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-0387783899c642a8b7eb4ba379bcdf5d | ord-a446da7f8266422f9bd324e68e376165 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1.O=C1CCCc2cccnc21>>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O.N1=CC=CC=2CCCC(C12)=O.C(#N)[BH3-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12 | O=C(OCc1ccccc1)[NH:28][CH2:27][CH2:26][CH2:25][C@H:24]([NH:23][C:21]([c:20]1[cH:19][cH:18][c:17]([CH2:16][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:43][cH:42]1)=[O:22])[C:39](=[O:40])[OH:41].O=[C:29]1[CH2:30][CH2:31][CH2:32][c:33]2[cH:34][cH:35][cH:36][n:... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1.O=C1CCCc2cccnc21 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1 | null | C(C)(=O)O.[Pd] | CO.O1CCOCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 5607f5fd0e2929fbf7a5ce89157402e33612104f64f31296b85141f220e298d4 | 753b3ed65f81f3c7612fd8854ab41e32f738996364629842b7b8ab85642e9f55 | O=C(NCCCCNC1CCCc2cccnc21)c1ccc(CNCc2ccccn2)nc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3].O=[C;H0;D3;+0:4](-[C:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:3]-[C:2]-[NH;D2;+0:1]-[CH;D3;+0:4](-[C:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10] | 20.5 | [{"value": 20.5, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | The compound obtained in Example 12-4 (149.9 mg) was dissolved in a dioxane/water (8/2) solution (7.5 ml). After the addition of 10% Pd—C (154.6 mg), the mixture was stirred for 4.5 hours under hydrogen atmosphere at room temperature. After the reaction, the catalyst was removed by filtration through celite and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether | Secondary amine | c1ccccc1.c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1ccncc1.c1ccncc1.c1cnc2c(c1)CCCC2 | HO- | C(C)(=O)O.[Pd].CO.O1CCOCC1.O | null | 4.5 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1.O=C1CCCc2cccnc21>C(C)(=O)O.[Pd].CO.O1CCOCC1.O>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba3b184e2c9341639bd6d7c29b775726 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1>>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)nc1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12.Cl.O1CCOCC1>>Cl.N1=C(C=CC=C1)CNCC1=NC=C(C=C1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12 | CC(C)(C)OC(=O)[N:28]([CH2:27][c:26]1[cH:25][cH:24][c:23]([C:3](=[O:2])[NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][CH:10]2[CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]32)[C:20](=[O:21])[OH:22])[cH:37][n:36]1)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][n:35]1>>[O:2]=[C:3]([NH:4][C@@H:5]([CH2:6][CH2:7][C... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1 | O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)nc1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCCCNC1CCCc2cccnc21)c1ccc(CNCc2ccccn2)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[C:5]-[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]-[C:5]-[NH;D2;+0:1]-[C:2]-[c:3]:[#7;a:4] | null | [] | null | null | 4.5 | HOUR | The compound obtained in Example 12-5 (26.8 mg) was dissolved in methanol (0.5 ml), and 4 mol/l hydrochloric acid/dioxane solution (0.5 ml) was added. The mixture was stirred for 4.5 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccncc1.c1ccncc1 | HO- | CO | null | 4.5 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cn1>CO>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a9513f02e8c489b998c3f5654a17c95 | CO.Cc1cnc(C(=O)O)cn1>>COC(=O)c1cnc(C)cn1 | CC=1N=CC(=NC1)C(=O)O.CO.ClCl>>COC(=O)C1=NC=C(N=C1)C | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]([CH3:9])[cH:10][n:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]([CH3:9])[cH:10][n:11]1 | CO.Cc1cnc(C(=O)O)cn1 | COC(=O)c1cnc(C)cn1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1cnccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | 4 | HOUR | Commercially available 5-methylpyrazine 2-carboxylic acid (2.05 g) was dissolved in methanol (0.6 ml) and chlorine gas was blown into the solution for 5 minutes. After four hours, the reaction solution was concentrated and 1 mol/l aqueous solution of sodium hydroxide was added, followed by extraction with chloroform. T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1cnccn1 | HO- | null | null | 4 | CO.Cc1cnc(C(=O)O)cn1>>COC(=O)c1cnc(C)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27b3171f15d74f3eb8897b1eb4d4be90 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 | CCN=C=NCCCN(C)C.Cl.C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC=1N=CC(=NC1)C(=O)O.C(C)NCC.C(=O)(OCC1=CC=CC=C1)NCCC[C@H](N)C(=O)O>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC=1N=CC(=NC1)C(=O)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O | O[C:21]([c:20]1[n:19][cH:18][c:17]([CH2:16][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:43][cH:42]1)=[O:22].[NH2:23][C@@H:24]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[C:39](=[O:40])[OH:41]>>[CH... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCCNC(=O)c1cnc(CNCc2ccccn2)cn1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1)-[C:12](=[O;D1;H0:13])-[O;D1;H1:14] | null | [] | null | null | 1 | HOUR | The compound obtained in Example 8-6 (160 mg) was dissolved in DMF (3.2 ml) and diethylamine (0.32 ml) was added. After one hour, the reaction solution was concebtrated and the residue obtained was dissolved in DMF (1 ml). Then, WSCI hydrochloride (73 mg), DMAP (31 mg), and a solution of the compound obtained in Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1cnccn1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 1 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>CN(C)C=1C=CN=CC1.CN(C)C=O>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1cnc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f1bdec720c284c5a909cb7ee228ab562 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)s1>>NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O | FC(C(=O)O)(F)F.C1(=CC=CC=C1)SC.C1=C(C=CC=C1O)C.C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(S1)C(=O)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O>>N1=C(C=CC=C1)CNCC1=CC=C(S1)C(=O)N[C@@H](CCCN)C(=O)O | CC(C)(C)OC(=O)[N:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([C:7]([NH:6][C@@H:5]([CH2:4][CH2:3][CH2:2][NH:1]C(=O)OCc2ccccc2)[C:23](=[O:24])[OH:25])=[O:8])[s:22]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][n:21]1>>[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH2:13][NH:14][CH2:15][c:16... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)s1 | NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O | null | null | null | Reduction | OtherReaction | db305e12bb22c0e06b500cae34ccc19c2401b08ed0140f539b17a6d9b3c802f5 | 05f7531bd2636778edfac6a26cd2353c7ae0b8f4cd794177adc3e85f154eabc1 | c1ccc(CNCc2cccs2)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[#16;a:4])-[C:5]-[c:6]:[#7;a:7].O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:8]-[C:9]-[C:10]>>[#16;a:4]:[c:3]-[C:2]-[NH;D2;+0:1]-[C:5]-[c:6]:[#7;a:7].[C:10]-[C:9]-[NH2;D1;+0:8] | 53.3 | [{"value": 53.3, "product": "N1=C(C=CC=C1)CNCC1=CC=C(S1)C(=O)N[C@@H](CCCN)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixed solution of trifluoroacetic acid (1.4 ml), thioanisole (0.36 ml), and m-cresol (0.32 ml) was added to the compound obtained in Example 14-3 (56.2 mg). After 1.5 hours, the reaction solution was concentrated. Methanol was added to the residue and the mixture was washed with hexane. The methanol layer was concent... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc | Primary amine.Secondary amine | c1ccccc1 | null | c1ccsc1.c1ccncc1 | HO- | null | null | 1.5 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)s1>>NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7479874898141028e1d5a7be0f6d12d | NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O.O=C1CCCc2cccnc21>>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)s1 | N1=C(C=CC=C1)CNCC1=CC=C(S1)C(=O)N[C@@H](CCCN)C(=O)O.C(C)(=O)O.N1=CC=CC=2CCCC(C12)=O.C(#N)[BH3-].[Na+]>>N1=C(C=CC=C1)CNCC1=CC=C(S1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12 | [O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7][NH2:8])[C:19](=[O:20])[OH:21])[c:22]1[cH:23][cH:24][c:25]([CH2:26][NH:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][n:34]2)[s:35]1.O=[C:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]21>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7][NH:8][CH:9]1[C... | NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O.O=C1CCCc2cccnc21 | O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)s1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 8a78537bd4beb037f975f95605700fd9f4fd57c27fb34d55c5286ac9db07202f | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(NCCCCNC1CCCc2cccnc21)c1ccc(CNCc2ccccn2)s1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[NH;D2;+0:10]-[C:9]-[C:8])-[c:4](:[c:5]):[#7;a:6]:[c:7] | 27 | [{"value": 27.0, "product": "N1=C(C=CC=C1)CNCC1=CC=C(S1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | The compound obtained in Example 14-4 (18.2 mg) was dissolved in methanol (0.6 ml), and acetic acid (0.06 ml), 5,6,7,8-tetrahydroquinolin-8-one (16 mg), and sodium cyanoborohydride (7 mg) were added. After 3 days, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (1 g,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2.c1ccsc1.c1ccncc1 | Other | CO | null | 72 | NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O.O=C1CCCc2cccnc21>CO>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e776eb67f904408b46f21893414ce16 | COC(=O)c1ccc(CBr)cc1.Nc1cccc2cccnc12>>COC(=O)c1ccc(CNc2cccc3cccnc23)cc1 | NC=1C=CC=C2C=CC=NC12.C([O-])([O-])=O.[K+].[K+].BrCC1=CC=C(C(=O)OC)C=C1>>N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)OC)C=C1 | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][n:19][c:20]23)[cH:21][cH:22]1 | COC(=O)c1ccc(CBr)cc1.Nc1cccc2cccnc12 | COC(=O)c1ccc(CNc2cccc3cccnc23)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2cccc3cccnc23)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8](:[c:9]):[#7;a:10]:[c:11] | 172.4 | [{"value": 172.4, "product": "N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 8-Aminoquinoline (1.26 g) was dissolved in DMF (20 ml), and potassium carbonate (1.2 g) and methyl 4-bromomethylbenzoate (1.0 g) were added. After stirring for 20 hours, the reaction solution was concentrated. The resulting residue was diluted with chloroform and water was added. The mixture was extracted with chlorofo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ncccc2c1 | HBr | CN(C)C=O | null | 20 | COC(=O)c1ccc(CBr)cc1.Nc1cccc2cccnc12>CN(C)C=O>COC(=O)c1ccc(CNc2cccc3cccnc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-333a087240e745fe8e998f895bad03a7 | COC(=O)c1ccc(CNc2cccc3cccnc23)cc1>>O=C(O)c1ccc(CNc2cccc3cccnc23)cc1 | N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)OC)C=C1.[OH-].[Na+]>>N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]23)[cH:20][cH:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]23)[cH:20][cH:21]1 | COC(=O)c1ccc(CNc2cccc3cccnc23)cc1 | O=C(O)c1ccc(CNc2cccc3cccnc23)cc1 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNc2cccc3cccnc23)cc1 | 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] | 58.8 | [{"value": 58.8, "product": "N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound obtained in Example 16-1 (1 g) was dissolved in methanol (10 ml), and 1 mol/l aqueous solution of sodium hydroxide (10 ml) was added. The reaction solution was dissolved in THF (10 ml). After the reaction for 7 hours, the reaction solution was concentrated. The obtained residue was dissolved in water and 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | CO.C1CCOC1 | null | null | COC(=O)c1ccc(CNc2cccc3cccnc23)cc1>CO.C1CCOC1>O=C(O)c1ccc(CNc2cccc3cccnc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91ef27d823e541ca8aed75174c6cb21c | C1COCCO1.CC(C)(C)OC(=O)NCCC[C@H](NC(=O)c1ccc(CNc2cccc3cccnc23)cc1)C(=O)O>>O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CNc2cccc3cccnc23)cc1 | N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)N[C@@H](CCCNC(=O)OC(C)(C)C)C(=O)O)C=C1.Cl.O1CCOCC1>>N1=CC=CC2=CC=CC(=C12)NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCNCC2=NC=CC=C2)C=C1 | O1[CH2:11][CH2:10]O[CH2:14][CH2:13]1.CC(C)(O[C:9](=O)[NH:8][CH2:7][CH2:6][CH2:5][C@H:4]([NH:3][C:2](=[O:1])[c:19]1[cH:20][cH:21][c:22]([CH2:23][NH:24][c:25]2[cH:26][cH:27][cH:28][c:29]3[cH:30][cH:31][cH:32][n:33][c:34]23)[cH:35][cH:36]1)[C:16](=[O:17])[OH:18])[CH3:12]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7][N... | C1COCCO1.CC(C)(C)OC(=O)NCCC[C@H](NC(=O)c1ccc(CNc2cccc3cccnc23)cc1)C(=O)O | O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CNc2cccc3cccnc23)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | a652afc6d1416e8a8b6a16d894707db2264368edc25cd6cb06f0be24ce675ebb | 5236369eda45f903c7b7aa54c4699da5c377cdc85ef012eb9454449607227618 | O=C(NCCCCNCc1ccccn1)c1ccc(CNc2cccc3cccnc23)cc1 | C-C(-C)(-[CH3;D1;+0:1])-O-[C;H0;D3;+0:2](=O)-[#7:3]-[C:4].O1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-O-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1>>[C:4]-[#7:3]-[CH2;D2;+0:2]-[c;H0;D3;+0:6]1:[#7;a:9]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:1]:[cH;D2;+0:5]:1 | null | [] | null | null | 15 | HOUR | The compound obtained in Example 16-3 (122.6 mg) was dissolved in methanol (1.2 ml) and 4 mol/l hydrochloric acid/dioxane solution (1.2 ml) was added. After the reaction for 1 hour, the reaction solution was concentrated and dried under reduced pressure. The resulting residue was dissolved in methanol (2 ml), and pyrid... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Boc | null | C1COCCO1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccc2ncccc2c1 | HO- | CO | null | 15 | C1COCCO1.CC(C)(C)OC(=O)NCCC[C@H](NC(=O)c1ccc(CNc2cccc3cccnc23)cc1)C(=O)O>CO>O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CNc2cccc3cccnc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8d808e82a4642758ddd699886c22acc | CO.Cc1ccc(C(=O)O)c2ccccc12>>COC(=O)c1ccc(C)c2ccccc12 | CC1=CC=C(C2=CC=CC=C12)C(=O)O.CO.Cl>>CC1=CC=C(C2=CC=CC=C12)C(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | CO.Cc1ccc(C(=O)O)c2ccccc12 | COC(=O)c1ccc(C)c2ccccc12 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2ccccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 19 | HOUR | Commercially available 4-methyl-1-naphthalenecarboxylic acid (250.6 mg) was dissolved in methanol (7.5 ml). Hydrogen chloride gas was blown into the solution for five minutes while cooling with ice. Then, the mixture was stirred for 19 hours at room temperature and the solvent was removed by distillation. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2ccccc2c1 | HO- | null | null | 19 | CO.Cc1ccc(C(=O)O)c2ccccc12>>COC(=O)c1ccc(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-556b3489715040888ff745b81e37a366 | COC(=O)c1ccc(C)c2ccccc12.O=C1CCC(=O)N1Br>>COC(=O)c1ccc(CBr)c2ccccc12 | CC1=CC=C(C2=CC=CC=C12)C(=O)OC.BrN1C(CCC1=O)=O.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC1=CC=C(C2=CC=CC=C12)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | COC(=O)c1ccc(C)c2ccccc12.O=C1CCC(=O)N1Br | COC(=O)c1ccc(CBr)c2ccccc12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2ccccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 96.6 | [{"value": 96.6, "product": "BrCC1=CC=C(C2=CC=CC=C12)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 6 | HOUR | The compound obtained in Example 17-1 (269.9 mg) was dissolved in carbontetrachloride (8 ml), and N-bromosuccinimide (252.6 mg) and azobisisobutylonitrile (22.1 mg) were added to the solution. The mixture was stirred for 6 hours at 70° C. After the completion of the reaction, the solid was removed using a glass filter ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2ccccc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | 70 | 6 | COC(=O)c1ccc(C)c2ccccc12.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)c1ccc(CBr)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65c497fe5d834364a584b9d25bebadc4 | NCCc1c[nH]c2ccccc12.O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>>O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1c[nH]c2ccccc12)OCc1ccccc1 | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.Cl.NCCC1=CNC2=CC=CC=C12>>N1C=C(C2=CC=CC=C12)CCNC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)CCCNC(=O)OCC1=CC=CC=C1)=O | [NH2:28][CH2:29][CH2:30][c:31]1[cH:32][nH:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]12.O[C:26]([C@H:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[O:40][CH2:41][c:42]1[cH:43][cH:44][cH:45][cH:46][cH:47]1)[NH:8][C:9](=[O:10])[O:11][CH2:12][CH:13]1[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:... | NCCc1c[nH]c2ccccc12.O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1 | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1c[nH]c2ccccc12)OCc1ccccc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1c[nH]c2ccccc12)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | 16 | HOUR | Commercially available Nα-Fmoc-Nδ-Cbz-L-ornithine (528.0 mg) was dissolved in DMF (10.6 ml), and HOBt (235 mg), WSCI hydrochloride (334 mg), and tryptamine (0.165 ml) were added to the solution. The mixture was stirred for 16 hours at room temperature. After the reaction, the solvent was removed by distillation. The re... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=O | null | 16 | NCCc1c[nH]c2ccccc12.O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>CN(C)C=O>O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1c[nH]c2ccccc12)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dc70e910fce4c9ba040b32abaa97152 | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCCNC(=O)OC(C)(C)C)C(=O)O.C(C)NCC>>C(=O)(OC(C)(C)C)NCCC[C@H](N)C(=O)O | O=C(OCC1c2ccccc2-c2ccccc21)[NH:13][C@@H:12]([CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:14](=[O:15])[OH:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:13])[C:14](=[O:15])[OH:16] | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O | null | null | CN(C)C=O | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | null | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 210 | [{"value": 210.0, "product": "C(=O)(OC(C)(C)C)NCCC[C@H](N)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The compound obtained in Example 23-1 (250.8 mg) was dissolved in DMF (5 ml). After the addition of diethylamine. (0.5 ml), the mixture was stirred for 2 hours at room temperature. After the reaction, the solvent was removed by distillation under reduced pressure and the residue was dried under vacuum to obtain the tit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | null | HO- | CN(C)C=O | null | 2 | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>CN(C)C=O>CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca2b518cac5f495b9803aa3ec5936836 | COC(=O)c1c(CN)cc(C(=O)OC(C)(C)C)c2ccccc12>>CC(C)(C)OC(=O)c1cc(CN)c(C(=O)O)c2ccccc12 | C(=O)(OC(C)(C)C)C1=CC(=C(C2=CC=CC=C12)C(=O)OC)CN.[OH-].[Na+]>>C(=O)(OC(C)(C)C)C1=CC(=C(C2=CC=CC=C12)C(=O)O)CN | C[O:16][C:14]([c:13]1[c:10]([CH2:11][NH2:12])[cH:9][c:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2)=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([CH2:11][NH2:12])[c:13]([C:14](=[O:15])[OH:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | COC(=O)c1c(CN)cc(C(=O)OC(C)(C)C)c2ccccc12 | CC(C)(C)OC(=O)c1cc(CN)c(C(=O)O)c2ccccc12 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2ccccc2c1 | 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] | 91.7 | [{"value": 91.7, "product": "C(=O)(OC(C)(C)C)C1=CC(=C(C2=CC=CC=C12)C(=O)O)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The compound obtained in Example 25-1 (266.6 mg) was dissolved in THF (2.7 ml) and methanol (2.7 ml). After the addition of 1 mol/l aqueous solution of sodium hydroxide (2.7 ml), the mixture was stirred for 5 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ccccc2c1 | Other | CO.C1CCOC1 | null | 5 | COC(=O)c1c(CN)cc(C(=O)OC(C)(C)C)c2ccccc12>CO.C1CCOC1>CC(C)(C)OC(=O)c1cc(CN)c(C(=O)O)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d0b5681f2aa4659be4d853e461c318f | NCc1ccc(C(=O)O)cc1.O=C(Cl)OCc1ccccc1>>O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1 | Cl.NCC1=CC=C(C(=O)O)C=C1.C(C1=CC=CC=C1)OC(=O)Cl>>C(=O)(OCC1=CC=CC=C1)NCC1=CC=C(C(=O)O)C=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1.Cl[C:2](=[O:1])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1)[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NCc1ccc(C(=O)O)cc1.O=C(Cl)OCc1ccccc1 | O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1 | null | null | [OH-].[Na+] | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | 3 | HOUR | Commercially available 4-aminomethylbenzoic acid (5 g) was dissolved in 1 mol/l aqueous solution of sodium hydroxide (33 ml). Benzylchloroformate (5.2 ml) and 1 mol/l aqueous solution sodium hydroxide (40 ml) were gradually and simultaneously added while stirring at room temperature. After 3 hours, 1 mol/l hydrochloric... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | [OH-].[Na+] | null | 3 | NCc1ccc(C(=O)O)cc1.O=C(Cl)OCc1ccccc1>[OH-].[Na+]>O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-447f2211d39544d9a51ee1929e302857 | CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O.O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1>>NCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O | C(=O)(OCC1=CC=CC=C1)NCC1=CC=C(C(=O)O)C=C1.CCN=C=NCCCN(C)C.Cl.C(=O)(OC(C)(C)C)NCCC[C@H](N)C(=O)O>>Cl.C(=O)(OCC1=CC=CC=C1)NCC1=CC=C(C(=O)N[C@@H](CCCN)C(=O)O)C=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:28](=[O:29])[OH:30].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1>>[NH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH2:14][N... | CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O.O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1 | NCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(NCc1ccccc1)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9].O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | 38 | [{"value": 38.0, "product": "C(=O)(OCC1=CC=CC=C1)NCC1=CC=C(C(=O)N[C@@H](CCCN)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 70 | MINUTE | The compound obtained in Example 23-2 (350 mg) was dissolved in DMF (7 ml). After the addition of WSCI hydrochloride (265.0 g), DMAP (169 mg), and the compound obtained in Example 41-1 (276.0 mg), the mixture was stirred for 24 hours at room temperature. After the reaction, the solvent was removed by distillation. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 1.166667 | CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)O.O=C(NCc1ccc(C(=O)O)cc1)OCc1ccccc1>CN(C)C=1C=CN=CC1.CN(C)C=O>NCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef91b828fa474015a55771cdc907c24a | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O)Cc1ccccn1>>CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1 | C(=O)(OCC1=CC=CC=C1)NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1>>NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1 | O=C(OCc1ccccc1)[NH:22][CH2:21][c:20]1[cH:19][cH:18][c:17]([C:15]([NH:14][C@@H:13]([CH2:12][CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][n:34]2)[C:25](=[O:26])[OH:27])=[O:16])[cH:24][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]... | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O)Cc1ccccn1 | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(NCCCCCNCc1ccccn1)c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 64.3 | [{"value": 64.3, "product": "NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The compound obtained in Example 41-4 (0.02 g) was dissolved in methanol (0.5 ml). After the addition of 10% Pd—C (0.02 g), the mixture was stirred for 2 hours under hydrogen atmosphere at room temperature. After the reaction, the catalyst was removed by filtration and solvent was removed by distillation. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccncc1 | HO- | [Pd].CO | null | 2 | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1)C(=O)O)Cc1ccccn1>[Pd].CO>CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b8da72fa0b543b09dd1bd7a4a052cdb | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1>>N=C(N)NCc1ccc(C(=O)N[C@@H](CCCCNCc2ccccn2)C(=O)O)cc1 | NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1.[N+](=O)([O-])[O-].C(C)N(CC)CC>>N(C(=N)N)CC1=CC=C(C(=O)N[C@H](C(=O)O)CCCCNCC2=NC=CC=C2)C=C1 | CC(C)(C)O[C:2](=O)[N:18]([CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([NH:12][C:10]([c:9]1[cH:8][cH:7][c:6]([CH2:5][NH2:4])[cH:30][cH:29]1)=[O:11])[C:26](=[O:27])[OH:28])[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][n:25]1>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][CH2... | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1 | N=C(N)NCc1ccc(C(=O)N[C@@H](CCCCNCc2ccccn2)C(=O)O)cc1 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 9c99f5f13a5234ccaea03980d7cd5ecd37fc66448c72bd52fa274e11fbb05537 | 0b77e58f0dc5119c54e374c50f6da4d9e2b9387d0ae0eb3faaa1b3b3f6746de7 | O=C(NCCCCCNCc1ccccn1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[N;H0;D3;+0:2](-[C:3]-[C:4])-[C:5]-[c:6]:[#7;a:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7;a:7]:[c:6]-[C:5]-[NH;D2;+0:2]-[C:3]-[C:4].[N;D1;H1:11]=[C;H0;D3;+0:1](-[N;D1;H2:12])-[NH;D2;+0:8]-[C:9]-[c:10] | null | [] | null | null | 3 | DAY | The compound obtained in Example 41-5 (0.01 g) was dissolved in DMF (0.3 ml). After the addition of dimethylpyrazolecarboxyamidine nitrate (0.01 g), the mixture was adjusted to pH 8 with triethylamine and stirred for 3 days. The reaction solution was concentrated. Chloroform was added to the residue and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine.Secondary amine | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C)C=O | null | 72 | CC(C)(C)OC(=O)N(CCCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O)Cc1ccccn1>CN(C)C=O>N=C(N)NCc1ccc(C(=O)N[C@@H](CCCCNCc2ccccn2)C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41eeeb2ebe654f5880ffb7bc1398ddda | Cc1cc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)c2ccccc2c1C(=O)O>>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)c2ccccc12 | CC1=C(C2=CC=CC=C2C(=C1)CN(CC1=NC=CC=C1)C(=O)OC(C)(C)C)C(=O)O.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C2=CC=CC=C12)C(=O)O | C[c:19]1[cH:18][c:17]([CH2:16][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[c:29]2[c:24]([c:20]1[C:21](=[O:22])[OH:23])[cH:25][cH:26][cH:27][cH:28]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1)[CH2:1... | Cc1cc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)c2ccccc2c1C(=O)O | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)c2ccccc12 | null | null | CO.C1CCOC1 | Miscellaneous | OtherReaction | bc69eab4aed79cb8a12c113134d9ed8784cfdc4986b6169db3b00e709fc6dc00 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(CNCc2cccc3ccccc23)nc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | 87.6 | [{"value": 87.6, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C2=CC=CC=C12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The compound obtained in Example 43-1 (1.60 g) was dissolved in THF (16 ml) and methanol (16 ml). After the addition of 1 mol/l aqueous solution of sodium hydroxide (16 ml), the mixture was stirred for 16 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved i... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccncc1.c1ccc2ccccc2c1 | Other | CO.C1CCOC1 | null | 16 | Cc1cc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)c2ccccc2c1C(=O)O>CO.C1CCOC1>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bfa4290bd144e32ab8ac973d4d7ed90 | CC(C)(C)OC(=O)N(Cc1ccc(C(=O)N[C@@H](CCCNc2cccc3cccnc23)C(=O)O)cc1)Cc1ccccn1>>O=C(N[C@@H](CCCNc1cccc2cccnc12)C(=O)O)c1ccc(CNCc2ccccn2)cc1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)N[C@H](C(=O)O)CCCNC=2C=CC=C3C=CC=NC23)C=C1.Cl.O1CCOCC1>>N1=C(C=CC=C1)CNCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCNC=2C=CC=C3C=CC=NC23)C=C1 | CC(C)(C)OC(=O)[N:27]([CH2:26][c:25]1[cH:24][cH:23][c:22]([C:2](=[O:1])[NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][n:17][c:18]23)[C:19](=[O:20])[OH:21])[cH:36][cH:35]1)[CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][n:34]1>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7... | CC(C)(C)OC(=O)N(Cc1ccc(C(=O)N[C@@H](CCCNc2cccc3cccnc23)C(=O)O)cc1)Cc1ccccn1 | O=C(N[C@@H](CCCNc1cccc2cccnc12)C(=O)O)c1ccc(CNCc2ccccn2)cc1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCCCNc1cccc2cccnc12)c1ccc(CNCc2ccccn2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | 2.5 | HOUR | The compound obtained in Example 53-3 (19.0 mg) was dissolved in methanol (0.19 ml) and 4 mol/l hydrochloric acid/dioxane (0.19 ml) was added. After 2.5 hours, the reaction solution was concentrated and azeotropically distilled with methanol. The residue was purified by silica gel column chromatography (1 g, chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccc2ncccc2c1.c1ccccc1.c1ccncc1 | HO- | CO | null | 2.5 | CC(C)(C)OC(=O)N(Cc1ccc(C(=O)N[C@@H](CCCNc2cccc3cccnc23)C(=O)O)cc1)Cc1ccccn1>CO>O=C(N[C@@H](CCCNc1cccc2cccnc12)C(=O)O)c1ccc(CNCc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7d03949ae1e54900937fdaebc8008d05 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@@H]2CCCc3cccnc32)C(=O)O)c2ccccc12>>O=C(N[C@@H](CCCN[C@@H]1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)c2ccccc12 | N1=C(C=CC=C1)CN(C(=O)OC(C)(C)C)CC1=CC=C(C2=CC=CC=C12)C(=O)N[C@H](C(=O)O)CCCN[C@@H]1CCCC=2C=CC=NC12.Cl.O1CCOCC1>>Cl.N1=C(C=CC=C1)CNCC1=CC=C(C2=CC=CC=C12)C(=O)N[C@H](C(=O)O)CCCN[C@@H]1CCCC=2C=CC=NC12 | CC(C)(C)OC(=O)[N:28]([CH2:27][c:26]1[cH:25][cH:24][c:23]([C:3](=[O:2])[NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]32)[C:20](=[O:21])[OH:22])[c:41]2[c:36]1[cH:37][cH:38][cH:39][cH:40]2)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][n:35]1>>[O:2]=[C:3](... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@@H]2CCCc3cccnc32)C(=O)O)c2ccccc12 | O=C(N[C@@H](CCCN[C@@H]1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)c2ccccc12 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCCCN[C@@H]1CCCc2cccnc21)c1ccc(CNCc2ccccn2)c2ccccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | 2 | HOUR | The compound obtained in Example 54-3 (7.2 mg) was dissolved in methanol (0.15 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.15 ml) was added. After 2 hours, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol/water=7/3/0.5). After the additi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccncc1.c1ccc2ccccc2c1 | HO- | CO | null | 2 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@@H]2CCCc3cccnc32)C(=O)O)c2ccccc12>CO>O=C(N[C@@H](CCCN[C@@H]1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ad50d0bff1c4952af0d652c13f73120 | CC(C)(C)OC(=O)NCC[C@H](NC(=O)c1ccc(CNC(=O)OC(C)(C)C)cc1)C(=O)O>>NCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O | C(=O)(OC(C)(C)C)NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCNC(=O)OC(C)(C)C)C=C1.Cl.O1CCOCC1>>NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCN)C=C1 | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][C@H:4]([NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][NH:13]C(=O)OC(C)(C)C)[cH:14][cH:15]1)[C:16](=[O:17])[OH:18]>>[NH2:1][CH2:2][CH2:3][C@H:4]([NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][NH2:13])[cH:14][cH:15]1)[C:16](=[O:17])[OH:18] | CC(C)(C)OC(=O)NCC[C@H](NC(=O)c1ccc(CNC(=O)OC(C)(C)C)cc1)C(=O)O | NCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O | null | null | CO | Reduction | OtherReaction | 46afa823531eb720870dfe550968a278ca78b2d48230eadae217f678fe9f4703 | ca6ddca0ebc9d1ff371f32035a46f1304744e0bd3993a09d469e1a625d8e0ac3 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[NH2;D1;+0:1].[NH2;D1;+0:4]-[C:5]-[c:6] | 189.4 | [{"value": 189.4, "product": "NCC1=CC=C(C(=O)N[C@H](C(=O)O)CCN)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | The compound obtained in Example 60-2 (49.7 mg) was dissolved in methanol (0.5 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.5 ml) was added. The mixture was stirred for 1.5 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dried using a vacuum pump to ob... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Primary amine.Primary amine | null | null | c1ccccc1 | HO- | CO | null | 1.5 | CC(C)(C)OC(=O)NCC[C@H](NC(=O)c1ccc(CNC(=O)OC(C)(C)C)cc1)C(=O)O>CO>NCC[C@H](NC(=O)c1ccc(CN)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88c344182a2a4d219be99f9edfe605f7 | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>COC(=O)[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21 | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCCNC(=O)OC(C)(C)C)C(=O)O.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O>>COC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)CCCNC(=O)OC(C)(C)C)=O | [OH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[NH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]1[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2-[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:... | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | COC(=O)[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21 | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | 102.8 | [{"value": 102.8, "product": "COC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)CCCNC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Commercially available Nα-Fmoc-Nδ-Boc-L-ornithine (1.00 g), WSCI hydrochloride (0.633 g), and HOBt (0.446 g) were reacted in methanol (20 ml) for 23 hours at room temperature. After the reaction, methanol was removed and the residue was extracted with chloroform. The extract was washed with water, saturated aqueous sol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2c(c1)Cc1ccccc12 | Other | CO | null | null | CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>CO>COC(=O)[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12f48c0cf7f24a37988025d4c331fd79 | COC(=O)[C@@H](CCCN(Cc1ccccn1)C(=O)OC(C)(C)C)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>>CC(C)(C)OC(=O)N(CCC[C@H](C(=O)O)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1)Cc1ccccn1 | COC([C@@H](CCCN(C(=O)OC(C)(C)C)CC1=NC=CC=C1)C(C1=CC=C(C=C1)CN(CC1=NC=CC=C1)C(=O)OC(C)(C)C)=O)=O.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)[C@@H](C(=O)O)CCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1 | C[O:15][C:13]([C@@H:12]([CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:40][c:41]1[cH:42][cH:43][cH:44][cH:45][n:46]1)[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH2:22][N:23]([CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][n:30]2)[C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[c... | COC(=O)[C@@H](CCCN(Cc1ccccn1)C(=O)OC(C)(C)C)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)N(CCC[C@H](C(=O)O)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1)Cc1ccccn1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CCCCNCc1ccccn1)c1ccc(CNCc2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]=[O;D1;H0:6] | 91.7 | [{"value": 91.7, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)[C@@H](C(=O)O)CCCN(C(=O)OC(C)(C)C)CC2=NC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | The compound obtained in Example 66-3 (8.96 g) was dissolved in methanol (134.4 ml) and 1 N aqueous solution of sodium hydroxide (134.4 ml) was added. The mixture was stirred for 1 day. After confirming completion of the reaction with TLC, the reaction solution was concentrated under reduced pressure. The residue was d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | Other | CO | null | 24 | COC(=O)[C@@H](CCCN(Cc1ccccn1)C(=O)OC(C)(C)C)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>CO>CC(C)(C)OC(=O)N(CCC[C@H](C(=O)O)C(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b85bed97867047cf9ea39fa5d22c1896 | COC(=O)c1ccc(CN(Cc2nccn2C)C(=O)OC(C)(C)C)c2ccccc12>>Cn1ccnc1CN(Cc1ccc(C(=O)O)c2ccccc12)C(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)N(CC=1N(C=CN1)C)CC1=CC=C(C2=CC=CC=C12)C(=O)OC.[OH-].[Na+].C1CCOC1>>C(=O)(OC(C)(C)C)N(CC=1N(C=CN1)C)CC1=CC=C(C2=CC=CC=C12)C(=O)O | C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([CH2:9][N:8]([CH2:7][c:6]2[n:2]([CH3:1])[cH:3][cH:4][n:5]2)[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2)=[O:15]>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1[CH2:7][N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[c:... | COC(=O)c1ccc(CN(Cc2nccn2C)C(=O)OC(C)(C)C)c2ccccc12 | Cn1ccnc1CN(Cc1ccc(C(=O)O)c2ccccc12)C(=O)OC(C)(C)C | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(CNCc3ncc[nH]3)cccc2c1 | 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] | 84.1 | [{"value": 84.1, "product": "C(=O)(OC(C)(C)C)N(CC=1N(C=CN1)C)CC1=CC=C(C2=CC=CC=C12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | The compound obtained in Example 74-2 (1.0526 g) was dissolved in methanol (10 ml), and 1 N aqueous solution of sodium hydroxide (10 ml) and THF (10 ml) were added. The mixture was stirred for 2.5 hours. Part of the solvent was removed by distillation while adding water to the reaction solution. After adjusting the pH ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ncc[nH]1.c1ccc2ccccc2c1 | Other | CO | null | 2.5 | COC(=O)c1ccc(CN(Cc2nccn2C)C(=O)OC(C)(C)C)c2ccccc12>CO>Cn1ccnc1CN(Cc1ccc(C(=O)O)c2ccccc12)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7caa3397b14e44faa54906917a8e33b6 | CO.Cc1ccc(C(=O)O)c2cccnc12>>COC(=O)c1ccc(C)c2ncccc12 | CC1=CC=C(C=2C=CC=NC12)C(=O)O.CO.Cl>>CC1=CC=C(C=2C=CC=NC12)C(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]2[n:11][cH:12][cH:13][cH:14][c:15]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]2[n:11][cH:12][cH:13][cH:14][c:15]12 | CO.Cc1ccc(C(=O)O)c2cccnc12 | COC(=O)c1ccc(C)c2ncccc12 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2ncccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C;D1;H3:8]):[c:4] | null | [] | null | null | 15 | HOUR | The compound obtained in Example 87-2 (1 g) was dissolved in methanol (25 ml). The solution was stirred for 15 hours while blowing hydrochloric acid gas, and the solvent was removed by distillation. The obtained residue was dissolved in water and 1 mol/l sodium hydroxide aqueous solution was added to cause a solid subs... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2ncccc2c1 | HO- | null | null | 15 | CO.Cc1ccc(C(=O)O)c2cccnc12>>COC(=O)c1ccc(C)c2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebd70d5959dd40d49b1ca0a2b29a7ea9 | COC(=O)c1ccc(CBr)c2ccccc12.Nc1ccccn1>>O=C(O)c1ccc(CNc2ccccn2)c2ccccc12 | BrCC1=CC=C(C2=CC=CC=C12)C(=O)OC.C([O-])([O-])=O.[K+].[K+].NC1=NC=CC=C1>>N1=C(C=CC=C1)NCC1=CC=C(C2=CC=CC=C12)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8]Br)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | COC(=O)c1ccc(CBr)c2ccccc12.Nc1ccccn1 | O=C(O)c1ccc(CNc2ccccn2)c2ccccc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 92415cd0d503587dbc9232020ecee975743c4b5ccf369938adbe25f985d01623 | 3a5c5926d99d81cbe840ec25b6cb76f2e082bfbc6b5b9f02c592b9a82d36478b | c1ccc(NCc2cccc3ccccc23)nc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8].[c:11]:[c:10](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:12]:[c:13] | 9.5 | [{"value": 9.5, "product": "N1=C(C=CC=C1)NCC1=CC=C(C2=CC=CC=C12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | The compound obtained in Example 17-2 (1.6728 g) was dissolved in DMF (33 ml). After the addition of potassium carbonate (1.66 g) and 2-aminopyridine (0.68 g), the mixture was stirred for 15 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissolved in chlorofor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Carboxylic acid.Secondary amine | null | null | c1ccncc1.c1ccc2ccccc2c1 | HBr | CN(C)C=O | null | 15 | COC(=O)c1ccc(CBr)c2ccccc12.Nc1ccccn1>CN(C)C=O>O=C(O)c1ccc(CNc2ccccn2)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d904a5a2c0ac422f89170732fdcdba69 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@H]2CCCc3cccnc32)C(=O)NCc2cccc3ccccc23)c2ccccc12>>O=C(N[C@@H](CCCN[C@H]1CCCc2cccnc21)C(=O)NCc1cccc2ccccc12)c1ccc(CNCc2ccccn2)c2ccccc12 | C1(=CC=CC2=CC=CC=C12)CNC([C@H](CCCN[C@H]1CCCC=2C=CC=NC12)NC(=O)C1=CC=C(C2=CC=CC=C12)CN(CC1=NC=CC=C1)C(=O)OC(C)(C)C)=O.Cl.O1CCOCC1>>Cl.C1(=CC=CC2=CC=CC=C12)CNC([C@H](CCCN[C@H]1CCCC=2C=CC=NC12)NC(=O)C1=CC=C(C2=CC=CC=C12)CNCC1=NC=CC=C1)=O | CC(C)(C)OC(=O)[N:39]([CH2:38][c:37]1[cH:36][cH:35][c:34]([C:3](=[O:2])[NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][C@H:10]2[CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]32)[C:20](=[O:21])[NH:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]23)[c:52]2[c:47]1[cH:48][cH:49][c... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@H]2CCCc3cccnc32)C(=O)NCc2cccc3ccccc23)c2ccccc12 | O=C(N[C@@H](CCCN[C@H]1CCCc2cccnc21)C(=O)NCc1cccc2ccccc12)c1ccc(CNCc2ccccn2)c2ccccc12 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(N[C@@H](CCCN[C@H]1CCCc2cccnc21)C(=O)NCc1cccc2ccccc12)c1ccc(CNCc2ccccn2)c2ccccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | The compound obtained in Example 90-2 (14.2 mg) was dissolved in methanol (0.3 ml), and 4 mol/l hydrochloric acid/dioxane solution (0.3 ml) was added to the solution. After the reaction for 3.5 hours, the reaction solution was concentrated. The residue obtained was purified by silica gel column chromatography (0.5 g, c... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccc2ccccc2c1.c1ccncc1.c1ccc2ccccc2c1 | HO- | CO | null | null | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCN[C@H]2CCCc3cccnc32)C(=O)NCc2cccc3ccccc23)c2ccccc12>CO>O=C(N[C@@H](CCCN[C@H]1CCCc2cccnc21)C(=O)NCc1cccc2ccccc12)c1ccc(CNCc2ccccn2)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-749372d48f064457a6708bf563870855 | CCC=CCCC=CC=CC=O.[OH-]>>CCC=CCCC=CC=CC(=O)O | C(C=CC=CCCC=CCC)=O.[OH-].[Na+]>>C(C=CC=CCCC=CCC)(=O)O | [CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=[O:12].[OH-:13]>>[CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][C:11](=[O:12])[OH:13] | CCC=CCCC=CC=CC=O.[OH-] | CCC=CCCC=CC=CC(=O)O | null | [Ag-]=O | O | Acylation | OtherReaction | 212580cf94343ba681451fe636f6c4d850d6e10e1bdc7e1852b33ddb4cd6898f | 37c4d4a9954dede23d940a212db876610ae18deb2faf143c8b44e17692b9193f | null | [C:1]=[C:2]-[C:3]=[C:4]-[CH;D2;+0:5]=[O;D1;H0:6].[OH-;D0:7]>>[C:1]=[C:2]-[C:3]=[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | 20 | CELSIUS | null | null | For example, the 2,4,8-undecatrienal is added to a suspension of silver (I) oxide (1.1 eq) in water. The mixture is stirred at 20° C. and 50% sodium hydroxide solution (equal weight to the aldehyde), is added over 30 minutes allowing the batch to exotherm to 60° C. The solution is filtered through celite, and the aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | null | null | [Ag-]=O.O | 20 | null | CCC=CCCC=CC=CC=O.[OH-]>[Ag-]=O.O>CCC=CCCC=CC=CC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbad221a573c49cda03a1bf66a5dc9ac | CCC=CCCC=CC=CC=O.[OH-]>>CCC=CCCC=CC=CC(=O)O | [OH-].[Na+].C(C=CC=CCCC=CCC)=O>>C(C=CC=CCCC=CCC)(=O)O | [CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=[O:12].[OH-:13]>>[CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][C:11](=[O:12])[OH:13] | CCC=CCCC=CC=CC=O.[OH-] | CCC=CCCC=CC=CC(=O)O | null | [Ag-]=O | O | Acylation | OtherReaction | 212580cf94343ba681451fe636f6c4d850d6e10e1bdc7e1852b33ddb4cd6898f | 37c4d4a9954dede23d940a212db876610ae18deb2faf143c8b44e17692b9193f | null | [C:1]=[C:2]-[C:3]=[C:4]-[CH;D2;+0:5]=[O;D1;H0:6].[OH-;D0:7]>>[C:1]=[C:2]-[C:3]=[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | 20 | CELSIUS | null | null | 2,4,8-Undecatrienal was added to a suspension of silver (I) oxide (1.1 eq) in water. The mixture was stirred at 20° C. and concentrated sodium hydroxide solution (equal weight to the aldehyde), was added over 30 minutes allowing the batch to exotherm to 60° C. The solution was filtered through celite, and the aqueous f... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | null | null | [Ag-]=O.O | 20 | null | CCC=CCCC=CC=CC=O.[OH-]>[Ag-]=O.O>CCC=CCCC=CC=CC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-041f2cc851b84257b82bcd81cc91efb6 | CC(=O)c1ccccn1.CCOC(=O)C(F)(F)F>>O=C(CC(=O)C(F)(F)F)c1ccccn1 | C(C)OC(C(F)(F)F)=O.N1=C(C=CC=C1)C(C)=O.C[O-].[Na+]>>FC(C(CC(=O)C1=NC=CC=C1)=O)(F)F | [O:1]=[C:2]([CH3:3])[c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1.CCO[C:4](=[O:5])[C:6]([F:7])([F:8])[F:9]>>[O:1]=[C:2]([CH2:3][C:4](=[O:5])[C:6]([F:7])([F:8])[F:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1 | CC(=O)c1ccccn1.CCOC(=O)C(F)(F)F | O=C(CC(=O)C(F)(F)F)c1ccccn1 | null | null | CO | C-C Coupling | OtherReaction | 32688b2be78fcb1623f924ded4f1da30562c8a1cc17a29844013a0b12a85add5 | da4745a356290ddd7ef0372302b86253afded9b0422422979166627a7dfa5740 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[#7;a:7]:[c:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[#7;a:7]:[c:8]-[C:9](=[O;D1;H0:11])-[CH2;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6] | 81.2 | [{"value": 81.0, "product": "FC(C(CC(=O)C1=NC=CC=C1)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "FC(C(CC(=O)C1=NC=CC=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Trifluoro-acetic acid ethyl ester (9.82 mL, 82.5 mmol) was added to a solution of 1-pyridin-2-yl-ethanone (5.00 g, 41.2 mmol) in methanol (40 mL) containing sodium methoxide (61.8 mmol). The reaction mixture was heated at reflux overnight, concentrated under reduced pressure and acidified with aqueous hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ketone | null | null | c1ccncc1 | HO- | CO | null | null | CC(=O)c1ccccn1.CCOC(=O)C(F)(F)F>CO>O=C(CC(=O)C(F)(F)F)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28a5b5cc6d534df2ab307d50f454482a | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccccn1>>O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 | FC(C(CC(=O)C1=NC=CC=C1)=O)(F)F.NC1=CC(=NN1)C(=O)O>>N1=C(C=CC=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[nH:21][n:22]1.O=[C:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[CH2:15][C:16](=O)[C:17]([F:18])([F:19])[F:20]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[n:21]2[n:22]1 | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccccn1 | O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | b8fee759f013fec5fe2a3bf3ba798d111186d3e8b5ba1db0552d6a12a8abef16 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-c2ccn3nccc3n2)nc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]):[c:7]:[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12].[NH2;D1;+0:13]-[c:14]1:[c:15]:[c:16](-[C:17](=[O;D1;H0:18])-[O;D1;H1:19]):[#7;a:20]:[nH;D2;+0:21]:1>>[F;D1;H0:10]-[C:9](-[F;D1;H0:11])(-[F;D1;H0:12])-[c;H0;D3;+0:1]1:[cH;D2;+0... | 71.5 | [{"value": 71.0, "product": "N1=C(C=CC=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "N1=C(C=CC=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4,4,4-Trifluoro-1-pyridin-2-yl-butane-1,3-dione (3.00g, 13.8 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (1.76 g, 13.8 mmol) in acetic acid (100 ml) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccncc1 | HO- | C(C)(=O)O | null | null | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccccn1>C(C)(=O)O>O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e3cd44aa54b46a5be88c3b168754af2 | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccc(Cl)c(Cl)c1>>O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | ClC=1C=C(C=CC1Cl)C(CC(C(F)(F)F)=O)=O.NC1=CC(=NN1)C(=O)O>>ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[nH:23][n:24]1.O=[C:8]([c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1)[CH2:17][C:18](=O)[C:19]([F:20])([F:21])[F:22]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]3)[cH:17][c:18]([C:19]([F:20])([F:21])[... | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccc(Cl)c(Cl)c1 | O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | b8fee759f013fec5fe2a3bf3ba798d111186d3e8b5ba1db0552d6a12a8abef16 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-c2ccn3nccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12].[NH2;D1;+0:13]-[c:14]1:[c:15]:[c:16](-[C:17](=[O;D1;H0:18])-[O;D1;H1:19]):[#7;a:20]:[nH;D2;+0:21]:1>>[F;D1;H0:10]-[C:9](-[F;D1;H0:11])(-[F;D1;H0:12])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]... | 90.9 | [{"value": 90.0, "product": "ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(3,4-Dichloro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (1.00 g, 3.51 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (0.446 g, 3.51 mmoL) in acetic acid (100 mL) was heated at reflux for 48 hours. The reaction concentrated under reduced pressure and the crude product was purified by column chromatography on silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccccc1 | HO- | C(C)(=O)O | null | null | Nc1cc(C(=O)O)n[nH]1.O=C(CC(=O)C(F)(F)F)c1ccc(Cl)c(Cl)c1>C(C)(=O)O>O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce58d50a47684e479766e3f10e08080e | N#CCC(=O)c1ccc(Cl)c(Cl)c1.Nc1cc(C(=O)O)n[nH]1>>Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12 | ClC=1C=C(C=CC1Cl)C(CC#N)=O.NC1=CC(=NN1)C(=O)O>>NC1=CC(=NC=2N1N=C(C2)C(=O)O)C2=CC(=C(C=C2)Cl)Cl | O=[C:4]([CH2:3][C:2]#[N:1])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1.[NH2:13][c:14]1[cH:15][c:16]([C:17](=[O:18])[OH:19])[n:20][nH:21]1>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]2)[n:13][c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[n:20][n:21]12 | N#CCC(=O)c1ccc(Cl)c(Cl)c1.Nc1cc(C(=O)O)n[nH]1 | Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | be74778d36133091bb4231e2c2d129b049f5d608b0bd76d7f006256331a580f2 | cba055f16bb6d8902fe3b7ee13bd8e7822896a26eeb51828f22dbf1978e995c7 | c1ccc(-c2ccn3nccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[NH2;D1;+0:10]-[c:11]1:[c:12]:[c:13](-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]):[#7;a:17]:[nH;D2;+0:18]:1>>[NH2;D1;+0:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[n;H0;D2;+0:10... | 8.3 | [{"value": 8.0, "product": "NC1=CC(=NC=2N1N=C(C2)C(=O)O)C2=CC(=C(C=C2)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.3, "product": "NC1=CC(=NC=2N1N=C(C2)C(=O)O)C2=CC(=C(C=C2)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3,4-Dichloro-phenyl)-3-oxo-propionitrile (1.00 g, 4.67 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (0.593 g, 4.67 mmol) in pyridine (50 mL) was heated at reflux for 3 days. The reaction was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 7-ami... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine | Primary amine | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cnc2ccnn2c1 | HO- | N1=CC=CC=C1 | null | null | N#CCC(=O)c1ccc(Cl)c(Cl)c1.Nc1cc(C(=O)O)n[nH]1>N1=CC=CC=C1>Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad52a17fa51e4b88856111c6d4ba70a8 | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1>>O=C(NCc1ccccc1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23]3)[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[n:30]2[n:31]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][c:13]2[n:14][c:15](-... | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | O=C(NCc1ccccc1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | null | null | O1CCCC1.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1cc2nc(-c3ccccc3)ccn2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:8]:[c:7]1:[c:9]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:4]:[#7;a:5]:1:[c:6] | 89.9 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.845 g, 1.91 mmol) was added to a suspension of 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.600 g, 1.59 mmol) and benzylamine (0.209 mL, 1.91 mmol) in tetrahydrofuran (25 ml) containing triethyl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ccnn2c1.c1ccccc1 | HO- | O1CCCC1.C(C)OCC | null | 8 | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1>O1CCCC1.C(C)OCC>O=C(NCc1ccccc1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-425c76a157aa4a56aa708107dad64d02 | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1>>O=C(NCc1ccccc1)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 | C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.N1=C(C=CC=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=NC=CC=C2)=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][n:21]3)[cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]2[n:29]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH... | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 | O=C(NCc1ccccc1)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 | null | null | O1CCCC1.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1cc2nc(-c3ccccn3)ccn2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:8]:[c:7]1:[c:9]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:4]:[#7;a:5]:1:[c:6] | 86.9 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=NC=CC=C2)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=NC=CC=C2)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.430 g, 0.973 mmol) was added to a suspension of 5-pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.250 g, 0.811 mmol) and benzylamine (0.106 mL, 0.973 mmol) in tetrahydrofuran (10 mL) containing triethylamine ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ccnn2c1.c1ccncc1 | HO- | O1CCCC1.C(C)OCC | null | 8 | NCc1ccccc1.O=C(O)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1>O1CCCC1.C(C)OCC>O=C(NCc1ccccc1)c1cc2nc(-c3ccccn3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-809a8008e6c74c43a0d2d0f98cab69c5 | NCc1ccccc1.Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12>>Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)NCc3ccccc3)nn12 | C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.NC1=CC(=NC=2N1N=C(C2)C(=O)O)C2=CC(=C(C=C2)Cl)Cl.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2N)C2=CC(=C(C=C2)Cl)Cl)=C1 | [NH2:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.O[C:17]([c:16]1[cH:15][c:14]2[n:13][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]3)[cH:3][c:2]([NH2:1])[n:28]2[n:27]1)=[O:18]>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]2)[n:13][c:14]2[cH:15][c:16]([C:17](=[O:... | NCc1ccccc1.Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12 | Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)NCc3ccccc3)nn12 | null | null | O1CCCC1.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1cc2nc(-c3ccccc3)ccn2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:8]:[c:7]1:[c:9]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:4]:[#7;a:5]:1:[c:6] | 55 | [{"value": 55.0, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2N)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.0, "product": "C(C1=CC=CC=C1)NC(=O)C1=NN2C(N=C(C=C2N)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.081 g, 0.184 mmol) was added to a suspension of 7-amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.050 g, 0.154 mmol) and benzylamine (0.034 mL, 0.308 mmol) in tetrahydrofuran (5 ml) containing triethylamine (0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ccnn2c1.c1ccccc1 | HO- | O1CCCC1.C(C)OCC | null | 8 | NCc1ccccc1.Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)O)nn12>O1CCCC1.C(C)OCC>Nc1cc(-c2ccc(Cl)c(Cl)c2)nc2cc(C(=O)NCc3ccccc3)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a92de8e942446ad891d617a6bf78e66 | NCc1cccs1.O=C(O)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1>>O=C(NCc1cccs1)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1 | C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.BrC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O.S1C(=CC=C1)CN>>S1C(=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Br)=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][s:9]1.O[C:2](=[O:1])[c:10]1[cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]3)[cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]2[n:29]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][s:9]1)[c:10]1[cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c:... | NCc1cccs1.O=C(O)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1 | O=C(NCc1cccs1)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1 | null | null | C1CCOC1.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1cccs1)c1cc2nc(-c3ccccc3)ccn2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[#16;a:10]:[c:11]-[C:12]-[NH2;D1;+0:13]>>[#16;a:10]:[c:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1 | 73.2 | [{"value": 73.0, "product": "S1C(=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Br)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "S1C(=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Br)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.144 g, 0.327 mmol) was added to a suspension of 5-(4-bromo-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.115 g, 0.298 mmol) and thiophene-2-methylamine (0.034 mL, 0.327 mmol) in THF (10 mL) containing triethylam... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1cnc2ccnn2c1.c1ccccc1 | HO- | C1CCOC1.C(C)OCC | null | 8 | NCc1cccs1.O=C(O)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1>C1CCOC1.C(C)OCC>O=C(NCc1cccs1)c1cc2nc(-c3ccc(Br)cc3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90de7fa601fe410ebfb5c3e3361413d4 | NCc1ccccn1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1>>O=C(NCc1ccccn1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)O.N1=C(C=CC=C1)CN>>N1=C(C=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1.O[C:2](=[O:1])[c:11]1[cH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23]3)[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[n:30]2[n:31]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1)[c:11]1[cH:12][c:13]2[n:14][c:15](-[c... | NCc1ccccn1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | O=C(NCc1ccccn1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 | null | null | O1CCCC1.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccn1)c1cc2nc(-c3ccccc3)ccn2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[#7;a:10]:[c:11]-[C:12]-[NH2;D1;+0:13]>>[#7;a:10]:[c:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1 | 59.1 | [{"value": 59.0, "product": "N1=C(C=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.1, "product": "N1=C(C=CC=C1)CNC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC(=C(C=C2)Cl)Cl)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.141 g, 0.319 mmol) was added to a suspension of 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.100 g, 0.265 mmol) and C-Pyridin-2-yl-methylamine (0.033 mL, 0.319 mmol) in tetrahydrofuran (10 mL) c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1cnc2ccnn2c1.c1ccccc1 | HO- | O1CCCC1.C(C)OCC | null | 8 | NCc1ccccn1.O=C(O)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1>O1CCCC1.C(C)OCC>O=C(NCc1ccccn1)c1cc2nc(-c3ccc(Cl)c(Cl)c3)cc(C(F)(F)F)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99d47705097443a5986f2a6fdfb02356 | CS(=O)(=O)c1cccc(N)c1.O=C(Cl)c1cc2nc(-c3ccc(Cl)cc3)cc(C(F)(F)F)n2n1>>CS(=O)(=O)c1cccc(NC(=O)c2cc3nc(-c4ccc(Cl)cc4)cc(C(F)(F)F)n3n2)c1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C2)C(=O)Cl.CS(=O)(=O)C=1C=C(C=CC1)N.N1=CC=CC=C1>>CS(=O)(=O)C=1C=C(C=CC1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Cl)=C1 | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:33]1.Cl[C:11](=[O:12])[c:13]1[cH:14][c:15]2[n:16][c:17](-[c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]3)[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[n:31]2[n:32]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[... | CS(=O)(=O)c1cccc(N)c1.O=C(Cl)c1cc2nc(-c3ccc(Cl)cc3)cc(C(F)(F)F)n2n1 | CS(=O)(=O)c1cccc(NC(=O)c2cc3nc(-c4ccc(Cl)cc4)cc(C(F)(F)F)n3n2)c1 | null | null | C(C)(=O)OCC.C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1cc2nc(-c3ccccc3)ccn2n1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](:[c:6]):[c:7](:[#7;a:8]):[c:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:8]:[c:7]1:[c:9]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:4]:[#7;a:5]:1:[c:6] | 93.4 | [{"value": 93.0, "product": "CS(=O)(=O)C=1C=C(C=CC1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Cl)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "CS(=O)(=O)C=1C=C(C=CC1)NC(=O)C1=NN2C(N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)Cl)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 5-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carbonyl chloride (0.100 g, 0.277 mmol) (prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid using standard procedures, e.g.; thionyl chloride) was added to a solution of 3-methanesulfonyl-phenylamine (0.052 mL... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ccnn2c1.c1ccccc1 | HCl | C(C)(=O)OCC.C(C)#N | null | 8 | CS(=O)(=O)c1cccc(N)c1.O=C(Cl)c1cc2nc(-c3ccc(Cl)cc3)cc(C(F)(F)F)n2n1>C(C)(=O)OCC.C(C)#N>CS(=O)(=O)c1cccc(NC(=O)c2cc3nc(-c4ccc(Cl)cc4)cc(C(F)(F)F)n3n2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f369b6f770fb42b39d21ef9339c14116 | N#Cc1ccc(N(CCc2ccc(OCc3ccccc3)cc2)n2cnnc2)cc1>>N#Cc1ccc(N(CCc2ccc(O)cc2)n2cnnc2)cc1 | C(C)(=O)OCC.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CCN(C1=CC=C(C#N)C=C1)N1C=NN=C1.C(C)O>>OC1=CC=C(C=C1)CCN(C1=CC=C(C#N)C=C1)N1C=NN=C1 | c1ccc(C[O:14][c:13]2[cH:12][cH:11][c:10]([CH2:9][CH2:8][N:7]([c:6]3[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:23][cH:22]3)[n:17]3[cH:18][n:19][n:20][cH:21]3)[cH:16][cH:15]2)cc1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]2)[n:17]2[cH:18][n:19][n:20][cH:21]2)[cH:22][c... | N#Cc1ccc(N(CCc2ccc(OCc3ccccc3)cc2)n2cnnc2)cc1 | N#Cc1ccc(N(CCc2ccc(O)cc2)n2cnnc2)cc1 | null | [Pd] | C1CCOC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCN(c2ccccc2)n2cnnc2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 28 | [{"value": 28.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.8, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirred solution of 4-{[2-(4-benzyloxyphenyl)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile (536 mg, 1.355 mmol) in distilled THF (15 mL) was added in succession absolute ethanol (30 mL) and Pd/C (10%, 54 mg). The black suspension was then stirred under an atmosphere of hydrogen (balloon) for 3 days. Upon removal b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1nnc[nH]1 | Other | [Pd].C1CCOC1 | null | 72 | N#Cc1ccc(N(CCc2ccc(OCc3ccccc3)cc2)n2cnnc2)cc1>[Pd].C1CCOC1>N#Cc1ccc(N(CCc2ccc(O)cc2)n2cnnc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40253bf90ce142bf9ca6e6e254b862e2 | BrCCCCCCCCCCBr.N#Cc1ccc(Nn2cnnc2)cc1>>N#Cc1ccc(N(CCCCCCCCCCBr)n2cnnc2)cc1 | C(C)(=O)OCC.[H-].[Na+].N=1N=CN(C1)NC1=CC=C(C#N)C=C1.BrCCCCCCCCCCBr>>BrCCCCCCCCCCN(C1=CC=C(C#N)C=C1)N1C=NN=C1 | Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][n:19]2[cH:20][n:21][n:22][cH:23]2)[cH:24][cH:25]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18])[n:19]2[cH:2... | BrCCCCCCCCCCBr.N#Cc1ccc(Nn2cnnc2)cc1 | N#Cc1ccc(N(CCCCCCCCCCBr)n2cnnc2)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(Nn2cnnc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5](-[NH;D2;+0:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[#7;a:10]:[c:11]:1):[c:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[#7;a:7]1:[c:8]:[#7;a:9]:[#7;a:10]:[c:11]:1)-[c:5](:[c:4]):[c:12] | null | [] | null | null | 8 | HOUR | Sodium hydride (60%, 240 mg, 6.0 mmol) was added to a solution of 4-([1,2,4]triazol-4-ylamino)-benzonitrile (926 mg, 5.0 mmol) in DMSO (25 mL) at r.t. The mixture was stirred for 1 hour at this temperature and 1,10-dibromodecane (5 mL) was added. The reaction mixture was stirred overnight and ethyl acetate (100 mL) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1nnc[nH]1 | HBr | CS(=O)C | null | 8 | BrCCCCCCCCCCBr.N#Cc1ccc(Nn2cnnc2)cc1>CS(=O)C>N#Cc1ccc(N(CCCCCCCCCCBr)n2cnnc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9485af3a607841f4825b672142d9a16a | CN(C)S(=O)(=O)c1ccc(C=O)cc1Br>>CN(C)S(=O)(=O)c1ccc(CO)cc1Br | BrC=1C=C(C=O)C=CC1S(N(C)C)(=O)=O.[BH4-].[Na+]>>BrC=1C=C(CO)C=CC1S(N(C)C)(=O)=O | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]1[Br:15]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][c:14]1[Br:15] | CN(C)S(=O)(=O)c1ccc(C=O)cc1Br | CN(C)S(=O)(=O)c1ccc(CO)cc1Br | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 96.7 | [{"value": 92.0, "product": "BrC=1C=C(CO)C=CC1S(N(C)C)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "BrC=1C=C(CO)C=CC1S(N(C)C)(=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of OBS02001 (6.0 g, 19.47 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.81 g, 21.42 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C1CCOC1 | null | 4 | CN(C)S(=O)(=O)c1ccc(C=O)cc1Br>C1CCOC1>CN(C)S(=O)(=O)c1ccc(CO)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7100408e04744a39debe8e7490bc02b | CN(C)S(=O)(=O)c1ccc(CO)cc1Br.O=S(Cl)Cl>>CN(C)S(=O)(=O)c1ccc(CCl)cc1Br | BrC=1C=C(CO)C=CC1S(N(C)C)(=O)=O.S(=O)(Cl)Cl>>BrC=1C=C(CCl)C=CC1S(N(C)C)(=O)=O | O[CH2:11][c:10]1[cH:9][cH:8][c:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[c:14]([Br:15])[cH:13]1.O=S(Cl)[Cl:12]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13][c:14]1[Br:15] | CN(C)S(=O)(=O)c1ccc(CO)cc1Br.O=S(Cl)Cl | CN(C)S(=O)(=O)c1ccc(CCl)cc1Br | null | null | C(Cl)Cl.CCCCCC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 99.4 | [{"value": 95.0, "product": "BrC=1C=C(CCl)C=CC1S(N(C)C)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.4, "product": "BrC=1C=C(CCl)C=CC1S(N(C)C)(=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of OBS02002 (5.0 g, 16.12 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (1.76 mL, 24.18 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give a yellow oil which solidi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HCl | C(Cl)Cl.CCCCCC | null | 2 | CN(C)S(=O)(=O)c1ccc(CO)cc1Br.O=S(Cl)Cl>C(Cl)Cl.CCCCCC>CN(C)S(=O)(=O)c1ccc(CCl)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bed968cd268c4dc9bd3f8edd0f8cf451 | CN(C)S(=O)(=O)c1c(Br)cc(C=O)cc1Br>>CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br | BrC=1C=C(C=O)C=C(C1S(N(C)C)(=O)=O)Br.[BH4-].[Na+]>>BrC=1C=C(CO)C=C(C1S(N(C)C)(=O)=O)Br | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[c:8]([Br:9])[cH:10][c:11]([CH:12]=[O:13])[cH:14][c:15]1[Br:16]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[c:8]([Br:9])[cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]1[Br:16] | CN(C)S(=O)(=O)c1c(Br)cc(C=O)cc1Br | CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 98.3 | [{"value": 94.0, "product": "BrC=1C=C(CO)C=C(C1S(N(C)C)(=O)=O)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "BrC=1C=C(CO)C=C(C1S(N(C)C)(=O)=O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of OBS02013 (5.5 g, 14.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.59 g, 15.63 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C1CCOC1 | null | 4 | CN(C)S(=O)(=O)c1c(Br)cc(C=O)cc1Br>C1CCOC1>CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-796fbe34d3a94319b39c4736b207ae20 | CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br.O=S(Cl)Cl>>CN(C)S(=O)(=O)c1c(Br)cc(CCl)cc1Br | BrC=1C=C(CO)C=C(C1S(N(C)C)(=O)=O)Br.S(=O)(Cl)Cl>>BrC=1C=C(CCl)C=C(C1S(N(C)C)(=O)=O)Br | O[CH2:12][c:11]1[cH:10][c:8]([Br:9])[c:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[c:15]([Br:16])[cH:14]1.O=S(Cl)[Cl:13]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[c:8]([Br:9])[cH:10][c:11]([CH2:12][Cl:13])[cH:14][c:15]1[Br:16] | CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br.O=S(Cl)Cl | CN(C)S(=O)(=O)c1c(Br)cc(CCl)cc1Br | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | To a solution of OBS02015 (3.93 g, 10.10 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (1.11 mL, 15.15 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give OBS02018 as a brown oil ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CN(C)S(=O)(=O)c1c(Br)cc(CO)cc1Br.O=S(Cl)Cl>C(Cl)Cl>CN(C)S(=O)(=O)c1c(Br)cc(CCl)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c11cc9676ab94e19a6703c7d9987902e | COc1cc(C=O)ccc1S(=O)(=O)N(C)C>>COc1cc(CO)ccc1S(=O)(=O)N(C)C | CN(S(=O)(=O)C1=C(C=C(C=O)C=C1)OC)C.[BH4-].[Na+]>>CN(S(=O)(=O)C1=C(C=C(CO)C=C1)OC)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16] | COc1cc(C=O)ccc1S(=O)(=O)N(C)C | COc1cc(CO)ccc1S(=O)(=O)N(C)C | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 98.4 | [{"value": 92.0, "product": "CN(S(=O)(=O)C1=C(C=C(CO)C=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.4, "product": "CN(S(=O)(=O)C1=C(C=C(CO)C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of OBS02011 (5.5 g, 21.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.88 g, 23.33 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C1CCOC1 | null | 4 | COc1cc(C=O)ccc1S(=O)(=O)N(C)C>C1CCOC1>COc1cc(CO)ccc1S(=O)(=O)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19c47b15572e4f0d927f5edbf6903370 | COc1cc(CO)ccc1S(=O)(=O)N(C)C.O=S(Cl)Cl>>COc1cc(CCl)ccc1S(=O)(=O)N(C)C | CN(S(=O)(=O)C1=C(C=C(CO)C=C1)OC)C.S(=O)(Cl)Cl>>CN(S(=O)(=O)C1=C(C=C(CCl)C=C1)OC)C | O[CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16])[cH:9][cH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][Cl:7])[cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16] | COc1cc(CO)ccc1S(=O)(=O)N(C)C.O=S(Cl)Cl | COc1cc(CCl)ccc1S(=O)(=O)N(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 104.6 | [{"value": 99.0, "product": "CN(S(=O)(=O)C1=C(C=C(CCl)C=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.6, "product": "CN(S(=O)(=O)C1=C(C=C(CCl)C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of OBS02014 (2.76 g, 10.55 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (1.15 mL, 15.82 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give OBS02016 as a brown oil ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 2 | COc1cc(CO)ccc1S(=O)(=O)N(C)C.O=S(Cl)Cl>C(Cl)Cl>COc1cc(CCl)ccc1S(=O)(=O)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f707e4cc83c42549e0c7b9fa77e3491 | COc1ccc(C=O)cc1S(=O)(=O)N(C)C>>COc1ccc(CO)cc1S(=O)(=O)N(C)C | CN(S(=O)(=O)C=1C=C(C=O)C=CC1OC)C.[BH4-].[Na+]>>CN(S(=O)(=O)C=1C=C(CO)C=CC1OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]([CH3:15])[CH3:16] | COc1ccc(C=O)cc1S(=O)(=O)N(C)C | COc1ccc(CO)cc1S(=O)(=O)N(C)C | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 62.7 | [{"value": 59.0, "product": "CN(S(=O)(=O)C=1C=C(CO)C=CC1OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "CN(S(=O)(=O)C=1C=C(CO)C=CC1OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of OBS02049 (5.5 g, 21.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.88 g, 23.33 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C1CCOC1 | null | 4 | COc1ccc(C=O)cc1S(=O)(=O)N(C)C>C1CCOC1>COc1ccc(CO)cc1S(=O)(=O)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-876474b7d56a4b3b88e8d5a4a4d44459 | CC(=O)Cl>>[Cl-].[Cl-] | C(C)(C)(C)C=1C=C([O-])C=C(C1)C(C)(C)C.C(C)(C)(C)C=1C=C([O-])C=C(C1)C(C)(C)C.C[SiH](C)[Zr+2](C1=C(CC=2C=CC3=C(C12)C=CC=C3)C)C3=C(CC=1C=CC2=C(C31)C=CC=C2)C.C(C)(=O)Cl>>[Cl-].[Cl-].C[SiH](C)[Zr+2](C1=C(CC=2C=CC3=C(C12)C=CC=C3)C)C3=C(CC=1C=CC2=C(C31)C=CC=C2)C | CC(=O)[Cl:33]>>[Cl-:33].[Cl-:34] | CC(=O)Cl | [Cl-].[Cl-] | null | null | C1(=CC=CC=C1)C | Functional Group Addition | OtherReaction | 8b076030aa392a55412a9120ce0f0944851bad8e888757c95f62a549bffd0c1f | 17d817805580a66098304d022891ad8b7ebc698f18dda2b00fe6f98c7e3c0ad6 | null | C-C(=O)-[Cl;H0;D1;+0:1]>>[Cl-;H0;D0:1] | null | [] | null | null | 4 | HOUR | 3.4 g of rac-dimethylsilylbis(2-methylbenzo[e]indenyl)zirconium bis(3,5-di-tert-butylphenoxide) (IV) from example 1 were suspended in 35.8 g of toluene in a dry round-bottomed flask which had been flushed with inert gas and was provided with stopcock and magnetic stirrer bar. At room temperature, 7.5 g of a 10% strengt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | HO- | C1(=CC=CC=C1)C | null | 4 | CC(=O)Cl>C1(=CC=CC=C1)C>[Cl-].[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37c79427ac8147a1b820d04799e1fa3a | Nc1c(Cl)cc(C(=O)O)cc1C(F)(F)F.O=S(Cl)Cl>>Nc1c(Cl)cc(C(=O)Cl)cc1C(F)(F)F | NC1=C(C=C(C(=O)O)C=C1C(F)(F)F)Cl.S(=O)(Cl)Cl>>ClC=1C=C(C(=O)Cl)C=C(C1N)C(F)(F)F | O[C:7]([c:6]1[cH:5][c:3]([Cl:4])[c:2]([NH2:1])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10]1)=[O:8].O=S(Cl)[Cl:9]>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[Cl:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | Nc1c(Cl)cc(C(=O)O)cc1C(F)(F)F.O=S(Cl)Cl | Nc1c(Cl)cc(C(=O)Cl)cc1C(F)(F)F | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 80 | [{"value": 80.0, "product": "ClC=1C=C(C(=O)Cl)C=C(C1N)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 13 g (0.0543 mol) of 4-amino-3-chloro-5-trifluoromethyl-benzoic acid was added to 32.5 ml of thionyl chloride. The suspension was heated until the crystals have dissolved, then refluxing was continued for another 2 h. After cooling to room temperature, the remaining thionyl chloride was evaporated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | 2 | Nc1c(Cl)cc(C(=O)O)cc1C(F)(F)F.O=S(Cl)Cl>>Nc1c(Cl)cc(C(=O)Cl)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5946892308ac4131bb6fd116f5fb02cd | CC(C)(C)N.Nc1c(Cl)cc(C2CO2)cc1C(F)(F)F>>CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 | NC1=C(C=C(C=C1C(F)(F)F)C1CO1)Cl.C(C)(C)(C)N>>NC1=C(C=C(C=C1C(F)(F)F)C(CO)NC(C)(C)C)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[NH2:5].[CH:6]1([c:9]2[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]2)[CH2:7][O:8]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][CH:6]([CH2:7][OH:8])[c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | CC(C)(C)N.Nc1c(Cl)cc(C2CO2)cc1C(F)(F)F | CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2392b40e60cedf65cac67885e88ff1a248596b43034e44f7ac1c981b15170aa3 | d7adf528712633f83e6bae148cdd27bcd1da32e03c86fb5a52b2cfb0297b6748 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH2;D1;+0:5].[c:6]:[c:7](-[CH;D3;+0:8]1-[C:9]-[O;H0;D2;+0:10]-1):[c:11]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[CH;D3;+0:8](-[C:9]-[OH;D1;+0:10])-[c:7](:[c:6]):[c:11] | 20 | [{"value": 20.0, "product": "NC1=C(C=C(C=C1C(F)(F)F)C(CO)NC(C)(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.2 g (0.022 mol) of (4-amino-3-chloro-5-trifluoromethyl-phenyl)-ethylene oxide was dissolved in 26 ml of anhydrous ethanol and treated with 5.1 ml (0.049 mol) of tert-butylamine. The mixture was refluxed for 13 h, and then evaporated. The residue was extracted with 2N hydrochloric acid for several times. Aqueous layer... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Primary alcohol.Secondary amine | C1CO1 | null | c1ccccc1 | null | C(C)O | null | null | CC(C)(C)N.Nc1c(Cl)cc(C2CO2)cc1C(F)(F)F>C(C)O>CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-484020b3048d494b90cf506b9fcdd076 | CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1>>CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 | ClC=1C=C(C=C(C1N)C(F)(F)F)C(CO)NC(C)(C)C.Br>>Br.NC1=C(C=C(C=C1C(F)(F)F)C(CO)NC(C)(C)C)Cl | [CH3:2][C:3]([CH3:4])([CH3:5])[NH:6][CH:7]([CH2:8][OH:9])[c:10]1[cH:11][c:12]([Cl:13])[c:14]([NH2:15])[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:2][C:3]([CH3:4])([CH3:5])[NH:6][CH:7]([CH2:8][OH:9])[c:10]1[cH:11][c:12]([Cl:13])[c:14]([NH2:15])[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 | CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 | null | null | C(C)OCC.C(C)(C)O.C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 80 | [{"value": 80.0, "product": "Br.NC1=C(C=C(C=C1C(F)(F)F)C(CO)NC(C)(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of 2-(3-chloro-4-amino-5-trifluoromethyl-phenyl)-2-tert-butylaminoethanol was dissolved in 20 ml of anhydrous diethyl ether and the solution was acidified to pH=2 by adding dropwise a solution of hydrobromic acid in isopropanol with stirring. The precipitate was collected by filtration, washed with small amount o... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)OCC.C(C)(C)O.C(C)O | null | null | CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1>C(C)OCC.C(C)(C)O.C(C)O>CC(C)(C)NC(CO)c1cc(Cl)c(N)c(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b7d1cffff564c4a9cb1d06f37c1aa66 | COC(=O)C(F)(F)F.NCC(=O)O>>O=C(O)CNC(=O)C(F)(F)F | Cl.FC(C(=O)OC)(F)F.C(C)N(CC)CC.NCC(=O)O>>FC(C(=O)NCC(=O)O)(F)F | CO[C:6](=[O:7])[C:8]([F:9])([F:10])[F:11].[O:1]=[C:2]([OH:3])[CH2:4][NH2:5]>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11] | COC(=O)C(F)(F)F.NCC(=O)O | O=C(O)CNC(=O)C(F)(F)F | null | null | CO.C(C)(=O)OCC | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[NH2;D1;+0:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | 87 | [{"value": 87.0, "product": "FC(C(=O)NCC(=O)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "FC(C(=O)NCC(=O)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Methyl trifluoroacetate (804 μL, 7.99 mmoles) and triethylamine (928 μL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | CO.C(C)(=O)OCC | null | 18 | COC(=O)C(F)(F)F.NCC(=O)O>CO.C(C)(=O)OCC>O=C(O)CNC(=O)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c353e953aaf34bf5a0978f79193a0a6e | COC(=O)C(F)(F)F.NCCCCCCCCCCCC(=O)O>>O=C(O)CCCCCCCCCCCNC(=O)C(F)(F)F | Cl.FC(C(=O)OC)(F)F.C(C)N(CC)CC.NCCCCCCCCCCCC(=O)O>>FC(C(=O)NCCCCCCCCCCCC(=O)O)(F)F | CO[C:16](=[O:17])[C:18]([F:19])([F:20])[F:21].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:18]([F:19])([F:20])[F:21] | COC(=O)C(F)(F)F.NCCCCCCCCCCCC(=O)O | O=C(O)CCCCCCCCCCCNC(=O)C(F)(F)F | null | null | CO.C(C)(=O)OCC | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6] | 97 | [{"value": 97.0, "product": "FC(C(=O)NCCCCCCCCCCCC(=O)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "FC(C(=O)NCCCCCCCCCCCC(=O)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Methyl trifluoroacetate (200 μL, 1.99 mmoles) and triethylamine (184 μL, 1.32 mmoles) were added to a suspension of 12-aminododecanoic acid (300 mg, 1.32 mmoles) in methanol (2 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | CO.C(C)(=O)OCC | null | 18 | COC(=O)C(F)(F)F.NCCCCCCCCCCCC(=O)O>CO.C(C)(=O)OCC>O=C(O)CCCCCCCCCCCNC(=O)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28b069d863c243e9b7e86e1ed5bab749 | CCCCC(NC(=O)CCc1ccccc1)C(=O)O.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O>>O=C(CCc1ccccc1)NCCCCCC(=O)ON1C(=O)CCC1=O | C(C)(=O)OCC.C(ON1C(CCC1=O)=O)(ON1C(CCC1=O)=O)=O.C(CCC1=CC=CC=C1)(=O)NC(C(=O)O)CCCC.N1=CC=CC=C1>>C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCC2=CC=CC=C2 | O=C(O)[CH:12]([NH:11][C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:13][CH2:14][CH2:15][CH3:16].O=C1CCC(=O)N1O[C:17](=[O:18])[O:19][N:20]1[C:21](=[O:22])[CH2:23][CH2:24][C:25]1=[O:26]>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16... | CCCCC(NC(=O)CCc1ccccc1)C(=O)O.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O | O=C(CCc1ccccc1)NCCCCCC(=O)ON1C(=O)CCC1=O | null | null | C(C)#N | C-C Coupling | OtherReaction | 93b0b6ada019dc48dd1969cd30fdb502c2060ad2bcb3136a86bf4bcbc2603af8 | e462bea03759d6b06e7e4a45a0246b428f72f63058c08857b19cd7d927939d72 | O=C(CCc1ccccc1)NCCCCCC(=O)ON1C(=O)CCC1=O | O-C(=O)-[CH;D3;+0:1](-[#7:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6]-[C:7]-[C:8]-[CH3;D1;+0:9].O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#8:12]-[#7:13](-[C:14]=[O;D1;H0:15])-[C:16]=[O;D1;H0:17]>>[C:4]-[C:3](=[O;D1;H0:5])-[#7:2]-[CH2;D2;+0:1]-[C:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#8:12]-[#7... | 72 | [{"value": 72.0, "product": "C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Disuccinimidyl carbonate (155 mg, 604 μmoles) was added to a solution of 31 (159 mg, 604 μmoles) and pyridine (97.7 μL, 1.21 mmoles) in acetonitrile (1 mL). The reaction mixture was stirred at room temperature for 2.5 h, during which the solution became clear and evolved gas. The solution was added to ethyl acetate (5 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.C1CC[NH]C1 | HO- | C(C)#N | null | 2.5 | CCCCC(NC(=O)CCc1ccccc1)C(=O)O.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O>C(C)#N>O=C(CCc1ccccc1)NCCCCCC(=O)ON1C(=O)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f33bd7733d2649b28c202fcf88b30a6f | COC(=O)C(F)(F)F.NCCCCCC(=O)O>>CCCCC(NC(=O)C(F)(F)F)C(=O)O | Cl.FC(C(=O)OC)(F)F.C(C)N(CC)CC.C(CCC(=O)O)CCN>>FC(C(=O)NC(C(=O)O)CCCC)(F)F | CO[C:7](=[O:8])[C:9]([F:10])([F:11])[F:12].[CH2:1]([CH2:2][CH2:3][CH2:4][CH2:5][NH2:6])[C:13](=[O:14])[OH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[C:9]([F:10])([F:11])[F:12])[C:13](=[O:14])[OH:15] | COC(=O)C(F)(F)F.NCCCCCC(=O)O | CCCCC(NC(=O)C(F)(F)F)C(=O)O | null | null | CO.C(C)(=O)OCC | C-C Coupling | OtherReaction | d74d0a5acd645dfea30de269d8ab70a6ac661872218a71741d60c7576a9da318 | 0b74b52e4fc5005a147b20905d595c7c40dd6bccfebbd593743baf9abee3e9c4 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[NH2;D1;+0:7]-[CH2;D2;+0:8]-[C:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[CH3;D1;+0:12]-[C:11]-[C:10]-[C:9]-[CH;D3;+0:8](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0... | null | [] | null | null | 8 | HOUR | Methyl trifluoroacetate (513 μL, 5.10 mmoles) and triethylamine (474 μL, 3.40 mmoles) were added to a suspension of aminocaproic acid (455 mg, 3.40 mmoles) in methanol (2 mL). After the mixture was stirred vigorously for 8 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | null | HO- | CO.C(C)(=O)OCC | null | 8 | COC(=O)C(F)(F)F.NCCCCCC(=O)O>CO.C(C)(=O)OCC>CCCCC(NC(=O)C(F)(F)F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95720159bc9c4e74bfd87770a2679b41 | COC(=O)C(F)(F)F.N[C@@H](Cc1ccc(C(=O)c2ccccc2)cc1)C(=O)O>>O=C(c1ccccc1)c1ccc(C[C@H](NC(=O)C(F)(F)F)C(=O)O)cc1 | Cl.FC(C(=O)OC)(F)F.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)C1=CC=C(C[C@H](N)C(=O)O)C=C1>>FC(C(=O)N[C@@H](CC1=CC=C(C=C1)C(C1=CC=CC=C1)=O)C(=O)O)(F)F | CO[C:16](=[O:17])[C:18]([F:19])([F:20])[F:21].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]([CH2:13][C@H:14]([NH2:15])[C:22](=[O:23])[OH:24])[cH:25][cH:26]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]([CH2:13][C@H:14]([NH:15][C:16](=[O:17])[C:18]([F:19])(... | COC(=O)C(F)(F)F.N[C@@H](Cc1ccc(C(=O)c2ccccc2)cc1)C(=O)O | O=C(c1ccccc1)c1ccc(C[C@H](NC(=O)C(F)(F)F)C(=O)O)cc1 | null | null | CO.C(C)(=O)OCC | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(c1ccccc1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | 18.3 | [{"value": 18.0, "product": "FC(C(=O)N[C@@H](CC1=CC=C(C=C1)C(C1=CC=CC=C1)=O)C(=O)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.3, "product": "FC(C(=O)N[C@@H](CC1=CC=C(C=C1)C(C1=CC=CC=C1)=O)C(=O)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Methyl trifluoroacetate (89.6 μL, 891 μmoles) and triethylamine (104 μL, 743 μmoles) were added to a suspension of 4-benzoylphenylalanine (200 mg, 743 μmoles) in methanol (0.5 mL). The reaction was stirred vigorously for 24 h and then acidified with 1 N HCl until a pH of 2 was obtained. The mixture was added to ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CO.C(C)(=O)OCC | null | 24 | COC(=O)C(F)(F)F.N[C@@H](Cc1ccc(C(=O)c2ccccc2)cc1)C(=O)O>CO.C(C)(=O)OCC>O=C(c1ccccc1)c1ccc(C[C@H](NC(=O)C(F)(F)F)C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c54cdbd8852148ac91f1b58babbae954 | CCOC(=O)c1cc2ccc(Cl)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>>CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | C(C)OC(=O)C1=CC=2C(=NC(=CC2)Cl)N1.CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1S(O[C@H](C1)C)(=O)=O>>C(C)OC(=O)C1=CC=2C(=NC(=CC2)Cl)N1[C@@H](CNC(=O)OC(C)(C)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[n:13][c:14]2[nH:15]1.O=S1(=O)O[C@@H:16]([CH3:17])[CH2:18][N:19]1[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[n:13][c:14]2[n:15]1[C@H:16]([CH3:17])[CH2... | CCOC(=O)c1cc2ccc(Cl)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1 | CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d1951b105958c0224d72add1f759995b14a1e0275bebbc04056db815a7f30cd1 | 34de9d8e288ec5d28c4b93823449d6a6677a5117e7f900876f17de38589f2b84 | c1cnc2[nH]ccc2c1 | O=S1(=O)-O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3]-[N;H0;D3;+0:4]-1-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:21]):[nH;D2;+0:22]:1>>[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:... | 98 | [{"value": 98.0, "product": "C(C)OC(=O)C1=CC=2C(=NC(=CC2)Cl)N1[C@@H](CNC(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 3.0 g (13.3 mmol) 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester in 70 ml N,N-dimethylformamide was cooled to 0 deg C. and 1.58 g (14.0 mmol) potassium tert-butoxide was added. After 30 min, 3.49 g (14.7 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl est... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Sulfamate | Carbamic ester | c1cnc2[nH]ccc2c1.C1COS[NH]1 | c1ccc2cc[nH]c2n1 | c1ccc2cc[nH]c2n1 | Other | CN(C=O)C | null | 0.5 | CCOC(=O)c1cc2ccc(Cl)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>CN(C=O)C>CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c012507fc04e49d28877f9bb49e6f4c1 | CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C>>C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21 | C(C)OC(=O)C1=CC=2C(=NC(=CC2)Cl)N1[C@@H](CNC(=O)OC(C)(C)C)C.FC(C(=O)O)(F)F.C([O-])([O-])=O.[K+].[K+]>>ClC=1N=C2N3[C@@H](CNC(C3=CC2=CC1)=O)C | CCO[C:5](=[O:6])[c:7]1[cH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[n:14][c:15]2[n:16]1[C@H:2]([CH3:1])[CH2:3][NH:4]C(=O)OC(C)(C)C>>[CH3:1][C@@H:2]1[CH2:3][NH:4][C:5](=[O:6])[c:7]2[cH:8][c:9]3[cH:10][cH:11][c:12]([Cl:13])[n:14][c:15]3[n:16]21 | CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21 | null | null | ClCCl.O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 980646861e090cb1209472fbff7ee587a3d7e2281610da63909549c3b75f47df | b0e3e4341a5ddf0d97948d9b8973adb58a5f8a4ab6888767daa512773c94bb45 | O=C1NCCn2c1cc1cccnc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]-[C:7]-[NH;D2;+0:8]-C(=O)-O-C(-C)(-C)-C):[c:9]:[#7;a:10]>>[#7;a:10]:[c:9]:[#7;a:5]1:[c:3](:[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6]-1 | null | [] | null | null | 2.5 | HOUR | A solution of 6.70 g (17.5 mmol) (R)-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester in 80 ml dichloromethane was cooled to 0 deg C. and 27 ml (0.35 mol) trifluoroacetic acid were added over 4 min. The cooling bath was removed and after 1 h the volatile com... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Secondary amide | null | c1cnc2c(c1)cc1n2CCNC1 | c1cnc2c(c1)cc1n2CCNC1 | HO- | ClCCl.O.C(C)(=O)OCC | null | 2.5 | CCOC(=O)c1cc2ccc(Cl)nc2n1[C@H](C)CNC(=O)OC(C)(C)C>ClCCl.O.C(C)(=O)OCC>C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0aa2ac51ea084ae5878736e83d8c7556 | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Cl)nc3N21 | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)Cl.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Cl | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][c:13]2[cH:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[n:20][c:21]3[n:22]21>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[n:20][c:21]3[N:22... | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Cl)nc3N21 | null | null | C(C)(=O)O | Reduction | OtherReaction | 3588f906d3b64048c6516264d01ca70a6d91527fcaf2de3139c67085dae9a866 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cnc2c(c1)C[C@@H]1CNCCN21 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14](:[#7;a:15]:[c:16]):[n;H0;D3;+0:17]:2-[C:18](-[C;D1;H3:19])-[C:20]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C@H;D3;+0:10]2-[CH2;D2... | 65.7 | [{"value": 65.7, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.65 g (2.0 mmol) (R)-6-chloro-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 10 ml acetic acid was added 0.64 g (10.1 mmol) sodium cyano borohydride. After 3 h the reaction mixture was poured into 10% aqueous sodium carbonate solution and extracted twice with ethy... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | null | C(C)(=O)O | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21>C(C)(=O)O>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Cl)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0b2eccfe6484bd781c52236855a5bd0 | CCOC(=O)c1cc2ccc(Br)nc2n1C(=O)OC(C)(C)C>>CCOC(=O)c1cc2ccc(Br)nc2[nH]1 | CCOC(=O)C1=CC=2C(=NC(=CC2)Br)N1C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1 | CC(C)(C)OC(=O)[n:15]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]2[nH:15]1 | CCOC(=O)c1cc2ccc(Br)nc2n1C(=O)OC(C)(C)C | CCOC(=O)c1cc2ccc(Br)nc2[nH]1 | null | null | ClCCl | Reduction | Boc amine deprotection | f701b9ee5aae8f5e2160be9618f00214bf46da08143bc69a5c09f14d92e091fb | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1cnc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4]):[c:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[c:7]1:[c:6]:[c:5]:[c:2](:[#7;a:3]:[c:4]):[nH;D2;+0:1]:1 | 95.5 | [{"value": 95.5, "product": "C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The solution of 18.4 g (0.05 mol) 6-bromo-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 165 ml dichloromethane was cooled to 0 deg C. and then 38.0 ml trifluoroacetic acid was added within 5 min. The cooling bath was removed and after 2 h at room temperature the reaction mixture was p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1ccc2cc[nH]c2n1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HO- | ClCCl | null | null | CCOC(=O)c1cc2ccc(Br)nc2n1C(=O)OC(C)(C)C>ClCCl>CCOC(=O)c1cc2ccc(Br)nc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a9a89ab74244856b7ae661c9abb9021 | CCOC(=O)c1cc2ccc(Br)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>>CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1.CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1S(O[C@H](C1)C)(=O)=O>>C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1[C@@H](CNC(=O)OC(C)(C)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]2[nH:15]1.O=S1(=O)O[C@@H:16]([CH3:17])[CH2:18][N:19]1[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]2[n:15]1[C@H:16]([CH3:17])[CH2... | CCOC(=O)c1cc2ccc(Br)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1 | CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d1951b105958c0224d72add1f759995b14a1e0275bebbc04056db815a7f30cd1 | 34de9d8e288ec5d28c4b93823449d6a6677a5117e7f900876f17de38589f2b84 | c1cnc2[nH]ccc2c1 | O=S1(=O)-O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3]-[N;H0;D3;+0:4]-1-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:21]):[nH;D2;+0:22]:1>>[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:... | null | [] | null | null | null | null | This compound was prepared in analogy to Example 1, intermediate a) from 6-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester, potassium tert-butoxide and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Sulfamate | Carbamic ester | c1cnc2[nH]ccc2c1.C1COS[NH]1 | c1ccc2cc[nH]c2n1 | c1ccc2cc[nH]c2n1 | Other | null | null | null | CCOC(=O)c1cc2ccc(Br)nc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>>CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e07af560f18e4cd3afc3bb14e37b2cbe | CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C>>C[C@@H]1CNC(=O)c2cc3ccc(Br)nc3n21 | ClC=1N=C2N3[C@@H](CNC(C3=CC2=CC1)=O)C.C(C)OC(=O)C1=CC=2C(=NC(=CC2)Br)N1[C@@H](CNC(=O)OC(C)(C)C)C>>BrC=1N=C2N3[C@@H](CNC(C3=CC2=CC1)=O)C | CCO[C:5](=[O:6])[c:7]1[cH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[n:14][c:15]2[n:16]1[C@H:2]([CH3:1])[CH2:3][NH:4]C(=O)OC(C)(C)C>>[CH3:1][C@@H:2]1[CH2:3][NH:4][C:5](=[O:6])[c:7]2[cH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[n:14][c:15]3[n:16]21 | CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C | C[C@@H]1CNC(=O)c2cc3ccc(Br)nc3n21 | null | null | null | Miscellaneous | OtherReaction | 980646861e090cb1209472fbff7ee587a3d7e2281610da63909549c3b75f47df | b0e3e4341a5ddf0d97948d9b8973adb58a5f8a4ab6888767daa512773c94bb45 | O=C1NCCn2c1cc1cccnc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]-[C:7]-[NH;D2;+0:8]-C(=O)-O-C(-C)(-C)-C):[c:9]:[#7;a:10]>>[#7;a:10]:[c:9]:[#7;a:5]1:[c:3](:[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6]-1 | null | [] | null | null | null | null | This compound was prepared in analogy to Example 1, intermediate b) from (R)-6-bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Secondary amide | null | c1cnc2c(c1)cc1n2CCNC1 | c1cnc2c(c1)cc1n2CCNC1 | HO- | null | null | null | CCOC(=O)c1cc2ccc(Br)nc2n1[C@H](C)CNC(=O)OC(C)(C)C>>C[C@@H]1CNC(=O)c2cc3ccc(Br)nc3n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a8b29b5053c40f587e0586b30fa4d8a | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | ClC=1N=C2N3[C@@H](CNC(C3=CC2=CC1)=O)C.C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][c:13]2[cH:14][c:15]3[cH:16][cH:17][c:18]([Br:19])[n:20][c:21]3[n:22]21>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([Br:19])[n:20][c:21]3[N:22... | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | null | null | null | Reduction | OtherReaction | 3588f906d3b64048c6516264d01ca70a6d91527fcaf2de3139c67085dae9a866 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cnc2c(c1)C[C@@H]1CNCCN21 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14](:[#7;a:15]:[c:16]):[n;H0;D3;+0:17]:2-[C:18](-[C;D1;H3:19])-[C:20]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C@H;D3;+0:10]2-[CH2;D2... | null | [] | null | null | null | null | This compound was prepared in analogy to Example 2, intermediate b) from (R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium cyano borohydride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | null | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e857f4086cd4f5592763c9b4669cb23 | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H]2Cc3ccc(Br)nc3N21 | ClC=1N=C2N3[C@@H](CNC(C3=CC2=CC1)=O)C.C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][c:13]2[cH:14][c:15]3[cH:16][cH:17][c:18]([Br:19])[n:20][c:21]3[n:22]21>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([Br:19])[n:20][c:21]3[N:2... | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H]2Cc3ccc(Br)nc3N21 | null | null | null | Reduction | OtherReaction | de3c416747686331d778a59a4f8f34c899868ed1590a5b701d48a91c8320a205 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cnc2c(c1)C[C@H]1CNCCN21 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14](:[#7;a:15]:[c:16]):[n;H0;D3;+0:17]:2-[C:18](-[C;D1;H3:19])-[C:20]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C@@H;D3;+0:10]2-[CH2;D... | null | [] | null | null | null | null | This compound was prepared in analogy to Example 2, intermediate b) from (R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium cyano borohydride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)C[C@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@H]1C[NH]CCN21 | null | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H]2Cc3ccc(Br)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45ca063676444665b7e575b5a775cc21 | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>>Cc1ccc2cc3n(c2n1)[C@H](C)CN(C(=O)OC(C)(C)C)C3 | [OH-].[Na+].C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C([O-])([O-])=O.[Na+].[Na+].CB1OB(OB(O1)C)C>>C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)C | Br[c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[n:8]([c:9]2[n:10]1)[C@H:11]([CH3:12])[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22]3>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[n:8]([c:9]2[n:10]1)[C@H:11]([CH3:12])[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22]3 | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21 | Cc1ccc2cc3n(c2n1)[C@H](C)CN(C(=O)OC(C)(C)C)C3 | 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 | C1CCOC1.COCCOC | Functional Group Interconversion | OtherReaction | fe223930198a3c5184e5893c54ed9eeda7d7c8a49947cece167900cc4407ed6f | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cnc2c(c1)cc1n2CCNC1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](:[c:8])-[C:9]>>[C:9]-[#7;a:7](:[c:8]):[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[C;D1;H3:10]):[c:6]:[c:5]:[c:4]:1 | 71.1 | [{"value": 71.1, "product": "C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 0.20 g (0.55 mmol) (R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate a) in 10 ml 1,2-dimethoxyethane was added 63 mg (55 μmol) tetrakis(triphenylphosphine)palladium. After 30 min, 5 ml saturated aqueous sodium carbonate solution and 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)cc1n2CC[NH]C1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.COCCOC | null | 0.5 | C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21>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.C1CCOC1.COCCOC>Cc1ccc2cc3n(c2n1)[C@H](C)CN(C(=O)OC(C)(C)C)C3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e401693ea07b49d8b2d0052599bf9d7b | CCB(CC)CC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>CCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | O.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)B(CC)CC.C([O-])([O-])=O.[K+].[K+].C(C)B(CC)CC>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CC | CCB(CC)[CH2:2][CH3:1].Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[N:9]1[C@H:10]([CH2:11]2)[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][C@H:22]1[CH3:23]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[N:9]1[C@H:10]([CH2:11]2)[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19... | CCB(CC)CC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | CCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | Cl[Pd]Cl.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | C1CCOC1.CN(C=O)C | C-C Coupling | OtherReaction | e617b556b59849d2e84a070e62a218de42a40fe6a1282b7371d9b2a4651abbda | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].C-C-B(-C-C)-[CH2;D2;+0:7]-[C;D1;H3:8]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:7]-[C;D1;H3:8]):[c:5]:[c:6] | 89.5 | [{"value": 89.5, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 0.70 g (1.90 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 14 ml N,N-dimethylformamide was added 73.0 mg [1,1′-bis(diphenyphosphino)ferrocene]-dichloropalladium(II) and after 15 min, 4.8 ml of a 1M triethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr.B | Cl[Pd]Cl.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C1CCOC1.CN(C=O)C | null | 0.25 | CCB(CC)CC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>Cl[Pd]Cl.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C1CCOC1.CN(C=O)C>CCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9de31a32fdc4c3f897713ad2e8c473b | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.O=C([O-])C(F)(F)F>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(F)(F)F)nc3N21 | C(C)(=O)OCC.O.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.FC(C(=O)[O-])(F)F.[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(F)(F)F | Brc1[cH:17][cH:16][c:15]2[c:24]([n:23]1)[N:25]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2.O=[C:18]([O-])[C:19]([F:20])([F:21])[F:22]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.O=C([O-])C(F)(F)F | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(F)(F)F)nc3N21 | null | [Cu](I)I | CN1C(CCC1)=O | Miscellaneous | OtherReaction | ce373e47514e8a459021808ec054a1c76779582dd6ee06da5ff855e079f71e0c | f004e58a958e83ed69c0f163c54d2c11d46ff03ec9dbfbb5a519e7e4cb2f94a4 | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4](:[n;H0;D2;+0:5]:1)-[#7:6](-[C:7])-[C:8].O=[C;H0;D3;+0:9](-[O-])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[C:7]-[#7:6](-[C:8])-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[n;H0;D2;+0:5]:1 | 27.7 | [{"value": 27.7, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 0.8 g (2.17 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 12 ml 1-methyl-2-pyrrolidone, 2.36 g (17.4 mmol) sodium trifluoroacetate was added. After a solution had formed, 1.65 g (8.7 mmol) copper iodide wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Br- | [Cu](I)I.CN1C(CCC1)=O | null | 2 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.O=C([O-])C(F)(F)F>[Cu](I)I.CN1C(CCC1)=O>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(F)(F)F)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90af6704e9c3417f9f4a191d574bb4d4 | C#CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C4CC4)nc3N21 | C12CCCC(CCC1)B2.C(C#C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C1CC1 | Br[CH2:21][C:20]#[CH:19].Br[c:18]1[cH:17][cH:16][c:15]2[c:23]([n:22]1)[N:24]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([C... | C#CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C4CC4)nc3N21 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | dea767f72d7a33d088e63eed048a0b1430ddeba68f366a76ef874757f7955b00 | 82709ffa7c42000a782cc2e52b480a4cd9032daa935d44c8267a1409cb7c73da | c1cc2c(nc1C1CC1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C;H0;D2;+0:2]#[CH;D1;+0:3].Br-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]-[#7:7]):[c:8]:[c:9]>>[#7:7]-[c:6]:[#7;a:5]:[c;H0;D3;+0:4](-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[CH2;D2;+0:1]-1):[c:8]:[c:9] | 35.2 | [{"value": 35.2, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C1CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 150.0 mg (1.23 mmol) 9-borabicyclo[3.3.1]nonane and 47 μl (0.62 mmol) propargyl bromide in 1 ml tetrahydrofuran was heated to reflux for 2 h. The mixture was cooled to room temperature then 0.61 ml (1.83 mmol) of a degassed 3M sodium hydroxide solution was added and after 1 h a mixture of 0.20 g (0.54 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Alkyne | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CC1 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CC1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(C)(=O)OCC.O1CCCC1 | null | null | C#CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(C)(=O)OCC.O1CCCC1>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C4CC4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7a4f3c997774bd4bc1869e396fb93b7 | C=CC(=O)OCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C=C)(=O)OCC.C(C)(=O)[O-].[Na+].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C=CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([n:13]1)[N:14]1[C@H:15]([CH2:16]2)[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][C@H:27]1[CH3:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([n:13]1)[N:14]1[C@H:15]([CH2... | C=CC(=O)OCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | [CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+] | C1(=CC=CC=C1)C | C-C Coupling | Heck terminal vinyl | 4dad991d2b32e9f4dfc4ed419a9977a70c8dfea43eb1d4c57f720c77feaa26a8 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH2;D1;+0:12]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH;D2;+0:12]=[C:11]-[C:9](=[O;D1;H0:10])-[#8:8]-[C:7]):[c:5]:[c:6] | 91.2 | [{"value": 91.2, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C=CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.0 g (2.71 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) and 0.36 ml (3.25 mmol) ethyl acrylate in 30 ml toluene were added 0.67 g (8.15 mmol) sodium acetate, 82.6 mg (0.27 mmol) tri(o-tolyl)phosphine and 0.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | [CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].C1(=CC=CC=C1)C | null | null | C=CC(=O)OCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].C1(=CC=CC=C1)C>CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c76cc796d2ea4b6895678bcd5aed63a0 | CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21 | C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[K+].C(C)(=O)OCC.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C=CC(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CCCO | CCO[C:21]([CH:20]=[CH:19][c:18]1[cH:17][cH:16][c:15]2[c:24]([n:23]1)[N:25]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2)=[O:22]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:... | CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21 | null | null | C(C)OCC | Reduction | OtherReaction | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]-[#7:9]>>[#7:9]-[c:8]:[#7;a:7]:[c:5](-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:6] | 50.5 | [{"value": 50.5, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 245.0 mg (0.63 mmol) (4R,9aR)-6-(2-ethoxycarbonyl-vinyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 12, intermediate) in 10 ml diethyl ether were added 50.0 mg (1.32 mmol) lithium aluminium hydride. After 2 h the reaction mixture was poured into s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Other | C(C)OCC | null | null | CCOC(=O)C=Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>C(C)OCC>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-660832ee65134c9f8989cfb890244cdf | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21>>COCCCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | CI.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CCCO.[H-].[Na+].O.CI>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CCCOC | I[CH3:1].[OH:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([n:11]1)[N:12]1[C@H:13]([CH2:14]2)[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][C@H:25]1[CH3:26]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([n:11]1)[N:12]1[C@H:13]([CH2:14]2)[CH2:15][N:16]([C:17](=... | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21 | COCCCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31b37b19ff6de58cf584e89bae19f862b01d058b473835fea10bbd4c0a53fd14 | f3e76c16e7df5a83f618c93f8745117d548e410efce45e89753f2c180a9b20f8 | c1cnc2c(c1)C[C@@H]1CNCCN21 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[OH;D1;+0:4]>>[C:2]-[C:3]-[O;H0;D2;+0:4]-[CH3;D1;+0:1] | 73.9 | [{"value": 73.9, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 160.0 mg (0.46 mmol) (4R,9aR)-6-(3-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 4 ml tetrahydrofuran was cooled to 0 deg C. and treated with 24.0 mg (0.51 mmol, 60% dispersion in mineral oil) sodium hydride. After 30 min 32 μl (0.51 mmol) met... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HI | O1CCCC1 | null | 8 | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CCCO)nc3N21>O1CCCC1>COCCCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22ed86cfb9ec4e0589ebac4532874db4 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C#N)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.[Cu]C#N>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C#N | Br[c:18]1[cH:17][cH:16][c:15]2[c:22]([n:21]1)[N:23]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([C:19]#[N:20])[n:21][c:22]3... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C#N)nc3N21 | null | [C-]#N.C(C)[N+](CC)(CC)CC.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O1CCOCC1 | Miscellaneous | OtherReaction | 1ad010d68d2cf3fc2c4c6afb45d15699c60a94e569f723de2590f8997ee1f3e8 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:5]:[c:6] | 98.4 | [{"value": 98.4, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 0.20 g (0.54 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 5 ml dioxane were added 195.0 mg (2.17 mmol) copper(I)cyanide, 22.5 mg (22 μmol) tris(dibenzylideneacetone)dipalladium(0), 48.2 mg (87 μmol) 1,1′-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Br- | [C-]#N.C(C)[N+](CC)(CC)CC.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1 | null | 1.5 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>[C-]#N.C(C)[N+](CC)(CC)CC.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1>C[C@@H]1CN(C(=O)OC... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8430ae839444098ab6a91097b86fa43 | CCOC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | O.C(C)(=O)OCC.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)N(CC)CC>>COC(=O)C=1N=C2N3[C@@H](CN(C[C@H]3CC2=CC1)C(=O)OC(C)(C)C)C | C[CH2:1][O:2][C:3](C)=[O:4].Br[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@H:24]1[CH3:25]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:... | CCOC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CO.[Cl-].[Na+].O | C-C Coupling | OtherReaction | 8a3c0bd6355491b24af5ada37a407cb52a1fe65c2737a92a816d4dca725c9d46 | d10596a8c19a2f73e75b45831843b0167b833766de35d70e5c827a0edd11483e | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].C-[CH2;D2;+0:7]-[#8:8]-[C;H0;D3;+0:9](-C)=[O;D1;H0:10]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[#8:8]-[CH3;D1;+0:7]):[c:5]:[c:6] | 74.4 | [{"value": 74.4, "product": "COC(=O)C=1N=C2N3[C@@H](CN(C[C@H]3CC2=CC1)C(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 6.0 g (16.3 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 60 ml methanol were added 0.57 g (0.8 mmol) and 3.4 ml (2.5 g, 24.4 mmol) triethylamine and the reaction mixture was stirred at 80 deg C. for 24 h ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | CO.[Cl-].[Na+].O | null | 24 | CCOC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>CO.[Cl-].[Na+].O>COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4c8a7c4280e4f479284330e5332aff7 | COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | COC(=O)C=1N=C2N3[C@@H](CN(C[C@H]3CC2=CC1)C(=O)OC(C)(C)C)C.[H-].C(C(C)C)[Al+]CC(C)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO | CO[C:19]([c:18]1[cH:17][cH:16][c:15]2[c:22]([n:21]1)[N:23]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2)=[O:20]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2:19][OH:... | COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]-[#7:7]>>[#7:7]-[c:6]:[#7;a:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | 67.3 | [{"value": 67.3, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4.2 g (12.1 mmol) (4R,9aR)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester in 100 ml tetrahydrofuran was cooled to 0 deg C. and treated dropwise with 48.4 ml diisobutylaluminium hydride (48.4 mmol; 1M solution in THF). The cooling bath was rem... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Other | O1CCCC1 | null | null | COC(=O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>O1CCCC1>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c60f96f3dfe4af09a1a02a0d2d06a2f | BrCC1CC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CC4)nc3N21 | BrCC1CC1.C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.[H-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCC1CC1 | Br[CH2:21][CH:22]1[CH2:23][CH2:24]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2:19][OH:20])[n:25][c:26]3[N:27]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3... | BrCC1CC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CC4)nc3N21 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cc2c(nc1COCC1CC1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#7;a:5]:[c:6]-[C:7]-[OH;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | 67.1 | [{"value": 67.1, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCC1CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 1.2 g (37.6 mmol) (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 30 ml N,N-dimethylformamide was added 0.18 g (41.4 mmol) sodium hydride. After 30 min 0.72 ml (1.01 g, 75.2 mmol) (bromomethyl)cyclopropane was added and the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CC1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 3 | BrCC1CC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>CN(C=O)C.C(C)(=O)OCC>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CC4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec280414291745f18f96f4f9f83936e4 | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>COCCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.[H-].[Na+].COCCBr>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCOC | Br[CH2:4][CH2:3][O:2][CH3:1].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]2)[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH3:27]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]2)[CH2:16][N... | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | COCCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7;a:4]:[c:5]-[C:6]-[OH;D1;+0:7]>>[#7;a:4]:[c:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[#8:3] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 15 intermediate c), from (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and 2-bromoethyl methyl ether.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | null | null | null | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>COCCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3096397b79924ba2b3dce04ecbaf743c | CCOC(=O)c1cc2cccnc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>>CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C | C(C)OC(=O)C1=CC=2C(=NC=CC2)N1.CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1S(O[C@H](C1)C)(=O)=O>>C(C)OC(=O)C1=CC=2C(=NC=CC2)N1[C@@H](CNC(=O)OC(C)(C)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[nH:14]1.O=S1(=O)O[C@@H:15]([CH3:16])[CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[n:14]1[C@H:15]([CH3:16])[CH2:17][NH:18][C:19... | CCOC(=O)c1cc2cccnc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1 | CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2df9a9c5f0820d04afaf4a0a0b292eab7ec40867851e37e8d6d095fc461acbde | 34de9d8e288ec5d28c4b93823449d6a6677a5117e7f900876f17de38589f2b84 | c1cnc2[nH]ccc2c1 | O=S1(=O)-O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3]-[N;H0;D3;+0:4]-1-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:21]):[nH;D2;+0:22]:1>>[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[c:18]:[c:19](:[#7;a:20]:[c:... | null | [] | null | null | null | null | This compound was prepared in analogy to Example 1 intermediate a), from 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester, potassium tert-butoxide and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Sulfamate | Carbamic ester | c1cnc2[nH]ccc2c1.C1COS[NH]1 | c1cc2cccnc2[nH]1 | c1cc2cccnc2[nH]1 | Other | null | null | null | CCOC(=O)c1cc2cccnc2[nH]1.C[C@H]1CN(C(=O)OC(C)(C)C)S(=O)(=O)O1>>CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba91640e69894163ae5a9e5f20c566cd | CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C>>C[C@@H]1CNC(=O)c2cc3cccnc3n21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)OC(=O)C1=CC=2C(=NC=CC2)N1[C@@H](CNC(=O)OC(C)(C)C)C>>C[C@@H]1CNC(C2=CC3=CC=CN=C3N12)=O | CCO[C:5](=[O:6])[c:7]1[cH:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[n:15]1[C@H:2]([CH3:1])[CH2:3][NH:4]C(=O)OC(C)(C)C>>[CH3:1][C@@H:2]1[CH2:3][NH:4][C:5](=[O:6])[c:7]2[cH:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:14]3[n:15]21 | CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C | C[C@@H]1CNC(=O)c2cc3cccnc3n21 | null | null | null | Miscellaneous | OtherReaction | 980646861e090cb1209472fbff7ee587a3d7e2281610da63909549c3b75f47df | b0e3e4341a5ddf0d97948d9b8973adb58a5f8a4ab6888767daa512773c94bb45 | O=C1NCCn2c1cc1cccnc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]-[C:7]-[NH;D2;+0:8]-C(=O)-O-C(-C)(-C)-C):[c:9]:[#7;a:10]>>[#7;a:10]:[c:9]:[#7;a:5]1:[c:3](:[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6]-1 | null | [] | null | null | null | null | This compound was prepared in analogy to Example 1 intermediate b), from (R)-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-pyrrolo [2,3-b]pyridine-2-carboxylic acid ethyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Secondary amide | null | c1cnc2c(c1)cc1n2CCNC1 | c1cnc2c(c1)cc1n2CCNC1 | HO- | null | null | null | CCOC(=O)c1cc2cccnc2n1[C@H](C)CNC(=O)OC(C)(C)C>>C[C@@H]1CNC(=O)c2cc3cccnc3n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03aca9a6eb014e909cc8f2829b9f72fc | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)CC2Cc3cccnc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1CC2=CC3=CC=CN=C3N2[C@@H](C1)C.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1CC2CC3=CC=CN=C3N2[C@@H](C1)C | Br[c:18]1[cH:17][cH:16][c:15]2[c:20]([n:19]1)[N:21]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18][n:19][c:20]3[N:21]12 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)CC2Cc3cccnc3N21 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | f9279971d86d9444594a7e21aa775d3f8f6ef2632d9e34346ec762d79f24bc4d | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cnc2c(c1)CC1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6]>>[#7:4]-[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:5]:[c:6] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 2 intermediate b), from (R)-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium cyano borohydride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)CC1C[NH]CCN21 | c1cnc2c(c1)CC1C[NH]CCN21 | Br- | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)CC2Cc3cccnc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89d931138c0b4e07bc6f2a3eb238b96d | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.N=C(c1ccccc1)c1ccccc1>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C1=CC=CC=C1)(C1=CC=CC=C1)=N.C([O-])(O)=O.[Na+].CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)N=C(C1=CC=CC=C1)C1=CC=CC=C1 | Br[c:18]1[cH:17][cH:16][c:15]2[c:34]([n:33]1)[N:35]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.N=C(c1ccccc1)c1ccccc1 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | cb8ea748659c76f4a076bd2db847e7a5b6bf41f45707ae143a775a7f11f91e13 | d6fdf3485f414343350878d3990b407f7838ca1f9344576c0f428d9ed6db7945 | c1ccc(C(=Nc2ccc3c(n2)N2CCNC[C@H]2C3)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[NH;D1;+0:7]=[C:8](-[c:9])-[c:10]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D2;+0:7]=[C:8](-[c:9])-[c:10]):[c:5]:[c:6] | 94.3 | [{"value": 94.3, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)N=C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture consisting of 0.20 g (0.54 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, 91 μl (0.54 mmol) benzophenone imine, 73.0 mg (0.76 mmol) sodium tert-butoxide, 5.6 mg (0.01 mmol) tris(dibenzylideneacetone)dipalladium chloroform complex and 10.1 mg (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted imine | Substituted imine | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.c1ccccc1.c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.N=C(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9420b90e3c944f184dd1ad0a0878ab9 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)N=C(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)N | c1ccc(C(c2ccccc2)=[N:19][c:18]2[cH:17][cH:16][c:15]3[c:21]([n:20]2)[N:22]2[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14]3)cc1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N)nc3N21 | null | [Pd] | CO | Miscellaneous | OtherReaction | fe28e0513c54643a2e998df32fe9ad14c978580c0e1fa51268908e5a62d5d818 | 69d38cb38c5a54a23121b1c97287244fbbd5b6f97c6a1faf8cb1a05e149dd1cc | c1cnc2c(c1)C[C@@H]1CNCCN21 | [#7:1]-[c:2]:[#7;a:3]:[c:4](-[N;H0;D2;+0:5]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:6]>>[#7:1]-[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6] | 58.9 | [{"value": 58.9, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 0.23 g (0.49 mmol) (4R,9aR)-6-(benzhydrylidene-amino)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 2.5 ml methanol were added 0.46 g (7.4 mmol) ammonium formate and 104 mg (0.05 mmol) 5% palladium on charcoal and the suspension was stirred for 1 h at 60 d... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Primary amine | c1ccccc1.c1ccccc1 | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Other | [Pd].CO | null | 1 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N=C(c4ccccc4)c4ccccc4)nc3N21>[Pd].CO>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(N)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9c2ecbcaca9440d991fda79c7080583 | CN(C)C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21>>C[C@@H]1CN(C(=O)O)Cc2c(C=O)c3ccc(Cl)nc3n21 | CN(C=O)C.P(=O)(Cl)(Cl)Cl.C(C)(C)(C)OC(=O)N1CC2=CC3=CC=C(N=C3N2[C@@H](C1)C)Cl.CN(C=O)C>>ClC=1N=C2N3[C@@H](CN(CC3=C(C2=CC1)C=O)C(=O)O)C | CN(C)[CH:11]=[O:12].CC(C)(C)[O:7][C:5]([N:4]1[CH2:3][C@@H:2]([CH3:1])[n:20]2[c:9]([cH:10][c:13]3[cH:14][cH:15][c:16]([Cl:17])[n:18][c:19]32)[CH2:8]1)=[O:6]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[OH:7])[CH2:8][c:9]2[c:10]([CH:11]=[O:12])[c:13]3[cH:14][cH:15][c:16]([Cl:17])[n:18][c:19]3[n:20]21 | CN(C)C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21 | C[C@@H]1CN(C(=O)O)Cc2c(C=O)c3ccc(Cl)nc3n21 | null | null | null | C-C Coupling | OtherReaction | fc504f89c15901e8ffedc928baf43672f35ff5ac2eb5e0f980a0bf67f51eb4c5 | 32cfc3631d78164a01e996da5e4578450505a2fe752dc7fb153a3394324bd13f | c1cnc2c(c1)cc1n2CCNC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[#7;a:7]2:[c:8](:[#7;a:9]:[c:10]):[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:2-[C:15]-1.C-N(-C)-[CH;D2;+0:16]=[O;D1;H0:17]>>[O;D1;H0:17]=[CH;D2;+0:16]-[c;H0;D3;+0:13]1:[c:11](:[c:12]):[c:8](:[#7;a:9]:[c:10]):[#7;a:7]2:[c:14]:1-[C:15]-[#7:4](-[C:2](=[O;D1;H0:3... | 55.2 | [{"value": 55.2, "product": "ClC=1N=C2N3[C@@H](CN(CC3=C(C2=CC1)C=O)C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N,N-Dimethylformamide (10 ml) was cooled to 1 deg C. and treated dropwise with 5.1 ml (56.0 mmol) phosphorus oxychloride. After the addition the temperature was again cooled to 1 deg C. and a solution of 1.0 g (3.11 mmol) (R)-6-chloro-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amide.Boc | Aldehyde.Carbamic acid | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)cc1n2CC[NH]C1 | c1cnc2c(c1)cc1n2CC[NH]C1 | Other | null | null | null | CN(C)C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Cl)nc3n21>>C[C@@H]1CN(C(=O)O)Cc2c(C=O)c3ccc(Cl)nc3n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05569ebd91214f03abdb2da47cce2309 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.OCc1ccccc1>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21 | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=C(C=C7)C)C8=CC=C(C=C8)C.C(C1=CC=CC=C1)O.[H-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1... | Br[c:18]1[cH:17][cH:16][c:15]2[c:28]([n:27]1)[N:29]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2.[OH:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.OCc1ccccc1 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 32dda3c635ec04b7d6d271ee7a833d4ba1050367b9a6734cc3e61bd879845a28 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2ccc3c(n2)N2CCNC[C@H]2C3)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[OH;D1;+0:7]-[C:8]-[c:9]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[C:8]-[c:9]):[c:5]:[c:6] | null | [] | null | null | 30 | MINUTE | To a solution of 3.0 g (8.15 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 30 ml toluene was added 0.20 g (0.29 mmol) (S)-(−)-2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl and 0.12 g (0.12 mmol) di-palladium-tris(dibenzyli... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | 0.5 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21.OCc1ccccc1>C1(=CC=CC=C1)C>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4de5f69c09a8424fa4014c420cfd14c6 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)OCC1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O | c1ccc(C[O:19][c:18]2[cH:17][cH:16][c:15]3[c:21]([n:20]2)[N:22]2[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14]3)cc1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([OH:19])[n:2... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 | null | [Pd] | CO.C(C)(=O)OCC | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1cnc2c(c1)C[C@@H]1CNCCN21 | [#7:1]-[c:2]:[#7;a:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7:1]-[c:2]:[#7;a:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3.90 g (9.86 mmol) (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 21, intermediate) in 30 ml methanol:ethyl acetate (1:1 v/v) 0.20 g 10% palladium on charcoal was added and the reaction was hydrogenated at atmospheric pressure for... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Other | [Pd].CO.C(C)(=O)OCC | null | 2 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCc4ccccc4)nc3N21>[Pd].CO.C(C)(=O)OCC>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-120c810d170145e48cb9f8656c3f06aa | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>>COc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | CI.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O.[H-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)OC | I[CH3:1].[OH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[N:9]1[C@H:10]([CH2:11]2)[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][C@H:22]1[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[N:9]1[C@H:10]([CH2:11]2)[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])... | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 | COc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1cnc2c(c1)C[C@@H]1CNCCN21 | I-[CH3;D1;+0:1].[#7:2]-[c:3]:[#7;a:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[#7:2]-[c:3]:[#7;a:4]:[c:5](-[O;H0;D2;+0:6]-[CH3;D1;+0:1]):[c:7] | null | [] | null | null | 30 | MINUTE | To a solution of 0.25 g (0.82 mmol) (4R,9aR)-6-hydroxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 2 ml N,N-dimethylformamide, 40 mg (0.90 mmol) sodium hydride (55–65% dispersion in oil) was added. After 30 min, 0.10 ml (0.23 g, 1.64 mmol) methyl iodide was added. After ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HI | CN(C=O)C | null | 0.5 | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>CN(C=O)C>COc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66a1909896b24caab495aec954787752 | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>>CCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O.[H-].[Na+].C(C)Br>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)OCC | Br[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[CH3:24]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([... | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 | CCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[c:4]:[#7;a:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#7:3]-[c:4]:[#7;a:5]:[c:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:8] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 22 intermediate b), from (4R,9aR)-6-hydroxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and ethyl bromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | null | null | null | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>>CCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-470b37aa1b554df0a01e828ed15e2e0e | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21.OCCBr>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCCO)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O.[H-].[Na+].BrCCO>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)OCCO | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([OH:19])[n:23][c:24]3[N:25]12.Br[CH2:20][CH2:21][OH:22]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:1... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21.OCCBr | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCCO)nc3N21 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[#7:4]-[c:5]:[#7;a:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:4]-[c:5]:[#7;a:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3]):[c:9] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 22 intermediate b), from (4R,9aR)-6-hydroxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and 2-bromoethanol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21.OCCBr>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(OCCO)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40073ed8883f49fdb37bae2621bbb1a1 | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>>COCCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)O.[H-].[Na+].COCCBr>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)OCCOC | Br[CH2:4][CH2:3][O:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([n:11]1)[N:12]1[C@H:13]([CH2:14]2)[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][C@H:25]1[CH3:26]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([n:11]1)[N:12]1[C@H:13]([CH2:14]2)[CH2:15][N:16]([C:17](=[O:... | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21 | COCCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]-[c:5]:[#7;a:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:4]-[c:5]:[#7;a:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:9] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 22 intermediate b), from (4R,9aR)-6-hydroxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and 2-bromoethyl methyl ether.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | null | null | null | COCCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(O)nc3N21>>COCCOc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b00a14b32cb4eb0989faf4d1d75bf10 | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>CCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.[H-].[Na+].C(C)Br>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCC | Br[CH2:2][CH3:1].[OH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@H:24]1[CH3:25]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C... | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | CCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4]-[C:5]-[OH;D1;+0:6]>>[#7;a:3]:[c:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 15 intermediate c), from (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and ethyl bromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HBr | null | null | null | CCBr.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>CCOCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43e098a75328405591d8f34e4766b09c | BrCC1CCCCC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CCCCC4)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.[H-].[Na+].BrCC1CCCCC1>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCC1CCCCC1 | Br[CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2:19][OH:20])[n:28][c:29]3[N:30]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12]... | BrCC1CCCCC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CCCCC4)nc3N21 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cc2c(nc1COCC1CCCCC1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[#7;a:5]:[c:6]-[C:7]-[OH;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 15 intermediate c), from (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and (bromomethyl)cyclohexane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CCCCC1 | HBr | null | null | null | BrCC1CCCCC1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCC4CCCCC4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a1470418a2d432e913bf306105f46ca | BrCCOC1CCCCO1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.[H-].[Na+].BrCCOC1OCCCC1>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCOC1OCCCC1 | Br[CH2:21][CH2:22][O:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:29]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2:19][OH:20])[n:30][c:31]3[N:32]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:... | BrCCOC1CCCCO1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cc2c(nc1COCCOC1CCCCO1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7;a:4]:[c:5]-[C:6]-[OH;D1;+0:7]>>[#7;a:4]:[c:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[#8:3] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 15 intermediate c), from (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and 2-(2-bromoethoxy)tetrahydro-2H-pyran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CCOCC1 | HBr | null | null | null | BrCCOC1CCCCO1.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f70284bb0ad4e6594155aded5cc3234 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCOC1OCCCC1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO | C1CCC([O:23][CH2:22][CH2:21][O:20][CH2:19][c:18]2[cH:17][cH:16][c:15]3[c:25]([n:24]2)[N:26]2[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14]3)OC1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1cnc2c(c1)C[C@@H]1CNCCN21 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3] | 71.6 | [{"value": 71.6, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To the solution of 0.16 g (0.36 mmol) (4R,9aR)-4-methyl-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxymethyl]-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3 ml methanol was added 0.136 g (0.71 mmol) para-toluenesulphonic acid. After 30 min, the solvent was removed on a rotary evaporator a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | CO | null | 0.5 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCOC4CCCCO4)nc3N21>CO>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb8ff8e70d0648c3ae6436d1841b5099 | CC(C)[CH2][Al]([CH2]C(C)C)[CH2]C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>CC(C)Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C(C)C)[Al](CC(C)C)CC(C)C.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.COCCOC.[OH-].[Na+].C(C(C)C)[Al](CC(C)C)CC(C)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CC(C)C | CC(C)[CH2][Al]([CH2]C(C)C)[CH2:1][CH:2](C)[CH3:3].O[CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@H:24]1[CH3:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14... | CC(C)[CH2][Al]([CH2]C(C)C)[CH2]C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | CC(C)Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | C-C Coupling | OtherReaction | 861590323101b9187e0da132999bd5db6e6f128995dfe411cf8248c6aee7d060 | 5086858461038ad8c4c4a388cee61b6d9e9118227e969bc00fcc5a7517669191 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-C(-C)-[CH2]-[Al](-[CH2;D2;+0:1]-[CH;D3;+0:2](-C)-[C;D1;H3:3])-[CH2]-C(-C)-C.O-[CH2;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]-[#7:9]>>[#7:9]-[c:8]:[#7;a:7]:[c:5](-[CH2;D2;+0:4]-[CH;D3;+0:2](-[C;D1;H3:3])-[CH3;D1;+0:1]):[c:6] | 76.2 | [{"value": 76.2, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 2.0 g (5.43 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 50 ml 1,2-dimethoxyethane 0.75 g (0.65 mmol) tetrakis(triphenylphosphine)palladium was added. After 20 min, 16.3 ml (16.3 mmol) triisobutylaluminiu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | null | null | 0.333333 | CC(C)[CH2][Al]([CH2]C(C)C)[CH2]C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>CC(C)Cc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a46fdafabe5249c698e36d7e815a119f | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C=O)nc3N21 | CN(C=O)C.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CO.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)(C)(C)[Li]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C=O | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2:19][OH:20])[n:21][c:22]3[N:23]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:18]([CH:19]=[O:20])... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C=O)nc3N21 | null | null | O1CCCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cnc2c(c1)C[C@@H]1CNCCN21 | [#7:1]-[c:2]:[#7;a:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7]>>[#7:1]-[c:2]:[#7;a:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7] | 40.1 | [{"value": 40.1, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2.0 g (5.43 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 15 ml tetrahydrofuran was cooled to −75 deg C. and treated with 4.40 ml (0.65 mmol) tert-butyllithium (1.5 M solution in n-pentane). After 30 min, 0.6... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | null | O1CCCC1 | null | 0.5 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CO)nc3N21>O1CCCC1>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C=O)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02cf394ff1174a2c8c2dd1ba46ed3904 | CCN(CC)S(F)(F)F.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CF)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)N(CC)S(F)(F)F>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CF | CCN(CC)S(F)(F)[F:20].OCCO[CH2:19][c:18]1[cH:17][cH:16][c:15]2[c:22]([n:21]1)[N:23]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17][c:... | CCN(CC)S(F)(F)F.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CF)nc3N21 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 6b7662b04cb434c5fe9d0583bd5f655ffda416a8f901054c2cea6807669e00d6 | 2526597d509453bcc2a938a0e6b64800134402e46803a382020459fab85a3703 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-C-C-O-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]-[#7:7]>>[#7:7]-[c:6]:[#7;a:5]:[c:3](-[CH2;D2;+0:2]-[F;H0;D1;+0:1]):[c:4] | 51.7 | [{"value": 51.7, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)CF", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 82.0 μl (0.11 g, 0.63 mmol) diethylaminosulphur trifluoride in 2 ml dichloromethane was cooled to −78 deg C. and treated with a solution of 0.20 g (0.63 mmol) (4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 15, intermed... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Tertiary amine | Primary halide | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HF | ClCCl | null | 1 | CCN(CC)S(F)(F)F.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>ClCCl>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(CF)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b99a44cabbc54b1fb8e18ab7df58ee0d | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | [Cl-].[NH4+].C(C)(C)(C)[Li].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)=O>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C)O | [CH3:1][CH:2]=[O:3].Br[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[CH3:24]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])(... | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | f2163f7cd19d59af81ad726594d3472f24b5d895933621c0a762f82441e2c0b3 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C;D1;H3:7]-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH;D3;+0:8](-[C;D1;H3:7])-[OH;D1;+0:9]):[c:5]:[c:6] | null | [] | null | null | 15 | MINUTE | A solution of 6.0 g (16.3 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 250 ml diethyl ether was cooled to −100 deg C. and treated with 11.9 ml (17.9 mmol) tert-butyllithium (1.5 M in n-pentane). After 15 min, 1.0 ml (0.79 g, 17.9 mmol) acetaldehyde ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Br- | C(C)OCC | null | 0.25 | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>C(C)OCC>CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-391941e392754a1e9238011a72cda5be | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>>C[C@H](O)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C)O.FC(C(=O)O)(F)F>>O[C@@H](C)C=1N=C2N3[C@@H](CNC[C@H]3CC2=CC1)C | CC(C)(C)OC(=O)[N:13]1[CH2:12][C@@H:11]2[N:10]([c:8]3[c:7]([cH:6][cH:5][c:4]([CH:2]([CH3:1])[OH:3])[n:9]3)[CH2:17]2)[C@H:15]([CH3:16])[CH2:14]1>>[CH3:1][C@H:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@@H:11]([CH2:12][NH:13][CH2:14][C@H:15]1[CH3:16])[CH2:17]2 | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C[C@H](O)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | null | null | ClCCl | Reduction | Boc amine deprotection | 9e539a19c640e3791557361844771d61b34639aec46582d78c8ac43e8a66b11e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | A solution of 3.09 g (9.27 mmol) (4R,9aR)-6-(1-(RS)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 38, intermediate) in 33 ml dichloromethane was cooled to 0 deg C. and treated with 8.8 ml (12.7 g, 0.11 mol) trifluoroacetic acid. The cooling bath was re... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1CNCCN21 | c1cnc2c(c1)C[C@@H]1CNCCN21 | HO- | ClCCl | null | null | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>ClCCl>C[C@H](O)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57b3fd38537f4e8580bbf0fb18d923ce | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc([C@@H](C)O)nc3N21>>CO[C@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | [Cl-].[NH4+].CI.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)[C@@H](C)O.[H-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)[C@@H](C)OC | I[CH3:1].[OH:2][C@H:3]([CH3:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@H:24]1[CH3:25]>>[CH3:1][O:2][C@H:3]([CH3:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18... | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc([C@@H](C)O)nc3N21 | CO[C@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | c1cnc2c(c1)C[C@@H]1CNCCN21 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[OH;D1;+0:6]>>[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | null | null | 30 | MINUTE | To a solution of 0.75 g (2.25 mmol) (4R,9aR)-6-(1-(R)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 ml N,N-dimethylformamide was added 0.12 g (2.70 mmol) sodium hydride (55–65% dispersion in oil). After 30 min, 0.28 ml (0.64 g, 4.50 mmol) methyl iodide was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HI | CN(C=O)C | null | 0.5 | CI.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc([C@@H](C)O)nc3N21>CN(C=O)C>CO[C@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
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