc2-c2ccc3ccccc3n2)cc1 | N-c1:c:c:c(-C(=O)-[O;H0;D2;+0:1]-[C;D1;H3:2]):c:c:1-C=O.O=C(-N1-C-C-C-C-1)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | 91 | [{"value": 91.0, "product": "ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 7 (3.06 g. 11.72 mmol) was reacted with compound 525a (2.1 g, 11.72 mmol) and KOH (2.32 g, 35.16 mmol) in EtOH (150 mL) according to the procedure in the preparation of Compound 259e. Purification by chromatography using CHCl3-MeOH (7:1) as the eluent gave the title intermediate (3.1 g, 91%). MS: 388.07 (M+H+)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Tertiary amide.Primary amine | Ether | c1ccccc1.C1CCNC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HO- | CCO | null | null | COC(=O)c1ccc(N)c(C=O)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>CCO>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a2f227c2a164f239c7c766c164959dc | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1>>CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)OC)C=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(C)OC(=O)C=1C=C2C(=NC1)N(C(=N2)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2)Br)C2CCCCC2>>C(C)OC(=O)C=1C=C2C(=NC1)N(C(=N2)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)OC)C2CCCCC2 | Brc1ccccc1-c1ccc2c(n1)[cH:16][cH:15][c:14](-[c:13]1[n:12][c:10]3[c:9]([n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]3)[n:39]1[CH:40]1[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1)[cH:38]2.O=C(O)c1cc[c:17]2[n:18][c:19](-[c:20]3[cH:21][c:22]([O:23][CH3:24])[cH:25][cH:26][c:27]3-[c:28]3[cH:29][cH:30][c:31]([Cl:32])... | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1 | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | CC(=O)O.CN(C)C=O | Miscellaneous | OtherReaction | 1dfd0569aef7fb1e689ca63ae202aacd76d224af600a64fd69ed9cf016c10412 | 3fbb180061815c1a91daf750f59d95354663c01e4c6076719644d5369bdccd52 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5cccnc5n4C4CCCCC4)ccc3n2)cc1 | Br-c1:c:c:c:c:c:1-c1:c:c:c2:[cH;D2;+0:1]:[c:2](-[c:3](:[#7;a:4]):[#7;a:5]):[c:6]:[cH;D2;+0:7]:c:2:n:1.O-C(=O)-c1:c:c:[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2:c:1>>[#7;a:4]:[c:3](-[c:2]1:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2:[cH;D2;+0:1]:1):[#7;a:5] | 40 | [{"value": 40.0, "product": "C(C)OC(=O)C=1C=C2C(=NC1)N(C(=N2)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)OC)C2CCCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The amine was reacted with Compound 525c (0.314 g, 0.805 mmol) in the presence of HBTU (0.32 g, 0.844 mmol) and DIEA (0.47 mL, 2.68 mmol) in DMF (10 mL), followed cyclization in AcOH (10 mL) according to procedure (2) and (3) in the preparation of Compound 477d. Separation by RP HPLC (from 20% of buffer B to 99% of buf... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | null | c1ccccc1.c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1cnc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | CC(=O)O.CN(C)C=O | null | null | CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1>CC(=O)O.CN(C)C=O>CCOC(=O)c1cnc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-455a65ed6b874538915b34bc7f320e6d | NC1CCCCC1.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>>O=C(O)c1ccc([N+](=O)[O-])c(NC2CCCCC2)c1 | FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-].C1(CCCCC1)N>>C1(CCCCC1)NC=1C=C(C(=O)O)C=CC1[N+](=O)[O-] | [NH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.F[c:11]1[c:7]([N+:8](=[O:9])[O-:10])[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[cH:19]1 | NC1CCCCC1.O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | O=C(O)c1ccc([N+](=O)[O-])c(NC2CCCCC2)c1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[#7;+:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11](-[C:10])-[C:13]):[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | 85 | CELSIUS | 6 | HOUR | A mixture of 3-fluoro-4-nitrobenzoic acid (0.35 g, 1.891 mmol) and cyclohexylamine (2.17 mL, 18.91 mmol) in NMP (10 mL) was stirred under Ar at 85° C. for 6 h. The solvent was evaporated under high vacuum. The residue was purified by chromatography using CH3Cl-MeOH (10:1) as the eluent to give the title intermediate in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HF | CN1CCCC1=O | 85 | 6 | NC1CCCCC1.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>CN1CCCC1=O>O=C(O)c1ccc([N+](=O)[O-])c(NC2CCCCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2267f3d53bda4933bade31f83b91eb23 | CN(C)C(On1nnc2ccccc21)=[N+](C)C.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1>>c1ccc2[nH]cnc2c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)OC)C=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>N1=CNC2=C1C=CC=C2 | CN(C)C(O[n:7]1nnc2ccccc21)=[N+](C)C.COc1ccc(-c2ccc(Cl)cc2)c(-[c:6]2cc[c:8]3[c:4]([cH:3][cH:2][c:1](C(=O)O)[cH:9]3)[n:5]2)c1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | CN(C)C(On1nnc2ccccc21)=[N+](C)C.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1 | c1ccc2[nH]cnc2c1 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 43f8c1d2e12fe8fe06ccbfc248e471b89c1229f77f22c63310f1a7ae77f052a5 | dc1e835f5a3e2840a5d662e45443561889bdafd4f3c7eaad8d82c6e795b1eb02 | c1ccc2[nH]cnc2c1 | C-N(-C)-C(-O-[n;H0;D3;+0:1]1:n:n:c2:c:c:c:c:c:1:2)=[N+](-C)-C.C-O-c1:c:c:c(-c2:c:c:c(-Cl):c:c:2):c(-[c;H0;D3;+0:2]2:[n;H0;D2;+0:3]:[c:4]3:[c:5]:[c:6]:[c;H0;D3;+0:7](-C(-O)=O):[c:8]:[c;H0;D3;+0:9]:3:c:c:2):c:1>>[c:6]1:[c:5]:[c:4]2:[nH;D2;+0:3]:[cH;D2;+0:2]:[n;H0;D2;+0:1]:[c;H0;D3;+0:9]:2:[c:8]:[cH;D2;+0:7]:1 | null | [] | null | null | 8 | HOUR | Compound 525c (0.38 g, 0.97 mmol) was reacted with HBTU (0.444 g, 1.2 mmol) in anhydrous DMF (5 mL) in the presence of DIEA (0.41 mL, 2.35 mmol) for 30 min. The mixture was then transferred to a suspension of amine-resin in DMF (5 mL). The reaction mixture was shaken at room temperature overnight. The solution was drai... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Amidinium.Carboxylic acid.Ether | null | c1ccc2[nH]nnc2c1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HCl | CN(C)C=O | null | 8 | CN(C)C(On1nnc2ccccc21)=[N+](C)C.COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(C(=O)O)ccc3n2)c1>CN(C)C=O>c1ccc2[nH]cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2af721953d1e433ba339919acca129b0 | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC4)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C1(CC1)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CC2)C=CC(=C3)C(=O)O)OC)C=C1 | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40]4)[n:39][c:38]3[cH:37][cH:36]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[CH:33]1[CH2:34][CH2:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bca9f6890a93da0c14d9f4e55f9655d1fdfb7c70773f09aaeafce39e8be0aed3 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CC4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH;D3;+0:9]1-[C:10]-[C:11]-1>>[c:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D3;+0:1]:1-[CH;D3;+0:9]1-[C:10]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and cyclopropylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1.C1CC1 | c1ccc2nc[nH]c2c1.C1CC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a1059e9eaba4776a1501cce895e62b3 | CC(C)N.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C(C)C)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(C)(C)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C(C)C)C=CC(=C3)C(=O)O)OC)C=C1 | CC(N)[CH3:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[c:14](-[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[CH2:33][CH3:34])[cH:36][cH:37][c:38]3[n:39]2)[cH:40]1>>[CH3:1][O:2][c:3]1[cH:4][cH:... | CC(C)N.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C(C)C)ccc3n2)c1 | null | null | null | C-C Coupling | C-methylation | 64373be5a33736ed2e1d3944b47a5ade48d6d0bd171709b9325375f360c184f2 | b4142dbc8aebf8ea5ecf50af61f2215c729ea5a2dcf1f9e7fd52e13ad01c499d | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5[nH]4)ccc3n2)cc1 | C-C(-N)-[CH3;D1;+0:1].[C;D1;H3:2]-[CH2;D2;+0:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[c:9]>>[C;D1;H3:2]-[CH;D3;+0:3](-[CH3;D1;+0:1])-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[c:9] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and isopropylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1 | Other | null | null | null | CC(C)N.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C(C)C)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ceb6250f88184346a918792c8b9c8f73 | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CCCC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCC4)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C1(CCCC1)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCC2)C=CC(=C3)C(=O)O)OC)C=C1 | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42]4)[n:41][c:40]3[cH:39][cH:38]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1>>[CH3:1][O:2... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CCCC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCC4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b41ceeb5a9ac63d4cb904d03247393491b717315be2d98da4355fbe2848c6a6 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCC4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-1>>[c:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D3;+0:1]:1-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-1 | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and cyclopentylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1.C1CCCC1 | c1ccc2nc[nH]c2c1.C1CCCC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CCCC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac87005d8e664fdf9948862b6b86dbd4 | CC(C)CN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC(C)C)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(C(C)C)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC(C)C)C=CC(=C3)C(=O)O)OC)C=C1 | N[CH2:33][CH:34]([CH3:35])[CH3:36].CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41]4)[n:40][c:39]3[cH:38][cH:37]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21>>[CH3:1][O:2][c:3]1[... | CC(C)CN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC(C)C)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e2ab8b98cf900440127ead862394c72c072386b0bf56fe859e56bb968c0d4253 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5[nH]4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])-[CH2;D2;+0:9]-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and isobutylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1 | Other | null | null | null | CC(C)CN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC(C)C)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e2b3249e2694788abdfe82fec322288 | CC(C)CCN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CCC(C)C)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(CC(C)C)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CCC(C)C)C=CC(=C3)C(=O)O)OC)C=C1 | N[CH2:33][CH2:34][CH:35]([CH3:36])[CH3:37].CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42]4)[n:41][c:40]3[cH:39][cH:38]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21>>[CH3:1][O:2... | CC(C)CCN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CCC(C)C)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e2ab8b98cf900440127ead862394c72c072386b0bf56fe859e56bb968c0d4253 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5[nH]4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH2;D2;+0:9]-[C:10]-[C:11]>>[C:11]-[C:10]-[CH2;D2;+0:9]-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and isoamylamine according to the procedure described in the preparation Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1 | Other | null | null | null | CC(C)CCN.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CCC(C)C)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-252469d1f4154aa39e4f99d256124b0c | CCC(N)CC.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>CCC(CC)n1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(C)C(CC)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C(CC)CC)C=CC(=C3)C(=O)O)OC)C=C1 | N[CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5].CC[n:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]3[n:12][c:13](-[c:14]4[cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20][c:21]4-[c:22]4[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]4)[cH:29][cH:30][c:31]3[cH:32]2)[n:33][c:34]2[cH:35][c:36]([C:37](=[O:38])[OH:39])[cH:40][cH:41][c:42]12>>[CH3:1][CH2:2... | CCC(N)CC.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | CCC(CC)n1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 25a293369dc0a6ca350c31a835bd70d8f78280ba657d6a9e499357771b52f0dc | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5[nH]4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:1-[c:8].N-[CH;D3;+0:9](-[C:10]-[C;D1;H3:11])-[C:12]-[C;D1;H3:13]>>[C;D1;H3:11]-[C:10]-[CH;D3;+0:9](-[C:12]-[C;D1;H3:13])-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:1-[c:8] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and 1-ethylpropylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | Other | null | null | null | CCC(N)CC.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>CCC(CC)n1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a3c1138f892438db2fb90c0ff35dc06 | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CC4)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C1(CC1)CN.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC2CC2)C=CC(=C3)C(=O)O)OC)C=C1 | CCn1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41]4)[n:40][c:39]3[cH:38][cH:37]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]12.[NH2:32][CH2:33][CH:34]1[CH2:35][CH2:36]1>>[CH3:1][O:2][c:3]... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CC4)ccc3n2)c1 | null | null | null | Miscellaneous | OtherReaction | 958cc1249ea91d53534fdf57a0de3ffefb807d9ef1528b3902a5c2f2d4c2484b | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4CC4CC4)ccc3n2)cc1 | C-C-n1:[c;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]):[#7;a:5]:[c:6](:[c:7]):[c;H0;D3;+0:8]:1:[c:9]:[c:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[n;H0;D3;+0:13]1:[c;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]):[#7;a:5]:[c:6](:[c:7]):[c;H0;D3;+0:8]:1:[c:9]:[c:10] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and cyclopropylmethylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b51835bb50f4ee2b859ce6fb63abef9 | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CCCO1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CCCO4)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(C1CCCO1)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC2OCCC2)C=CC(=C3)C(=O)O)OC)C=C1 | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43]4)[n:42][c:41]3[cH:40][cH:39]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[CH2:33][CH:34]1[CH2:35][CH2:36][CH2:37][O:38]1>>[CH3:... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CCCO1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CCCO4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e2ab8b98cf900440127ead862394c72c072386b0bf56fe859e56bb968c0d4253 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4CC4CCCO4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH2;D2;+0:9]-[C:10](-[C:11])-[#8:12]-[C:13]>>[C:11]-[C:10](-[CH2;D2;+0:9]-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[#8:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and tetrahydrofurfurylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCOC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCC1CCCO1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4CC4CCCO4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21030ef7b5d6451fb179be2887730b6f | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC2CCC1C2>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC5CCC4C5)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].NC1C2CCC(C1)C2.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>C12C(CC(CC1)C2)N2C(=NC1=C2C=CC(=C1)C(=O)O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)OC | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]4)[n:43][c:42]3[cH:41][cH:40]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[CH:33]1[CH2:34][CH:35]2[CH2:36][CH2:37][CH:38]1[CH2:3... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC2CCC1C2 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC5CCC4C5)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0926909704c881cb54268272553e278ad999675801d46787e69580b6b2154531 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CC5CCC4C5)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-1-[C:14]>>[C:14]-[C:13]1-[C:12]-[C:11]-[C:10]-[CH;D3;+0:9]-1-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and 2-aminonorbornane according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1.C1CC2CCC1C2 | C1CC2CCC1C2.c1ccc2nc[nH]c2c1 | C1CC2CCC1C2.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NC1CC2CCC1C2>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC5CCC4C5)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85aae62cdf464e669bee6474f376901c | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 | C[C@@H]1CC[C@H](CC1)N.ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCC(CC2)C)C=CC(=C3)C(=O)O)OC)C=C1 | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]4)[n:43][c:42]3[cH:41][cH:40]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[C@H:33]1[CH2:34][CH2:35][C@H:36]([CH3:37])[CH2:38][CH... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49b984735c916b875c4d6b41bd581cd6aee28172bfc5c4a35fa470763ec90d74 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[C@@H;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[C:11]-[C:10]-[CH;D3;+0:9](-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and a mixture of cis and trans 4-methylcyclohexyl-amine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1.C1CCCCC1 | c1ccc2nc[nH]c2c1.C1CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a69b478981884fc6ae0f767259691dae | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 | C[C@@H]1CC[C@H](CC1)N.ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCC(CC2)C)C=CC(=C3)C(=O)O)OC)C=C1 | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]4)[n:43][c:42]3[cH:41][cH:40]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[C@H:33]1[CH2:34][CH2:35][C@H:36]([CH3:37])[CH2:38][CH... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49b984735c916b875c4d6b41bd581cd6aee28172bfc5c4a35fa470763ec90d74 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[C@@H;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[C:11]-[C:10]-[CH;D3;+0:9](-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and a mixture of cis and trans 4-methylcyclohexyl-amine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1.C1CCCCC1 | c1ccc2nc[nH]c2c1.C1CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.C[C@H]1CC[C@H](N)CC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCC(C)CC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dda83994225470db26d050c1f5260e3 | CC1CC(N)CC(C)(C)C1.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC(C)CC(C)(C)C4)ccc3n2)c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].CC1(CC(CC(C1)C)N)C.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CC(CC(C2)C)(C)C)C=CC(=C3)C(=O)O)OC)C=C1 | N[CH:33]1[CH2:34][CH:35]([CH3:36])[CH2:37][C:38]([CH3:39])([CH3:40])[CH2:41]1.CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:46]4)[n:45][c:44]3[cH:43][cH:42]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])... | CC1CC(N)CC(C)(C)C1.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC(C)CC(C)(C)C4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49b984735c916b875c4d6b41bd581cd6aee28172bfc5c4a35fa470763ec90d74 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[C:11]-[C:10]-[CH;D3;+0:9](-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared from Resin 534a and 3,3,5-trimethylcyclohexylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | C1CCCCC1.c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1.C1CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CC1CC(N)CC(C)(C)C1.CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CC(C)CC(C)(C)C4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-879bf9131e944162837b5e78db54c54a | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2oc(-c3ccccc3)cc(=O)c2c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3oc(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.O=C1C=C(OC2=CC=C(C=C12)C(=O)O)C1=CC=CC=C1.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O.[OH-].[Na+]>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(C=C(OC1=CC2)C2=CC=CC=C2)=O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:29][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[c:8]([NH2:10])[cH:9]1.O=[C:11](O)[c:12]1[cH:13][cH:14][c:15]2[o:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25](=[O:26])[c:27]2[cH:28]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:... | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2oc(-c3ccccc3)cc(=O)c2c1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3oc(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | f9accb00a91792d96b39ff02a375537b38d03b722e594e100a63bed216907510 | 385ce9ca1706b429744c9f3c46c58dcbcde24114867b5a7a37ed5c314fda0c62 | O=c1cc(-c2ccccc2)oc2ccc(-c3nc4ccccc4n3C3CCCCC3)cc12 | 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].O-[C;H0;D3;+0:14](=O)-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18](:[#8;a:19]):[c:20]:[c:21]:1>>[#8;a:19]:[c:18]1:[c:17]:[c:16]:[c;H0;D3;+0:15](-[c;H0;D3;+0:14]2:[n;H0;D2;+0:7]:[c:6](:[c:5]:[c:4]-[C:2](=... | null | [] | null | null | 15 | MINUTE | 4-Oxo-2-phenyl-4H-chromene-6-carboxylic acid (280 mg, 1.05 mmol) was dissolved in DMF (5 mL), and HATU (418 mg, 1.1 eq.) and diisopropyl ethylamine (402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (303 mg, 1.1 eq.) dissolved in 2 mL DMF was added... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine.Secondary amine | Carboxylic acid | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.c1ccc2occcc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=O | null | 0.25 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2oc(-c3ccccc3)cc(=O)c2c1>CN(C)C=O>O=C(O)c1ccc2c(c1)nc(-c1ccc3oc(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f04f0a8359e4e8fb01a48ccab0a1caa | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O.[OH-].[Na+].O=C1C=C(NC2=CC=C(C=C12)C(=O)O)C1=CC=CC=C1.O=C1C=C(NC2=CC=C(C=C12)C(=O)O)C1=CC=CC=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(C=C(NC1=CC2)C2=CC=CC=C2)=O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:29][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[c:8]([NH2:10])[cH:9]1.O=[C:11](O)[c:12]1[cH:13][cH:14][c:15]2[nH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25](=[O:26])[c:27]2[cH:28]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n... | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | f9accb00a91792d96b39ff02a375537b38d03b722e594e100a63bed216907510 | 385ce9ca1706b429744c9f3c46c58dcbcde24114867b5a7a37ed5c314fda0c62 | O=c1cc(-c2ccccc2)[nH]c2ccc(-c3nc4ccccc4n3C3CCCCC3)cc12 | 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].O-[C;H0;D3;+0:14](=O)-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18](:[#7;a:19]):[c:20]:[c:21]:1>>[#7;a:19]:[c:18]1:[c:17]:[c:16]:[c;H0;D3;+0:15](-[c;H0;D3;+0:14]2:[n;H0;D2;+0:7]:[c:6](:[c:5]:[c:4]-[C:2](=... | null | [] | null | null | 15 | MINUTE | 4-Oxo-2-phenyl-1,4-dihydro-quinoline-6-carboxylic acid (298.5 mg, 1.05 mmol), (Compound 481c), was dissolved in DMF (5 mL), and HATU (440 mg, 1.1 eq.) and diisopropyl ethylamine (402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (303 mg, 1.1 eq.) d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine.Secondary amine | Carboxylic acid | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=O | null | 0.25 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>CN(C)C=O>O=C(O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e7b6eba073f491490bf87ec3ec55f8d | CCOC(=O)CC(=O)c1ccccc1.CCOC(=O)c1ccc(N)cc1>>CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1 | C(C)OC(C1=CC=C(C=C1)N)=O.C(C)OC(CC(C1=CC=CC=C1)=O)=O>>C(C)OC(C1=CC=C(C=C1)N=C(CC(=O)OCC)C1=CC=CC=C1)=O | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[N:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:18][cH:19]1)[c:20]1... | CCOC(=O)CC(=O)c1ccccc1.CCOC(=O)c1ccc(N)cc1 | CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1 | null | null | C1CCCCC1 | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | cb968592dec1a2c40e9f51052b6ef3c2d7edca4da22c8c4bb0fad7e1c1c69433 | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | C(=Nc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7](:[c:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 4-Amino-benzoic acid ethyl ester (66 g, 0.4 mol) and 3-oxo-3-phenyl-propionic acid ethyl ester (0.4 mol, 1 eq.) were dissolved in 500 mL cyclohexane and refluxed for 2 days using a Dean-Stark trap. The solution was filtered, the solvent evaporated and the residue recrystallized to give 4-(2-ethoxycarbonyl-1-phenyl-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCCCC1 | null | null | CCOC(=O)CC(=O)c1ccccc1.CCOC(=O)c1ccc(N)cc1>C1CCCCC1>CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a577073ebe364a4c82297261bf042f78 | CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1>>CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | C(C)OC(C1=CC=C(C=C1)N=C(CC(=O)OCC)C1=CC=CC=C1)=O>>C(C)OC(=O)C=1C=C2C(C=C(NC2=CC1)C1=CC=CC=C1)=O | CCO[C:19]([CH2:18][C:11](=[N:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22][cH:21]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[nH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19](=[O:20])[c:21]2[cH:22]1 | CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1 | CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | null | null | C1(=CC=CC=C1)C(=O)C1=CC=CC=C1.C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | ad2231f333301a6c1317ab17a456ae386fddce0d862bc4e6f091f7fead5dfa17 | 59b6a5a3b1598e876490d57467df4ab7e65df3931d028663a836ca05e9c53f3d | O=c1cc(-c2ccccc2)[nH]c2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=[N;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]-[C:11](-[#8:12])=[O;D1;H0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[#8:12]-[C:11](=[O;D1;H0:13])-[c:10]:[c:9]:[c;H0;D3;+0:8]1:[c:6](:[c:7]):[nH;D2;+0:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:14](:[c:... | null | [] | 250 | CELSIUS | null | null | 4-Amino-benzoic acid ethyl ester (66 g, 0.4 mol) and 3-oxo-3-phenyl-propionic acid ethyl ester (0.4 mol, 1 eq.) were dissolved in 500 mL cyclohexane and refluxed for 2 days using a Dean-Stark trap. The solution was filtered, the solvent evaporated and the residue recrystallized to give 4-(2-ethoxycarbonyl-1-phenyl-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Substituted imine | null | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HO- | C1(=CC=CC=C1)C(=O)C1=CC=CC=C1.C(C)OCC | 250 | null | CCOC(=O)CC(=Nc1ccc(C(=O)OCC)cc1)c1ccccc1>C1(=CC=CC=C1)C(=O)C1=CC=CC=C1.C(C)OCC>CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5532319ae53f40b48ac9e0eb52596179 | CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>>O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | C(C)OC(=O)C=1C=C2C(C=C(NC2=CC1)C1=CC=CC=C1)=O.[OH-].[Na+]>>O=C1C=C(NC2=CC=C(C=C12)C(=O)O)C1=CC=CC=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][c:17](=[O:18])[c:19]2[cH:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][c:17](=[O:18])[c:19]2[cH:20]1 | CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc(-c2ccccc2)[nH]c2ccccc12 | 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 | [] | 40 | CELSIUS | 4 | HOUR | Saponification proceeded with dissolving 26.5 g (0.1 mol) 4-oxo-2-phenyl-1,4-dihydro-quinoline-6-carboxylic acid ethyl ester in ethanol (100 mL), adding 10 eq. of 1N NaOH solution and stirring at 40° C. for 4 hr. The ethanol was evaporated, water was added and acidified, and the precipitate filtered. The white product ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1.c1ccccc1 | Other | C(C)O | 40 | 4 | CCOC(=O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>C(C)O>O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92ddba25f3974eceba02eade2621de1b | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.O=C1C=C(NC2=CC=C(C=C12)C(=O)O)C1=CC=CC=C1.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(C=C(NC3=CC2)C2=CC=CC=C2)=O)C2CCCCC2)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[c:10]([NH2:12])[cH:11]1.O=[C:13](O)[c:14]1[cH:15][cH:16][c:17]2[nH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26][c:27](=[O:28])[c:29]2[cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][... | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 3156d9713af60742570144f202f54886c4ea29704490be82acf553ad4b890d81 | 2c7e28df6187a1559bf3bdf429be12550f69083c743a14154a096b0d7c5276e7 | O=c1cc(-c2ccccc2)[nH]c2ccc(-c3nc4ccccc4n3C3CCCCC3)cc12 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](:[#7;a:6]):[c:7]:[c:8]:1.[C:9]-[C:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14](-[NH2;D1;+0:15]):[c:16])-[C:17]>>[#7;a:6]:[c:5]1:[c:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:15]:[c:14](:[c:16]):[c:12](:[c:13]):[n;H0;D3;+0:11]:2-[C:10](-[C:9])-[C:17]):[c:8]:[... | 800.1 | [{"value": 800.1, "product": "C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(C=C(NC3=CC2)C2=CC=CC=C2)=O)C2CCCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 4-Oxo-2-phenyl-1,4-dihydro-quinoline-6-carboxylic acid (2.78 g, 1.05 mmol) was dissolved in DMF (50 mL), and HATU (1.1 eq.) and diisopropyl ethylamine (2.2 eq, 402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (2.89 g, 1.1 eq.) dissolved in 20 mL D... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=O | null | 0.25 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2[nH]c(-c3ccccc3)cc(=O)c2c1>CN(C)C=O>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3e64b83fe1941a496c990845a45cb8a | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1.O=P(Cl)(Cl)Cl>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(C=C(NC3=CC2)C2=CC=CC=C2)=O)C2CCCCC2)C=C1.P(=O)(Cl)(Cl)Cl>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1 | O=[c:27]1[cH:26][c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH: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:31]3[CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:30][c:29]21.O=P(Cl)(Cl)[Cl:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1.O=P(Cl)(Cl)Cl | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 438e974ce5f8b1c45ff57c7a7dddacdfe9d2415c193d181f3fd6e6e5ac7f9d1c | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[nH;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10] | null | [] | 100 | CELSIUS | null | null | 1-Cyclohexyl-2-(4-oxo-2-phenyl-1,4-dihydro-quinolin-6-yl)-1H-benzoimidazole-5-carboxylic acid ethyl ester acid (4 g, 8.14 mmol) was dissolved in phosphorous oxy chloride and heated at 100° C. overnight. After evaporation of the solvent the product was recrystallized from methanol/water to give 3.96 g of crude product. ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HCl | null | 100 | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3[nH]c(-c4ccccc4)cc(=O)c3c1)n2C1CCCCC1.O=P(Cl)(Cl)Cl>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36172fd882c8461fabaa669a99e3754e | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.ClNc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Nc4ccc(Cl)cc4)c3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.ClNC1=CC=CC=C1>>ClC1=CC=C(C=C1)NC1=CC(=NC2=CC=C(C=C12)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C2=CC=CC=C2 | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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:36]3[CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)[cH:35][c:34]21.[NH:26]([c:27]1[cH:28][cH:29][cH:30][cH:32][cH:33]1)[Cl:31]>>[O:1]=[C:... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.ClNc1ccccc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Nc4ccc(Cl)cc4)c3c1)n2C1CCCCC1 | null | null | null | Functional Group Interconversion | OtherReaction | c0fe4b02c352dbb9ceac8aa76b612387291b560eabef8734aef984ee68162f1e | 24f91e21fc7bbbae3ad65033508fd0c79fa40ac8de84e0b35479006fae934cde | c1ccc(Nc2cc(-c3ccccc3)nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc23)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[Cl;H0;D1;+0:10]-[NH;D2;+0:11]-[c:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[c:17]:1>>[Cl;H0;D1;+0:10]-[c;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]2:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:2:[c:9]):[c:17]:[c:1... | null | [] | null | null | null | null | The title compound was prepared using the method described for Compound 481. In this reaction 102 mg (0.2 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used. The nucleophile used wasp-chlorophenylamine. Yield: 89 mg.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tertiary amine | Aromatic halide.Secondary amine | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.ClNc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Nc4ccc(Cl)cc4)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66afaa298b0647eda13e4be36dd69ac2 | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCCO>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCCO)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.NCCCCO>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)NCCCCO | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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]21.[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31]>>[O:1]=[C:2]([OH:3])[c... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCCO | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCCO)c3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7f9db3cafec3e5e8d7d36dd860c54b065cb18888ec353baecb67d2885ae686c0 | 11f5b5e0b1e60cd85ba81b4fbd6d432c2ec0e112bb718efd046623781920966e | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 102 mg (0.2 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used in the same reaction sequence as that used for Compound 481. The nucleophile used was 4-amino-butan-1-ol. Yield: 59 mg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCCO>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCCO)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c72001d47fa4633b55549ce9ad7c27d | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCn1ccnc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCn4ccnc4)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.N1(C=NC=C1)CCCN>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)NCCCN2C=NC=C2 | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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]21.[NH2:26][CH2:27][CH2:28][CH2:29][n:30]1[cH:31][cH:32][n:33][cH:34]1>>[... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCn1ccnc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCn4ccnc4)c3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7f9db3cafec3e5e8d7d36dd860c54b065cb18888ec353baecb67d2885ae686c0 | 11f5b5e0b1e60cd85ba81b4fbd6d432c2ec0e112bb718efd046623781920966e | c1ccc(-c2cc(NCCCn3ccnc3)c3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 102 mg (0.2 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used in the same reaction sequence as that used for Compound 481. The nucleophile used was 3-imidazol-1-yl-propylamine. Yield: 31 mg.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1c[nH]cn1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NCCCn1ccnc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(NCCCn4ccnc4)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4821a24cb09948238f23ab6b82a30229 | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccccc4)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.C1(=CC=CC=C1)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)OC2=CC=CC=C2 | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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]21.[OH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]([OH:3]... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccccc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccccc4)c3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c8a11ffc273ff0eaced293f97dc35357051c617137fa514af0f5ab8c0870b35d | b181e0a0e5d49064f20e24382a661fd07e16e36c9c15ea6db1c62799e1f728d2 | c1ccc(Oc2cc(-c3ccccc3)nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc23)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:7]:[c:6]1:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 51 mg (0.1 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used in the same reaction sequence as that used for Compound 481. The nucleophile used was phenol. Yield: 19 mg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Tertiary amine | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccccc4)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af4d234f064842669017ccdfe28e22f8 | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccc2ccc(O)cc2c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccc5ccc(O)cc5c4)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.C1=C(C=CC2=CC=C(C=C12)O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)OC2=CC1=CC(=CC=C1C=C2)O | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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:40]3[CH:41]3[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]3)[cH:39][c:38]21.[OH:26][c:27]1[cH:28][cH:29][c:30]2[cH:31][cH:32][c:33]([OH:34])[cH:35... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccc2ccc(O)cc2c1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccc5ccc(O)cc5c4)c3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c8a11ffc273ff0eaced293f97dc35357051c617137fa514af0f5ab8c0870b35d | b181e0a0e5d49064f20e24382a661fd07e16e36c9c15ea6db1c62799e1f728d2 | c1ccc(-c2cc(Oc3ccc4ccccc4c3)c3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:7]:[c:6]1:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 51 mg (0.1 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used in the same reaction sequence as that used for Compound 481. The nucleophile used was naphthalene-2,7-diol. Yield: 6.2 mg.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Tertiary amine | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccc2ccccc2c1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Oc1ccc2ccc(O)cc2c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Oc4ccc5ccc(O)cc5c4)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa14fd58b6d1427a9dc5fa7265be2ca5 | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Sc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Sc4ccccc4)c3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C.C1(=CC=CC=C1)S>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)SC2=CC=CC=C2 | CN(C)[c:25]1[cH:24][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[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]21.[SH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]([OH:3]... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Sc1ccccc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Sc4ccccc4)c3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1dce00dabbf26de0ee096b23e3cf18b71947f33210212c762d571c127e6b03ed | 23872d7b85fe7d0fd9537bb0b47ba722cb38a3589862fa47f37552520593f1ab | c1ccc(Sc2cc(-c3ccccc3)nc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc23)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:7]:[c:6]1:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 51 mg (0.1 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used in the same reaction sequence as that used for Compound 481. The nucleophile used was benzenethiol. Yield: 36 mg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Aromatic thiol | Monosulfide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.Sc1ccccc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Sc4ccccc4)c3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5db50e0236924a6abcb3d528a899adb3 | CC(=O)c1cc([N+](=O)[O-])ccc1Br.CCO.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>CCOc1ccc([N+](=O)[O-])cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | Cl.BrC1=C(C=C(C=C1)[N+](=O)[O-])C(C)=O.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.C(C)O.[OH-].[K+]>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)[N+](=O)[O-])OCC | O=[C:13]([c:12]1[c:4](Br)[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1)[CH3:14].[CH3:1][CH2:2][OH:3].CC[O:26][C:24]([c:23]1[cH:22][c:21]2[n:20][c:19](-[c:18]3[cH:17][c:16]([CH:15]=O)[c:39]([NH2:40])[cH:38][cH:37]3)[n:30]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[c:29]2[cH:28][cH:27]1)=[O:25]>>[CH3:1][CH2:2]... | CC(=O)c1cc([N+](=O)[O-])ccc1Br.CCO.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | CCOc1ccc([N+](=O)[O-])cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d20f6735abe3efde20755fde59aec6a16292c08679eaece18cd7a1157e58e382 | b7d9b01209a4bbd88cfbcd60b2e8c6a2ace013c5b913407a84572cc98b9d8b4c | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D3;+0:7](=O)-[CH3;D1;+0:8].C-C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12].O=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18].[C;D1;H3:19]-[C:20]-[OH;D1;+0:21]>>[C;D1;H3:19]-[C:20]-[O;H0;D2;+0:21]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0... | null | [] | 75 | CELSIUS | 8 | HOUR | 1-(2-Bromo-5-nitro-phenyl)-ethanone (61 mg, 0.25 mmol) prepared similarly to the procedure described in Meisenheimer, J., Zimmermann P., and v. Kummer, U. Ann. der. Chem. 446, pp. 205-228) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Ketone.Ester.Primary alcohol.Primary amine | Carboxylic acid.Ether | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | null | 75 | 8 | CC(=O)c1cc([N+](=O)[O-])ccc1Br.CCO.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>CCOc1ccc([N+](=O)[O-])cc1-c1ccc2cc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4019479c4c134858b9dfdacc9546d653 | CC(=O)c1ccnc2ccccc12.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccnc5ccccc45)ccc3c1)n2C1CCCCC1 | Cl.N1=CC=C(C2=CC=CC=C12)C(C)=O.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>N1=C(C=CC2=CC(=CC=C12)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C2=CC=NC1=CC=CC=C21 | O=[C:17]([c:18]1[cH:19][cH:20][n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12)[CH3:28].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]([NH2:16])[c:30]([CH:29]=O)[cH:31]1)[n:32]2[CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][... | CC(=O)c1ccnc2ccccc12.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccnc5ccccc45)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | c1ccc2c(-c3ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n3)ccnc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17](:[c:18]):[c:19]:1:[c:20]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:10]:[c:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:11](-[c;H0;D3;+0:13]2:[c:14]... | 19.3 | [{"value": 19.3, "product": "N1=C(C=CC2=CC(=CC=C12)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C2=CC=NC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | (1-Quinolin-4-yl-ethanone (43 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were then added. The reaction was stirred at 75° C. overnight. The reaction was acidified with 4N hyd... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccc2ncccc2c1.C1CCCCC1 | HO- | C(C)O | 75 | 8 | CC(=O)c1ccnc2ccccc12.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccnc5ccccc45)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db6a3b04c04d45caaa23c9fa24f0ced6 | CC(=O)c1cc([N+](=O)[O-])ccc1Br.OB(O)c1ccc(Cl)cc1>>CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1 | CO.ClC1=CC=C(C=C1)B(O)O.BrC1=C(C=C(C=C1)[N+](=O)[O-])C(C)=O.C([O-])(O)=O.[Na+]>>ClC1=CC=C(C2=CC=C(C=C2C(C)=O)[N+](=O)[O-])C=C1 | Br[c:12]1[c:4]([C:2]([CH3:1])=[O:3])[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1-[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | CC(=O)c1cc([N+](=O)[O-])ccc1Br.OB(O)c1ccc(Cl)cc1 | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | null | [] | 80 | CELSIUS | null | null | 1-(2-Bromo-5-nitro-phenyl)-ethanone (1 g, 4 mmol; prepared similarly to the procedure described in Meisenheimer, J., Zimmermann P., and v. Kummer, U. Ann. der. Chem. 446, pp. 205-228), p-Chlorophenylboronic acid (768 mg, 1.2 eq.), and tetrakis(triphenylphosphine)-palladium(0) (473 mg, 0.1 eq.), were dissolved in 25 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | 80 | null | CC(=O)c1cc([N+](=O)[O-])ccc1Br.OB(O)c1ccc(Cl)cc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f538b2ec01b4155a5f2694438a7c789 | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc([N+](=O)[O-])ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | Cl.ClC1=CC=C(C2=CC=C(C=C2C(C)=O)[N+](=O)[O-])C=C1.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)[N+](=O)[O-])C=C1 | O=[C:17]([c:18]1[cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]1)[CH3:34].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]([NH2:16])[c:36]([CH:35]=O)[cH:37]1)[n:38]2[CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][... | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc([N+](=O)[O-])ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[c:17]):[c:18]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:10]:[c:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:11](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[... | 22.6 | [{"value": 22.6, "product": "ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)[N+](=O)[O-])C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | 1-(4′-Chloro-4-nitro-biphen-2-yl)-ethanone (69 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overnight. The reaction was acidified... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | C(C)O | 75 | 8 | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc([N+](=O)[O-])ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f7d4870ad9a4abf8a731fdf8d91007d | N#Cc1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1>>N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | O.ClC1=C(C=C(C#N)C=C1)[N+](=O)[O-].C1(CCCCC1)N>>C1(CCCCC1)NC1=C(C=C(C#N)C=C1)[N+](=O)[O-] | Cl[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][c:14]1[N+:15](=[O:16])[O-:17].[NH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | N#Cc1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1 | N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | null | null | CN(C)C=O | 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] | 100 | [{"value": 100.0, "product": "C1(CCCCC1)NC1=C(C=C(C#N)C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C1(CCCCC1)NC1=C(C=C(C#N)C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1 g (5.48 mmol) 4-chloro-3-nitrobenzonitrile, Compound 126, and 1.14 g (11.51 mmol) of cyclohexylamine were heated overnight in 5 mL anhydrous DMF. After cooling to room temperature, the solution was added dropwise into 100 mL H2O stirring vigorously. The solids were collected by filtration and dried unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HCl | CN(C)C=O | null | null | N#Cc1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1>CN(C)C=O>N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0095f0c8461a44d6ade5ffbb54532335 | N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>>O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | C1(CCCCC1)NC1=C(C=C(C#N)C=C1)[N+](=O)[O-].C1(CCCCC1)NC1=C(C=C(C#N)C=C1)[N+](=O)[O-].[Sn](C)(C)(C)N=[N+]=[N-]>>C1(CCCCC1)NC1=C(C=C(C=C1)C1=NN=NN1)[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([C:7]#[N:11])[cH:12][cH:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.[CH3][Sn]([CH3])([CH3])[N:8]=[N+:9]=[N-:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9][n:10][nH:11]2)[cH:12][cH:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]... | N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-] | O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | d793d4dee9d5a39dbd122d04a35a5f691674657d5f6e422ae31ce158ea438a57 | 95e338ac8e3158e8ab88ebe03ba7338cec0c32ed80de2cb9f73834a6f54aede3 | c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | [CH3]-[Sn](-[CH3])(-[CH3])-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[nH;D2;+0:4]:1):[c:9]:[c:10] | 88.1 | [{"value": 88.0, "product": "C1(CCCCC1)NC1=C(C=C(C=C1)C1=NN=NN1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "C1(CCCCC1)NC1=C(C=C(C=C1)C1=NN=NN1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.10 g (4.49 mmol) of 4-cyclohexylamino-3-nitrobenzonitrile, Compound 127, and 1.11 g (5.39 mmol) of Me3SnN3 in 50 mL toluene was refluxed overnight. The crystals were collected by filtration, washed with toluene, dried, and treated with 50 mL 4M HCl in dioxane for 4 h. The solids were collected by filtra... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Tin | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.C1CCCCC1 | Sn | C1(=CC=CC=C1)C | null | null | N#Cc1ccc(NC2CCCCC2)c([N+](=O)[O-])c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>C1(=CC=CC=C1)C>O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85c31d8126c4464c93b23e2402334dc3 | O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1>>Nc1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O.C1(CCCCC1)NC1=C(C=C(C=C1)C1=NN=NN1)[N+](=O)[O-]>>C1(CCCCC1)NC=1C(=CC(=CC1)C1=NN=NN1)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][n:7][n:8][nH:9]2)[cH:10][cH:11][c:12]1[NH:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][n:7][n:8][nH:9]2)[cH:10][cH:11][c:12]1[NH:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1 | O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | Nc1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title intermediate was prepared from 1.20 g (4.16 mmol) Compound 128 as described for Compound 11 to yield 0.9 g (83%). MS: 259.18 (M+H+).
Conditions: See reaction.notes.procedure_details.
Workup: to yield 0.9 g (83%) | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1nnn[nH]1.C1CCCCC1 | Other | null | null | null | O=[N+]([O-])c1cc(-c2nnn[nH]2)ccc1NC1CCCCC1>>Nc1cc(-c2nnn[nH]2)ccc1NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7165482d1b544f339b673f77c011c5ae | CC(=O)C(c1ccccc1)c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(c4ccccc4)c4ccccc4)ccc3c1)n2C1CCCCC1 | 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(=O)N3CCCC3)C=C1.C(C)(=O)C1=CC=CC=C1.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1)=O.C1(=CC=CC=C1)C(C(=O)C)C1=CC=CC=C1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC... | CC(=O)[CH:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.O=C(c1ccc(-c2ccc(Cl)cc2)c(-[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]... | CC(=O)C(c1ccccc1)c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(c4ccccc4)c4ccccc4)ccc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 488fec9809a3d37598ae7ae8adc1c78acb03a280236585a13e6ce1667748cecd | 40ed9ee77e576c7a7966ecf3d09e3babedf3ae404a067023e77064d728a09f11 | c1ccc(C(c2ccccc2)c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C(=O)-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].Cl-c1:c:c:c(-c2:c:c:c(-C(=O)-N3-C-C-C-C-3):c:c:2-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[c:11]:[c:12]):c:c:1>>[c:10]:[#7;a:9]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]):[c:11]:[c:12] | null | [] | null | null | null | null | The title compound was synthesized in four steps as described for Compound 13, Compound 25, Compound 27, Q=ethyl and Compound 204, respectively, except 1,1-diphenylacetone was used in the first step, instead of acetophenone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Tertiary amide | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1CCNC1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | CC(=O)C(c1ccccc1)c1ccccc1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(c4ccccc4)c4ccccc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be5034d2404c402f953fb1dc96bb4aaf | CC(=O)c1ccccc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 | 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(=O)N3CCCC3)C=C1.C(C)(=O)C1=CC=CC=C1.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1)=O.BrC1=C(C=CC=C1)C(C)=O>>BrC1=C(C=CC=C1)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][cH:22][c:23]1[Br:24].O=C(c1ccc(-c2ccc(Cl)cc2)c(-[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:29]4[CH:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)[cH:28][c:27]3[cH:26][cH:25]2)c1)N1CCCC1>>[O:1]=[C:2]([OH:3])[c:4]1... | CC(=O)c1ccccc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | c5e96f9ff00a145d4f9f2280da199e21f4b5b6eb061cb22431bfff34c779ce7d | 40ed9ee77e576c7a7966ecf3d09e3babedf3ae404a067023e77064d728a09f11 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].Cl-c1:c:c:c(-c2:c:c:c(-C(=O)-N3-C-C-C-C-3):c:c:2-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]):c:c:1>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | The title compound was synthesized in four steps as described for Compound 13, Compound 25, Compound 27 Q=ethyl and Compound 204, respectively, except 2′-bromoacetophenon was used in the first step instead of acetophenone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Tertiary amide | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1CCNC1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | CC(=O)c1ccccc1Br.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4Br)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d74673d792cc4db19d725f1bf05d5c6e | CC(C)=O.Nc1ccc(Cl)cc1>>CC(C)Nc1ccc(Cl)cc1 | ClC1=CC=C(N)C=C1.CC(=O)C.[BH3-]C#N.[Na+].[O-]S(=O)(=O)[O-].[Mg+2]>>ClC1=CC=C(C=C1)NC(C)C | O=[C:2]([CH3:1])[CH3:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1 | CC(C)=O.Nc1ccc(Cl)cc1 | CC(C)Nc1ccc(Cl)cc1 | null | null | CC(=O)O.CCO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 64.7 | [{"value": 64.7, "product": "ClC1=CC=C(C=C1)NC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 1 g (7.84 mmol) of 4-chloroaniline, 0.91 g (15.68 mmol) of acetone, 0.99 g (15.68 mmol) of NaCNBH3, 4 g of MgSO4 in 99 mL anhydrous EtOH and 1 mL AcOH was stirred at room temperature overnight, filtered and the solvent was removed. The residue was dissolved in 50 mL EtOAc, washed with 50 mL H2O, dried (Na2... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | CC(=O)O.CCO | null | 8 | CC(C)=O.Nc1ccc(Cl)cc1>CC(=O)O.CCO>CC(C)Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93f36f4283284a6bb8c6a986ff4ff83f | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.CNc1ccc(Cl)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)OCC)C=2C=C1C=CC(=NC1=CC2)C(=O)O.CCN(C(C)C)C(C)C.ClC1=CC=C(NC)C=C1>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NCC2=CC=C(C=C2)Cl)=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: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:21].[NH:22]([CH3:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][O:3]... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.CNc1ccc(Cl)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | CN(C)C=1C=CN=CC1 | O=S(Cl)Cl | Acylation | OtherReaction | 4a6cfa6e2eddb05d9863d7ea41150d1d826cc51a5fcc63444bd4e505c01580aa | 9b702924f2df230008ea1edd297d6a4305f6e78d7804dff7e838c4286e010bf9 | O=C(NCc1ccccc1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[CH3;D1;+0:7]-[NH;D2;+0:8]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[CH2;D2;+0:7]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 48.3 | [{"value": 48.3, "product": "C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NCC2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 100 mg (0.23 mmol) Compound 402a in 1 mL SOCl2 was allowed to stand at room temperature for 10 min and SOCl2 was removed. The residue was dissolved in 5 mL anhydrous CH2Cl2; 89 mg (0.69 mmol) DIEA, 84 mg (0.69 mmol) DMAP, 98 mg (0.69 mmol) 4-chloro-N-methylaniline were added; and the solution was vortexed... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=1C=CN=CC1.O=S(Cl)Cl | null | 0.166667 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)O)ccc3c1)n2C1CCCCC1.CNc1ccc(Cl)cc1>CN(C)C=1C=CN=CC1.O=S(Cl)Cl>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e28513a172e944558539493e46709591 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NCC2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1>>ClC1=CC=C(C=C1)CNC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | 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])[NH:20][CH2:21][c:22]4[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]4)[cH:29][cH:30][c:31]3[cH:32]1)[n:33]2[CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6]... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | CCO.[OH-].[Na+].C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCc1ccccc1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | 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] | 10.1 | [{"value": 10.1, "product": "ClC1=CC=C(C=C1)CNC(=O)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 63 mg (0.11 mmol) of Compound 546c in 0.55 mL THF, 0.44 mL of EtOH and 0.11 mL of 2 N aq. NaOH was allowed to stand at room temperature overnight. The reaction was quenched with 0.22 mL 1 M aq. HCl. The solvents were removed and the residue was purified by HPLC to yield 6 mg of the title compound.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | Other | CCO.[OH-].[Na+].C1CCOC1 | null | 8 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>CCO.[OH-].[Na+].C1CCOC1>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba599b2e995c47369e7fe96361377003 | CC(C)Nc1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C(C)C)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NCC2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1.ClC1=CC=C(C=C1)NC(C)C>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(N(C(C)C)C2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1 | [NH:22]([c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1)[CH:30]([CH3:31])[CH3:32].Clc1ccc(CN[C:20]([c:19]2[n:18][c:17]3[cH:16][cH:15][c:14](-[c:13]4[n:12][c:10]5[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]5)[n:37]4[CH:38]4[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]4)[cH:36][c:35]3[cH:34][cH:33]2)=[... | CC(C)Nc1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C(C)C)ccc3c1)n2C1CCCCC1 | null | null | null | Acylation | OtherReaction | 3c1ebc2d0788b67a4285083a16d0313f4ac4512b333d83cff9f96cbde1b6f903 | c26fe3b33dc55496b8ce8902a1392c0b396b38c9e491c53f1913d677055b8b8b | O=C(Nc1ccccc1)c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1 | Cl-c1:c:c:c(-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]):c:c:1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | The title compound was prepared as described for Compound 546c using Compound 546a in place of 4-chloro-N-methylaniline. MS: 595.27 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide.Secondary amine | Tertiary amide | c1ccccc1 | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | CC(C)Nc1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C(C)C)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e51b810aaa854df5bdc71ee4878dfb71 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.Clc1ccc(NC2CCCCC2)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C4CCCCC4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(NCC2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1.ClC1=CC=C(C=C1)NC1CCCCC1>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C(N(C2CCCCC2)C2=CC=C(C=C2)Cl)=O)C2CCCCC2)C=C1 | Clc1ccc(C[NH:22][C:20]([c:19]2[n:18][c:17]3[cH:16][cH:15][c:14](-[c:13]4[n:12][c:10]5[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]5)[n:40]4[CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]4)[cH:39][c:38]3[cH:37][cH:36]2)=[O:21])cc1.N([c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1)[CH:30]1[CH2:31]... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.Clc1ccc(NC2CCCCC2)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C4CCCCC4)ccc3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 14a6fa9139e38ea102aa07dd618ebf420ce9b403db1cd1ad139f3d9bce0728be | 191709a82d4a82123df243375b3c77a35a4966846090fe61cd569dfad6758fb5 | O=C(c1ccc2cc(-c3nc4ccccc4n3C3CCCCC3)ccc2n1)N(c1ccccc1)C1CCCCC1 | Cl-c1:c:c:c(-C-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]):c:c:1.[C:6]-[C:7]-[CH;D3;+0:8](-N-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])-[C:14]-[C:15]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[N;H0;D3;+0:1](-[CH;D3;+0:8](-[C:7]-[C:6])-[C:14]-[C:15])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | null | [] | null | null | null | null | The title compound was prepared as described for Compound 546c using Compound 546b in place of 4-chloro-N-methylaniline. MS: 635.31 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide.Secondary amine | Tertiary amide | c1ccccc1.c1ccccc1.C1CCCCC1 | c1ccccc1.C1CCCCC1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1.C1CCCCC1 | HCl | null | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)NCc4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.Clc1ccc(NC2CCCCC2)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(C(=O)N(c4ccc(Cl)cc4)C4CCCCC4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-522247ab19904367b2b43558f6c84fd9 | CCc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>CCc1ccc(-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)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)CC)OC | OB(O)[c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:44][cH:43]1.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)... | CCc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1 | CCc1ccc(-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] | 48 | [{"value": 48.0, "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)CC)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-ethylphenylboronic acid (39 mg, 0.2625 mmol) to produce the title compound (48 mg, 48% 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 | CCc1ccc(B(O)O)cc1.COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1>>CCc1ccc(-c2ccc(OC)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-161853aa92d94646a7cab1f725f99b08 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)c(F)c1>>COc1ccc(-c2ccc(F)c(F)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.FC=1C=C(C=CC1F)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)F)F)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]([F:11])[c:12]([F:13])[cH:... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)c(F)c1 | COc1ccc(-c2ccc(F)c(F)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] | 25 | [{"value": 25.0, "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)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 3,4-difluorophenylboronic acid (42 mg, 0.2625 mmol) to produce the title compound (26 mg, 25% 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(F)c(F)c1>>COc1ccc(-c2ccc(F)c(F)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-225889013ad64142ad59648337bb5142 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1cc(Cl)cc(Cl)c1>>COc1ccc(-c2cc(Cl)cc(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=C(C1)Cl)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)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][c:9]([Cl:10])[cH:11][c:12]([Cl:13])[c... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1cc(Cl)cc(Cl)c1 | COc1ccc(-c2cc(Cl)cc(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] | 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(=CC(=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 3,5-dichlorophenylboronic acid (50 mg, 0.2625 mmol) to produce the title compound (17 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.OB(O)c1cc(Cl)cc(Cl)c1>>COc1ccc(-c2cc(Cl)cc(Cl)c2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-861b872cbe294a6282742e68370f0170 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccccc1F>>COc1ccc(-c2ccccc2F)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.FC1=C(C=CC=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=C(C=CC=C2)F)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][cH:11][c:12]1[F:13]>>[CH... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OC)ccc4Br)ccc3c1)n2C1CCCCC1.OB(O)c1ccccc1F | COc1ccc(-c2ccccc2F)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](-[F;D1;H0:16]):[c:17]>>[#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](-[F;D1;H0:16]):[c:17]):[c:2]:[c:3].[O;D1;H0:10]=[C:9](-[OH;D... | 25 | [{"value": 25.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=C(C=CC=C2)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 2-fluorophenylboronic acid (37 mg, 0.2625 mmol) to produce the title compound (9 mg, 25% 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)c1ccccc1F>>COc1ccc(-c2ccccc2F)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d561aa8de7184e83af868602a51ae444 | COc1ccc(C2CCCCC2)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>>COc1ccc(C2CCCCC2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | [OH-].[K+].C1(CCCCC1)C1=C(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=C(C=CC(=C2)OC)C2CCCCC2 | CC(=O)[c:13]1[c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42]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[... | COc1ccc(C2CCCCC2)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1 | COc1ccc(C2CCCCC2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | C(C)O | C-C Coupling | OtherReaction | b0005d85f44f8fd2e5347e57b6d8612a6bcb7f2f6961e5711380421da946a83b | f34555a5c6bd5f7f28302c4b82e779fa0b15fb240c98b7acf87941b8ccbcbc8b | c1ccc(C2CCCCC2)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](:[c:7]:[c:8]):[c:9](-[C:10]):[c:11]>>[C: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] | 21 | [{"value": 21.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC(=C2)OC)C2CCCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure and workup for Compound 354, Compound 354e (86 mg, 0.22 mmol) was reacted with Compound 545a (50 mg, 0.22 mmol) in ethanol (3 mL) using 10% w/v KOH in Ethanol (436 μL, 0.66 mmol) to produce the title compound (26 mg, 21% yield).
Conditions: See reaction.notes.procedure_details. | 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 | COc1ccc(C2CCCCC2)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Br)ccc4O)ccc3c1)n2C1CCCCC1>C(C)O>COc1ccc(C2CCCCC2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-180008a4e1d843148585643ac69fb651 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4I)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=C(C=CC(=C2)C(=O)N2CCCC2)I)C2CCCCC2)C=C1.FC1=CC=C(C=C1)B(O)O.C(=O)(O)[O-].[Na+]>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2)C2CCCCC2)C=C1 | I[c:32]1[c:20](-[c:19]2[n:18][c:17]3[cH:16][cH:15][c:14](-[c:13]4[n:12][c:10]5[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]5)[n:44]4[CH:45]4[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]4)[cH:43][c:42]3[cH:41][cH:40]2)[cH:21][c:22]([C:23](=[O:24])[N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[cH:30][cH:31]1.OB(... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4I)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)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 | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | I-[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] | null | [] | 90 | CELSIUS | null | null | A mixture of 200 mg (0.29 mmol) Compound 419d 62 mg (0.44 mmol) 4-fluorophenyl-boronic acid, 32 mg (0.029 mmol) Pd(PPh3)4 and 2 mL sat. NaHCO3 in 16 mL degassed MeOH was heated at 90° C. under Ar overnight. The mixture was evaporated to dryness, the residue was taken up in CH2Cl2 and purified on silica gel using CH2Cl2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HI.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 | 90 | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4I)ccc3c1)n2C1CCCCC1.OB(O)c1ccc(F)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>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-592a02326f1c4ac6a087683397ce4ce4 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2)C2CCCCC2)C=C1.Cl>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2 | 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]4[cH:19][c:20]([C:21](=[O:22])[N:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[cH:28][cH:29][c:30]4-[c:31]4[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]4)[cH:38][cH:39][c:40]3[cH:41]1)[n:42]2[CH:43]1[CH2:44][CH... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 | null | null | CO.[OH-].[Na+].C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | 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] | 34.4 | [{"value": 34.4, "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)F)C(=O)N2CCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A solution of 197 mg (0.30 mmol) Compound 549a in 3.75 mL THF, 3 mL MeOH and 0.75 mL 2 N NaOH was stirred at room temperature overnight and then heated at 50° C. for 1.5 h. After the addition of 1.5 mL 1 M HCl, the solution was evaporated to dryness and the residue was purified on HPLC to yield 66 mg yellow solid.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | Other | CO.[OH-].[Na+].C1CCOC1 | 50 | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1>CO.[OH-].[Na+].C1CCOC1>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6054d0a7a46c45edbff9ad48fe883552 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(OC)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2)C2CCCCC2)C=C1.COC1=CC=C(C=C1)B(O)O>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)OC)C(=O)N2CCCC2)C2CCCCC2)C=C1 | Fc1ccc(-[c:32]2[c:20](-[c:19]3[n:18][c:17]4[cH:16][cH:15][c:14](-[c:13]5[n:12][c:10]6[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]6)[n:45]5[CH:46]5[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]5)[cH:44][c:43]4[cH:42][cH:41]3)[cH:21][c:22]([C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[cH:30][cH:3... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(OC)cc4)ccc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 438ea9fb2f1e2bd442e752627ef66a09bf142d9e1b00bd87c35f5c3609c407f2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | F-c1:c:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:1.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] | null | [] | null | null | null | null | Prepared as described for Compound 549a using 4-methoxyphenylboronic acid instead of 4-fluorophenylboronic acid.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HF.B | null | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.COc1ccc(B(O)O)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(OC)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e44b3fef14649678b5212d63bf7d029 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2.C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2)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)OC)C(=O)N2CCCC2 | C[CH2:1][O:2]C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.F[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][c:19]2-[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])[c... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1 | COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 19f3de88c1ff494b5964ae21423caf2b486a88be4918172c6174e1b0b9d47238 | d8d94c1bd173874c0f14ff424cfaadb9d4ddef05edf07b3bc37ea23445da7932 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | C-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-C(=O)-c1:c:c:c2:c(:c:1):n:c(-c1:c:c:c3:n:c(-c4:c:c(-C(=O)-N5-C-C-C-C-5):c:c:c:4-c4:c:c:c(-F):c:c:4):c:c:c:3:c:1):n:2-C1-C-C-C-C-C-1.F-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | null | [] | null | null | null | null | Prepared as described for Compound 549 using Compound 561a instead Compound 549a.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Tertiary amide | Ether | c1ccc2[nH]cnc2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCNC1.c1ccccc1.C1CCCCC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HF | null | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(C(=O)N3CCCC3)cc2-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a81c8e2a4db4ee29e2e549c8369a27e | CC(=O)c1cc(F)ccc1Br.OB(O)c1ccc(Cl)cc1>>CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1 | BrC1=C(C=C(C=C1)F)C(C)=O.ClC1=CC=C(C=C1)B(O)O.C([O-])(O)=O.[Na+].CO>>ClC1=CC=C(C2=CC=C(C=C2C(C)=O)F)C=C1 | Br[c:10]1[c:4]([C:2]([CH3:1])=[O:3])[cH:5][c:6]([F:7])[cH:8][cH:9]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1 | CC(=O)c1cc(F)ccc1Br.OB(O)c1ccc(Cl)cc1 | CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | 82.5 | [{"value": 82.5, "product": "ClC1=CC=C(C2=CC=C(C=C2C(C)=O)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 1-(2-Bromo-5-fluoro-phenyl)-ethanone (868 mg, 4 mmol), p-chlorophenylboronic acid (768 mg, 1.2 eq.), and tetrakis (triphenylphosphine)palladium(0) (473 mg, 0.1 eq.), were dissolved in 25 mL toluene, 6 mL methanol and 2.5 mL sat. sodium bicarbonate solution. After degassing/sonicating the solution, the sealed reaction v... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | C1(=CC=CC=C1)C | 80 | null | CC(=O)c1cc(F)ccc1Br.OB(O)c1ccc(Cl)cc1>C1(=CC=CC=C1)C>CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8352f928c7e34d6bb53ce46f2706993e | CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | Cl.ClC1=CC=C(C2=CC=C(C=C2C(C)=O)F)C=C1.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)F)C=C1 | O=[C:17]([c:18]1[cH:19][c:20]([F:21])[cH:22][cH:23][c:24]1-[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1)[CH3:32].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]([NH2:16])[c:34]([CH:33]=O)[cH:35]1)[n:36]2[CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1>>[O:1]=[... | CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[c:17]):[c:18]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:10]:[c:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:11](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[... | 58.3 | [{"value": 58.3, "product": "ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | 1-(4′-Chloro-4-fluoro-biphen-2-yl)-ethanone (62 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overnight. The reaction was acidifie... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | C(C)O | 75 | 8 | CC(=O)c1cc(F)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31f9c0f61d9249b9b6c327d0605ace27 | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>Nc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | Cl.ClC1=CC=C(C2=CC=C(C=C2C(C)=O)[N+](=O)[O-])C=C1.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>NC=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 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13]([C:14](=O)[CH3:15])[cH:42]1.CC[O:27][C:25]([c:24]1[cH:23][c:22]2[n:21][c:20](-[c:19]3[cH:18][c:17]([CH:16]=O)[c:40]([NH2:41])[cH:39][cH:38]3)[n:31]([CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[c:30]2[cH:29][cH:28]1)=[O:2... | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | Nc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | b44160b7cb9fd63a77a88ac79c05dd59660f10678fcd44a5556e4fb03ee031e6 | 084fa52e5dbb55f7858474c48a310680c20d4b7f3bab6f5807b5e0665d0d4c50 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13]1:[c:14]:[c:15](-[N+;H0;D3:16](=O)-[O-]):[c:17]:[c:18]:[c:19]:1-[c:20]>>[NH2;D1;+0:16]-[c:15]1:[c:17]:[c:18]:[c:19](-[c:20]):[c;H0;D3;+0:13](-[c;H0;D3;+0:11]2:[cH;D2;+... | 12.6 | [{"value": 12.6, "product": "NC=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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 3 | DAY | 1-(4′-Chloro-4-nitro-biphen-2-yl)-ethanone (69 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. for 3 days. The reaction was acidifie... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Nitro group.Primary amine | Carboxylic acid.Primary amine | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | C(C)O | 75 | 72 | CC(=O)c1cc([N+](=O)[O-])ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>Nc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d05b9a35d6b640619d0c5b71820127fe | CC(=O)c1cc(Cl)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Cl)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | Cl.ClC1=CC=C(C2=CC=C(C=C2C(C)=O)Cl)C=C1.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>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 | O=[C:17]([c:18]1[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]1-[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1)[CH3:32].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]([NH2:16])[c:34]([CH:33]=O)[cH:35]1)[n:36]2[CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1>>[O:1]=... | CC(=O)c1cc(Cl)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Cl)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[c:17]):[c:18]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:10]:[c:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:11](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[... | 89.1 | [{"value": 89.1, "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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | 1-(4′-Chloro-4-chloro-biphen-2-yl)-ethanone (132 mg, 0.5 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overnight. The reaction was acidifie... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | C(C)O | 75 | 8 | CC(=O)c1cc(Cl)ccc1-c1ccc(Cl)cc1.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(Cl)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c81dd56e7d224caf9b58cfef39785b59 | CC(=O)c1cc2c(cc1-c1ccc(Cl)cc1)OCCCO2.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5c(cc4-c4ccc(Cl)cc4)OCCCO5)ccc3c1)n2C1CCCCC1 | Cl.ClC1=CC=C(C=C1)C=1C(=CC2=C(OCCCO2)C1)C(C)=O.C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C=O)C2CCCCC2)C=C1.[OH-].[K+]>>ClC1=CC=C(C=C1)C=1C(=CC2=C(OCCCO2)C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | O=[C:17]([c:18]1[cH:19][c:20]2[c:21]([cH:22][c:23]1-[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1)[O:31][CH2:32][CH2:33][CH2:34][O:35]2)[CH3:36].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]([NH2:16])[c:38]([CH:37]=O)[cH:39]1)[n:40]2[CH:41]1[CH2:42][CH2:43][CH... | CC(=O)c1cc2c(cc1-c1ccc(Cl)cc1)OCCCO2.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5c(cc4-c4ccc(Cl)cc4)OCCCO5)ccc3c1)n2C1CCCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | c1ccc(-c2cc3c(cc2-c2ccc4cc(-c5nc6ccccc6n5C5CCCCC5)ccc4n2)OCCCO3)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]-[#8:16]):[c:17](-[c:18]):[c:19]>>[#8:16]-[c:15]:[c:14]:[c;H0;D3;+0:13](-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[n;H0;... | 83.8 | [{"value": 83.8, "product": "ClC1=CC=C(C=C1)C=1C(=CC2=C(OCCCO2)C1)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | 1-[8-(4-Chloro-phenyl)-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl]-ethanone (76 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overn... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccc2c(c1)OCCCO2.C1CCCCC1 | HO- | C(C)O | 75 | 8 | CC(=O)c1cc2c(cc1-c1ccc(Cl)cc1)OCCCO2.CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C=O)c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc5c(cc4-c4ccc(Cl)cc4)OCCCO5)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ba2bb4cec354b52a5f09a1610b62ab4 | CC(C)(C)OC(=O)NCCN.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1>>CC(C)(C)OC(=O)NCCNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.C(C)(C)(C)OC(NCCN)=O>>C(C)(C)(C)OC(=O)NCCNC1=CC(=NC2=CC=C(C=C12)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O)C2=CC=CC=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11].CC[O:33][C:31]([c:30]1[cH:29][c:28]2[n:27][c:26](-[c:25]3[cH:24][cH:23][c:22]4[n:21][c:14](-[c:15]5[cH:16][cH:17][cH:18][cH:19][cH:20]5)[cH:13][c:12](Cl)[c:45]4[cH:44]3)[n:37]([CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)[c:36]2[cH:35][c... | CC(C)(C)OC(=O)NCCN.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1 | CC(C)(C)OC(=O)NCCNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c03dd276f853a05b864f0f8dd086804c533a46cb3dd4cc5b91e4f2cfc8071ede | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-[c;H0;D3;+0:5]1:[c:6]:[c:7](-[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].[C:14]-[C:15]-[NH2;D1;+0:16]>>[C:14]-[C:15]-[NH;D2;+0:16]-[c;H0;D3;+0:5]1:[c:6]:[c:7](-[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | In this reaction 51 mg (0.1 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used. The nucleophile used was (2-amino-ethyl)-carbamic acid tert-butyl ester. Yield: 21 mg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HCl | null | null | null | CC(C)(C)OC(=O)NCCN.CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cc(Cl)c3c1)n2C1CCCCC1>>CC(C)(C)OC(=O)NCCNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7dd4b2a4ef5644a1bfb4229c4d0aa572 | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NN>>NNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C(=CC(=NC3=CC2)C2=CC=CC=C2)Cl)C2CCCCC2)C=C1.NN.C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)N(C)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C(=CC(=NC1=CC2)C2=CC=CC=C2)NN | CN(C)[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][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][c:36]12.[NH2:1][NH2:2]>>[NH2:1][NH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:... | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NN | NNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bc1341e7acb58109f82d458a218a63ba2a21b474e7a9a13824ee72ca9b64cd33 | 9229b618803dd30f15247e7f4d1f3e1653e4aad0cb96238da3411af756adcb84 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-N(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[N;D1;H2:10]-[NH2;D1;+0:11]>>[N;D1;H2:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | In this reaction 102 mg (0.2 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester was reacted with hydrazine as the nucleophile as described for the preparation of Compound 481. Yield: 3.7 mg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Tertiary amine | Hydrazine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | null | null | null | CN(C)c1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12.NN>>NNc1cc(-c2ccccc2)nc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b322e11520841b196169d5d56e9306f | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCc1ccccc1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4Cc4ccccc4)ccc3n2)c1 | C(C1=CC=CC=C1)N.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2CC)C=CC(=C3)C(=O)O)OC)C=C1>>C(C1=CC=CC=C1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)OC | CC[n:32]1[c:21](-[c:20]2[cH:19][c:18]3[cH:17][cH:16][c:15](-[c:14]4[c:6](-[c:7]5[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]5)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44]4)[n:43][c:42]3[cH:41][cH:40]2)[n:22][c:23]2[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]21.N[CH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[... | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCc1ccccc1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4Cc4ccccc4)ccc3n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e2ab8b98cf900440127ead862394c72c072386b0bf56fe859e56bb968c0d4253 | 4952f8086f73a314806faeb15b92936d3e88816f200b8db1be44046279de05fa | c1ccc(Cn2c(-c3ccc4nc(-c5ccccc5-c5ccccc5)ccc4c3)nc3ccccc32)cc1 | C-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].N-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[c:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D3;+0:1]:1-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The title compound was prepared from resin 534a and benzylamine according to the procedure described in the preparation of Compound 534.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2[nH]cnc2c1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.c1ccccc1 | Other | null | null | null | CCn1c(-c2ccc3nc(-c4cc(OC)ccc4-c4ccc(Cl)cc4)ccc3c2)nc2cc(C(=O)O)ccc21.NCc1ccccc1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4Cc4ccccc4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb2c15bd615d4f6794cd3558a526f54a | CCO.O=C(O)c1cccc([N+](=O)[O-])c1Cl>>CCOC(=O)c1cccc([N+](=O)[O-])c1Cl | ClC1=C(C(=O)O)C=CC=C1[N+](=O)[O-].Cl.CCO>>C(C)OC(C1=C(C(=CC=C1)[N+](=O)[O-])Cl)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[Cl:15] | CCO.O=C(O)c1cccc([N+](=O)[O-])c1Cl | CCOC(=O)c1cccc([N+](=O)[O-])c1Cl | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | To a solution of 2-chloro-3-nitrobenzoic acid (0.85 g, 4.22 mmol) in anhydrous EtOH (50 mL) was bubbled with dry hydrogen chloride for 2 h at room temperature and the mixture was then stirred at room temperate overnight. After evaporation of solvent, water (100 mL) was added and the precipitates were collected by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | 8 | CCO.O=C(O)c1cccc([N+](=O)[O-])c1Cl>>CCOC(=O)c1cccc([N+](=O)[O-])c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32973439968e48cc92f147eea162d254 | CCOC(=O)c1cccc([N+](=O)[O-])c1Cl.NC1CCCCC1>>CCOC(=O)c1cccc([N+](=O)[O-])c1NC1CCCCC1 | C(C)OC(C1=C(C(=CC=C1)[N+](=O)[O-])Cl)=O.C1(CCCCC1)N>>C(C)OC(C1=C(C(=CC=C1)[N+](=O)[O-])NC1CCCCC1)=O | Cl[c:14]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][c:10]1[N+:11](=[O:12])[O-:13].[NH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | CCOC(=O)c1cccc([N+](=O)[O-])c1Cl.NC1CCCCC1 | CCOC(=O)c1cccc([N+](=O)[O-])c1NC1CCCCC1 | null | null | 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](-[#7;+:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]>>[#7;+:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[NH;D2;+0:13]-[C:12](-[C:11])-[C:14]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10] | 95 | [{"value": 95.0, "product": "C(C)OC(C1=C(C(=CC=C1)[N+](=O)[O-])NC1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The crude 2-chloro-3-nitro-benzoic acid ethyl ester was dissolved in acetonitrile (100 mL) and cyclohexylamine (2.5 mL, 21.83 mmol) was added. The mixture was stirred at reflux overnight. After evaporation of solvent, water (100 mL) was added and the precipitates were collected by filtration and dried to give 2-cyclohe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HCl | C(C)#N | null | null | CCOC(=O)c1cccc([N+](=O)[O-])c1Cl.NC1CCCCC1>C(C)#N>CCOC(=O)c1cccc([N+](=O)[O-])c1NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89880c3395ed477f8d233ada3d738e6a | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc(B(O)O)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(C(=O)O)cc4)ccc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)F)C(=O)N2CCCC2)C2CCCCC2)C=C1.C(=O)(O)C1=CC=C(C=C1)B(O)O>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)C(=O)O)C(=O)N2CCCC2)C2CCCCC2)C=C1 | Fc1ccc(-[c:32]2[c:20](-[c:19]3[n:18][c:17]4[cH:16][cH:15][c:14](-[c:13]5[n:12][c:10]6[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]6)[n:46]5[CH:47]5[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]5)[cH:45][c:44]4[cH:43][cH:42]3)[cH:21][c:22]([C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[cH:30][cH:3... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc(B(O)O)cc1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(C(=O)O)cc4)ccc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 438ea9fb2f1e2bd442e752627ef66a09bf142d9e1b00bd87c35f5c3609c407f2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | F-c1:c:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:1.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] | null | [] | null | null | null | null | Prepared as described for Compound 549a using 4-carboxyphenylboronic acid instead of 4-fluorophenylboronic acid.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HF.B | null | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(F)cc4)ccc3c1)n2C1CCCCC1.O=C(O)c1ccc(B(O)O)cc1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(C(=O)O)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e10bdcdc08734a1eb2de660877144002 | CCCCCCBr.[OH-]>>CCCCCCOc1ccc(Br)cc1 | [OH-].[Na+].BrCCCCCC>>C(CCCCC)OC1=CC=C(C=C1)Br | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:12].[OH-:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CCCCCCBr.[OH-] | CCCCCCOc1ccc(Br)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 237b39c74d9ac316ab5fa82490d6e28fcabc1fba8f9788c4e332d859dc17e1aa | 0982cd6efc6319765d94a87d57678d456858cbe5beb9beb8aa85dffb8650d81d | c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[OH-;D0:5]>>[Br;H0;D1;+0:1]-[c:6]1:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:5]-[CH2;D2;+0:2]-[C:3]-[C:4]):[c:10]:[c:11]:1 | 164.4 | [{"value": 164.4, "product": "C(CCCCC)OC1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 4 | HOUR | 50.0 g (0.290 mol) of p-bromophenyl was dissolved in 300 ml of ethanol and 14.2 g (0.340 mol) of sodium hydroxide and 49.5 g (0.300 mol) of 1-bromohexane were added thereto. The resulting solution was stirred at 70° C. for 4 hours to complete the reaction and the solvent was removed by distillation. Then 150 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide.Ether | null | c1ccccc1 | c1ccccc1 | null | C(C)O | 70 | 4 | CCCCCCBr.[OH-]>C(C)O>CCCCCCOc1ccc(Br)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f5adceea13d94cc8a530bea2105e798e | CCCCCCOc1ccc(Br)cc1>>[Li][c]1ccc(OCCCCCC)cc1 | C(CCCCC)OC1=CC=C(C=C1)Br.CCCCCC.C(CCC)[Li]>>C(CCCCC)OC1=CC=C(C=C1)[Li] | Br[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[cH:13][cH:14]1>>[Li:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[cH:13][cH:14]1 | CCCCCCOc1ccc(Br)cc1 | [Li][c]1ccc(OCCCCCC)cc1 | null | null | C1=CC=CC=C1 | Miscellaneous | Preparation of organolithium compounds | 09779d25a04d5c0f9dabfacc40aa046c53f91c14a1d59b1794183fd92ad3e2b7 | b74e09b9a6bbb0311fc1db764a25c5a719efefaac386e11fdf0023b3ff360a3e | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[Li;D1;H0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 24.0 g (0.093 mol) of 4-hexyloxybromobenzene was dissolved in 30ml of benzene and stirred at room temperature in a stream of nitrogen. To the resulting solution was added drop-wise 50 ml of hexane solution including 15% of butyllithium was added drop-wise for 30 minutes and the solution was maintained under stirring fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aryl lithium | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C1=CC=CC=C1 | null | null | CCCCCCOc1ccc(Br)cc1>C1=CC=CC=C1>[Li][c]1ccc(OCCCCCC)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0c3e91422e8b4735b26950b5d98d588a | Brc1ccccc1.CCCCC(=O)Cl>>CCCCC(=O)c1ccc(Br)cc1 | Cl.[Cl-].[Al+3].[Cl-].[Cl-].C(CCCC)(=O)Cl.BrC1=CC=CC=C1>>C(CCCC)(=O)C1=CC=C(C=C1)Br | [cH:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1 | Brc1ccccc1.CCCCC(=O)Cl | CCCCC(=O)c1ccc(Br)cc1 | null | null | C(=S)=S | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 61.6 | [{"value": 61.6, "product": "C(CCCC)(=O)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 104.5 g (0.76 mol) of anhydrous aluminum chloride and 92.1 g (0.76 mol) of valeroylchloride were added to 350 ml of carbon disulfide chilled at 0° C. To the resulting mixture with chilling and stirring, 100 g (0.64 mol) of bromobenzene was added and the solution was stirred at room temperature for 24 hours. After compl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(=S)=S | 0 | null | Brc1ccccc1.CCCCC(=O)Cl>C(=S)=S>CCCCC(=O)c1ccc(Br)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5f3fca7fc7f642fd8856543eb8ea740b | CCCCC(=O)c1ccc(Br)cc1>>CCCCCc1ccc(Br)cc1 | C(CCCC)(=O)C1=CC=C(C=C1)Br.C(COCCO)O.[OH-].[K+]>>C(CCCC)C1=CC=C(C=C1)Br | O=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | CCCCC(=O)c1ccc(Br)cc1 | CCCCCc1ccc(Br)cc1 | null | null | O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c:4](:[c:5]):[c:6] | 85.1 | [{"value": 85.1, "product": "C(CCCC)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 3 | HOUR | 95 g (0.39 mol) of 4-pentanoylbromobenzene, 300 ml of diethyleneglycol, 40 ml (0.80 mol) of 100% hydradine hydrate and 45 g (0.80 mol) of potassium hydroxide were heated at 130° C. for 1 hour and then at 180° C. with stirring for 3 hour. Water was added to the reaction solution and the organic layer was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | O | 180 | 3 | CCCCC(=O)c1ccc(Br)cc1>O>CCCCCc1ccc(Br)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d7f6df83e92a485783227fecb2b9c12a | CCCCCc1ccc(Br)cc1>>[Li][c]1ccc(CCCCC)cc1 | C(CCCC)C1=CC=C(C=C1)Br.CCCCCC.C(CCC)[Li]>>C(CCCC)C1=CC=C(C=C1)[Li] | Br[c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[cH:11][cH:12]1>>[Li:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[cH:11][cH:12]1 | CCCCCc1ccc(Br)cc1 | [Li][c]1ccc(CCCCC)cc1 | null | null | C1=CC=CC=C1 | Miscellaneous | Preparation of organolithium compounds | 09779d25a04d5c0f9dabfacc40aa046c53f91c14a1d59b1794183fd92ad3e2b7 | b74e09b9a6bbb0311fc1db764a25c5a719efefaac386e11fdf0023b3ff360a3e | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[Li;D1;H0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 18.35 g (0.081 mol) of 4-pentylbromobenzene was dissolved in 30 ml of benzene and the solution was stirred at room temperature in a stream of nitrogen. To the resulting solution was added drop-wise 50 ml (0.081 mol) of hexane solution including 15% butyllithium for 30 minutes and the solution was stirred for 2 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aryl lithium | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C1=CC=CC=C1 | null | null | CCCCCc1ccc(Br)cc1>C1=CC=CC=C1>[Li][c]1ccc(CCCCC)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c2c91aacfc624edc84b39cb1c3b96db2 | CCCCBr.CCCCCc1ccc(-c2ccc(O)cn2)cc1>>CCCCCc1ccc(-c2ccc(OCCCC)cn2)cc1 | C(CCCC)C1=CC=C(C=C1)C1=NC=C(C=C1)O.BrCCCC.[OH-].[K+]>>C(CCCC)C1=CC=C(C=C1)C1=NC=C(C=C1)OCCCC | Br[CH2:15][CH2:16][CH2:17][CH3:18].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:19][n:20]2)[cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[cH:19][n:20]2)[cH:21][cH:22]1 | CCCCBr.CCCCCc1ccc(-c2ccc(O)cn2)cc1 | CCCCCc1ccc(-c2ccc(OCCCC)cn2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 49.3 | [{"value": 49.3, "product": "C(CCCC)C1=CC=C(C=C1)C1=NC=C(C=C1)OCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.8 g of the resulting 2-(p-pentylphenyl)-5-hydroxypyridine, 2 g of 1-bromobutane and 0.8 g of potassium hydroxide placed in 60 ml of ethanol were heated under reflux for 4 hours. The potassium bromide precipitated during the reaction was removed by filtration. The ethanol was removed by distillation. The residue was e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccncc1 | HBr | C(C)O | null | null | CCCCBr.CCCCCc1ccc(-c2ccc(O)cn2)cc1>C(C)O>CCCCCc1ccc(-c2ccc(OCCCC)cn2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bb937fb985da4e238ffa165721bf85a6 | O=C(O)Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>Nc1ccc(CC(=O)[O-])c(N)c1 | [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])CC(=O)O.C(O)([O-])=O.[Na+].[H][H]>>[Na+].NC1=C(C=CC(=C1)N)CC(=O)[O-] | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[OH:9])[c:10]([N+:11](=O)[O-])[cH:12]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[O-:9])[c:10]([NH2:11])[cH:12]1 | O=C(O)Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | Nc1ccc(CC(=O)[O-])c(N)c1 | null | [Pd] | O | Functional Group Interconversion | OtherReaction | 985c83169f1ea733a240d70c7d10e3369a4b00a3eed471bef31f8bfa057a4312 | 033c2406eedbd148c9470f0f34cbfd0cf2d0a011923cc271f49dc24c589d39b9 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]:[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]):[c:7]-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[NH2;D1;+0:1]-[c:2](:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6]):[c:7]-[C:8]-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10] | 84.1 | [{"value": 84.1, "product": "[Na+].NC1=C(C=CC(=C1)N)CC(=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Five grams of 2,4-dinitrophenylacetic acid were dissolved in a solution of 1.9 gm of sodium hydrogen carbonate in 200 ml water and reduced with hydrogen in the presence of 0.3 gm of palladium on charcoal at room temperature. After completion of the uptake of hydrogen, the catalyst was filtered off, and the filtrate was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1 | Other | [Pd].O | null | null | O=C(O)Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>[Pd].O>Nc1ccc(CC(=O)[O-])c(N)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0ace83c6371546509178e06bffa6169c | CC(Oc1ccc(N)cc1N)C(=O)O.O=C(O)CCc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>CC(Oc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)O | C(O)([O-])=O.[Na+].[Na].[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])CCC(=O)O.[Na].NC1=C(OC(C(=O)O)C)C=CC(=C1)N>>[N+](=O)([O-])C1=C(OC(C(=O)O)C)C=CC(=C1)[N+](=O)[O-].[Na] | [CH3:1][CH:2]([O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:11][c:12]1[NH2:13])[C:16](=[O:17])[OH:18].O=C(O)CCc1ccc([N+](=[O:9])[O-:10])cc1[N+](=[O:14])[O-:15]>>[CH3:1][CH:2]([O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15])[C:16](=[O:17])[OH:18] | CC(Oc1ccc(N)cc1N)C(=O)O.O=C(O)CCc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | CC(Oc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)O | null | null | null | Functional Group Addition | OtherReaction | 177a832897d4868b1dbf2fc969184d29936fb85fee4ab2995b34293e7ced9bf5 | 0f5679596c87acc55854b40f0c3af636a713e900df497ffc04b11aafbdd76288 | c1ccccc1 | O-C(=O)-C-C-c1:c:c:c(-[N+](-[O-;H0;D1:1])=[O;H0;D1;+0:2]):c:c:1-[N+](-[O-;H0;D1:3])=[O;H0;D1;+0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[O-;H0;D1:1]-[N+;H0;D3:10](=[O;H0;D1;+0:2])-[c:9](:[c:11]):[c:8]:[c:6](-[N+;H0;D3:5](-[O-;H0;D1:3])=[O;H0;D1;+0:4]):[c:7] | null | [] | null | null | null | null | The 2-(2,4-dinitrophenoxy)-propionic acid from step (a) was converted into the sodium salt with sodium hydrogen carbonate and reduced in aqueous solution, using procedures analogous to those set forth in A, and the sodium salt was then isolated. Five grams of 2-(2,4-dinitrophenoxy)-propionic acid yielded 2.4 gm of sodi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Nitro group.Primary amine.Primary amine | Nitro group.Nitro group | c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | CC(Oc1ccc(N)cc1N)C(=O)O.O=C(O)CCc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>CC(Oc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-64cc2f3f72124fc4b36ee3e2ffc56dd7 | COCCOc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl>>COCCOc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 | NC1=NC(=CC(=N1)OCCOC)C.ClC1=C(C=CC=C1)S(=O)(=O)N=C=O>>COCCOC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)Cl | [CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([NH2:12])[n:26]1.[C:13](=[O:14])=[N:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[Cl:25]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20... | COCCOc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl | COCCOc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6])-[NH;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13] | null | [] | null | null | 2 | HOUR | To a dry stirred solution of 18.3 parts of 2-amino-4-(2-methoxyethoxy)-6-methylpyrimidine in 300 parts of methylene chloride at ambient temperature and pressure was added 22 parts of 2-chlorobenzenesulfonylisocyanate. The mixture was stirred for 2 hours and then the methylene chloride was removed under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | COCCOc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl>C(Cl)Cl>COCCOc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6731f9ed826a4a9ba7f301a84a813528 | COC(=O)COc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1cccs1>>COC(=O)COc1cc(C)nc(NC(=O)NS(=O)(=O)c2cccs2)n1 | [OH-].[Na+].NC1=NC(=CC(=N1)OCC(=O)OC)C.S1C(=CC=C1)S(=O)(=O)N=C=O>>CC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C=1SC=CC1)OCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([CH3:10])[n:11][c:12]([NH2:13])[n:25]1.[C:14](=[O:15])=[N:16][S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][s:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([CH3:10])[n:11][c:12]([NH:13][C:14](=[O:15])[NH:16][S:17](=[O:18])(=[O:19])[c:20]2[cH:21... | COC(=O)COc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1cccs1 | COC(=O)COc1cc(C)nc(NC(=O)NS(=O)(=O)c2cccs2)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1cccs1 | [#16;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D2;+0:6]=[C;H0;D2;+0:7]=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[#16;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | null | [] | null | null | 3 | HOUR | To a dry stirred solution of 18 parts of methyl (2-amino-6-methylpyrimidin-4-yloxy)acetate in 300 parts of methylene chloride at ambient temperature was added 20 parts of 2-thiophenesulfonylisocyanate. The solution was allowed to stand for 3 hours and was then poured onto ice. The pH of the aqueous layer was adjusted t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccsc1 | null | C(Cl)Cl | null | 3 | COC(=O)COc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1cccs1>C(Cl)Cl>COC(=O)COc1cc(C)nc(NC(=O)NS(=O)(=O)c2cccs2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6e67689ddc2b42cbafc28f9da9834950 | CNc1nc(C)cc(SCCOC)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-]>>COCCSc1cc(C)nc(N(C)C(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 | CNC1=NC(=CC(=N1)SCCOC)C.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COCCSC1=NC(=NC(=C1)C)N(C(=O)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])C | [CH3:1][O:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([NH:12][CH3:13])[n:29]1.[C:14](=[O:15])=[N:16][S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[N+:26](=[O:27])[O-:28]>>[CH3:1][O:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([N:12]([CH3:13])[C:14](=[O:15])[NH:16][S:17... | CNc1nc(C)cc(SCCOC)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-] | COCCSc1cc(C)nc(N(C)C(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 80efce6ceeace49536a85672860e2a5e31d8b9c94341eecb2be7c2c049271cea | c54c1ed6f5693fe7284d99bae8ce6ef1af2bc669c2b604d5d1041c83f556df82 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [C;D1;H3:1]-[NH;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;H0;D3;+0:9](=[O;D1;H0:8])-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | By using the procedure of Equation 2 with an equivalent amount of appropriate 2-methylaminopyrimidines or 2-methylamino-1,3,5-triazines and appropriately substituted benzenesulfonylisocyanates or isothiocyanates, the compounds of Table 3 can be prepared. For example, to a dry stirred solution of 19.7 parts of 2-methyla... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccccc1 | null | C(Cl)Cl | null | null | CNc1nc(C)cc(SCCOC)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-]>C(Cl)Cl>COCCSc1cc(C)nc(N(C)C(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d0a84019eb034faf8ec13c567c2ac205 | CNc1nc(C)cc(OCC(F)(F)F)n1.O=C=NS(=O)(=O)c1cccs1>>Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)NS(=O)(=O)c2cccs2)n1 | CNC1=NC(=CC(=N1)OCC(F)(F)F)C.S1C(=CC=C1)S(=O)(=O)N=C=O>>FC(COC1=NC(=NC(=C1)C)N(C(=O)NS(=O)(=O)C=1SC=CC1)C)(F)F | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[n:11][c:12]([NH:13][CH3:14])[n:26]1.[C:15](=[O:16])=[N:17][S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][s:25]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[n:11][c:12]([N:13]([CH3:14])[C:15](=[O:16])[NH:17][S:18](=[O:19])(=[O:20]... | CNc1nc(C)cc(OCC(F)(F)F)n1.O=C=NS(=O)(=O)c1cccs1 | Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)NS(=O)(=O)c2cccs2)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 80efce6ceeace49536a85672860e2a5e31d8b9c94341eecb2be7c2c049271cea | c54c1ed6f5693fe7284d99bae8ce6ef1af2bc669c2b604d5d1041c83f556df82 | O=C(Nc1ncccn1)NS(=O)(=O)c1cccs1 | [#16;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D2;+0:6]=[C;H0;D2;+0:7]=[O;D1;H0:8].[C;D1;H3:9]-[NH;D2;+0:10]-[c:11](:[#7;a:12]:[c:13]):[#7;a:14]:[c:15]>>[#16;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[N;H0;D3;+0:10](-[C;D1;H3:9])-[c:11](:[#7;a:12]:[c:13]):[#7;a:... | null | [] | null | null | null | null | To a dry stirred solution of 22.1 parts of 2-methylamino-4-(2,2,2-trifluorethoxy)-6-methylpyrimidine in 250 parts of methylene chloride at ambient temperature was added 18.9 parts of 2-thiophenesulfonyl isocyanate. That mixture was stirred and refluxed for 2 hours. The methylene chloride was removed under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccsc1 | null | C(Cl)Cl | null | null | CNc1nc(C)cc(OCC(F)(F)F)n1.O=C=NS(=O)(=O)c1cccs1>C(Cl)Cl>Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)NS(=O)(=O)c2cccs2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2e8a46510293438e9de6699f29e47925 | COCCSc1cc(C)nc(NC(=O)NS(=O)(=O)c2cc(Cl)ccc2Cl)n1.COS(=O)(=O)OC>>COCCSc1cc(C)nc(NC(=O)N(C)S(=O)(=O)c2cc(Cl)ccc2Cl)n1 | [H-].[Na+].COCCSC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl.[H][H].COS(=O)(=O)OC>>COCCSC1=NC(=NC(=C1)C)NC(=O)N(S(=O)(=O)C1=C(C=CC(=C1)Cl)Cl)C | [CH3:1][O:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][S:17](=[O:18])(=[O:19])[c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]2[Cl:27])[n:28]1.COS(=O)(=O)O[CH3:16]>>[CH3:1][O:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[N:15]([CH3:16])[... | COCCSc1cc(C)nc(NC(=O)NS(=O)(=O)c2cc(Cl)ccc2Cl)n1.COS(=O)(=O)OC | COCCSc1cc(C)nc(NC(=O)N(C)S(=O)(=O)c2cc(Cl)ccc2Cl)n1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | DMS Amine methylation | 354daa71b3e29fc6fa87eaadaed25e6121c7a619ccf9ef2a220ec4bd4ef68d79 | 21c6889e9277d51b6a9002d5913bbe8c174a36698e110e091e4baeead067f76b | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[#7;a:2]:[c:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]):[#7;a:12]>>[#7;a:2]:[c:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]):[#7;a:12] | null | [] | null | null | 12 | HOUR | An equivalent amount of sodium hydride (50% mineral oil dispersion) is added to a solution of N-[[4-(2-methoxyethylthio)-6-methylpyrimidin-2-yl]aminocarbonyl]-2,5-dichlorobenzenesulfonamide in dimethylformamide under a nitrogen atmosphere. After hydrogen evolution ceases, an equivalent amount of dimethylsulfate is adde... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Urea | Urea | null | null | c1cncnc1.c1ccccc1 | HO- | O.CN(C=O)C | null | 12 | COCCSc1cc(C)nc(NC(=O)NS(=O)(=O)c2cc(Cl)ccc2Cl)n1.COS(=O)(=O)OC>O.CN(C=O)C>COCCSc1cc(C)nc(NC(=O)N(C)S(=O)(=O)c2cc(Cl)ccc2Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0b1a851124e54824b1b40b05b43c9841 | CN(C(=O)Cl)S(=O)(=O)c1ccccc1Cl.CNc1nc(C)cc(OCC(F)(F)F)n1>>Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)N(C)S(=O)(=O)c2ccccc2Cl)n1 | ClC1=C(C=CC=C1)S(=O)(=O)N(C(=O)Cl)C.O1CCCC1.CNC1=NC(=CC(=N1)OCC(F)(F)F)C>>FC(COC1=NC(=NC(=C1)C)N(C(=O)N(S(=O)(=O)C1=C(C=CC=C1)Cl)C)C)(F)F | Cl[C:15](=[O:16])[N:17]([CH3:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[Cl:28].[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[n:11][c:12]([NH:13][CH3:14])[n:29]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[n:11][c:12]([N:13]([CH3:14])[C:15](=[O:16])[N:17... | CN(C(=O)Cl)S(=O)(=O)c1ccccc1Cl.CNc1nc(C)cc(OCC(F)(F)F)n1 | Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)N(C)S(=O)(=O)c2ccccc2Cl)n1 | null | null | C(C)N(CC)CC | Acylation | N-alkylation of secondary amines with alkyl halides | 21141392b95d6b95cd118c7c0b595c90f08886f6a08d558238622ce18df3aa9b | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[#16:4])-[C;D1;H3:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[#16:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C;D1;H3:6])-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | To 18 parts of N-[(2-chlorophenyl)sulfonyl]N-methylcarbamyl chloride in 300 parts of tetrahydrofuran containing 10 parts of triethylamine is added 22 parts of 2-methylamino-4-(2,2,2-trifluoroethoxy)-6-methylpyrimidine. After stirring at reflux for 10 hours, the precipitated salts are filtered off and the filtrate is co... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | null | null | c1cncnc1.c1ccccc1 | HCl | C(C)N(CC)CC | null | null | CN(C(=O)Cl)S(=O)(=O)c1ccccc1Cl.CNc1nc(C)cc(OCC(F)(F)F)n1>C(C)N(CC)CC>Cc1cc(OCC(F)(F)F)nc(N(C)C(=O)N(C)S(=O)(=O)c2ccccc2Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eb991366bcba4f99849aa733add047f5 | COc1ccc2c(c1)C(N)CCC2.CSC(=NC#N)SC>>COc1ccc2c(c1)C(NC(=NC#N)SC)CCC2 | Cl.COC1=CC=C2CCCC(C2=C1)N.CSC(=NC#N)SC>>C(#N)N=C(NC1CCCC2=CC=C(C=C12)OC)SC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([NH2:10])[CH2:17][CH2:18][CH2:19]2.CS[C:11](=[N:12][C:13]#[N:14])[S:15][CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([NH:10][C:11](=[N:12][C:13]#[N:14])[S:15][CH3:16])[CH2:17][CH2:18][CH2:19]2 | COc1ccc2c(c1)C(N)CCC2.CSC(=NC#N)SC | COc1ccc2c(c1)C(NC(=NC#N)SC)CCC2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 629a5fed094069cdb419990b860f0cd06e96d8c9b7fd9bcaf56232f2358c71b0 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[#7:4]-[C:5]#[N;D1;H0:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[c:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[#7:4]-[C:5]#[N;D1;H0:6])-[c:10] | 86.8 | [{"value": 86.8, "product": "C(#N)N=C(NC1CCCC2=CC=C(C=C12)OC)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a stirred solution of 17.8 g of 7-methoxy-1,2,3,4-tetrahydro-1-naphthylamine hydrochloride in 150 ml of ethanol at 0° C. was added 15.5 g of dimethyl cyanodithioiminocarbonate over a period of 30 minutes. The mixture was then allowed to remain at room temperature for 2 days after which the reaction mixture was coole... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | 48 | COc1ccc2c(c1)C(N)CCC2.CSC(=NC#N)SC>C(C)O>COc1ccc2c(c1)C(NC(=NC#N)SC)CCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fd8d95a478864dbfb59b2f37d2043780 | CCN.CSC(=NC#N)NC1CCCc2ccccc21>>CCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(C)N>>C(#N)N=C(NCC)NC1CCCC2=CC=CC=C12 | [CH3:1][CH2:2][NH2:3].CS[C:4](=[N:5][C:6]#[N:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][NH:3][C:4](=[N:5][C:6]#[N:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CCN.CSC(=NC#N)NC1CCCc2ccccc21 | CCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7] | null | [] | null | null | 20 | HOUR | A solution of 6.13 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 10 ml of 70 percent aqueous ethylamine in 90 ml of ethanol was heated at reflux with stirring for 20 hours. The reaction mixture was cooled in a refrigerator to give 2.44 g of N"-cyano-N-ethyl-N'-(1,2,3,4-tetrahydro-1-naphthyl)-g... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | 20 | CCN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)O>CCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db048911c46a4e7fbece0f2029e0bf2d | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21>>CC(C)NC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(C)(C)N>>C(#N)N=C(NC(C)C)NC1CCCC2=CC=CC=C12 | [CH3:1][CH:2]([CH3:3])[NH2:4].CS[C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21 | CC(C)NC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:10]-[C:8](-[C;D1;H3:7])-[C;D1;H3:9] | null | [] | null | null | 154 | HOUR | A solution of 30.0 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 40 ml of isopropylamine in 300 ml of acetonitrile was heated at reflux with stirring for 154 hours. The solvent and excess isopropylamine were removed by evaporation in vacuo, leaving the crude product as a tacky, white solid. Cr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 154 | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21>C(C)#N>CC(C)NC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-43cdb080e7ac40e783406697db52c005 | CCCN.CSC(=NC#N)NC1CCCc2ccccc21>>CCCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(CC)N>>C(#N)N=C(NCCC)NC1CCCC2=CC=CC=C12 | [CH3:1][CH2:2][CH2:3][NH2:4].CS[C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CCCN.CSC(=NC#N)NC1CCCc2ccccc21 | CCCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | 20 | HOUR | A solution of 12.3 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 16 ml of n-propylamine in 100 ml of acetonitrile was heated at reflux with stirring for 20 hours. The reaction mixture was then allowed to stand in a refrigerator to give 8.63 g of N"-cyano-N-n-propyl-N'-(1,2,3,4-tetrahydro-1-nap... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 20 | CCCN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)#N>CCCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-69bb52a824db4c9e93cac19f6247b419 | CCCCN.CSC(=NC1CCCc2ccccc21)NC#N>>CCCCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)NC(SC)=NC1CCCC2=CC=CC=C12.C(CCC)N>>C(#N)N=C(NCCCC)NC1CCCC2=CC=CC=C12 | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].CS[C:6]([NH:7][C:8]#[N:9])=[N:10][CH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[N:7][C:8]#[N:9])[NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | CCCCN.CSC(=NC1CCCc2ccccc21)NC#N | CCCCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 529ff872960bf0eff1efa8c234064efd414f833a682a85913d3211ca2ab1c5b1 | e0f9f5fb30bfd7c68a5d07c09bbed764708cecbed4d3c1c2625d81ab303ad27b | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[C:3](-[C:4])-[c:5])-[NH;D2;+0:6]-[C:7]#[N;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:4]-[C:3](-[NH;D2;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[C:7]#[N;D1;H0:8])-[NH;D2;+0:11]-[C:10]-[C:9])-[c:5] | null | [] | null | null | 100 | HOUR | A solution of 12.3 g of N-cyano-N'-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 20 ml of n-butylamine in 100 ml of acetonitrile was heated at reflux with stirring for 100 hours. The solvent was removed by evaporation in vacuo. The residual oil was dissolved in methylene chloride, and the solution was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine.Monosulfide | Secondary amine.Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 100 | CCCCN.CSC(=NC1CCCc2ccccc21)NC#N>C(C)#N>CCCCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db01fe2c132d47d2a201a259adc7b8ec | CC(C)CN.CSC(=NC1CCCc2ccccc21)NC#N>>CC(C)CNC(=NC#N)NC1CCCc2ccccc21 | C(#N)NC(SC)=NC1CCCC2=CC=CC=C12.C(C(C)C)N>>C(#N)N=C(NCC(C)C)NC1CCCC2=CC=CC=C12 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].CS[C:6]([NH:7][C:8]#[N:9])=[N:10][CH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][C:6](=[N:7][C:8]#[N:9])[NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | CC(C)CN.CSC(=NC1CCCc2ccccc21)NC#N | CC(C)CNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 529ff872960bf0eff1efa8c234064efd414f833a682a85913d3211ca2ab1c5b1 | e0f9f5fb30bfd7c68a5d07c09bbed764708cecbed4d3c1c2625d81ab303ad27b | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[C:3](-[C:4])-[c:5])-[NH;D2;+0:6]-[C:7]#[N;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:4]-[C:3](-[NH;D2;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[C:7]#[N;D1;H0:8])-[NH;D2;+0:11]-[C:10]-[C:9])-[c:5] | null | [] | null | null | 100 | HOUR | A solution of 12.3 g of N-cyano-N'-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 20 ml of isobutylamine in 100 ml of acetonitrile was heated at reflux with stirring for 100 hours. The solvent was then removed by evaporation in vacuo. The residual oil was dissolved in methylene chloride and the solution was wa... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine.Monosulfide | Secondary amine.Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 100 | CC(C)CN.CSC(=NC1CCCc2ccccc21)NC#N>C(C)#N>CC(C)CNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-204270000ad042b79f64aead2300a0f3 | CSC(=NC#N)NC1CCCc2ccccc21.NC1CC1>>N#CN=C(NC1CC1)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C1(CC1)N>>C(#N)N=C(NC1CC1)NC1CCCC2=CC=CC=C12 | CS[C:4](=[N:3][C:2]#[N:1])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21.[NH2:5][CH:6]1[CH2:7][CH2:8]1>>[N:1]#[C:2][N:3]=[C:4]([NH:5][CH:6]1[CH2:7][CH2:8]1)[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CSC(=NC#N)NC1CCCc2ccccc21.NC1CC1 | N#CN=C(NC1CC1)NC1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | N=C(NC1CC1)NC1CCCc2ccccc21 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[NH2;D1;+0:7]-[C:8]1-[C:9]-[C:10]-1>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:7]-[C:8]1-[C:9]-[C:10]-1 | null | [] | null | null | 120 | HOUR | A solution of 24.6 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 25.0 g of cyclopropylamine in 250 ml of ethanol was heated at reflux with stirring for ca. 120 hours. The solvent was then removed by evaporation in vacuo. The residual oil was dissolved in a mixture of hot isopropyl acetate and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | C1CC1.c1ccc2c(c1)CCCC2 | Other | C(C)O | null | 120 | CSC(=NC#N)NC1CCCc2ccccc21.NC1CC1>C(C)O>N#CN=C(NC1CC1)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d77170d1529842b2876b4d1481bfd655 | CCN.COc1ccc2c(c1)C(N=C(NC#N)SC)CCC2>>CCNC(=NC#N)NC1CCCc2ccc(OC)cc21 | C(#N)NC(SC)=NC1CCCC2=CC=C(C=C12)OC.C(C)N>>C(#N)N=C(NCC)NC1CCCC2=CC=C(C=C12)OC | [CH3:1][CH2:2][NH2:3].CS[C:4]([NH:5][C:6]#[N:7])=[N:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]21>>[CH3:1][CH2:2][NH:3][C:4](=[N:5][C:6]#[N:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]21 | CCN.COc1ccc2c(c1)C(N=C(NC#N)SC)CCC2 | CCNC(=NC#N)NC1CCCc2ccc(OC)cc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 529ff872960bf0eff1efa8c234064efd414f833a682a85913d3211ca2ab1c5b1 | e0f9f5fb30bfd7c68a5d07c09bbed764708cecbed4d3c1c2625d81ab303ad27b | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[C:3](-[C:4])-[c:5])-[NH;D2;+0:6]-[C:7]#[N;D1;H0:8].[C;D1;H3:9]-[C:10]-[NH2;D1;+0:11]>>[C:4]-[C:3](-[NH;D2;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[C:7]#[N;D1;H0:8])-[NH;D2;+0:11]-[C:10]-[C;D1;H3:9])-[c:5] | null | [] | null | null | null | null | A solution of 5.5 g of N-cyano-N'-(1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)-S-methylisothiourea and 10 ml of 70 percent aqueous ethylamine in 100 ml of ethanol was heated at reflux for 37 hours. The solvent was removed by evaporation in vacuo, and the residue was chromatographed on silica gel, using ethyl acetate as el... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine.Monosulfide | Secondary amine.Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | null | CCN.COc1ccc2c(c1)C(N=C(NC#N)SC)CCC2>C(C)O>CCNC(=NC#N)NC1CCCc2ccc(OC)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc8d76d9bbd3464eaacc9e16c95fb543 | CS(=O)(=O)Cl.OCC1(c2ccccc2)CCCC1>>CS(=O)(=O)OCC1(c2ccccc2)CCCC1 | O.CS(=O)(=O)Cl.OCC1(CCCC1)C1=CC=CC=C1.C(C)N(CC)CC>>CS(=O)(=O)OCC1(CCCC1)C1=CC=CC=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17]1 | CS(=O)(=O)Cl.OCC1(c2ccccc2)CCCC1 | CS(=O)(=O)OCC1(c2ccccc2)CCCC1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2CCCC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 103.4 | [{"value": 103.4, "product": "CS(=O)(=O)OCC1(CCCC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of methanesulphonyl chloride (1.62 g) in dry dichloromethane (10 ml) was added over 20 minutes to a stirred mixture of 1-hydroxymethyl-1-phenylcyclopentane (1.91 g) and triethylamine (1.64 g) in dry dichloromethane (50 ml) at 0° C. (white precipitate). After 1 hour, all at about 0° C., water was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.C1CCCC1 | HCl | ClCCl | null | 1 | CS(=O)(=O)Cl.OCC1(c2ccccc2)CCCC1>ClCCl>CS(=O)(=O)OCC1(c2ccccc2)CCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dc9ee49832794fa68de60f9cd2a0a860 | CCCC(C(=O)OCC)C(=O)OCC.CCOC(=O)CBr>>CCCC(CC(=O)OCC)(C(=O)OCC)C(=O)OCC | C(CC)C(C(=O)OCC)C(=O)OCC.[H-].[Na+].BrCC(=O)OCC>>C(CC)C(C(=O)OCC)(CC(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][CH2:3][CH:4]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20].Br[CH2:5][C:6](=[O:7])[O:8][CH2:9][CH3:10]>>[CH3:1][CH2:2][CH2:3][C:4]([CH2:5][C:6](=[O:7])[O:8][CH2:9][CH3:10])([C:11](=[O:12])[O:13][CH2:14][CH3:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20] | CCCC(C(=O)OCC)C(=O)OCC.CCOC(=O)CBr | CCCC(CC(=O)OCC)(C(=O)OCC)C(=O)OCC | null | null | O.CN(C=O)C | C-C Coupling | OtherReaction | dec10cb828d6c9aa4008bd81821647b14cbf4051f2ffdf4834e81f8194810df1 | d90cee3721df093fb64e8221977d6193e09ece59001f733c44e92eb64ac1d82f | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11]-[C:12])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D4;+0:10](-[C:11]-[C:12])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16] | 97.2 | [{"value": 97.0, "product": "C(CC)C(C(=O)OCC)(CC(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "C(CC)C(C(=O)OCC)(CC(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diethyl prop-1-ylmalonate (70.23 g) was added dropwise to a stirred suspension of sodium hydride (8.35 g) in dimethylformamide (400 ml) under an atmosphere of nitrogen at 10° to 15° C. Following the addition, the mixture was allowed to stir at room temperature until effervescence ceased. The resulting clear solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Ester | Ester.Ester.Ester | null | null | null | HBr | O.CN(C=O)C | null | null | CCCC(C(=O)OCC)C(=O)OCC.CCOC(=O)CBr>O.CN(C=O)C>CCCC(CC(=O)OCC)(C(=O)OCC)C(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c66b4c32006947549b21495daa76d09c | CCCC(CC(=O)OCC)C(=O)OCC>>CCCC(CO)CCO | [Al].C(CC)C(C(=O)OCC)CC(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>OCC(CCO)CCC | CCO[C:5]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:7][C:8](OCC)=[O:9])=[O:6]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][OH:6])[CH2:7][CH2:8][OH:9] | CCCC(CC(=O)OCC)C(=O)OCC | CCCC(CO)CCO | null | null | C(C)OCC | Reduction | OtherReaction | 8eb0b0948ba02d6bff2e6dcc47886480a262869f201923801796429d5f921f16 | 3906c52a610c5241bd14656b0a46d01a4c70864c3b16d9b6e34a49708e61df8d | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C-C>>[C:4]-[C:3](-[C:5]-[CH2;D2;+0:6]-[OH;D1;+0:7])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 67 | [{"value": 67.0, "product": "OCC(CCO)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.8, "product": "OCC(CCO)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of diethyl 2-prop-1-ylsuccinate (23.47 g) in diethyl ether (100 ml) was added dropwise to a cooled and stirred suspension of lithium aluminium hydride (6.19 g) in dry diethyl ether (500 ml) under an atmosphere of nitrogen. When the addition was complete, the reaction mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Primary alcohol | null | null | null | HO- | C(C)OCC | null | null | CCCC(CC(=O)OCC)C(=O)OCC>C(C)OCC>CCCC(CO)CCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b735e5a5475e4b5385211bc2dd514f1b | CCCC(CO)CCO.CS(=O)(=O)Cl>>CCCC(CCOS(C)(=O)=O)COS(C)(=O)=O | CS(=O)(=O)Cl.OCC(CCO)CCC>>CS(=O)(=O)OCCC(CCC)COS(=O)(=O)C | [CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][OH:7])[CH2:12][OH:13].Cl[S:8]([CH3:9])(=[O:10])=[O:11]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][O:7][S:8]([CH3:9])(=[O:10])=[O:11])[CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17] | CCCC(CO)CCO.CS(=O)(=O)Cl | CCCC(CCOS(C)(=O)=O)COS(C)(=O)=O | null | null | N1=CC=CC=C1.O | Oxidation | OtherReaction | 4225dbf9ca6419601d7093c59ed8f6dec5f6f903b74d9e70e0044407d75531b0 | 0b809a80885d0bf1313fef97c4ea534ac69c0315a0c84ce01b11db749864b1db | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:11]-[#16:12](=[O;D1;H0:13])(=[O;D1;H0:14])-[O;H0;D2;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | 0 | CELSIUS | 1.5 | HOUR | Methanesulphonyl chloride (16.95 g) was added dropwise to a stirred solution of 3-hydroxymethylhexan-1-ol (8.94 g) in pyridine (39.5 g), maintaining the temperature at less than 5° C. Following the addition, the reaction mixture was stirred at 0° C. for 1.5 hours, then diluted with water and extracted with dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Sulfonyl halide | Mesylate.Mesylate | null | null | null | null | N1=CC=CC=C1.O | 0 | 1.5 | CCCC(CO)CCO.CS(=O)(=O)Cl>N1=CC=CC=C1.O>CCCC(CCOS(C)(=O)=O)COS(C)(=O)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a5ca049c5eda4598a16a6e6dcc623604 | N=C(N)c1ccc(C(F)(F)F)cc1>>CCCc1cnc(-c2ccc(C(F)(F)F)cc2)nc1 | [Na].Cl.FC(C1=CC=C(C(=N)N)C=C1)(F)F.C[O-].[Na+]>>C(CC)C=1C=NC(=NC1)C1=CC=C(C=C1)C(F)(F)F | [cH:1]1[cH:9][c:8]([C:7]([NH2:6])=[NH:18])[cH:17][cH:16][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[n:18][cH:19]1 | N=C(N)c1ccc(C(F)(F)F)cc1 | CCCc1cnc(-c2ccc(C(F)(F)F)cc2)nc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 35e78eb18897945d55a5a0b39b3f45325cb467501ec422e880c6b3a36ad7b38c | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc(-c2ncccn2)cc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[CH3;D1;+0:13]-[C:14]-[C:15]-[c:16]1:[c:17]:[n;H0;D2;+0:11]:[c;H0;D3;+0:9](-[c;H0;D3;+0:8]2:[c:7]:[c:6]:[c;H0;D3;+0:5](-[C:2](-[F;D1;H0:1])(-[F;D1;H0:3]... | 100 | [{"value": 100.0, "product": "C(CC)C=1C=NC(=NC1)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Trifluoromethylbenzamidine hydrochloride (5 g, 0.02 mol) and α-propyl-β-dimethylaminoacrolein (3 g, 0.02 mol) were added to a sodium methylate solution having metallic sodium (1 g) dissolved in anhydrous methanol (50 ml), followed by boiling the mixture for 4 hours with stirring, distilling off methanol, adding tolue... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | Other | CO | null | null | N=C(N)c1ccc(C(F)(F)F)cc1>CO>CCCc1cnc(-c2ccc(C(F)(F)F)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-44a33c27360e44e3a871e894dde8af47 | NCC(=O)O.O=CC=O.O=CC=O>>O=C(O)CNCC(=O)O | C(=O)C=O.S(=O)=O.N.C(=O)C=O.S(=O)=O.N.NCC(=O)O.S(=O)=O.C(=O)C=O.N>>N(CC(=O)O)CC(=O)O | [NH2:5][CH2:6][C:7](=[O:8])[OH:9].O=[CH:4][CH:2]=[O:1].O=CC=[O:3]>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][CH2:6][C:7](=[O:8])[OH:9] | NCC(=O)O.O=CC=O.O=CC=O | O=C(O)CNCC(=O)O | null | null | null | Protection | OtherReaction | 9d06cb638b706d4cb79fc6e46ecb956048b6ef3145f01102d0b89a43c1e14092 | be29133c75e6c5b4af558db4572199de5c79a857193a184a114a91fe0842ec28 | null | O=C-C=[O;H0;D1;+0:1].O=[CH;D2;+0:2]-[CH;D2;+0:3]=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[CH2;D2;+0:2]-[NH;D2;+0:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | null | null | Using the apparatus and procedure of Example 6, two runs were carried out in which glyoxal was reacted with sulfur dioxide and ammonia. In the first run, one equivalent of sulfur dioxide and one equivalent of glyoxal were charged per mole of ammonia. In the second run, two moles of glyoxal and two moles of sulfur dioxi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Aldehyde.Aldehyde.Primary amine | Carboxylic acid.Secondary amine | null | null | null | HO- | null | null | null | NCC(=O)O.O=CC=O.O=CC=O>>O=C(O)CNCC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-208c234460af47f4a565f140bd3ccc36 | N#Cc1ccc(-c2ccc(F)cc2)nc1Cl>>N#Cc1ccc(-c2ccc(F)cc2)nc1 | C(C)N(CC)CC.FC1=CC=C(C=C1)C1=NC(=C(C=C1)C#N)Cl.N1=CC=CC=C1>>FC1=CC=C(C=C1)C1=NC=C(C=C1)C#N | Cl[c:15]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[n:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[n:14][cH:15]1 | N#Cc1ccc(-c2ccc(F)cc2)nc1Cl | N#Cc1ccc(-c2ccc(F)cc2)nc1 | null | [Pd] | C(C)(=O)OCC | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 51.9 | [{"value": 51.9, "product": "FC1=CC=C(C=C1)C1=NC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(4-Fluorophenyl)-5-cyano-6-chloropyridine (8.6 g) prepared in Example 1 was dissolved in ethyl acetate (300 ml), followed by adding to the solution, Pd-C (1 g) and triethylamine (12 ml), subjecting the above pyridine derivative to catalytic reduction at ordinary temperature and ordinary pressure, thereafter adding wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | N#Cc1ccc(-c2ccc(F)cc2)nc1Cl>[Pd].C(C)(=O)OCC>N#Cc1ccc(-c2ccc(F)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-99a00e326a5c4ebba98eaae64e5e9821 | CCC[C@@H]1CC[C@@H](c2ccc(C#N)c(Cl)n2)CC1>>CCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1 | C(C)OCCO.C(CC)[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)C#N)Cl>>C(CC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=C1)C#N | Cl[c:14]1[c:11]([C:12]#[N:13])[cH:10][cH:9][c:8]([C@H:7]2[CH2:6][CH2:5][C@H:4]([CH2:3][CH2:2][CH3:1])[CH2:17][CH2:16]2)[n:15]1>>[CH3:1][CH2:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][n:15]2)[CH2:16][CH2:17]1 | CCC[C@@H]1CC[C@@H](c2ccc(C#N)c(Cl)n2)CC1 | CCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1 | null | [Zn] | O | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(C2CCCCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 33.8 | [{"value": 33.8, "product": "C(CC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Ethoxyethanol (200 ml), water (40 ml) and zinc powder (20 g) were added to 2-(trans-4-n-propylcyclohexyl)-5-cyano-6-chloropyridine (17.0 g) of Example 6, followed by heating the mixture under reflux for 28 hours, cooling, thereafter filtering, adding toluene (200 ml) and water (500 ml) to the filtrate, stirring, stil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | C1CCCCC1.c1ccncc1 | Other | [Zn].O | null | null | CCC[C@@H]1CC[C@@H](c2ccc(C#N)c(Cl)n2)CC1>[Zn].O>CCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8beeaa93f1014c5996470b38568fc2a7 | CCCCI.N#Cc1ccc(-c2ccc(F)cc2)nc1.[OH-]>>CCCCC(=O)c1ccc(-c2ccc(F)cc2)nc1 | [OH-].[Na+].FC1=CC=C(C=C1)C1=NC=C(C=C1)C#N.C(CCC)I.Cl>>FC1=CC=C(C=C1)C1=NC=C(C=C1)C(CCCC)=O | I[CH2:4][CH2:3][CH2:2][CH3:1].N#[C:5][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[n:18][cH:19]1.[OH-:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[n:18][cH:19]1 | CCCCI.N#Cc1ccc(-c2ccc(F)cc2)nc1.[OH-] | CCCCC(=O)c1ccc(-c2ccc(F)cc2)nc1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 73fc1a088a11ac9d138d2f5eeb74f6beb643d3e34583c692a5036a7114d95e06 | 49ea73709104ecdb961ad27f6a5019157a5cb4ba5f32cdf331765a695e32f2fc | c1ccc(-c2ccccn2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].N#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9].[OH-;D0:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4](=[O;H0;D1;+0:10])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | null | null | null | null | A solution of 2-(4-fluorophenyl)-5-cyanopyridine (3.1 g) of Example 11 in tetrahydrofuran (30 ml) was added to a tetrahydrofuran solution (50 ml) of a Grignard reagent prepared from metallic Mg (0.6 g) and n-butyl iodide (4.4 g), followed by reacting the mixture at 60° C. for 5 hours, pouring the resulting solution in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile | Ketone | null | null | c1ccncc1.c1ccccc1 | HI | O1CCCC1.C1(=CC=CC=C1)C | null | null | CCCCI.N#Cc1ccc(-c2ccc(F)cc2)nc1.[OH-]>O1CCCC1.C1(=CC=CC=C1)C>CCCCC(=O)c1ccc(-c2ccc(F)cc2)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-242e8fa6a2dc4836961364eb4f990cd4 | CCCCBr.CCCCCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1.[OH-]>>CCCCCC[C@@H]1CC[C@@H](c2ccc(C(=O)CCCC)cn2)CC1 | [OH-].[Na+].C(CCCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=C1)C#N.Cl.C(CCC)Br>>C(CCCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=C1)C(CCCC)=O | Br[CH2:17][CH2:18][CH2:19][CH3:20].N#[C:15][c:14]1[cH:13][cH:12][c:11]([C@H:10]2[CH2:9][CH2:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:24][CH2:23]2)[n:22][cH:21]1.[OH-:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[CH2:17][CH2:18]... | CCCCBr.CCCCCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1.[OH-] | CCCCCC[C@@H]1CC[C@@H](c2ccc(C(=O)CCCC)cn2)CC1 | null | null | C1(=CC=CC=C1)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 73fc1a088a11ac9d138d2f5eeb74f6beb643d3e34583c692a5036a7114d95e06 | 49ea73709104ecdb961ad27f6a5019157a5cb4ba5f32cdf331765a695e32f2fc | c1ccc(C2CCCCC2)nc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].N#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9].[OH-;D0:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4](=[O;H0;D1;+0:10])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | 35 | CELSIUS | 5 | HOUR | An ethyl ether solution (30 ml) of 2-(trans-4-n-hexylcyclohexyl)-5-cyanopyridine (13.2 g) of Example 16 was added to an ethyl ether solution (50 ml) of a Grignard reagent prepared from metallic Mg (2.5 g) and butyl bromide (13.8 g), followed by agitating the mixture at 35° C. for 5 hours, pouring the resulting solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile | Ketone | null | null | C1CCCCC1.c1ccncc1 | HBr | C1(=CC=CC=C1)C.C(C)OCC | 35 | 5 | CCCCBr.CCCCCC[C@@H]1CC[C@@H](c2ccc(C#N)cn2)CC1.[OH-]>C1(=CC=CC=C1)C.C(C)OCC>CCCCCC[C@@H]1CC[C@@H](c2ccc(C(=O)CCCC)cn2)CC1 |
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