dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6b54782d3d54a7482681e2989745206 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNCC(=O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | BrCC([C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)=O.C(C)(C)O.[C@@H]1(CCCC2=CC=CC=C12)N.BrCC([C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)=O>>FC=1C=C(C[C@@H](C(CNCC2=CC(=CC=C2)OC)=O)NC(OC(C)(C)C)=O)C=C(C1)F | Br[CH2:10][C:11](=[O:12])[C@H:13]([CH2:14][c:15]1[cH:16][c:17]([F:18])[cH:19][c:20]([F:21])[cH:22]1)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].[CH3:1][CH:3]([OH:2])[CH3:4].c1c[c:31]2[c:7]([cH:6][cH:5]1)[C@@H:8]([NH2:9])CCC2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C:11](=[O:1... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr.CC(C)O.N[C@H]1CCCc2ccccc21 | COc1cccc(CNCC(=O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3581b7d91b024c9d8f21a9b657df737dbe8f8adeb35760e3ed337ec3f3466828 | a4609538d3f37322096c41cccfcd6680961cc560d17981006cedfbf8f1fba62f | O=C(CCc1ccccc1)CNCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[CH3;D1;+0:5]-[CH;D3;+0:6](-[CH3;D1;+0:7])-[OH;D1;+0:8].[NH2;D1;+0:9]-[C@H;D3;+0:10]1-C-C-C-[c;H0;D3;+0:11]2:c:c:[cH;D2;+0:12]:[c:13]:[c:14]:2-1>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[c:14]1:[c:13]:[cH;D2;+0:12]:[cH;D2;+0:7]:[c;H0;D3;+0:6](-[O;H0... | null | [] | null | null | null | null | tert-butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate (III, EXAMPLE 1, 1 equivalent) is dissolved in isopropanol and treated with 3-methoxybenzylamine (VI, 5 equivalents). The reaction is heated at reflux for 2 hours and monitored by TLC for disappearance of the ketone (III). Upon completion, the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary alcohol.Primary amine | Ketone.Ether.Secondary amine | c1ccc2c(c1)CCCC2 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNCC(=O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-248a10502437472580dade79efab34be | CCO.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)c1 | O1[C@H](C1)[C@H](CC1=CC=CC=C1)NC(OCC1=CC=CC=C1)=O.[C@@H]1(CCCC2=CC=CC=C12)N.C(C)O>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(OCC1=CC=CC=C1)=O | C[CH2:1][OH:2].C1C[C@H:8]([NH2:9])[c:7]2[cH:6][cH:5][cH:4][cH:3][c:32]2C1.[CH2:10]1[C@H:11]([C@H:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[NH:21][C:22](=[O:23])[O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[O:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]([OH:1... | CCO.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c0b5b17ac3394c5c8093fd7290c9f820512ea169bd4f38fc3d5b10f13a22ddc2 | 13cf7e1851bdd95448f362feecdb7dbbbad6007407240fb9bb9ba68898b35e75 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)OCc1ccccc1 | C-[CH2;D2;+0:1]-[OH;D1;+0:2].[C:3]-[C:4](-[#7:5]-[C:6]=[O;D1;H0:7])-[C@H;D3;+0:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1.[NH2;D1;+0:11]-[C@H;D3;+0:12]1-C-C-C-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[c:15]:[c:16]:[c:17]:[c:18]:2-1>>[C:3]-[C:4](-[#7:5]-[C:6]=[O;D1;H0:7])-[C@H;D3;+0:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[NH;D2;+0:11]-[CH2;D2... | null | [] | null | null | null | null | A mixture of benzyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate (V, 0.22 g, 0.74 mmol), 3-methoxybenzylamine (VI, 0.13 g, 0.92 mmol), and ethanol (2 mL) is stirred at reflux for 2.3 hours and then cooled and concentrated under reduced pressure. The residue is chouromatographed (silica gel; methanol/dichloromethane/am... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Primary amine | Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)CCCC2.C1CO1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCO.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d482f4816a14eb0bd2a19510aac6c7a | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.COc1cccc(CN(C[C@@H](O)[C@@H](N)Cc2ccccc2)C(=O)OC(C)(C)C)c1>>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1 | C(#N)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.N[C@H]([C@@H](CN(C(OC(C)(C)C)=O)CC1=CC(=CC=C1)OC)O)CC1=CC=CC=C1.C(C)OP(OCC)(=O)C#N.C(C)N(CC)CC>>C(#N)C=1C=C(C(=O)N[C@H]([C@@H](CN(C(OC(C)(C)C)=O)CC2=CC(=CC=C2)OC)O)CC2=CC=CC=C2)C=C(C1)C(=O)N(CCC)CCC | O[C:17]([c:16]1[cH:15][c:12]([C:13]#[N:14])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:48]1)=[O:18].[NH2:19][C@@H:20]([CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[C@H:28]([OH:29])[CH2:30][N:31]([CH2:32][c:33]1[cH:34][cH:35][cH:36][c:37]([O:38][CH3:39])[cH:40]1)[C:41](=[O:42]... | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.COc1cccc(CN(C[C@@H](O)[C@@H](N)Cc2ccccc2)C(=O)OC(C)(C)C)c1 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 65 | HOUR | To a mixture of 3-cyano-5-[(dipropylamino)carbonyl]benzoic acid (IX/XXXII, PREPARATION 7, 0.086 g, 0.314 mmol) and tert-butyl (2R,3S)-3-amino-2-hydroxy-4-phenylbutyl(3-methoxybenzyl)carbamate (XXXV, EXAMPLE 584, 0.126 g, 0.314 mmol) in dichloromethane (0.3 mL) is added diethylcyanophosphonate (0.062 g, 0.330 mmol) and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 65 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.COc1cccc(CN(C[C@@H](O)[C@@H](N)Cc2ccccc2)C(=O)OC(C)(C)C)c1>ClCCl>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd1c8afcc5204909840a2902caba583c | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1>>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | C(#N)C=1C=C(C(=O)N[C@H]([C@@H](CN(C(OC(C)(C)C)=O)CC2=CC(=CC=C2)OC)O)CC2=CC=CC=C2)C=C(C1)C(=O)N(CCC)CCC.ClCCl.Cl>>Cl.C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C#N)=O | CC(C)(C)OC(=O)[N:31]([CH2:30][C@H:28]([C@@H:20]([NH:19][C:17]([c:16]1[cH:15][c:12]([C:13]#[N:14])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:41]1)=[O:18])[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[OH:29])[CH2:32][c:33]1[cH:34][cH:35][cH:36][c:37]([O:38][CH3:39])[cH:40]1>>[... | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | 8 | HOUR | A mixture of tert-butyl (2R,3S)-3-({3-cyano-5-[(dipropylamino)carbonyl]benzoyl}amino)-2-hydroxy-4-phenylbutyl(3-methoxybenzyl)carbamate (XXXVI, EXAMPLE 585, 0.080 g, 0.122 mmol), dichloromethane (1 mL), and methanol saturated with hydrochloric acid (1 mL) is stirred for 8 hours, after which time the solvents are remove... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CO | null | 8 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(Cc2cccc(OC)c2)C(=O)OC(C)(C)C)c1>CO>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bba5ef2be2842d79d4d8719ca773bd4 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.C(C)N(CC)CC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(=O)C1=CC(=CC(=C1)C(=O)N)C(=O)N(CCC)CCC | O[C:18]([c:17]1[cH:16][c:12]([C:13]([NH2:14])=[O:15])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:42]1)=[O:19].F[c:25]1[cH:24][c:23]([CH2:22][C@H:21]([NH2:20])[C@H:29]([OH:30])[CH2:31][NH:32][CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([O:39][CH3:40])[cH:41]2)[cH:28][c:27](F)[cH:26]1>>... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | CN(C)C=O | Acylation | OtherReaction | bbb264be94a4fc72235a1eeb5059eaade41a0470bc462e3c864b07715b8e8337 | 36ad82ec23ff54b317ae61ab7073aab8c4c44a03106bdb4e02cabb6fe9023e93 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]-[C:5](-[C:6])-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9](-F):[c:10]:1.O-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15]>>[C:6]-[C:5](-[C:4]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c:10]:[cH;D2;+0:9]:[c:8]:1)-[NH;D2;+0:7]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15] | null | [] | 22.5 | CELSIUS | 3 | DAY | To a mixture of 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid (IX, PREPARATION 6, 0.18 g, 0.616 mmol) in dry DMF (16 mL) is added EDC (0.182 9, 0.9 mmol), HOBT (0.127 g, 0.9 mmol), triethylamine (0.062 g, 0.616 mol), and (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.185... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | CN(C)C=O | 22.5 | 72 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>CN(C)C=O>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8c978de386f45d793555bdd7d820963 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN1CCOCC1.N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21>>O=C(CCCC(=O)N1CCCCC1)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21 | C=1C=CC2=C(C1)N=NN2O.C(CCl)Cl.NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.Cl.N[C@H]([C@@H](CN(C(OCC1C2=CC=CC=C2C=2C=CC=CC12)=O)CC1=CC(=CC=C1)I)O)CC1=CC(=CC(=C1)F)F.CN1CCOCC1>>FC=1C=C(C=C(C1)F)C[C@@H]([C@@H](CN(C(OCC1C2=CC=CC=C2C=2C=CC=CC12)=O)CC1=CC(=CC=C1)I)O)NC(CCCC(N1CCCCC1)=O)=O | CCC[N:8]([C:6]([c:5]1cc(C(=O)O)c[c:3]([C:2](N)=[O:1])[cH:4]1)=[O:7])[CH2:9][CH2:10][CH3:11].CN1CCO[CH2:12][CH2:13]1.[NH2:14][C@@H:15]([CH2:16][c:17]1[cH:18][c:19]([F:20])[cH:21][c:22]([F:23])[cH:24]1)[C@H:25]([OH:26])[CH2:27][N:28]([CH2:29][c:30]1[cH:31][cH:32][cH:33][c:34]([I:35])[cH:36]1)[C:37](=[O:38])[O:39][CH2:40]... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN1CCOCC1.N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21 | O=C(CCCC(=O)N1CCCCC1)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21 | null | null | CN(C)C=O | Acylation | OtherReaction | cac388f056fd19b8d291e8c95cd02196574fe57bfb322e6ee0acefe66a912fe8 | 456c6f534fb693d4ef33552c275997d036b6f08ea46e1be546645f68dda57d28 | O=C(CCCC(=O)N1CCCCC1)N[C@H](CCN(Cc1ccccc1)C(=O)OCC1c2ccccc2-c2ccccc21)Cc1ccccc1 | C-C-C-[N;H0;D3;+0:1](-[C:2]-[C:3]-[CH3;D1;+0:4])-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[C;H0;D3;+0:10](-N)=[O;D1;H0:11]):c:c(-C(-O)=O):c:1.C-N1-C-C-O-[CH2;D2;+0:12]-[CH2;D2;+0:13]-1.[C:14]-[C:15](-[C:16])-[NH2;D1;+0:17]>>[C:14]-[C:15](-[C:16])-[NH;D2;+0:17]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[CH2... | null | [] | null | null | 60 | MINUTE | HOBt (81 mg, 0.6 mmole) and EDC (105 mg, 0.55 mmole) are added to 1-carboxy-5-piperdinylglutaramide (IX, 100 mg, 0.5 mmole) in DMF (2 ml). The acid is activated 60 minutes then treated with 1-9H-fluoren-9-ylmethyl (2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl(3-iodobenzyl)carbamate hydrochloride (XXXV, EXAMPLE ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amide.Tertiary amide.Primary amine.Tertiary amine | Secondary amide.Tertiary amide | c1ccccc1.C1COCCN1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=O | null | 1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN1CCOCC1.N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21>CN(C)C=O>O=C(CCCC(=O)N1CCCCC1)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN(Cc1cccc(I)c1)C(=O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-357b9e9632e94076a4cb47c31f35dba0 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(S(N)(=O)=O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCNC(=O)c1cc(C(=O)N(CCC)[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(S(N)(=O)=O)c1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C.NS(=O)(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F>>NS(=O)(=O)C=1C=C(C=C(C(=O)N(CCC)[C@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)CC2=CC=CC=C2)C1)C(=O)NCCC | O[C:10]([c:9]1[cH:8][c:7]([C:5]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:13][CH2:14][CH3:15])=[O:6])[cH:43][c:38]([S:39]([NH2:40])(=[O:41])=[O:42])[cH:37]1)=[O:11].F[c:20]1[cH:19][c:18]([CH2:17][C@H:16]([NH2:12])[C@H:24]([OH:25])[CH2:26][NH:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][c:33]([O:34][CH3:35])[cH:36]2)[cH:23][c:22](F)[... | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(S(N)(=O)=O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCNC(=O)c1cc(C(=O)N(CCC)[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(S(N)(=O)=O)c1 | null | null | CN(C)C=O | Acylation | OtherReaction | 2b34b0a76a49a17c30539e788caed9cb2c66509e428a62269dcd131c2d3a6cb6 | 7fc764d84551ecc818368ae0856b7c0691434c84863c648f0d7e0f8f36d9557c | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]-[C:5](-[C:6])-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9](-F):[c:10]:1.O-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15]:[c:16]-[C:17](=[O;D1;H0:18])-[N;H0;D3;+0:19](-[C:20]-[C:21])-[CH2;D2;+0:22]-[C:23]-[C;D1;H3:24]>>[C:6]-[C:5](-[C:4]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c:10]:[cH;D2;+0:9]:[c... | null | [] | null | null | 18 | HOUR | O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.0928 9, 0.244 mmol) is added to a mixture of, 3-(aminosulfonyl)-5-[(dipropylamino)-carbonyl]benzoic acid (XXXIX, PREPARATION 13, 0.0800 g, 0.244 mmol) and (2R,3S)-3-amino-1-[(3-methoxybenzyl)-amino]-4-phenyl-2-butanol (VIII, EXAMPLE 17... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Tertiary amide.Primary amine | Secondary amide.Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | CN(C)C=O | null | 18 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(S(N)(=O)=O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>CN(C)C=O>CCCNC(=O)c1cc(C(=O)N(CCC)[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(S(N)(=O)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6e0f5db8aa84ae6a11cc6a360d8c8ad | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CCN(CC)CC.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | C(#N)P(OCC)(OCC)=O.NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C(C)N(CC)CC>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)CC)=O | N[C:13](=O)[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:41][c:16]([C:17](O)=[O:18])[cH:15]1.CCN(CC)C[CH3:14].F[c:24]1[cH:23][c:22]([CH2:21][C@H:20]([NH2:19])[C@H:28]([OH:29])[CH2:30][NH:31][CH2:32][c:33]2[cH:34][cH:35][cH:36][c:37]([O:38][CH3:39])[cH:40]2)[cH:27][c:26](F)[cH:2... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CCN(CC)CC.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | ClCCl | Acylation | OtherReaction | 17186f8cf62cc95acd2e345a80051f13012094b744c213c5c91f2b20a68194e9 | 24132b9cdab9d3ba117bf7d7fe90237ca4c3e797cedf53c4daa04c180424b99f | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].F-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]):[c:9]:[c;H0;D3;+0:10](-F):[c:11]:1.N-[C;H0;D3;+0:12](=O)-[c:13](:[c:14]):[c:15]:[c:16](-[C;H0;D3;+0:17](-O)=[O;D1;H0:18]):[c:19]>>[C:7]-[C:6](-[C:5]-[c:4]1:[c:3]:[cH;D2;+0:2]:[c:11]:[cH;D2;+0:10]:[c:9]:1)-[NH;D2;+0:8]-[C;H0;D3... | null | [] | 22.5 | CELSIUS | 1 | HOUR | Diethyl cyanophosphonate (0.132 mL, 0.870 mmol) is added to a mixture of 3-[(dipropylamino)carbonyl]-5-ethylbenzoic acid (IX, PREPARATION 21, 0.200 g, 0.720 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.216 mg, 0.720 mmol), and triethylamine (0.121 mL, 0.870 mmol) in dichlor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Primary amide.Primary amine.Tertiary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | ClCCl | 22.5 | 1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CCN(CC)CC.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>ClCCl>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a944467d662f44c485c0d9a3c183a573 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCC(=O)N(CCC)c1cc(C)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C(C)N(CC)CC.ClCCl.C(#N)P(OCC)(OCC)=O>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(=CC(=C1)C)N(CCC)C(CCC)=O)=O | N[C:13](=O)[c:12]1[cH:11][c:10]([C:4](=[O:5])[N:6]([CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][CH3:9])[cH:40][c:15]([C:16](O)=[O:17])[cH:14]1.F[c:23]1[cH:22][c:21]([CH2:20][C@H:19]([NH2:18])[C@H:27]([OH:28])[CH2:29][NH:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][c:36]([O:37][CH3:38])[cH:39]2)[cH:26][c:25](F)[cH:24]1>>[CH3:1][CH2:... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCC(=O)N(CCC)c1cc(C)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | null | Acylation | OtherReaction | d7ad5b4f78b72662f669de6e0d85052056588a440530abbee7c70931b6136efa | 8634dfee5cb5a864d77819149e0eda23f385c1c8bc7963fd14971e2cc7d99964 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]-[C:5](-[C:6])-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9](-F):[c:10]:1.N-[C;H0;D3;+0:11](=O)-[c:12]1:[c:13]:[c;H0;D3;+0:14](-[C;H0;D3;+0:15](=[O;D1;H0:16])-[N;H0;D3;+0:17](-[C:18]-[C:19])-[CH2;D2;+0:20]-[C:21]-[C;D1;H3:22]):[c:23]:[c:24](-[C;H0;D3;+0:25](-O)=[O;D1;H0:26]):[c:27]:1>>[C:6]-[C... | null | [] | 22.5 | CELSIUS | 1 | HOUR | Following the procedure of EXAMPLE 570 and making non-critical variations, diethyl cyanophosphonate (0.0760 mL, 0.550 mmol) is added to a mixture of 3-[butyryl(propyl)amino]-5-methylbenzoic acid (IX, 0.120 g, 0.460 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, 0.137 g, 0.460 mmol), and tri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Primary amide.Tertiary amide.Primary amine | Secondary amide.Tertiary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | 22.5 | 1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCC(=O)N(CCC)c1cc(C)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fc1fe4668e845838c414cb306ad9243 | CCOC(=O)c1cc(C(=O)[O-])cc(C(=O)OCC)c1>>CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1 | C1(=CC(=CC(=C1)C(=O)[O-])C(=O)OCC)C(=O)OCC.CO>>OCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC | O=[C:9]([c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:18][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:11]1)[O-:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][OH:10])[cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:18]1 | CCOC(=O)c1cc(C(=O)[O-])cc(C(=O)OCC)c1 | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1 | null | null | C1CCOC1 | Reduction | OtherReaction | 3ee00ae8302f5a9cabfd43f47c90c2bc696c7c0e2b77ca13873c453d0520692e | c2c13922fe3c9358e6ba38897f2383764691ea247b267e6643408d03716a3879 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O-;H0;D1:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of diethyl 1,3,5-benzenetricarboxylate (5.2 g) and borane methylsulfide complex (6.1 g) is stirred in THF (150 mL) at 20-25 degrees C. overnight. The mixture is then treated with methanol, concentrated to dryness, and chouromatographed (silica gel) to give diethyl 5-(hydroxymethyl)isophthalate. Diethyl 5-(hyd... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | null | CCOC(=O)c1cc(C(=O)[O-])cc(C(=O)OCC)c1>C1CCOC1>CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-628bf9c19d46473e8f9be5f1a7bed15e | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1>>CCOC(=O)c1cc(CO)cc(C(=O)O)c1 | OCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC.O.O.[OH-].[Li+]>>C(C)OC(=O)C=1C=C(C(=O)O)C=C(C1)CO | CC[O:15][C:13]([c:12]1[cH:11][c:8]([CH2:9][OH:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:16]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][OH:10])[cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16]1 | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1 | CCOC(=O)c1cc(CO)cc(C(=O)O)c1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A mixture of diethyl 1,3,5-benzenetricarboxylate (5.2 g) and borane methylsulfide complex (6.1 g) is stirred in THF (150 mL) at 20-25 degrees C. overnight. The mixture is then treated with methanol, concentrated to dryness, and chouromatographed (silica gel) to give diethyl 5-(hydroxymethyl)isophthalate. Diethyl 5-(hyd... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1>C(C)O>CCOC(=O)c1cc(CO)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a178ecf83f346c0b9b4d34eb4fb567d | CCCNCCC.CCOC(=O)c1cc(CO)cc(C(=O)O)c1>>CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1 | C(C)OC(=O)C=1C=C(C(=O)O)C=C(C1)CO.C(CCl)Cl.C(C)(C)N(CC)C(C)C.C(CC)NCCC>>C(CC)N(C(=O)C=1C=C(C(=O)OCC)C=C(C1)CO)CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH3:7].O[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])[cH:22]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])[cH:22]... | CCCNCCC.CCOC(=O)c1cc(CO)cc(C(=O)O)c1 | CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of diethyl 1,3,5-benzenetricarboxylate (5.2 g) and borane methylsulfide complex (6.1 g) is stirred in THF (150 mL) at 20-25 degrees C. overnight. The mixture is then treated with methanol, concentrated to dryness, and chouromatographed (silica gel) to give diethyl 5-(hydroxymethyl)isophthalate. Diethyl 5-(hyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | CN(C)C=O | null | null | CCCNCCC.CCOC(=O)c1cc(CO)cc(C(=O)O)c1>CN(C)C=O>CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad094caf47d64ebfadec8d260ca7aae5 | BrP(Br)Br.CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1>>CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1 | C(CC)N(C(=O)C=1C=C(C(=O)OCC)C=C(C1)CO)CCC.P(Br)(Br)Br>>BrCC=1C=C(C(=O)OCC)C=C(C1)C(=O)N(CCC)CCC | BrP(Br)[Br:14].O[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:22][c:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])[cH:15]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][Br:14])[cH:15][c:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21]... | BrP(Br)Br.CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1 | CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1 | null | null | ClCCl | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 50 | CELSIUS | 4 | HOUR | A mixture of ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate (1.5 g) and phosphorous tribromide (0.95 mL) is stirred in dichloromethane (10 mL) and heated at 50 degrees C. for 4 hours and then cooled and partitioned between dichloromethane and water. The organic phase is separated and washed with aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | ClCCl | 50 | 4 | BrP(Br)Br.CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)OCC)c1>ClCCl>CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-201e05753f71425baafa4ec66518f560 | CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1.[C-]#N>>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1 | BrCC=1C=C(C(=O)OCC)C=C(C1)C(=O)N(CCC)CCC.[C-]#N.[Na+]>>C(#N)CC=1C=C(C(=O)OCC)C=C(C1)C(=O)N(CCC)CCC | Br[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:23][c:17]([C:18](=[O:19])[O:20][CH2:21][CH3:22])[cH:16]1.[C-:14]#[N:15]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][C:14]#[N:15])[cH:16][c:17]([C:18](=[O:19])[O:20][CH2:21][... | CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1.[C-]#N | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3.5 | HOUR | A mixture of ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate (1.5 g) and phosphorous tribromide (0.95 mL) is stirred in dichloromethane (10 mL) and heated at 50 degrees C. for 4 hours and then cooled and partitioned between dichloromethane and water. The organic phase is separated and washed with aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | CS(=O)C | null | 3.5 | CCCN(CCC)C(=O)c1cc(CBr)cc(C(=O)OCC)c1.[C-]#N>CS(=O)C>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5abba60dc17c4279a0fabe86a30603c5 | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1>>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)O)c1 | O.[OH-].[Li+].C(#N)CC=1C=C(C(=O)OCC)C=C(C1)C(=O)N(CCC)CCC.Cl>>C(#N)CC=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC | CC[O:20][C:18]([c:17]1[cH:16][c:12]([CH2:13][C:14]#[N:15])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:21]1)=[O:19]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][C:14]#[N:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]1 | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1 | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)O)c1 | null | null | O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A mixture of ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate (1.5 g) and phosphorous tribromide (0.95 mL) is stirred in dichloromethane (10 mL) and heated at 50 degrees C. for 4 hours and then cooled and partitioned between dichloromethane and water. The organic phase is separated and washed with aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O.C(C)O | null | null | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)OCC)c1>O.C(C)O>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aaa13892175e420d857b8d19e4bda8cd | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)CC#N)=O | O=[C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:42][c:17]([C:18](O)=[O:19])[cH:16]1)[NH2:15].CN(C)[C:14](On1nnc2cccnc21)=[N+](C)C.F[c:25]1[cH:24][c:23]([CH2:22][C@H:21]([NH2:20])[C@H:29]([OH:30])[CH2:31][NH:32][CH2:33][c:34]2[cH:35][cH:36][cH:37][c:38]([O:39][CH3:40])[cH... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | ClCCl | Acylation | OtherReaction | c0a1559fb1dd6482f8d01781c65df907fa5f2c8e3a0adcb79acf25b7fd5bc6a4 | 47dbc2bce8c4a5b7558c17b523404899fdeee19be7c6b5382ce5c641dbd9a9fc | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-N(-C)-[C;H0;D3;+0:1](-O-n1:n:n:c2:c:c:c:n:c:2:1)=[N+](-C)-C.F-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]):[c:9]:[c;H0;D3;+0:10](-F):[c:11]:1.O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:16]:[c:17](-[C;H0;D3;+0:18](=O)-[NH2;D1;+0:19]):[c:20]>>[C:7]-[C:6](-[C:5]-[c:4]1:[c:3]:[cH;D2;+0:2]:[c:1... | null | [] | 40 | CELSIUS | null | null | A mixture of 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid (IX, 0.13 g), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, 0.14 g), HATU (0.17 g), and dichloromethane (10 mL) is stirred at 40 degrees C. overnight. After cooling, the mixture is washed with water and the organic phase is sepa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Amidinium.Carboxylic acid.Primary amide.Primary amine | Nitrile.Secondary amide | c1cnc2[nH]nnc2c1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | ClCCl | 40 | null | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>ClCCl>CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33c4ecf85a674a66b17a5aed8c96e3e8 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)CO)=O | N[C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:41][c:16]([C:17](O)=[O:18])[cH:15]1)=[O:14].F[c:24]1[cH:23][c:22]([CH2:21][C@H:20]([NH2:19])[C@H:28]([OH:29])[CH2:30][NH:31][CH2:32][c:33]2[cH:34][cH:35][cH:36][c:37]([O:38][CH3:39])[cH:40]2)[cH:27][c:26](F)[cH:25]1>>[CH3:1]... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | null | Acylation | OtherReaction | 42ade9cc36b1912b4516610b597820102657a5b0a84e6371e69896bd4f173802 | 4cea0d2f2e8208a1bbd83729c5f7c60a1c6d2b65556e903829a454edb4b0b3eb | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]-[C:5](-[C:6])-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9](-F):[c:10]:1.N-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]:[c:16](-[C;H0;D3;+0:17](-O)=[O;D1;H0:18]):[c:19]>>[C:6]-[C:5](-[C:4]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c:10]:[cH;D2;+0:9]:[c:8]:1)-[NH;D2;+0:7]-[C;H0;D3;+0:17](=[O;D1;H... | null | [] | null | null | null | null | Following the procedure of CHART P and EXAMPLE 739 and making non-critical variations but using 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoic acid (IX) and (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII), the title compound is obtained, HRMS (FAB)=615.3571.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Primary amide.Primary amine | Secondary amide.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(CO)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cc9933a50ad48efa13736bc46712902 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>>C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1 | BrC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.C[Si](C)(C)C#C>>C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C#C)CCC | Br[c:3]1[cH:4][c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]([C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH3:20])[cH:21]1>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]([C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH3:20])[cH:21]1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 | C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1 | null | [Cu]I | O.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 95b76df7bbd0ba7aef764b8988925515b3c4e00700642b1df2a075a9fb68bd8a | 3328c8f87c438567981cd74666102f3c9878dcf86df57abda9cd69bae6cfdc49 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:12]#[C;D1;H1:13]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11] | 111.3 | [{"value": 111.3, "product": "C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C#C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, 200 mg, 0.58 mmol), PdCl2(Ph3P) 2 (16 mg, 0.03 mol %) and copper (I) iodide (6 mg, 0.05 mol %) in triethylamine (1.2 mL) is heated to reflux. (Trimethylsilyl) acetylene (100 microliter, 0.7 mmol) is added, and the mixture stirred for 3 hours, cooled ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [Cu]I.O.C(C)N(CC)CC | null | 3 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>[Cu]I.O.C(C)N(CC)CC>C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c86006caf014907a3b6434f084f3b0a | C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1>>C#Cc1cc(C(=O)O)cc(C(=O)N(CCC)CCC)c1 | [OH-].[K+].C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C#C)CCC>>C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)C#C)CCC | C[O:8][C:6]([c:5]1[cH:4][c:3]([C:2]#[CH:1])[cH:20][c:10]([C:11](=[O:12])[N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])[cH:9]1)=[O:7]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]([C:11](=[O:12])[N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])[cH:20]1 | C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1 | C#Cc1cc(C(=O)O)cc(C(=O)N(CCC)CCC)c1 | null | null | O.C(Cl)(Cl)Cl.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 4 | HOUR | To a stirred mixture of the protected methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate (XXXII, Step 1, 185.3 mg, 0.49 mmol) in methanol (2.5 mL) is added a mixture of potassium hydroxide (2.9 mL of a 1 M mixture in water, 2.9 mmol). The reaction mixture is stirred for 4 hours diluted with chloroform (40 mL), the ph... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O.C(Cl)(Cl)Cl.CO | null | 4 | C#Cc1cc(C(=O)OC)cc(C(=O)N(CCC)CCC)c1>O.C(Cl)(Cl)Cl.CO>C#Cc1cc(C(=O)O)cc(C(=O)N(CCC)CCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af5cefa77e1345fc8b935d28226f1a56 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.OB(O)c1cccc2cccnc12>>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1 | COC(C1=CC(=CC(=C1)C(=O)N(CCC)CCC)Br)=O.N1=CC=CC2=CC=CC(=C12)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C=1C=CC=C2C=CC=NC12)CCC | Br[c:18]1[cH:17][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:29]1.OB(O)[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][n:27][c:28]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[O:15]... | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.OB(O)c1cccc2cccnc12 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3cccnc23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#7:10])=[O;D1;H0:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](:[c:16]):[#7;a:17]:[c:18]>>[#7:10]-[C:9](=[O;D1;H0:11])-[c:8]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](:[c:16]):[#7;a:17]:[c:18]):[c:2]:[c:3]-[C:4](-[#8:... | 77.7 | [{"value": 77.7, "product": "C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C=1C=CC=C2C=CC=NC12)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | null | null | A mixture of methyl-3-bromo-5-[(dipropylamino)carbonyl]benzoate (XLVIII, 200 mg, 0.58 mmol), 8-quinolineboronic acid (200.6 mg, 1.2 mmol), sodium carbonate (870 Micro Liter of a 2 M mixture in water, 1.74 mmol) in toluene (6 mL) is degassed under reduced pressure for 15 minutes and purged with argon. Palladium tetrakis... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C1(=CC=CC=C1)C | 22.5 | null | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.OB(O)c1cccc2cccnc12>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C1(=CC=CC=C1)C>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac552957142044ebb2aebdba7d216c4b | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1>>CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2cccc3cccnc23)c1 | C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C=1C=CC=C2C=CC=NC12)CCC.[OH-].[Li+].O>>C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)C=1C=CC=C2C=CC=NC12)CCC | C[O:15][C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:28][c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]3[cH:23][cH:24][cH:25][n:26][c:27]23)[cH:16]1)=[O:14]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][c:17... | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2cccc3cccnc23)c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cccc3cccnc23)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] | null | [] | null | null | 8 | HOUR | To a mixture of methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate (XLIX, step 1, 175.5 mg, 0.45 mmol) in methanol (2 mL) is added lithium hydroxide (32.3 mg, 1.4 mmol) and water (500 microliter). After stirring overnight, the reaction mixture is partitioned between ethyl acetate (10 mL) and water (10 mL). The... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | CO | null | 8 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2cccc3cccnc23)c1>CO>CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2cccc3cccnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12bdcba360e24f0399f05dc0a8e328a4 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccc(OC)cc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccc(OC)cc2)c1.Cl | C(CC)N(C(=O)C=1C=C(C=C(C1)C1=CC=C(C=C1)OC)C(=O)O)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1.C(CCl)Cl>>Cl.C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(=O)C=1C=C(C=C(C1)C(=O)N(CCC)CCC)C1=CC=C(C=C1)OC | O[C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:47][c:38](-[c:39]2[cH:40][cH:41][c:42]([O:43][CH3:44])[cH:45][cH:46]2)[cH:37]1)=[O:14].F[c:20]1[cH:19][c:18]([CH2:17][C@H:16]([NH2:15])[C@H:24]([OH:25])[CH2:26][NH:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][c:33]([O:34][CH3:35]... | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccc(OC)cc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl | CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccc(OC)cc2)c1.Cl | null | null | CN(C=O)C.C(Cl)Cl | Acylation | OtherReaction | cee1875b3b75a383cf35f695f02ef0d0f775d067bb15da83f67f8c72821156e3 | 416aa8acb8e1963e35f7fb5e1f21f3659f811d81cec6dcf7bdf86b46bf705a40 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1cccc(-c2ccccc2)c1 | Cl-C-C-[Cl;H0;D1;+0:1].F-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]):[c:9]:[c;H0;D3;+0:10](-F):[c:11]:1.O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:16]>>[C:7]-[C:6](-[C:5]-[c:4]1:[c:3]:[cH;D2;+0:2]:[c:11]:[cH;D2;+0:10]:[c:9]:1)-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:1... | null | [] | null | null | 4.5 | HOUR | A mixture of 5-[(dipropylamino)carbonyl]-4′-methoxy[1,1′-biphenyl]-3-carboxylic acid (IX-L, step 1, 316 mg, 0.89 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol dihydrochloride (VIII, 332 mg, 0.89 mmol), HOBt (181 mg, 1.34 mmol), and N-methylmorpholine (0.37 g, 3.56 mmol) in methylene chloride (8 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide.Primary halide.Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HF | CN(C=O)C.C(Cl)Cl | null | 4.5 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccc(OC)cc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>CN(C=O)C.C(Cl)Cl>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccc(OC)cc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d727ed7dc474db2a346b15daf990376 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.[C@@H]1(CCCC2=CC=CC=C12)N.CC(C)O>>FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(OC(C)(C)C)=O)C=C(C1)F | [CH2:10]1[C@H:11]([C@H:13]([CH2:14][c:15]2[cH:16][c:17]([F:18])[cH:19][c:20]([F:21])[cH:22]2)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[O:12]1.C[CH:3]([CH3:1])[OH:2].c1[cH:4][cH:5][cH:6][c:7]2[c:31]1CCC[C@@H:8]2[NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]([OH:12... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21 | COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | null | null | null | Functional Group Interconversion | OtherReaction | b5acb2fc8300276c87d14fb61e5880239a98818e5d9bd804b2744c5ce6887d14 | fe5795a4443c9bc6454ec29387895fbed9eb4d86cd89c198a74f9ee933f66271 | c1ccc(CCCCNCc2ccccc2)cc1 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[OH;D1;+0:3].[C:4]-[C:5](-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C@H;D3;+0:14]1-[CH2;D2;+0:15]-[O;H0;D2;+0:16]-1.[NH2;D1;+0:17]-[C@H;D3;+0:18]1-C-C-C-[c;H0;D3;+0:19]2:c:[cH;D2;+0:20]:[c:21]:[c:22]:[c:23]:2-1>>[C:4]-[C:5](-[#7:6]-[C:7](=[O;D1;... | null | [] | 22.5 | CELSIUS | null | null | A mixture of tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, 500 mg, 1.67 mmol) and 3-methoxybenzylamine (VI, 0.34g, 2.51 mmol) in 2-propanol (3 mL) is heated at reflux overnight, allowed to cool to 20-25 degrees C., and concentrated under reduced pressure. The residue is crystallized from et... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Primary amine | Ether.Secondary alcohol.Secondary amine | C1CO1.c1ccc2c(c1)CCCC2 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | 22.5 | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-908d4e226c5c4e56b0d0b662f0bc9296 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccccc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccccc2)c1.Cl | C(CC)N(C(=O)C=1C=C(C=C(C1)C1=CC=CC=C1)C(=O)O)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1.C(CCl)Cl>>Cl.FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(=O)C=2C=C(C=C(C2)C(=O)N(CCC)CCC)C2=CC=CC=C2)C=C(C1)F | O[C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:47][c:40](-[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:39]1)=[O:14].[NH2:15][C@@H:16]([CH2:17][c:18]1[cH:19][c:20]([F:21])[cH:22][c:23]([F:24])[cH:25]1)[C@H:26]([OH:27])[CH2:28][NH:29][CH2:30][c:31]1[cH:32][cH:33][cH:34]... | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccccc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl | CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccccc2)c1.Cl | null | null | CN(C=O)C.C(Cl)Cl | Acylation | OtherReaction | 99edef57664ae1ea214b930248c307cc67480c5683ee3f8c2d2ffd197db8c978 | acf27917ff30a79c78bd4d7b221e71a2836d529262fa23e93598d0ad5d644426 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1cccc(-c2ccccc2)c1 | Cl-C-C-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[C:9])-[NH2;D1;+0:10]>>[C:7]-[C:8](-[C:9])-[NH;D2;+0:10]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[ClH;D0;+0:1] | null | [] | 22.5 | CELSIUS | null | null | A mixture of 5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylic acid (IX, 188 mg, 0.56 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, Step 2, 230 mg, 0.56 mmol), HOBt (114 mg, 0.84 mmol), and N-methylmorpholine (0.23 g, 2.24 mmol) in methylene chloride (6 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.C(Cl)Cl | 22.5 | null | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccccc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>CN(C=O)C.C(Cl)Cl>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccccc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bcdcc36dd6d44ec80d1dda3af44d1d1 | CCCN(CCC)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc(C(=O)OC)c1.CN(C)S(=O)(=O)c1ccc(Br)cc1>>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)B1OC(C(O1)(C)C)(C)C)CCC.CN(C)S(=O)(=O)C1=CC=C(C=C1)Br.C([O-])([O-])=O.[Na+].[Na+]>>CN(S(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC(=C1)C(=O)N(CCC)CCC)C(=O)OC)C | CC1(C)OB([c:18]2[cH:17][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:31]2)OC1(C)C.Br[c:19]1[cH:20][cH:21][c:22]([S:23](=[O:24])(=[O:25])[N:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[... | CCCN(CCC)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc(C(=O)OC)c1.CN(C)S(=O)(=O)c1ccc(Br)cc1 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6](:[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11]):[c:12]:[c:13]-[C:14](-[#7:15])=[O;D1;H0:16])-O-C-1(-C)-C>>[#7:15]-[C:14](=[O;D1;H0:16])-[c:13]:[c:12]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11] | null | [] | 22.5 | CELSIUS | null | null | A mixture of methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step 1, 534 mg, 1.4 mmol), 4-bromobenzenedimethyl-sulfonamide (363 mg, 1.4 mmol), and sodium carbonate (2 mL of a 2 M mixture in water, 4.1 mmol) in toluene (10 mL) is degassed under reduced pressure for 15 minutes ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C1(=CC=CC=C1)C | 22.5 | null | CCCN(CCC)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc(C(=O)OC)c1.CN(C)S(=O)(=O)c1ccc(Br)cc1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C1(=CC=CC=C1)C>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50c88d8ff7af471884f42a673ba80eb4 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1.CO>>CCCN(CCC)C(=O)c1cc(C(=O)O)c(C)c(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 | CN(S(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC(=C1)C(=O)N(CCC)CCC)C(=O)OC)C.CO>>CC1=C(C=C(C=C1C(=O)O)C(=O)N(CCC)CCC)C1=CC=C(C=C1)S(=O)(=O)N(C)C | C[O:15][C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:31][c:18](-[c:19]2[cH:20][cH:21][c:22]([S:23](=[O:24])(=[O:25])[N:26]([CH3:27])[CH3:28])[cH:29][cH:30]2)[cH:16]1)=[O:14].O[CH3:17]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:... | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1.CO | CCCN(CCC)C(=O)c1cc(C(=O)O)c(C)c(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 | null | null | O.[OH-].[Na+] | C-C Coupling | OtherReaction | 27413f11c35950587d2ede79b7c0ec2777f3a747a4df538f3bf795eb3c990de2 | 8fb1dfe94a77e1d4cf0cd3e4e184a4d169bd9164a787c5974edec4da8a424e47 | c1ccc(-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[c:8]):[c:9].O-[CH3;D1;+0:10]>>[CH3;D1;+0:10]-[c;H0;D3;+0:6](:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:5]):[c:7](-[c:8]):[c:9] | null | [] | 22.5 | CELSIUS | 4 | HOUR | A mixture of methyl 4′-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylate (XXXVIII, step 2, 555 mg, 1.24 mmol) in methanol (6 mL) and sodium hydroxide (2 mL of a 6.0 M mixture in water, 12 mmol) is stirred at 20-25 degrees C. for 4 hours. The reaction mixture is partitioned between ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O.[OH-].[Na+] | 22.5 | 4 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccc(S(=O)(=O)N(C)C)cc2)c1.CO>O.[OH-].[Na+]>CCCN(CCC)C(=O)c1cc(C(=O)O)c(C)c(-c2ccc(S(=O)(=O)N(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-567d03dbb38e445499582682a8997659 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccsc2)c1>>CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)C1=CSC=C1)CCC>>C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)C1=CSC=C1)CCC | C[O:15][C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:23][c:17](-[c:18]2[cH:19][cH:20][s:21][cH:22]2)[cH:16]1)=[O:14]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][c:17](-[c:18]2[cH:19][cH:20][s:21][cH:2... | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccsc2)c1 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1 | null | null | O.C1CCOC1.CO.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccsc2)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] | null | [] | 40 | CELSIUS | 2 | HOUR | A mixture of methyl 3-[(dipropylamino)carbonyl]-5-(3-thienyl)benzoate (XLIX, step 3, 0.31 g, 0.88 mmol) in THF/methanol/sodium hydroxide (3/1/1, 5 mL) is stirred at 40 degrees C. for 2 hours. The reaction is cooled to 20-25 degrees C., diluted with water and extracted with ethyl acetate. The aqueous phase is acidified ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | O.C1CCOC1.CO.[OH-].[Na+] | 40 | 2 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(-c2ccsc2)c1>O.C1CCOC1.CO.[OH-].[Na+]>CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e576d813046458695d3ac8247f24ec8 | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccsc2)c1.Cl | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)C1=CSC=C1)CCC.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C=1C=CC2=C(C1)N=NN2O.C(C)N(CC)CC.C(CCl)Cl>>Cl.C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C1=CSC=C1)=O | O[C:13]([c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:44][c:38](-[c:39]2[cH:40][cH:41][s:42][cH:43]2)[cH:37]1)=[O:14].F[c:20]1[cH:19][c:18]([CH2:17][C@H:16]([NH2:15])[C@H:24]([OH:25])[CH2:26][NH:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][c:33]([O:34][CH3:35])[cH:36]2)[cH:23][c:22]... | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl | CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccsc2)c1.Cl | null | null | O.CN(C)C=O | Acylation | OtherReaction | cee1875b3b75a383cf35f695f02ef0d0f775d067bb15da83f67f8c72821156e3 | 416aa8acb8e1963e35f7fb5e1f21f3659f811d81cec6dcf7bdf86b46bf705a40 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1cccc(-c2ccsc2)c1 | Cl-C-C-[Cl;H0;D1;+0:1].F-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]):[c:9]:[c;H0;D3;+0:10](-F):[c:11]:1.O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:16]>>[C:7]-[C:6](-[C:5]-[c:4]1:[c:3]:[cH;D2;+0:2]:[c:11]:[cH;D2;+0:10]:[c:9]:1)-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:1... | null | [] | 22.5 | CELSIUS | null | null | A mixture of 3-[(dipropylamino)carbonyl]-5-(3-thienyl)benzoic acid (IX-L, step 4, 0.26 g, 0.79 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol dihydrochloride (VIII, 0.26 g, 0.71 mmol), HOBt (0.16 g, 1.18 mmol), and triethylamine (0.44 mL, 3.15 mmol) in DMF (4 mL) is stirred at 20-25 degrees C. for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide.Primary halide.Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccsc1 | HF | O.CN(C)C=O | 22.5 | null | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ccsc2)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.ClCCCl>O.CN(C)C=O>CCCN(CCC)C(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc(-c2ccsc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2e3ee405f934b399acec0e50178d74a | CCCCC(=O)c1cc(C)cc(C(=O)OC)c1>>CCCCC(=O)c1cc(C)cc(C(=O)O)c1 | CC=1C=C(C(=O)OC)C=C(C1)C(CCCC)=O.C1CCOC1.CO.[OH-].[Na+]>>CC=1C=C(C(=O)O)C=C(C1)C(CCCC)=O | C[O:15][C:13]([c:12]1[cH:11][c:9]([CH3:10])[cH:8][c:7]([C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[cH:16]1)=[O:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16]1 | CCCCC(=O)c1cc(C)cc(C(=O)OC)c1 | CCCCC(=O)c1cc(C)cc(C(=O)O)c1 | null | null | CO.C(C)(=O)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A mixture of methyl 3-methyl-5-pentanoylbenzoate (LXXVI, step 2. 133 mg, 0.605 mmol) in methanol (1 mL) is stirred with tetrahydrofuran/methanol/sodium hydroxide (2 N) (3/1/1, 3 mL) for 3 days. The reaction mixture is diluted with ethyl acetate and washed with water. The aqueous phase is separated and acidified with hy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.C(C)(=O)OCC | null | null | CCCCC(=O)c1cc(C)cc(C(=O)OC)c1>CO.C(C)(=O)OCC>CCCCC(=O)c1cc(C)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8237904813f545a79abe0272158bcf6a | CCCCC(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCCC(=O)c1cc(C)cc(C(=O)N[C@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 | CC=1C=C(C(=O)O)C=C(C1)C(CCCC)=O.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1.C(CCl)Cl>>FC=1C=C(C[C@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(C2=CC(=CC(=C2)C(CCCC)=O)C)=O)C=C(C1)F | O[C:13]([c:12]1[cH:11][c:9]([CH3:10])[cH:8][c:7]([C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[cH:39]1)=[O:14].[NH2:15][C@@H:16]([CH2:17][c:18]1[cH:19][c:20]([F:21])[cH:22][c:23]([F:24])[cH:25]1)[C@H:26]([OH:27])[CH2:28][NH:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][c:35]([O:36][CH3:37])[cH:38]1>>[CH3:1][CH2:2][CH2:3][CH2:4]... | CCCCC(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCCC(=O)c1cc(C)cc(C(=O)N[C@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | To a mixture of 3-methyl-5-pentanoylbenzoic acid (IX-LXXVII, 112 mg, 0.589 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, 239 mg, 0.589 mmol), HOBt (80 mg, 0.589 mmol), and N-methylmorpholine (250 mg, 2.47 mmol) in methylene chloride (3 mL) is added EDC (203 mg... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CCCCC(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>C(Cl)Cl>CCCCC(=O)c1cc(C)cc(C(=O)N[C@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3aecd9dcca040f5a2c51b55d9e31b18 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)C(=O)O | C(C1=CC=CC=C1)OC1=CC=C(C=C1)C[C@@H](C(=O)OC)NC(=O)OC(C)(C)C.[OH-].[Li+]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C | C[O:27][C:25]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1)=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH... | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)C(=O)O | null | null | C1CCOC1.CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 22.5 | CELSIUS | 12 | HOUR | To a mixture of methyl (2S)-3-[4-(benzyloxy)phenyl]-2-(tert-butoxycarbonyl)aminopropanoate (1.79 g, 4.65 mmol) in a THF/methanol/water (1/2/1, 16 ml) is added lithium hydroxide (340 mg, 13.9 mmol) and the mixture stirred at 20-25 degrees C. for 12 hours. The mixture is quenched with citric acid (10%). The resulting mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1.CO.O | 22.5 | 12 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OC(C)(C)C>C1CCOC1.CO.O>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04d1c6a4cb3f4effa6f331b317a06a66 | CCCN.O=C(O)CCCOCc1ccccc1>>CCCNC(=O)CCCOCc1ccccc1 | C(C1=CC=CC=C1)OCCCC(=O)O.C(CC)N.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1.C(CCl)Cl>>C(C1=CC=CC=C1)OCCCC(=O)NCCC | [CH3:1][CH2:2][CH2:3][NH2:4].O[C:5](=[O:6])[CH2:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCCN.O=C(O)CCCOCc1ccccc1 | CCCNC(=O)CCCOCc1ccccc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 79.8 | [{"value": 79.8, "product": "C(C1=CC=CC=C1)OCCCC(=O)NCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | 18 | HOUR | A mixture of 4-benzyloxybutyric acid (2.69 g, 13.8 mmol), propylamine (0.82 g, 13.8 mmol), HOBt (2.05 g, 15.2 mmol), N-methylmorpholine (1.68 g, 16.6 mmol) and EDC (2.91 g, 15.2 mmol) in DMF (6 mL) is stirred at 20-25 degrees C. for 18 hours. The mixture is diluted with ethyl acetate (40 mL) and washed with water (10 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | 22.5 | 18 | CCCN.O=C(O)CCCOCc1ccccc1>CN(C)C=O.C(C)(=O)OCC>CCCNC(=O)CCCOCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-112a9928d3d74d2e96621611ea0bf5af | CCCNC(=O)CCCOCc1ccccc1>>CCCNCCCCOCc1ccccc1 | C(C1=CC=CC=C1)OCCCC(=O)NCCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)OCCCCNCCC | O=[C:5]([NH:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CCCNC(=O)CCCOCc1ccccc1 | CCCNCCCCOCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccccc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[C:5] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OCCCCNCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 5 | HOUR | To an ice-cold, stirred mixture of 4-(benzyloxy)-N-propylbutanamide (2.59 g, 11.0 mmol) in THF (8 mL) is added lithium aluminum hydride (0.54 g, 14.3 mmol). The reaction mixture is heated to 40-50 degrees C. for 5 hours. The cooled reaction mixture is quenched with water (0.5 mL), sodium hydroxide (2 N, 1.0 mL), and sa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1 | Other | C1CCOC1 | 45 | 5 | CCCNC(=O)CCCOCc1ccccc1>C1CCOC1>CCCNCCCCOCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23e496ea885548ffbc6df0a19418a27c | CCCNCCCCOCc1ccccc1.CCOC(=O)c1cc(C)cc(C(=O)O)c1>>CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1 | C(C1=CC=CC=C1)OCCCCNCCC.C(C)OC(=O)C=1C=C(C(=O)O)C=C(C1)C.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1.C(CCl)Cl>>C(C1=CC=CC=C1)OCCCCN(C(=O)C=1C=C(C(=O)OCC)C=C(C1)C)CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.O[C:17](=[O:18])[c:19]1[cH:20][c:21]([CH3:22])[cH:23][c:24]([C:25](=[O:26])[O:27][CH2:28][CH3:29])[cH:30]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:... | CCCNCCCCOCc1ccccc1.CCOC(=O)c1cc(C)cc(C(=O)O)c1 | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCCCOCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 41.7 | [{"value": 41.7, "product": "C(C1=CC=CC=C1)OCCCCN(C(=O)C=1C=C(C(=O)OCC)C=C(C1)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | 18 | HOUR | A mixture of N-[4-(benzyloxy)butyl]-N-propylamine (2.31 g, 10.44 mmol), 3-(ethoxycarbonyl)-5-methylbenzoic acid (2.18 g, 10.44 mmol), HOBt (1.56 g, 11.49 mmol), N-methylmorpholine (1.37 mL, 12.52 mmol), and EDC (2.20 g, 11.49 mmol) in DMF (12 mL) is stirred at 20-25 degrees C. for 18 hours. The reaction mixture is dilu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | 22.5 | 18 | CCCNCCCCOCc1ccccc1.CCOC(=O)c1cc(C)cc(C(=O)O)c1>CN(C)C=O.C(C)(=O)OCC>CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a4999de904a4fd5ac09b499f7e54ad3 | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1>>CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)O)c1 | C(C1=CC=CC=C1)OCCCCN(C(=O)C=1C=C(C(=O)OCC)C=C(C1)C)CCC.[OH-].[Li+].Cl>>C(C1=CC=CC=C1)OCCCCN(C(=O)C=1C=C(C(=O)O)C=C(C1)C)CCC | CC[O:27][C:25]([c:24]1[cH:23][c:21]([CH3:22])[cH:20][c:19]([C:17]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)=[O:18])[cH:28]1)=[O:26]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:... | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1 | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)O)c1 | null | null | C1CCOC1.C(C)O.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCCCOCc1ccccc1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)OCCCCN(C(=O)C=1C=C(C(=O)O)C=C(C1)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of ethyl 3-{[[4-(benzyloxy)butyl](propyl)-amino]carbonyl}-5-methylbenzoate (1.75 g, 4.25 mmol) in THF/ethanol/water (1/2/1, 30 mL) is added lithium hydroxide (0.31 g, 12.76 mmol). The reaction mixture is stirred for 2 h and then acidified to pH=3 with concentrated hydrochloric acid (0.5 mL). The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1.C(C)O.O | null | 2 | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)OCC)c1>C1CCOC1.C(C)O.O>CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04d9af13482f4ee0a0c68b6a5023c3fe | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccc(OCc3ccccc3)cc2)NC(=O)OC(C)(C)C)c1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.[C@@H]1(CCCC2=CC=CC=C12)N.C(C)(C)O>>C(C1=CC=CC=C1)OC1=CC=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(OC(C)(C)C)=O)C=C1 | [CH2:10]1[C@H:11]([C@H:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28]2)[NH:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[O:12]1.C[CH:3]([CH3:1])[OH:2].c1[cH:4][cH:5][cH:6][c:7]2[c:37]1CCC[C@@H:8]2[NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccc(OCc3ccccc3)cc2)NC(=O)OC(C)(C)C)c1 | null | null | null | Functional Group Interconversion | OtherReaction | b5acb2fc8300276c87d14fb61e5880239a98818e5d9bd804b2744c5ce6887d14 | fe5795a4443c9bc6454ec29387895fbed9eb4d86cd89c198a74f9ee933f66271 | c1ccc(CNCCCCc2ccc(OCc3ccccc3)cc2)cc1 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[OH;D1;+0:3].[C:4]-[C:5](-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C@H;D3;+0:14]1-[CH2;D2;+0:15]-[O;H0;D2;+0:16]-1.[NH2;D1;+0:17]-[C@H;D3;+0:18]1-C-C-C-[c;H0;D3;+0:19]2:c:[cH;D2;+0:20]:[c:21]:[c:22]:[c:23]:2-1>>[C:4]-[C:5](-[#7:6]-[C:7](=[O;D1;... | null | [] | 90 | CELSIUS | 4 | HOUR | A mixture of tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (V, 1.58 g, 4.28 mmol) and 3-methoxybenzylamine (VI, 825 microliter, 6.42 mmol) in isopropanol (45 mL) is heated to 90 degrees C. for 4 hours. Upon cooling to 20-25 degrees C., the reaction mixture is concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Primary amine | Ether.Secondary alcohol.Secondary amine | C1CO1.c1ccc2c(c1)CCCC2 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | 90 | 4 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)[C@H]1CO1.CC(C)O.N[C@H]1CCCc2ccccc21>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccc(OCc3ccccc3)cc2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72bcc2ed2cd440258279a92022e1e9cc | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1>>CCCN(CCCCO)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)C(O)CNCc2cccc(OC)c2)c1 | C(C1=CC=CC=C1)OC1=CC=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(C2=CC(C(=O)N(CCC)CCCCOCC3=CC=CC=C3)=CC(=C2)C)=O)C=C1>>OCCCCN(C(C1=CC(C(=O)N[C@H](C(CNCC2=CC(=CC=C2)OC)O)CC2=CC=C(C=C2)O)=CC(=C1)C)=O)CCC | c1ccc(C[O:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[C:10](=[O:11])[c:12]2[cH:13][c:14]([CH3:15])[cH:16][c:17]([C:18](=[O:19])[NH:20][C@@H:21]([CH2:22][c:23]3[cH:24][cH:25][c:26]([O:27]Cc4ccccc4)[cH:28][cH:29]3)[C@H:30]([OH:31])[CH2:32][NH:33][CH2:34][c:35]3[cH:36][cH:37][cH:38][c:39]([O:40][CH3:41])[cH... | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1 | CCCN(CCCCO)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)C(O)CNCc2cccc(OC)c2)c1 | null | [Pd] | C(C)(=O)O | Deprotection | OtherReaction | 2f9d0a413f1720a1c2af1e39e35138382c37db7bcca9a728062743c035ee6048 | 0019c7eff1b5e27bd389d7453db70f02f82e6eb53fc11519e24abebafecd8503 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1.[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1):[c:7]>>[C:1]-[C:2]-[OH;D1;+0:3].[OH;D1;+0:6]-[c:5](:[c:4]):[c:7] | null | [] | null | null | 5 | HOUR | A mixture of N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide (X, 100 mg, 0.130 mmol) and palladium on carbon (10%, 100 mg) in absolute glacial acetic acid (5 mL) is shaken under an atmosphere of hydrogen at 35 psi for 5 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)O | null | 5 | CCCN(CCCCOCc1ccccc1)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1>[Pd].C(C)(=O)O>CCCN(CCCCO)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)C(O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49c78949a2c04ac882f087cc3b012b59 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)[C@H](O)CNCc2cccc(OC)c2)c1 | C(C1=CC=CC=C1)OC1=CC=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C1>>O[C@@H]([C@H](CC1=CC=C(C=C1)O)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)CNCC1=CC(=CC=C1)OC | c1ccc(C[O:25][c:24]2[cH:23][cH:22][c:21]([CH2:20][C@H:19]([NH:18][C:16]([c:15]3[cH:14][c:12]([CH3:13])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:41]3)=[O:17])[C@H:28]([OH:29])[CH2:30][NH:31][CH2:32][c:33]3[cH:34][cH:35][cH:36][c:37]([O:38][CH3:39])[cH:40]3)[cH:27][cH:26]2)cc1>>[CH3... | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | [Pd] | C(C)(=O)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | [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] | null | [] | null | null | 5 | HOUR | A mixture of N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide (140 mg, 0.215 mmol) and palladium on carbon (10%, 140 mg) in absolute glacial acetic acid (5 mL) is shaken under an atmosphere of hydrogen at 35 psi for 5 hours The resulting mixture is fi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)O | null | 5 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(OCc3ccccc3)cc2)[C@H](O)CNCc2cccc(OC)c2)c1>[Pd].C(C)(=O)O>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2ccc(O)cc2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-070cbe7140af4a7f9d59e645beb1e279 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)[O-])ccc2C)c1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)O)ccc2C)c1 | C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(=O)C=1C=C(C(=O)[O-])C=CC1C.[OH-].[Li+]>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(=O)C=1C=C(C(=O)O)C=CC1C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]([OH:12])[C@H:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([C:27](=[O:28])[O-:29])[cH:30][cH:31][c:32]2[CH3:33])[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]... | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)[O-])ccc2C)c1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)O)ccc2C)c1 | null | null | C1CCOC1.CO.O | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | [O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 22.5 | CELSIUS | 8 | HOUR | 3-[({(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}amino) carbonyl]-4-methylbenzoate (200 mg, 0.42 mmol) is treated with lithium hydroxide (39 mg, 0.96 mmol) in tetrahydrofuran/methanol/water (2/1/1, 2 ml), and the mixture stirred overnight at 20-25 degrees C. The mixture is decanted and the supernatant c... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1CCOC1.CO.O | 22.5 | 8 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)[O-])ccc2C)c1>C1CCOC1.CO.O>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C(=O)O)ccc2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c299e4b8c5a4140b994f980f26e1995 | COc1cccc(CNC[C@@H](O)[C@@H](Cc2ccccc2)NC(=O)c2cc(C)cc(Br)c2)c1.OB(O)c1ccco1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(-c3ccco3)c2)c1 | C(C1=CC=CC=C1)[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(=CC(=C1)C)Br)=O.O1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(=CC(=C1)C)C=1OC=CC1)=O | Br[c:29]1[cH:28][c:26]([CH3:27])[cH:25][c:24]([C:22]([NH:21][C@@H:13]([C@@H:11]([CH2:10][NH:9][CH2:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36]2)[OH:12])[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)=[O:23])[cH:35]1.OB(O)[c:30]1[cH:31][cH:32][cH:33][o:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8... | COc1cccc(CNC[C@@H](O)[C@@H](Cc2ccccc2)NC(=O)c2cc(C)cc(Br)c2)c1.OB(O)c1ccco1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(-c3ccco3)c2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(Cl)(Cl)Cl.CN(C=O)C | C-C Coupling | Suzuki coupling with boronic acids | 30fc6308f19ce3843efeacd1221e72dfe83900ec8748d35f98195a6635a23482 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1cccc(-c2ccco2)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#7:7])=[O;D1;H0:8].O-B(-O)-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | N-{(1R,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-bromo-5-methylbenzamide (X, EXAMLE 761, 295 mg, 0.59 mmol), 2-furanylboronic acid (133 mg, 1.19 mmol) and sodium carbonate (366 mg, 2.95 mmol) are combined in dimethylformamide (5 ml) and sparged under a flow of nitrogen for 15 minutes. Tetrakis(tripheny... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccoc1 | c1ccccc1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccoc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)Cl.CN(C=O)C | 100 | null | COc1cccc(CNC[C@@H](O)[C@@H](Cc2ccccc2)NC(=O)c2cc(C)cc(Br)c2)c1.OB(O)c1ccco1>C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)Cl.CN(C=O)C>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(-c3ccco... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-869d5d2e367a4478bd6388917c4fbdfe | COC(=O)c1cc(C)cc(Br)c1.OB(O)c1cccs1>>COC(=O)c1cc(C)cc(-c2ccsc2)c1 | S1C(=CC=C1)B(O)O.BrC=1C=C(C(=O)OC)C=C(C1)C>>CC=1C=C(C(=O)OC)C=C(C1)C1=CSC=C1 | Br[c:10]1[cH:9][c:7]([CH3:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16]1.OB(O)[c:11]1[cH:12][cH:13][cH:15][s:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[cH:9][c:10](-[c:11]2[cH:12][cH:13][s:14][cH:15]2)[cH:16]1 | COC(=O)c1cc(C)cc(Br)c1.OB(O)c1cccs1 | COC(=O)c1cc(C)cc(-c2ccsc2)c1 | null | null | null | C-C Coupling | OtherReaction | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccsc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[s;H0;D2;+0:13]:1>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[s;H0;D2;+0:13]:[cH;D2;+0:12]:1):[c:7]:[c:8] | null | [] | null | null | null | null | Following the general procedure of EXAMPLE 766 and making non-critical variations but using 2-thiopheneboronic acid and methyl 3-bromo-5-methylbenzoate, methyl 3-methyl-5-(3-thienyl)benzoate is obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | null | null | null | COC(=O)c1cc(C)cc(Br)c1.OB(O)c1cccs1>>COC(=O)c1cc(C)cc(-c2ccsc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6587c42cea104036bcb62b522d741943 | COC(=O)c1cc(C)cc(-c2ccsc2)c1>>Cc1cc(C(=O)O)cc(-c2ccsc2)c1 | CC=1C=C(C(=O)OC)C=C(C1)C1=CSC=C1.[OH-].[Li+]>>CC=1C=C(C(=O)O)C=C(C1)C1=CSC=C1 | C[O:7][C:5]([c:4]1[cH:3][c:2]([CH3:1])[cH:15][c:9](-[c:10]2[cH:11][cH:12][s:13][cH:14]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9](-[c:10]2[cH:11][cH:12][s:13][cH:14]2)[cH:15]1 | COC(=O)c1cc(C)cc(-c2ccsc2)c1 | Cc1cc(C(=O)O)cc(-c2ccsc2)c1 | null | null | O1CCCC1.CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccsc2)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] | null | [] | 22.5 | CELSIUS | 2 | HOUR | Methyl 3-methyl-5-(3-thienyl)benzoate (257 mg, 1.1 mmol) is treated with lithium hydroxide (186 mg, 4.4 mmol) in tetrahydrofuran/methanol/water (8 ml, 2:1:1) and the mixture is stirred for 2 hours at 20-25 degrees C. The mixture is acidified and concentrated to give the title compound, MS [M+H]+=217.0.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | O1CCCC1.CO.O | 22.5 | 2 | COC(=O)c1cc(C)cc(-c2ccsc2)c1>O1CCCC1.CO.O>Cc1cc(C(=O)O)cc(-c2ccsc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87705186f99d4b92b870c1ad70445a8b | CCCCC1CO1.COCCOCCOC.COCCOCCOC.[OH-]>>CCCCC1CC1C(=O)O | [H-].[Na+].COCCOCCOC.COCCOCCOC.O1CC1CCCC.COCCOCCOC.[OH-].[Na+].[H][H]>>C(CCC)C1C(C1)C(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][O:9]1.COCCOCCO[CH3:8].COCCOCCO[CH3:7].[OH-:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH:7]1[C:8](=[O:9])[OH:10] | CCCCC1CO1.COCCOCCOC.COCCOCCOC.[OH-] | CCCCC1CC1C(=O)O | null | null | O | Acylation | OtherReaction | 94ed567d976acf44a5e57391fef4ef02436a3b39ede3a4fd6d40312be9233c47 | a6005a0af1710b6cb0dc114c114fe4d537bca68fc1583250246e57e00485dfd3 | C1CC1 | C-O-C-C-O-C-C-O-[CH3;D1;+0:1].C-O-C-C-O-C-C-O-[CH3;D1;+0:2].[C:3]-[C:4]-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1.[OH-;D0:8]>>[C:3]-[C:4]-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH;D3;+0:2]-1-[C;H0;D3;+0:1](=[O;H0;D1;+0:7])-[OH;D1;+0:8] | null | [] | 25 | CELSIUS | 1 | DAY | A solution of triethylphosphonoacetate (22.4 g, 0.1 mol) in 13 mL of diglyme is added to a mixture of 13 mL of diglyme and sodium hydride (60%, 5.7 g, 0.12 mol) in mineral oil. When hydrogen evolution ceased, 1,2-epoxyhexane (12 g, 0.12 mol) in diglyme (12 mL) is added. The mixture is stirred for 1 day at 25 degrees C.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether.Ether.Ether.Ether | Carboxylic acid | C1CO1 | C1CC1 | C1CC1 | HO- | O | 25 | 24 | CCCCC1CO1.COCCOCCOC.COCCOCCOC.[OH-]>O>CCCCC1CC1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-baadfe228970474f9ccf855c160cc0da | Cc1noc(C)c1CCl.N>>Cc1noc(C)c1CN | ClCC=1C(=NOC1C)C.N>>NCC=1C(=NOC1C)C | Cl[CH2:8][c:7]1[c:2]([CH3:1])[n:3][o:4][c:5]1[CH3:6].[NH3:9]>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[CH2:8][NH2:9] | Cc1noc(C)c1CCl.N | Cc1noc(C)c1CN | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 141e57e7b467ef1af7390eea74d28aab60295f9a2146f5e9c32bccbe8d06fe6f | 14467bdca40cd5f74ac0c15917a737e6b818cd36a46b0668375c9383066b6e0b | c1cnoc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#8;a:6]:[c:7]:1-[C;D1;H3:8].[NH3;D0;+0:9]>>[C;D1;H3:4]-[c:3]1:[#7;a:5]:[#8;a:6]:[c:7](-[C;D1;H3:8]):[c:2]:1-[CH2;D2;+0:1]-[NH2;D1;+0:9] | null | [] | null | null | null | null | 4-Chloromethyl-3,5-dimethylisoxazole (700 mg, 4.8 mmol) is suspended in concentrated aqueous ammonia at 20-25 degrees C., and vigorously stirred overnight. The reaction mixture is extracted with isopropyl alcohol/chloroform (10/90, 2×). The combined organic phases are concentrated under nitrogen flow. The residue is pu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary amine | null | null | c1cnoc1 | HCl | null | null | null | Cc1noc(C)c1CCl.N>>Cc1noc(C)c1CN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8909ab9c1bbb4052a6f662c3ef28501b | CC(C)CC(N)=S.CCOC(=O)C(Cl)C=O>>CC(C)Cc1ncc(CO)s1 | C([O-])(O)=O.[Na+].C(CC(C)C)(N)=S.C(=O)C(C(=O)OCC)Cl.O>>OCC1=CN=C(S1)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C:5]([NH2:6])=[S:11].CCO[C:9]([CH:8](Cl)[CH:7]=O)=[O:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][OH:10])[s:11]1 | CC(C)CC(N)=S.CCOC(=O)C(Cl)C=O | CC(C)Cc1ncc(CO)s1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | e68044ee5188b864640d108d5429795f5c1c710f8b7f392caeaa187d2cf45ab5 | 8b901d2ed5111dacd25f5694d037526276a1bc99ab06e4d896eeb1a4f7c36ad2 | c1cscn1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-Cl)-[CH;D2;+0:4]=O.[C:5]-[C:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]>>[C:5]-[C:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[cH;D2;+0:4]:[c;H0;D3;+0:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[s;H0;D2;+0:9]:1 | null | [] | 95 | CELSIUS | 4 | HOUR | Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ester.Thioamide | Primary alcohol | null | c1cscn1 | c1cscn1 | HCl | CN(C)C=O | 95 | 4 | CC(C)CC(N)=S.CCOC(=O)C(Cl)C=O>CN(C)C=O>CC(C)Cc1ncc(CO)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92664d0da051407c83e8edbff8cbe339 | CCOC(=O)c1cnc(CC(C)C)s1>>CC(C)Cc1ncc(CO)s1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O.CC(CC=1SC(=CN1)C(=O)OCC)C>>OCC1=CN=C(S1)CC(C)C | CCO[C:9]([c:8]1[cH:7][n:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[s:11]1)=[O:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][OH:10])[s:11]1 | CCOC(=O)c1cnc(CC(C)C)s1 | CC(C)Cc1ncc(CO)s1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cscn1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1 | null | [] | 22.5 | CELSIUS | 1 | HOUR | A solution of ethyl 2-(2-methylpropyl)thiazole-5-carboxylate (2.05 g, 9.6 mmol) in THF (10 mL) is added dropwise with stirring to a suspension of lithium aluminum hydride (730 mg, 19 mmol) in dry THF (50 mL) at 0 degrees C. Upon complete addition, the reaction mixture is allowed to stir at 20-25 degrees C. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cscn1 | HO- | C1CCOC1 | 22.5 | 1 | CCOC(=O)c1cnc(CC(C)C)s1>C1CCOC1>CC(C)Cc1ncc(CO)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6f7460725c1446c903c60665af942d3 | O=C(O)C1(c2ccccc2)CC1>>NC1(c2ccccc2)CC1 | [N-]=[N+]=[N-].[Na+].C1(=CC=CC=C1)C1(CC1)C(=O)O>>C1(=CC=CC=C1)C1(CC1)N | O=C(O)[C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10]1>>[NH2:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10]1 | O=C(O)C1(c2ccccc2)CC1 | NC1(c2ccccc2)CC1 | null | null | ClCCl.S(O)(O)(=O)=O | Miscellaneous | Schmidt reaction acid_amine | 5c92e3b8174ad11d5f849d8f8180ac2e2fac2854913704a10a1a00f2a5fce63f | f6539489e23e870a77b49bacaebcd4efedb6a9c737a80e1e5866f398c3113bf2 | c1ccc(C2CC2)cc1 | O-C(=O)-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5]-[C:6]-1>>[N;D1;H2:7]-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5]-[C:6]-1 | null | [] | 50 | CELSIUS | 17 | HOUR | Following the procedure described in N. W. Werner et.al., J. Org. Syn. Coll. Vol. 5, 273-276, sodium azide (0.915 g, 14.1 mmol) is slowly added to a solution of 1-phenyl-cyclopropanecarboxlic acid (1.0 g, 6.1 mmol) in concentrated sulfuric acid (5 ml) and dichloromethane (10 ml). The sodium sulfate precipitated out of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amine | C1CC1 | C1CC1 | c1ccccc1.C1CC1 | Other | ClCCl.S(O)(O)(=O)=O | 50 | 17 | O=C(O)C1(c2ccccc2)CC1>ClCCl.S(O)(O)(=O)=O>NC1(c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5807476d8d4e47919a916fd1a588f127 | COc1ccccc1.O=C1CCCO1>>C1C2CC3C4CC5CC(C14)C(C2)C3C5 | C1(CCCO1)=O.C1(=CC=CC=C1)OC>>C1C2CC3C4C1C5CC(C4)CC3C5C2 | O([c:5]1[cH:6][cH:3][cH:2][cH:1][cH:10]1)[CH3:9].O=[C:12]1O[CH2:14][CH2:13][CH2:11]1>>[CH2:1]1[CH:2]2[CH2:3][CH:4]3[CH:5]4[CH2:6][CH:7]5[CH2:8][CH:9]([CH:10]14)[CH:11]([CH2:12]2)[CH:13]3[CH2:14]5 | COc1ccccc1.O=C1CCCO1 | C1C2CC3C4CC5CC(C14)C(C2)C3C5 | null | null | null | C-C Coupling | OtherReaction | 9415fc43541f0bc61dd7b21347441002aa892115da878296b140dad178b16581 | c671014c4bd265e3243b8edb29db18ceb7aa1d582e586eda338e7f5deec40006 | C1C2CC3C4CC5CC(C14)C(C2)C3C5 | O=[C;H0;D3;+0:1]1-O-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[CH3;D1;+0:5]-O-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[C:12]1-[C:13]2-[CH2;D2;+0:2]-[CH;D3;+0:3]3-[C:14]4-[CH2;D2;+0:10]-[CH;D3;+0:9]5-[CH2;D2;+0:1]-[CH;D3;+0:4]-3-[CH;D3;+0:5]-1-[CH;D3;+0:7](-[CH2;D2;+0:8]-5... | null | [] | null | null | null | null | 1.0 g of the polymer (A-12) produced in Production Example 1 was dissolved under heat in a mixed solvent of 5.0 ml of gamma-butyrolactone and 5.0 ml of anisole to prepare a coating solution. The ratio of all carbon atoms of the cage structure (diamantane) to all carbon atoms of the total solid content of the insulating... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | null | c1ccccc1.C1CCOC1 | C1C2CC3C4CC5CC(C14)C(C2)C3C5 | C1C2CC3C4CC5CC(C14)C(C2)C3C5 | null | null | null | null | COc1ccccc1.O=C1CCCO1>>C1C2CC3C4CC5CC(C14)C(C2)C3C5 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da7925d1e221449597eedc6d7ef7eec3 | BrCCCCCCBr.N#Cc1ccc(-c2ccc(O)cc2)cc1>>N#Cc1ccc(-c2ccc(OCCCCCCBr)cc2)cc1 | OC1=CC=C(C=C1)C1=CC=C(C=C1)C#N.BrCCCCCCBr>>BrCCCCCCOC1=CC=C(C=C1)C1=CC=C(C=C1)C#N | Br[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](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:19][cH:20]2)[cH:21][cH:22]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | BrCCCCCCBr.N#Cc1ccc(-c2ccc(O)cc2)cc1 | N#Cc1ccc(-c2ccc(OCCCCCCBr)cc2)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 58.3 | [{"value": 58.0, "product": "BrCCCCCCOC1=CC=C(C=C1)C1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "BrCCCCCCOC1=CC=C(C=C1)C1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.2 mol (39 g) of 4-hydroxy-4′-cyanobiphenyl, 2 mol (487.5 g) of 1,6-dibromohexane, 1.45 mol (200 g) of potassium carbonate anhydride and 800 ml of acetone were placed in a 2 l three-neck flask equipped with a mechanical stirrer and the mixture was reacted under reflux for 20 hours by using a water bath. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | null | BrCCCCCCBr.N#Cc1ccc(-c2ccc(O)cc2)cc1>CC(=O)C>N#Cc1ccc(-c2ccc(OCCCCCCBr)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b66bd81feb74d5f85c175b33f2e7d3a | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1>>CCOC(=O)c1cccc(C(=O)OCC)c1 | BrCCCCCCOC1=CC=C(C=C1)C1=CC=C(C=C1)C#N.OC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC.CC(=O)C>>C(C1=CC(C(=O)OCC)=CC=C1)(=O)OCC | O[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:16][c:10]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[cH:9]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[cH:16]1 | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1 | CCOC(=O)c1cccc(C(=O)OCC)c1 | null | null | O | Reduction | OtherReaction | 0b15258bc3b0efb75716a15093f26f3ade1fb35d0d50493dcb65925b9449d16a | 27ebe27a5e17883303ac9a42d30f2cb918c0044de7ff3c79776e1ddb80cc53d9 | c1ccccc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#8:10]-[C:9](=[O;D1;H0:11])-[c:8]:[c:7]:[cH;D2;+0:1]:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 90 | [{"value": 90.0, "product": "C(C1=CC(C(=O)OCC)=CC=C1)(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.08 mol (28.8 g) of 4-(6-bromohexyloxy)-4′-cyanobiphenyl, 0.08 mol (16.6 g) of diethyl 5-hydroxyisophthalate, 0.12 mol (19.2 g) of potassium carbonate anhydride and 400 ml of acetone were placed in a 1 l three-neck flask and the mixture was reacted under reflux for 24 hours by using a water bath. After the reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O | null | null | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1>O>CCOC(=O)c1cccc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1cf23f40774480182d68cd7193c2a56 | BrCCCCCCBr.Cc1ccc(N=Nc2ccc(O)cc2)cc1>>Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1 | OC1=CC=C(C=C1)N=NC1=CC=C(C=C1)C.BrCCCCCCBr.OC1=CC=CC=C1>>BrCCCCCCOC1=CC=C(C=C1)N=NC1=CC=C(C=C1)C | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Br:19].[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[N:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:20][cH:21]2)[cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[N:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Br:19])[cH:20][cH:21]2)[cH:22]... | BrCCCCCCBr.Cc1ccc(N=Nc2ccc(O)cc2)cc1 | Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N=Nc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 20 | HOUR | A 2 l three-neck flask equipped with a mechanical stirrer was charged with 42.4 g (0.2 mol) of 4-hydroxy-4′-methylazobenzene synthesized in the same manner as in the Example, 448 g (2 mol) of 1,6-dibromohexane and 212 g (1.5 mol) of potassium carbonate anhydride. To the mixture was added 800 ml of acetone and the resul... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | 20 | BrCCCCCCBr.Cc1ccc(N=Nc2ccc(O)cc2)cc1>CC(=O)C>Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8735bffa835f4857a0342a600b807818 | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1.Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1>>CCOC(=O)c1cccc(C(=O)OCC)c1OCCCCCCOc1ccc(N=Nc2ccc(C)cc2)cc1 | CC(=O)C.OC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC.BrCCCCCCOC1=CC=C(C=C1)N=NC1=CC=C(C=C1)C>>CC1=CC=C(C=C1)N=NC1=CC=C(OCCCCCCOC2=C(C(=O)OCC)C=CC=C2C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:17])[cH:9][c:10]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[cH:16]1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][c:25]1[cH:26][cH:27][c:28]([N:29]=[N:30][c:31]2[cH:32][cH:33][c:34]([CH3:35])[cH:36][cH:37]2)[cH:38][cH:39]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:... | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1.Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1 | CCOC(=O)c1cccc(C(=O)OCC)c1OCCCCCCOc1ccc(N=Nc2ccc(C)cc2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 23149dacdaebd504e79f1460639cdf4dc78dff873b7f37b250b388ce89c7cfcd | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N=Nc2ccc(OCCCCCCOc3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c;H0;D3;+0:10](-[OH;D1;+0:11]):[c:12]:[c:13](-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17]):[cH;D2;+0:18]:1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[cH;D2;+0:10]:[c:12]:[c:13](-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17]):[c;H0;D3;+0:18]:1-[O;H0;D2;+0:... | 83 | [{"value": 83.0, "product": "CC1=CC=C(C=C1)N=NC1=CC=C(OCCCCCCOC2=C(C(=O)OCC)C=CC=C2C(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1 l three-neck flask was charged with 16.6 g (0.07 mol) of diethyl 5-hydroxyisophthalate, 26.1 g (0.07 mol) of 4-(6-bromohexyloxy)-4′-methylazobenzene and 15.1 g (0.11 mol) of potassium carbonate anhydride. To the mixture was added 300 ml of acetone and the system was refluxed under heating to react for 24 hours. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O | null | null | CCOC(=O)c1cc(O)cc(C(=O)OCC)c1.Cc1ccc(N=Nc2ccc(OCCCCCCBr)cc2)cc1>O>CCOC(=O)c1cccc(C(=O)OCC)c1OCCCCCCOc1ccc(N=Nc2ccc(C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3ae525c31934931932ff4147ee1322c | NN.O=C1c2ccccc2-c2ccccc21>>NN=C1c2ccccc2-c2ccccc21 | C1=CC=CC=2C3=CC=CC=C3C(C12)=O.NN>>C1=CC=CC=2C3=CC=CC=C3C(C12)=NN | [NH2:1][NH2:2].O=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21>>[NH2:1][N:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | NN.O=C1c2ccccc2-c2ccccc21 | NN=C1c2ccccc2-c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ccc0a14f8c3fdf62e7efedef58920d09145f00264c0781efad48c689ddb905d2 | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | N=C1c2ccccc2-c2ccccc21 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[c:5]:[c:6]-1:[c:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[N;D1;H2:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[c:5]:[c:6]-1:[c:7] | null | [] | null | null | null | null | Symmetrical charge transport materials can be prepared by the following procedure. In the first step a 9-fluorenone or a derivative compound reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a 9-fluorenone hydrazone compound or derivative thereof. Then, the 9-fluorenone hydrazone compound can be ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HO- | null | null | null | NN.O=C1c2ccccc2-c2ccccc21>>NN=C1c2ccccc2-c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a453f07d5aa04e16a4fa21fb7c6c9382 | NN.O=C1c2ccccc2-c2ccccc21>>NN=C1c2ccccc2-c2ccccc21 | C1=CC=CC=2C3=CC=CC=C3C(C12)=O.NN>>C1=CC=CC=2C3=CC=CC=C3C(C12)=NN | [NH2:1][NH2:2].O=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21>>[NH2:1][N:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | NN.O=C1c2ccccc2-c2ccccc21 | NN=C1c2ccccc2-c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ccc0a14f8c3fdf62e7efedef58920d09145f00264c0781efad48c689ddb905d2 | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | N=C1c2ccccc2-c2ccccc21 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[c:5]:[c:6]-1:[c:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[N;D1;H2:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[c:5]:[c:6]-1:[c:7] | null | [] | null | null | null | null | Unsymmetrical charge transport materials can be prepared by using an unsymmetrical linking compound such as 6-dimethyl-1, 4-benzoquinone. Alternatively, unsymmetrical charge transport materials can be prepared by the following procedure. In the first step, a first 9-fluorenone or a derivative thereof reacts with an exc... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HO- | null | null | null | NN.O=C1c2ccccc2-c2ccccc21>>NN=C1c2ccccc2-c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c0dd087e7d649ed800a35b09df06bfc | O=C[C@@H](O)[C@@H](O)[C@H](O)CO>>OC[C@@H](O)C(O)[C@H](O)CO | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@@H](O)[C@@H](O)[C@H](O)CO>>C([C@H](C([C@@H](CO)O)O)O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | [O:13]=[CH:14][C@@H:15]([OH:16])[C@@H:17]([OH:18])[C@H:19]([OH:20])[CH2:21][OH:22]>>[OH:13][CH2:14][C@@H:15]([OH:16])[CH:17]([OH:18])[C@H:19]([OH:20])[CH2:21][OH:22] | O=C[C@@H](O)[C@@H](O)[C@H](O)CO | OC[C@@H](O)C(O)[C@H](O)CO | null | null | null | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | null | [C:1]-[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5]>>[C:1]-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[OH;D1;+0:5] | null | [] | null | null | null | null | Production of D-lyxose, which is a rare sugar, from D-glucose was carried out. By using yeast Candida famata R28, D-arabitol was produced from D-glucose with a yield of 50%. This reaction was carried out by a fermentation method. The produced D-arabitol was converted into D-xylulose by an acetic acid bacterium Acetobac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | null | null | null | null | null | O=C[C@@H](O)[C@@H](O)[C@H](O)CO>>OC[C@@H](O)C(O)[C@H](O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bbbb27521d247fb9f8aa4127e917a6f | N[C@@H](Cc1c[nH]cn1)C(=O)O>>NCCCC[C@H](N)C(=O)O | N[C@@H](CC1=CNC=N1)C(=O)O.N1=CN=C2N=CNC2=C1N>>N[C@@H](CCCCN)C(=O)O | [nH]1[cH:2][n:1][c:4]([CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10])[cH:3]1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10] | N[C@@H](Cc1c[nH]cn1)C(=O)O | NCCCC[C@H](N)C(=O)O | null | null | null | Miscellaneous | OtherReaction | e98cb4e427b1f834a3f369f733cfa94afa7e6bdf0b0a2dce6316f3b771d436b2 | 80432e902bdf083999b5ae9998b9b267b83df62fea0bbbdf4989ab850ab363f2 | null | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[nH]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:1>>[NH2;D1;+0:9]-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3] | null | [] | null | null | null | null | An ADE2 fragment and a LYS2 fragment were also prepared under similar reaction conditions using A451 genomic DNA as a template and ADE-1 (5′ ATG GAT TCT AGA ACA GTT GGT 3′ (SEQ ID NO: 127)) and ADE-2 (5′ TTA CTT GTT TTC TAG ATA AGC 3′ (SEQ ID NO: 128)) or LYS-1 (5′ ATG ACT AAC GAA AAG GTC TGG 3′ (SEQ ID NO: 129)) and L... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1c[nH]cn1 | null | null | Other | null | null | null | N[C@@H](Cc1c[nH]cn1)C(=O)O>>NCCCC[C@H](N)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-872cc659c4874c6cbc6f67a10392e496 | O=Cc1cc(O)ccc1[N+](=O)[O-].OCCCBr>>O=Cc1cc(OCCCO)ccc1[N+](=O)[O-] | C(Cl)Cl.BrCCCO.OC=1C=CC(=C(C=O)C1)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C1=C(C=O)C=C(C=C1)OCCCO | [O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16].Br[CH2:7][CH2:8][CH2:9][OH:10]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])[cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16] | O=Cc1cc(O)ccc1[N+](=O)[O-].OCCCBr | O=Cc1cc(OCCCO)ccc1[N+](=O)[O-] | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 96 | [{"value": 96.0, "product": "[N+](=O)([O-])C1=C(C=O)C=C(C=C1)OCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "[N+](=O)([O-])C1=C(C=O)C=C(C=C1)OCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Bromo-1-propanol (3.34 g, 24 mmol) was refluxed in 80 ml of anhydrous acetonitrile with 5-hydroxy-2-nitrobenzaldehyde (3.34 g, 20 mmol), K2CO3 (3.5 g), and KI (100 mg) overnight (15 h). The reaction mixture was cooled to room temperature and 150 ml of methylene chloride was added. The mixture was filtered and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | null | O=Cc1cc(O)ccc1[N+](=O)[O-].OCCCBr>C(C)#N>O=Cc1cc(OCCCO)ccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95048697cb86400084462103892b86f1 | c1ccc(Nc2ccc3ncccc3c2)cc1>>c1ccc(Nc2ccc3c(c2)CCCN3)cc1 | N(C1=CC=CC=C1)C=1C=C2C=CC=NC2=CC1>>C1(=CC=CC=C1)NC=1C=C2CCCNC2=CC1 | [cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[cH:12][cH:13][cH:14][n:15]3)[cH:16][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[CH2:12][CH2:13][CH2:14][NH:15]3)[cH:16][cH:17]1 | c1ccc(Nc2ccc3ncccc3c2)cc1 | c1ccc(Nc2ccc3c(c2)CCCN3)cc1 | null | [Pt](=O)=O | C(C)(=O)O | Reduction | OtherReaction | 0f501d7f6563b973124f46b9ac99227bf4e9d23710ef3fe61283d96ce59150d0 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(Nc2ccc3c(c2)CCCN3)cc1 | [c:1]:[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[c:7]:1:[c:8]>>[c:1]:[c:2]1:[c:7](:[c:8])-[NH;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-1 | 98.2 | [{"value": 98.2, "product": "C1(=CC=CC=C1)NC=1C=C2CCCNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 20.4 grams of 6-anilinoquinoline (prepared as described in Buu-Hoi, Royer and Hubert-Habart, J. Chem. Soc., 1956, 2048-2051) in 400 mL of acetic acid containing 1.3 grams of platinum(IV) oxide was hydrogenated at 30 psi for 4.2 hours on a Parr low-pressure hydrogenator. The solution was filtered; and the ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2ncccc2c1 | c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCCN2 | null | [Pt](=O)=O.C(C)(=O)O | null | null | c1ccc(Nc2ccc3ncccc3c2)cc1>[Pt](=O)=O.C(C)(=O)O>c1ccc(Nc2ccc3c(c2)CCCN3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-801f1dbefbd2482bb4cff0e1cae83ede | CC(C)(C)c1ccc(Br)cc1.Nc1cccc2cccnc12>>CC(C)(C)c1ccc(Nc2cccc3c2NCCC3)cc1 | NC=1C=CC=C2C=CC=NC12.C(C)(C)(C)C1=CC=C(C=C1)Br.CC(C)([O-])C.[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)NC=1C=CC=C2CCCNC12 | Br[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:21][cH:20]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][cH:18][cH:19]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[NH:16][CH2:17][CH2:18][CH2:19]3)[cH:20][cH:21]1 | CC(C)(C)c1ccc(Br)cc1.Nc1cccc2cccnc12 | CC(C)(C)c1ccc(Nc2cccc3c2NCCC3)cc1 | null | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 9f3303f7d64e81c40939d38cfebdbb37828fc7f74cee5ec10c91ec728073f17b | a80285b10533b001971933d28ff9ea0e1bc6ead83a15f0ed3aaf0722d61e5913 | c1ccc(Nc2cccc3c2NCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]1:[n;H0;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c:14]:1:[c:15]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]1:[c:14](:[c:15])-[CH2;D2;+0:13]-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[NH;D2;+0:10]-1 | 82 | [{"value": 82.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)NC=1C=CC=C2CCCNC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added 8-aminoquinoline (14.4 grams, 0.10 moles), 4-tert-butyl bromobenzene (21.3 grams, 0.10 moles), tris(dibenzylideneacetone)dipalladium (0) (1.8 grams, 0.002 moles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (2.5 grams, 0.004 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCCN2 | Br- | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | CC(C)(C)c1ccc(Br)cc1.Nc1cccc2cccnc12>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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>CC(C)(C)c1ccc(Nc2cccc3c2NCCC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f06d3551e324d909cd31afe338b56fc | Brc1ccc2ccccc2c1.Nc1ccc2ncccc2c1>>c1ccc2cc(Nc3ccc4c(c3)CCCN4)ccc2c1 | NC=1C=C2C=CC=NC2=CC1.BrC1=CC2=CC=CC=C2C=C1.CC(C)([O-])C.[Na+]>>C1=C(C=CC2=CC=CC=C12)NC=1C=C2CCCNC2=CC1 | Br[c:6]1[cH:5][c:4]2[cH:3][cH:2][cH:1][cH:21][c:20]2[cH:19][cH:18]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[cH:14][cH:15][cH:16][n:17]2>>[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13]3)[CH2:14][CH2:15][CH2:16][NH:17]4)[cH:18][cH:19][c:20]2[cH:21]1 | Brc1ccc2ccccc2c1.Nc1ccc2ncccc2c1 | c1ccc2cc(Nc3ccc4c(c3)CCCN4)ccc2c1 | null | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | d5ff64f0f0cd8549a04dc259a75ba7e3503ab0124a3126ace4800b2649f744fa | a80285b10533b001971933d28ff9ea0e1bc6ead83a15f0ed3aaf0722d61e5913 | c1ccc2cc(Nc3ccc4c(c3)CCCN4)ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[c:14]:2:[c:15]:[c:16]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]2:[c:14](:[c:15]:[c:16]:1)-[NH;D2;+0:13]-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-2):[c:4]:[c:5... | 70.9 | [{"value": 70.9, "product": "C1=C(C=CC2=CC=CC=C12)NC=1C=C2CCCNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 6-aminoquinoline (6.69 grams, 46.4 mmoles), 2-bromonapthalene (9.15 grams, 44.2 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.80 grams, 0.87 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (1.10 grams, 1.77 mmole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1ccc2ccccc2c1.c1ccc2ncccc2c1 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCN2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCN2 | Br- | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | Brc1ccc2ccccc2c1.Nc1ccc2ncccc2c1>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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>c1ccc2cc(Nc3ccc4c(c3)CCCN4)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5861cf62eb94184b8a6f8b14f7bdda8 | Brc1ccc2ccccc2c1.Nc1cccc2cccnc12>>c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | NC=1C=CC=C2C=CC=NC12.BrC1=CC2=CC=CC=C2C=C1.CC(C)([O-])C.[Na+]>>C1=C(C=CC2=CC=CC=C12)NC=1C=CC=C2CCCNC12 | Br[c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1.[cH:1]1[cH:2][c:3]2[c:4]([c:5]([NH2:6])[cH:17]1)[n:18][cH:19][cH:20][cH:21]2>>[cH:1]1[cH:2][c:3]2[c:4]([c:5]([NH:6][c:7]3[cH:8][cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16]3)[cH:17]1)[NH:18][CH2:19][CH2:20][CH2:21]2 | Brc1ccc2ccccc2c1.Nc1cccc2cccnc12 | c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | null | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | d5ff64f0f0cd8549a04dc259a75ba7e3503ab0124a3126ace4800b2649f744fa | a80285b10533b001971933d28ff9ea0e1bc6ead83a15f0ed3aaf0722d61e5913 | c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]1:[n;H0;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c:14]:1:[c:15]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]1:[c:14](:[c:15])-[CH2;D2;+0:13]-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[NH;D2;+0:10]-1):[c:4]:[c:5] | 52 | [{"value": 52.0, "product": "C1=C(C=CC2=CC=CC=C12)NC=1C=CC=C2CCCNC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 8-aminoquinoline (6.81 grams, 47.2 mmoles), 2-bromonapthalene (9.58 grams, 46.3 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.84 grams, 0.92 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.6 grams, 0.92 mmoles... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1ccc2ccccc2c1.c1ccc2ncccc2c1 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCN2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCN2 | Br- | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | Brc1ccc2ccccc2c1.Nc1cccc2cccnc12>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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-993bc91a09f64394813bc9f46ed5fd8c | c1ccc2cc(Nc3cccc4cccnc34)ccc2c1>>c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | C1=C(C=CC2=CC=CC=C12)NC=1C=CC=C2C=CC=NC12.C(C)(=O)OCC>>C1=C(C=CC2=CC=CC=C12)NC=1C=CC=C2CCCNC12 | [cH:1]1[cH:2][c:3]2[c:4]([c:5]([NH:6][c:7]3[cH:8][cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16]3)[cH:17]1)[n:18][cH:19][cH:20][cH:21]2>>[cH:1]1[cH:2][c:3]2[c:4]([c:5]([NH:6][c:7]3[cH:8][cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16]3)[cH:17]1)[NH:18][CH2:19][CH2:20][CH2:21]2 | c1ccc2cc(Nc3cccc4cccnc34)ccc2c1 | c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | null | [Pt](=O)=O | C(C)(=O)O | Reduction | OtherReaction | 0f501d7f6563b973124f46b9ac99227bf4e9d23710ef3fe61283d96ce59150d0 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 | [c:1]:[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[c:7]:1:[c:8]>>[c:1]:[c:2]1:[c:7](:[c:8])-[NH;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-1 | 101.4 | [{"value": 101.4, "product": "C1=C(C=CC2=CC=CC=C12)NC=1C=CC=C2CCCNC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 4.08 grams of N-2-naphthylquinolin-8-amine from above in acetic acid (10 mL) and ethyl acetate (150 mL) containing 0.24 grams of platinum(IV) oxide was hydrogenated at 45 psi for four hours on a Parr low-pressure hydrogenator. The solution was filtered through diatomaceous earth; concentrated in vacuo; an... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2ncccc2c1 | c1ccc2c(c1)CCCN2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCN2 | null | [Pt](=O)=O.C(C)(=O)O | null | 4 | c1ccc2cc(Nc3cccc4cccnc34)ccc2c1>[Pt](=O)=O.C(C)(=O)O>c1cc2c(c(Nc3ccc4ccccc4c3)c1)NCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea18611cf15946028f90f6758ed02185 | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)CCO2>>CC(C)(C)c1ccc(Nc2ccc3c(c2)CCO3)cc1 | O1CCC2=C1C=CC(=C2)N.C(C)(C)(C)C1=CC=C(C=C1)Br.CC(C)([O-])C.[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)NC=1C=CC2=C(CCO2)C1 | Br[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:20][cH:19]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH2:16][CH2:17][O:18]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[CH2:16][CH2:17][O:18]3)[cH:19][cH:20]1 | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)CCO2 | CC(C)(C)c1ccc(Nc2ccc3c(c2)CCO3)cc1 | null | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3c(c2)CCO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 2,3-dihydro-1-benzofuran-5-amine (11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 4-tert-butyl bromobenzene (18.1 grams, 85 mmoles), tris(dibenzylideneacetone)dipalladium (0) (1.6 grams, 1.7 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)CCO2>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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>CC(C)(C)c1ccc(Nc2ccc3c(c2)CCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3da1bc801bf499aa4187a62983239bd | Brc1ccc2c(c1)CCO2.CCN(CC)c1ccc(N)cc1>>CCN(CC)c1ccc(Nc2ccc3c(c2)CCO3)cc1 | C(C)N(C1=CC=C(C=C1)N)CC.BrC=1C=CC2=C(CCO2)C1.C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[Na+]>>O1CCC2=C1C=CC(=C2)NC2=CC=C(C=C2)N(CC)CC | Br[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[CH2:17][CH2:18][O:19]2.[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:20][cH:21]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[CH2:17][CH2:18][O:19]3)[cH:20][cH:21]1 | Brc1ccc2c(c1)CCO2.CCN(CC)c1ccc(N)cc1 | CCN(CC)c1ccc(Nc2ccc3c(c2)CCO3)cc1 | null | 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)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 3eefa8c0242a0dbc67760ed46fbbe572c7b05262288867a6644b519cc5731092 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3c(c2)CCO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | 87 | [{"value": 87.0, "product": "O1CCC2=C1C=CC(=C2)NC2=CC=C(C=C2)N(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added N,N-diethyl-1,4-phenylenediamine (3.35 grams, 20.4 mmoles), 5-bromo-2,3-dihydrobenzofuran (3.4 grams, 17.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.39 grams, 0.43 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | 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)C | 80 | null | Brc1ccc2c(c1)CCO2.CCN(CC)c1ccc(N)cc1>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)C>CCN(CC)c1ccc(Nc2ccc3c(c2)CCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab04477b1174495d94878c314fd9ebe5 | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)OC=CO2>>CC(C)(C)c1ccc(Nc2ccc3c(c2)OCCO3)cc1 | O1C=COC2=C1C=CC(=C2)N.C(C)(C)(C)C1=CC=C(C=C1)Br.CC(C)([O-])C.[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)NC1=CC2=C(OCCO2)C=C1 | Br[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:21][cH:20]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH:17]=[CH:18][O:19]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[O:16][CH2:17][CH2:18][O:19]3)[cH:20][cH:21]1 | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)OC=CO2 | CC(C)(C)c1ccc(Nc2ccc3c(c2)OCCO3)cc1 | null | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 5b9c864ebe5e9c55fc676b3c6cab7f5de49ffdfe3ed86c0d8e9f4d74d8f0bb4f | 073f62a3818e3c589c6cf905d1f7b64adb426c91fc96c232669654b3fe83ad5b | c1ccc(Nc2ccc3c(c2)OCCO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[c:10]1:[c:11]-[#8:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[#8:15]-1>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10]1:[c:11]-[#8:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[#8:15]-1 | 55 | [{"value": 55.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)NC1=CC2=C(OCCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added 1,4-benzodioxin-6-amine (5.26 grams, 34.8 mmoles), 4-tert-butyl bromobenzene (6.83 grams, 32.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.58 grams, 0.6 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.79 gra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary amine | Ether.Ether.Secondary amine | c1ccccc1.C1=COc2ccccc2O1 | c1ccccc1.c1ccc2c(c1)OCCO2 | c1ccccc1.c1ccc2c(c1)OCCO2 | Br- | 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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | CC(C)(C)c1ccc(Br)cc1.Nc1ccc2c(c1)OC=CO2>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(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>CC(C)(C)c1ccc(Nc2ccc3c(c2)OCCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-971429994703405483d8e251b6062dda | O=P(Cl)(Cl)Cl.Oc1ccnc2cccnc12>>Clc1ccnc2cccnc12 | OC1=CC=NC2=CC=CN=C12.P(=O)(Cl)(Cl)Cl.O.N>>ClC1=CC=NC2=CC=CN=C12 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]12>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]12 | O=P(Cl)(Cl)Cl.Oc1ccnc2cccnc12 | Clc1ccnc2cccnc12 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 160cc0635727e0449f6d143a0e3aa86d4f5c6cc2cf65b0d83794017f0973d942 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cnc2cccnc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10] | null | [] | null | null | null | null | To 700 mg of 4-hydroxy-1,5-naphthyridine (CAS No. 5423-54-1, purchased from Specs), phosphorous oxychloride (15 ml) was added and heated to reflux for an hour. The reaction was put back to room temperature. The mixture was poured to ice, made alkaline with ammonia water and extracted with ethyl acetate. The ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1ccnc2cccnc12>>Clc1ccnc2cccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-399ffb68b68542eb948a6d964532f4fb | Cc1nc2ccc(C(=O)O)cc2o1.Nc1ccnc2cccnc12.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>Cc1nc2ccc(NC(=O)Nc3ccnc4cccnc34)cc2o1 | NC1=CC=NC2=CC=CN=C12.CC=1OC2=C(N1)C=CC(=C2)C(=O)O.C(C)N(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>CC=1OC2=C(N1)C=CC(=C2)NC(=O)NC2=CC=NC1=CC=CN=C21 | O[C:9]([c:7]1[cH:6][cH:5][c:4]2[n:3][c:2]([CH3:1])[o:24][c:23]2[cH:22]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][n:15][c:16]2[cH:17][cH:18][cH:19][n:20][c:21]12.[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[NH:11][c:12]3[cH:13][cH:14][n:15][c:16]4[cH:17][cH:18][cH:1... | Cc1nc2ccc(C(=O)O)cc2o1.Nc1ccnc2cccnc12.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | Cc1nc2ccc(NC(=O)Nc3ccnc4cccnc34)cc2o1 | null | null | C1(=CC=CC=C1)C.CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | 667da69e1722da205cfeb2bffdfa049b4e0879435afda60fae68c2533a39df95 | ecf755b1d63c4b17ff77f75423f1cd2cb4c01eea455beb7cf8e0b1c6c992ada1 | O=C(Nc1ccc2ncoc2c1)Nc1ccnc2cccnc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[c:5]2:[#8;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1.O=P(-[N;H0;D2;+0:12]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[NH2;D1;+0:13]-[c:14]1:[c:15]:[c:16]:[#7;a:17]:[c:18]:[c:19]:1:[#7;a:20]:[c:21]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:13]-[c:14]1:[c:15]:[c:16]:[#7... | null | [] | 65 | CELSIUS | null | null | To 2-methyl-6-benzoxazole carboxylic acid (1.060 g) in toluene (111 ml) solution, triethylamine (0.867 ml) and N,N-dimethylformamide (22 ml) were added. To this mixture, diphenyl phosphoryl azide (1.65 ml) was added and stirred at 65° C. for an hour. The reaction mixture was cooled to room temperature, added with 4-ami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Primary amine | Urea | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1cnc2cccnc2c1 | HO- | C1(=CC=CC=C1)C.CN(C=O)C.C(C)(=O)OCC | 65 | null | Cc1nc2ccc(C(=O)O)cc2o1.Nc1ccnc2cccnc12.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C.CN(C=O)C.C(C)(=O)OCC>Cc1nc2ccc(NC(=O)Nc3ccnc4cccnc34)cc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2e54bf2162441c3ba25b67ddacf4642 | COCCl.Cc1nn(C)c2[nH]c(=O)c3ccccc3c12>>COCOc1nc2c(c(C)nn2C)c2ccccc12 | CC1=NN(C=2NC(C=3C=CC=CC3C21)=O)C.[H-].[Na+].COCCl>>CC1=NN(C=2N=C(C=3C=CC=CC3C21)OCOC)C | Cl[CH2:3][O:2][CH3:1].[O:4]=[c:5]1[nH:6][c:7]2[c:8]([c:9]([CH3:10])[n:11][n:12]2[CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][O:2][CH2:3][O:4][c:5]1[n:6][c:7]2[c:8]([c:9]([CH3:10])[n:11][n:12]2[CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | COCCl.Cc1nn(C)c2[nH]c(=O)c3ccccc3c12 | COCOc1nc2c(c(C)nn2C)c2ccccc12 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 35111ca09411e1f0ce39d2ae2925c8a8e8bf31410100a1901734dc9a487af197 | 1ae223d47d2f78a378f0f091748197aa526bfab373b8a34a73f210aacea8defb | c1ccc2c(c1)cnc1[nH]ncc12 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[C;D1;H3:4]-[#7;a:5]1:[#7;a:6]:[c:7]:[c:8]2:[c:9]:[c:10](:[c:11]):[c;H0;D3;+0:12](=[O;H0;D1;+0:13]):[nH;D2;+0:14]:[c:15]:1:2>>[C;D1;H3:4]-[#7;a:5]1:[#7;a:6]:[c:7]:[c:8]2:[c:9]:[c:10](:[c:11]):[c;H0;D3;+0:12](-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3]):[n;H0;D2;+0:14]:[c:15]:1:... | null | [] | 70 | CELSIUS | null | null | 1,3-Dimethyl-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one (10 g) was suspended in dimethylsulfoxide (100 mL), and sodium hydride (60%, 2.1 g) was added at room temperature. The mixture was stirred with heating at 70° C. for 2 hrs, and cooled to room temperature. Chloromethyl methyl ether (4.6 mL) was added, and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether.Ether | c1ccc2c(c1)cnc1n[nH]cc12 | c1nc2n[nH]cc2c2ccccc12 | c1nc2n[nH]cc2c2ccccc12 | HCl | CS(=O)C | 70 | null | COCCl.Cc1nn(C)c2[nH]c(=O)c3ccccc3c12>CS(=O)C>COCOc1nc2c(c(C)nn2C)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fd17aec7f0a4092953b0d83d57d440f | COCOc1nc2c(c(C)nn2C)c2ccccc12.O=C1CCC(=O)N1Br>>COCOc1nc2c(c(CBr)nn2C)c2ccccc12 | CC1=NN(C=2N=C(C=3C=CC=CC3C21)OCOC)C.BrN1C(CCC1=O)=O>>BrCC1=NN(C=2N=C(C=3C=CC=CC3C21)OCOC)C | [CH3:1][O:2][CH2:3][O:4][c:5]1[n:6][c:7]2[c:8]([c:9]([CH3:10])[n:12][n:13]2[CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12.O=C1CCC(=O)N1[Br:11]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[n:6][c:7]2[c:8]([c:9]([CH2:10][Br:11])[n:12][n:13]2[CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | COCOc1nc2c(c(C)nn2C)c2ccccc12.O=C1CCC(=O)N1Br | COCOc1nc2c(c(CBr)nn2C)c2ccccc12 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2c(c1)cnc1[nH]ncc12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[c:5](-[CH3;D1;+0:6]):[#7;a:7]:[#7;a:8]:1-[C;D1;H3:9]>>[#7;a:2]:[c:3]1:[c:4]:[c:5](-[CH2;D2;+0:6]-[Br;H0;D1;+0:1]):[#7;a:7]:[#7;a:8]:1-[C;D1;H3:9] | 74.3 | [{"value": 74.3, "product": "BrCC1=NN(C=2N=C(C=3C=CC=CC3C21)OCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,3-Dimethyl-5-methoxymethoxy-3H-pyrazolo[3,4-c]isoquinoline (1.03 g), N-bromosuccinimide (0.72 g) and benzoyl peroxide (0.05 g) were dissolved in carbon tetrachloride (20 mL), and the mixture was heated under reflux for 4 hrs. After the completion of the reaction, the reaction mixture was cooled to room temperature, w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1nc2n[nH]cc2c2ccccc12 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl | null | null | COCOc1nc2c(c(C)nn2C)c2ccccc12.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl>COCOc1nc2c(c(CBr)nn2C)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d49fe7db0444eacaa2175ac7a59ed16 | CC(C)CCON=O.Cc1ccc2c(c1)C(=O)CC2>>Cc1ccc2c(c1)C(=O)C(=NO)C2 | CC1=CC=C2CCC(C2=C1)=O.N(=O)OCCC(C)C.Cl.O1CCOCC1>>CC1=CC=C2CC(C(C2=C1)=O)=NO | CC(C)CCO[N:11]=[O:12].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][CH2:13]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[N:11][OH:12])[CH2:13]2 | CC(C)CCON=O.Cc1ccc2c(c1)C(=O)CC2 | Cc1ccc2c(c1)C(=O)C(=NO)C2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2b42c255b68a0c682e66edfe0ce9f8aa20628d7c2a3d9f5c123a2a086bbd4a8d | 31357763b1be60679a29f55afc8815d0b4a90e485d09aebc6e88f16eae688399 | N=C1Cc2ccccc2C1=O | C-C(-C)-C-C-O-[N;H0;D2;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[C:4]1-[CH2;D2;+0:5]-[C:6]-[c:7]:[c:8]-1>>[O;D1;H0:3]=[C:4]1-[c:8]:[c:7]-[C:6]-[C;H0;D3;+0:5]-1=[N;H0;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | 6-Methyl-1-indanone (40.4 g) and isoamyl nitrite (40.6 mL) were dissolved in ethanol (300 mL), and 4N hydrogen chloride-dioxane (10 mL) was added dropwise under ice-cooling. After the completion of the reaction, the precipitated crystals were collected by filtration and washed with ether to give 6-methyl-2-hydroxyimino... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitroso | Ketone.Oxime | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(C)O | null | null | CC(C)CCON=O.Cc1ccc2c(c1)C(=O)CC2>C(C)O>Cc1ccc2c(c1)C(=O)C(=NO)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d701be4f7e5458e98f5a8f5e6b675b1 | Cc1ccc2c(c1)C(=O)C(=NO)C2.O=C(O)CC(O)(CC(=O)O)C(=O)O>>Cc1ccc(CC#N)c(C(=O)O)c1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CC1=CC=C2CC(C(C2=C1)=O)=NO.[OH-].[Na+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C(#N)CC1=C(C(=O)O)C=C(C=C1)C | O[N:8]=[C:7]1[CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:13][c:9]2[C:10]1=[O:11].O=C(O)CC(O)(CC(=O)O)C(=O)[OH:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]#[N:8])[c:9]([C:10](=[O:11])[OH:12])[cH:13]1 | Cc1ccc2c(c1)C(=O)C(=NO)C2.O=C(O)CC(O)(CC(=O)O)C(=O)O | Cc1ccc(CC#N)c(C(=O)O)c1 | null | null | O | Acylation | OtherReaction | 524619af1fd7f44ca86fa2282de7b7ca264cbfe95c949bf850afd878c7659049 | da2299b1c6a114d908fd8b75e0d1d80f833ccf06edffadbe2c8374073d47e391 | c1ccccc1 | O-C(=O)-C-C(-O)(-C-C(-O)=O)-C(=O)-[OH;D1;+0:1].O-[N;H0;D2;+0:2]=[C;H0;D3;+0:3]1-[C:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;D1;H0:9]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[C:4]-[c:5]:[c:6](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[OH;D1;+0:1]):[c:7] | 44.1 | [{"value": 44.1, "product": "C(#N)CC1=C(C(=O)O)C=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 6-Methyl-2-hydroxyimino-1-indanone (37 g) and sodium hydroxide (19.7 g) were dissolved in water (287 mL), and p-toluenesulfonyl chloride (44.3 g) was added with stirring at 50° C. After the completion of the reaction, aqueous citric acid solution was added to acidify the reaction mixture, and the mixture was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Ketone.Tertiary alcohol.Oxime | Carboxylic acid.Nitrile | c1ccc2c(c1)CCC2 | null | c1ccccc1 | HO- | O | 50 | null | Cc1ccc2c(c1)C(=O)C(=NO)C2.O=C(O)CC(O)(CC(=O)O)C(=O)O>O>Cc1ccc(CC#N)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5302a0223cf146c2a418b84a39eda23c | Cc1ccc(CC#N)c(C(=O)O)c1>>Cc1ccc(CC#N)c(C(N)=O)c1 | C(#N)CC1=C(C(=O)O)C=C(C=C1)C.CN(C=O)C.C(C(=O)Cl)(=O)Cl>>C(#N)CC1=C(C(=O)N)C=C(C=C1)C | O[C:10]([c:9]1[c:5]([CH2:6][C:7]#[N:8])[cH:4][cH:3][c:2]([CH3:1])[cH:13]1)=[O:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]#[N:8])[c:9]([C:10]([NH2:11])=[O:12])[cH:13]1 | Cc1ccc(CC#N)c(C(=O)O)c1 | Cc1ccc(CC#N)c(C(N)=O)c1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 2-Cyanomethyl-5-methylbenzoic acid (16.3 g) and dimethylformamide (0.1 mL) were suspended in tetrahydrofuran (160 mL), and oxalyl dichloride (12.2 mL) was added dropwise under ice-cooling. After cease of foaming, the solvent was evaporated. The obtained residue was dissolved in tetrahydrofuran, and the solution was add... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1 | null | O1CCCC1 | null | null | Cc1ccc(CC#N)c(C(=O)O)c1>O1CCCC1>Cc1ccc(CC#N)c(C(N)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-620af7f975654029a3f778eca92d95f2 | Cc1ccc(CC#N)c(C(N)=O)c1>>Cc1ccc2cc(N)[nH]c(=O)c2c1 | C(#N)CC1=C(C(=O)N)C=C(C=C1)C.C([O-])([O-])=O.[K+].[K+]>>NC=1NC(C2=CC(=CC=C2C1)C)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]#[N:8])[c:12]([C:10]([NH2:9])=[O:11])[cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[nH:9][c:10](=[O:11])[c:12]2[cH:13]1 | Cc1ccc(CC#N)c(C(N)=O)c1 | Cc1ccc2cc(N)[nH]c(=O)c2c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 089be77f0f9830a6dc6557a8722311670051d026f3595c3115c4c372bcf16348 | 59b14427dcac06ff9979a8f84d82770b6a433a93052ad16fffc1b05f15a420b9 | O=c1[nH]ccc2ccccc12 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[O;D1;H0:9]):[c:10]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:10]):[c;H0;D3;+0:7](=[O;D1;H0:9]):[nH;D2;+0:8]:1 | 88.1 | [{"value": 88.1, "product": "NC=1NC(C2=CC(=CC=C2C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Cyanomethyl-5-methylbenzamide (10.9 g) was suspended in methanol (100 mL), and 10% aqueous potassium carbonate solution (100 mL) was added. The mixture was heated under reflux for 1 hr. The precipitated crystals were collected by filtration to give 3-amino-7-methyl-2H-isoquinolin-1-one (9.6 g).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amide | Primary amine | c1ccccc1 | c1ccc2ccncc2c1 | c1ccc2ccncc2c1 | null | CO | null | null | Cc1ccc(CC#N)c(C(N)=O)c1>CO>Cc1ccc2cc(N)[nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cddb9af07abf41b494cfeb8ed3d46cb9 | CC(=O)C(C#N)c1ccc(F)cc1.CNN>>Cc1nn(C)c(N)c1-c1ccc(F)cc1 | C(C)(=O)C(C#N)C1=CC=C(C=C1)F.CNN>>NC1=C(C(=NN1C)C)C1=CC=C(C=C1)F | O=[C:2]([CH3:1])[CH:8]([C:6]#[N:7])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1.[NH2:3][NH:4][CH3:5]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([NH2:7])[c:8]1-[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1 | CC(=O)C(C#N)c1ccc(F)cc1.CNN | Cc1nn(C)c(N)c1-c1ccc(F)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 5313ea2b547a7e97f846d9307e42ac2925475188c06332e189417467db3f09a0 | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-c2cn[nH]c2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[C;D1;H3:11]-[NH;D2;+0:12]-[NH2;D1;+0:13]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[n;H0;D3;+0:12](-[C;D1;H3:11]):[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[c;H0;D3;+0:3]:1-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[... | null | [] | null | null | null | null | α-Acetyl-4-fluorophenylacetonitrile (65.1 g) and methylhydrazine (30.9 mL) were dissolved in ethanol (320 mL), and the mixture was heated under reflux for 3 hrs. After the completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent was evaporated. The obtained solid was collected by... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CC(=O)C(C#N)c1ccc(F)cc1.CNN>C(C)O>Cc1nn(C)c(N)c1-c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0de85afc5504ce0a68ce8a449cd283a | Cc1nn(C)c(N)c1-c1ccc(F)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>Cc1nn(C)c2[nH]c(=O)c3cc(F)ccc3c12 | NC1=C(C(=NN1C)C)C1=CC=C(C=C1)F.N1=CC=CC=C1.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>FC=1C=CC=2C3=C(NC(C2C1)=O)N(N=C3C)C | [CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([NH2:7])[c:17]1-[c:16]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1.ClC(Cl)(Cl)O[C:8](OC(Cl)(Cl)Cl)=[O:9]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]2[nH:7][c:8](=[O:9])[c:10]3[cH:11][c:12]([F:13])[cH:14][cH:15][c:16]3[c:17]12 | Cc1nn(C)c(N)c1-c1ccc(F)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | Cc1nn(C)c2[nH]c(=O)c3cc(F)ccc3c12 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 57168be243203dca8521b07d6728297eb35523e266a8977764f9e83327ca7b3a | 85b4bf2087a5481ace7d95ffc08f83fb4764d9f3312671f9f9fd96f76b74e60a | O=c1[nH]c2[nH]ncc2c2ccccc12 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C;D1;H3:3]-[c:4]1:[#7;a:5]:[#7;a:6](-[C;D1;H3:7]):[c:8](-[NH2;D1;+0:9]):[c;H0;D3;+0:10]:1-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:1>>[C;D1;H3:3]-[c:4]1:[#7;a:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]2:[nH;D2;+0:9]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H... | 146 | [{"value": 146.0, "product": "FC=1C=CC=2C3=C(NC(C2C1)=O)N(N=C3C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 5-amino-4-(4-fluorophenyl)-1,3-dimethylpyrazole (20.0 g) and pyridine (23.6 mL) in dichloromethane (150 mL) was added dropwise over 30 min to a solution of triphosgene (11.6 g) in dichloromethane (100 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. The reaction solution w... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | null | c1cn[nH]c1.c1ccccc1 | c1ccc2c(c1)cnc1n[nH]cc12 | c1ccc2c(c1)cnc1n[nH]cc12 | HCl | ClCCl | null | 2 | Cc1nn(C)c(N)c1-c1ccc(F)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl>Cc1nn(C)c2[nH]c(=O)c3cc(F)ccc3c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60683cf36ac5418d8f27950efd500f7f | CC(=O)C(C#N)c1ccccc1.CC(O)NN>>Cc1nn(CCO)c(N)c1-c1ccccc1 | C(C)(=O)C(C#N)C1=CC=CC=C1.CO.N(N)C(C)O>>NC1=C(C(=NN1CCO)C)C1=CC=CC=C1 | O=[C:2]([CH3:1])[CH:10]([C:8]#[N:9])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH:3]([NH2:4])[CH:6]([CH3:5])[OH:7]>>[CH3:1][c:2]1[n:3][n:4]([CH2:5][CH2:6][OH:7])[c:8]([NH2:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CC(=O)C(C#N)c1ccccc1.CC(O)NN | Cc1nn(CCO)c(N)c1-c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0b4e3b1b20af613a00c89df7dcf03941ab54fce12f4ac8ea24b392089dd84738 | 2bccc335924a626069ba73d340529656710cb833164707efd73d8db8c8289086 | c1ccc(-c2cn[nH]c2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[CH3;D1;+0:11]-[CH;D3;+0:12](-[O;D1;H1:13])-[NH;D2;+0:14]-[NH2;D1;+0:15]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[n;H0;D3;+0:15](-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[O;D1;H1:13]):[c;H0;D3;+0:4](-[NH2;D1... | null | [] | null | null | null | null | α-Acetylphenylacetonitrile (10 g) was dissolved in methanol (100 mL), and hydrazinoethanol (5.3 g) was added, and the mixture was heated under reflux for 4 hrs. After the completion of the reaction, the solvent was evaporated. The obtained residue was subjected to silica gel column chromatography, and the fraction elut... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile.Secondary alcohol | Primary alcohol.Primary amine | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | null | null | null | CC(=O)C(C#N)c1ccccc1.CC(O)NN>>Cc1nn(CCO)c(N)c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a6b477751c442beb270a365d9549d41 | COC(=O)c1ccccc1C(=O)c1ccncc1>>O=c1occ(-c2ccncc2)c2ccccc12 | O.[H-].[Na+].[I-].C[S+](=O)(C)C.C(C1=CC=NC=C1)(=O)C1=C(C(=O)OC)C=CC=C1>>N1=CC=C(C=C1)C1=COC(=O)C2=CC=CC=C12 | O=[C:5]([c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:2](=[O:1])[O:3][CH3:4]>>[O:1]=[c:2]1[o:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | COC(=O)c1ccccc1C(=O)c1ccncc1 | O=c1occ(-c2ccncc2)c2ccccc12 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 2645b55234e0291c2b84dde40da1fa018fa13eebb03ef077159365914ef1a18e | 90d91da8fe4a4df48cab6f211982834fddab85bdecacddc95412489737467fb5 | O=c1occ(-c2ccncc2)c2ccccc12 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:8]):[c:9])-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:6]=[c;H0;D3;+0:5]1:[o;H0;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2):[c:2](:[c:3]):[c:4]:1:[c:9] | 48.1 | [{"value": 48.1, "product": "N1=CC=C(C=C1)C1=COC(=O)C2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (purity 60%, 2.0 g) was suspended in dimethylformamide (100 mL), and trimethylsulfoxonium iodide (11 g) was added, and the mixture was stirred at room temperature for 1 hr. Then, methyl 2-isonicotinoylbenzoate (11 g) was added, and the mixture was further stirred at room temperature for 1 hr. Water was a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | null | c1ccccc1 | c1cocc2ccccc12 | c1ccncc1.c1cocc2ccccc12 | HO- | CN(C=O)C | null | 1 | COC(=O)c1ccccc1C(=O)c1ccncc1>CN(C=O)C>O=c1occ(-c2ccncc2)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13f482487fc84e3b839642656948beb4 | N.O=c1occ(-c2ccncc2)c2ccccc12>>O=c1[nH]cc(-c2ccncc2)c2ccccc12 | N.N1=CC=C(C=C1)C1=COC(=O)C2=CC=CC=C12.Cl.C([O-])([O-])=O.[K+].[K+]>>N1=CC=C(C=C1)C1=CNC(C2=CC=CC=C12)=O | [NH3:3].o1[c:2](=[O:1])[c:17]2[c:12]([c:5](-[c:6]3[cH:7][cH:8][n:9][cH:10][cH:11]3)[cH:4]1)[cH:13][cH:14][cH:15][cH:16]2>>[O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | N.O=c1occ(-c2ccncc2)c2ccccc12 | O=c1[nH]cc(-c2ccncc2)c2ccccc12 | null | null | C(C)O | Miscellaneous | OtherReaction | 68502af5b6925df8a62d4a7bc8b03fb1d312bf012f95aaa9daf86ec32ada4d68 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1[nH]cc(-c2ccncc2)c2ccccc12 | [NH3;D0;+0:1].[O;D1;H0:2]=[c;H0;D3;+0:3]1:o:[cH;D2;+0:4]:[c:5](-[c:6]):[c:7]:[c:8]:1:[c:9]>>[O;D1;H0:2]=[c;H0;D3;+0:3]1:[nH;D2;+0:1]:[cH;D2;+0:4]:[c:5](-[c:6]):[c:7]:[c:8]:1:[c:9] | null | [] | null | null | 1 | HOUR | 4-(Pyridin-4-yl)isocoumarin (4.9 g) was suspended in ethanol and 28% aqueous ammonia, and the mixture was heated under reflux for 1 hr. Concentrated hydrochloric acid was added to acidify the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. After the completion of the reaction, aqueou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cocc2ccccc12 | c1cncc2ccccc12 | c1ccncc1.c1cncc2ccccc12 | HO- | C(C)O | null | 1 | N.O=c1occ(-c2ccncc2)c2ccccc12>C(C)O>O=c1[nH]cc(-c2ccncc2)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e4fe25b8cb34040a55b9da4c01046c5 | CCOC(=O)C1CCN(C(=O)OCC)CC1.N#CCc1ccccc1>>CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1 | C1(=CC=CC=C1)CC#N.C(C)OC(=O)N1CCC(C(=O)OCC)CC1.[H-].[Na+]>>C(C)OC(=O)N1CCC(CC1)C(=O)C(C#N)C1=CC=CC=C1 | CCO[C:10]([CH:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:22][CH2:21]1)=[O:11].[CH2:12]([C:13]#[N:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([C:10](=[O:11])[CH:12]([C:13]#[N:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]... | CCOC(=O)C1CCN(C(=O)OCC)CC1.N#CCc1ccccc1 | CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccccc1)C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:8](-[C:7]#[N;D1;H0:6])-[c:9](:[c:10]):[c:11])-[C:5] | 61.9 | [{"value": 61.9, "product": "C(C)OC(=O)N1CCC(CC1)C(=O)C(C#N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | Phenylacetonitrile (5.8 g), ethyl 1-ethoxycarbonylisonipecotate (11.5 g), sodium hydride (purity 60%, 2.0 g) and toluene (25 mL) were mixed, and the mixture was stirred at 80° C. for 3 hrs. After the completion of the reaction, the reaction mixture was cooled to room temperature, and the insoluble material was washed b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | C1CC[NH]CC1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 80 | 3 | CCOC(=O)C1CCN(C(=O)OCC)CC1.N#CCc1ccccc1>C1(=CC=CC=C1)C>CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51deee21f82a43f0bff6a58bf56afe54 | CN(C)CC(=O)O.Nc1cc2ccccc2c(=O)[nH]1>>CN(C)CC(=O)c1c(N)[nH]c(=O)c2ccccc12 | [Cl-].ClC1[NH+](CCN1C)C.NC=1NC(C2=CC=CC=C2C1)=O.Cl.CN(CC(=O)O)C.N1=CC=CC=C1>>NC=1NC(C2=CC=CC=C2C1C(CN(C)C)=O)=O | O[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[O:6].[cH:7]1[c:8]([NH2:9])[nH:10][c:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5](=[O:6])[c:7]1[c:8]([NH2:9])[nH:10][c:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CN(C)CC(=O)O.Nc1cc2ccccc2c(=O)[nH]1 | CN(C)CC(=O)c1c(N)[nH]c(=O)c2ccccc12 | null | null | C(Cl)Cl.C(Cl)(Cl)Cl.CO | C-C Coupling | Friedel-Crafts acylation | 39dd43fec205820c68835b9bdf2605f5b5729bd0a497eb3912d24042e0c3b77e | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=c1[nH]ccc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[N;D1;H2:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](:[c:11]):[cH;D2;+0:12]:1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:12]1:[c:10](:[c:11]):[c:9]:[c:8]:[#7;a:7]:[c:6]:1-[N;D1;H2:5] | 39.9 | [{"value": 39.9, "product": "NC=1NC(C2=CC=CC=C2C1C(CN(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-Amino-2H-isoquinolin-1-one (9.0 g), dimethylglycine hydrochloride (10.2 g) and pyridine (22.7 mL) were suspended in methylene chloride (100 mL), and 2-chloro-1,3-dimethylimidazolinium chloride (12.4 g) was added under ice-cooling. Then the mixture was stirred at room temperature for 2 hrs. After the completion of the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1cc2ccccc2cn1 | c1cc2ccccc2cn1 | c1cc2ccccc2cn1 | HO- | C(Cl)Cl.C(Cl)(Cl)Cl.CO | null | 2 | CN(C)CC(=O)O.Nc1cc2ccccc2c(=O)[nH]1>C(Cl)Cl.C(Cl)(Cl)Cl.CO>CN(C)CC(=O)c1c(N)[nH]c(=O)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e7798d870ed40f6ba75e1445dc7f489 | O=c1[nH]cc(C2CCNCC2)c2ccccc12.OCCBr>>O=c1[nH]cc(C2CCN(CCO)CC2)c2ccccc12 | Cl.N1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O.C([O-])([O-])=O.[K+].[K+].BrCCO>>OCCN1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O | [O:1]=[c:2]1[nH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:13][CH2:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12.Br[CH2:10][CH2:11][OH:12]>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][OH:12])[CH2:13][CH2:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | O=c1[nH]cc(C2CCNCC2)c2ccccc12.OCCBr | O=c1[nH]cc(C2CCN(CCO)CC2)c2ccccc12 | null | null | CC(CC)=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]cc(C2CCNCC2)c2ccccc12 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3])-[C:7]-[C:8] | 55.9 | [{"value": 55.9, "product": "OCCN1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(Piperidin-4-yl)-2H-isoquinolin-1-one hydrochloride (0.8 g) obtained in Example 31, potassium carbonate (2.0 g) and 2-bromoethanol (1.88 g) were dissolved in 2-butanone and water (1 mL), and the mixture was heated under reflux for 4 hrs. After the completion of the reaction, the solvent was evaporated, and water was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cncc2ccccc12 | HBr | CC(CC)=O.O | null | null | O=c1[nH]cc(C2CCNCC2)c2ccccc12.OCCBr>CC(CC)=O.O>O=c1[nH]cc(C2CCN(CCO)CC2)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e741d8f6fb54038b7f7b283502e6682 | C=O.O=c1[nH]cc(C2CCNCC2)c2ccccc12>>CN1CCC(c2c[nH]c(=O)c3ccccc23)CC1 | Cl.Cl.N1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O.C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CN1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][nH:8][c:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][nH:8][c:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1 | C=O.O=c1[nH]cc(C2CCNCC2)c2ccccc12 | CN1CCC(c2c[nH]c(=O)c3ccccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]cc(C2CCNCC2)c2ccccc12 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 19.2 | [{"value": 19.2, "product": "CN1CCC(CC1)C1=CNC(C2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 4-(Piperidin-4-yl)-2H-isoquinolin-1-one hydrochloride (0.5 g) obtained in Example 31 and 35% aqueous formalin solution (0.33 g) were dissolved in acetonitrile (20 mL), and sodium triacetoxyborohydride (0.81 g) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. After the completion o... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cncc2ccccc12 | Other | C(C)#N | null | 3 | C=O.O=c1[nH]cc(C2CCNCC2)c2ccccc12>C(C)#N>CN1CCC(c2c[nH]c(=O)c3ccccc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86a30e2990794aef9bb19dd83a50b9d6 | C1CCNCC1.C=O.Cc1cc2ccccc2c(=O)[nH]1>>Cc1[nH]c(=O)c2ccccc2c1CN1CCCCC1 | N1CCCCC1.C=O.CC=1NC(C2=CC=CC=C2C1)=O>>CC=1NC(C2=CC=CC=C2C1CN1CCCCC1)=O | [NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.O=[CH2:13].[CH3:1][c:2]1[nH:3][c:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1>>[CH3:1][c:2]1[nH:3][c:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1 | C1CCNCC1.C=O.Cc1cc2ccccc2c(=O)[nH]1 | Cc1[nH]c(=O)c2ccccc2c1CN1CCCCC1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | c79dca3e762abcf2201397b65c82e21b3f5000e5ce9f495e78918a4978163749 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]cc(CN2CCCCC2)c2ccccc12 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](:[c:8]):[cH;D2;+0:9]:1.[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c;H0;D3;+0:9]1:[c:7](:[c:8]):[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[C;D1;H3:2])-[C:13]-[C:14] | null | [] | 70 | CELSIUS | 5 | MINUTE | Piperidine (0.747 mL) and paraformaldehyde (271 mg) were dissolved in acetic acid (3 mL), and the mixture was stirred at 70° C. for 5 min. 3-Methyl-2H-isoquinolin-1-one (302 mg) was added to the reaction mixture, and the mixture was heated under reflux for 2.5 hrs. After the completion of the reaction, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1.c1cc2ccccc2cn1 | c1cc2ccccc2cn1.C1CC[NH]CC1 | c1cc2ccccc2cn1.C1CC[NH]CC1 | HO- | C(C)(=O)O | 70 | 0.083333 | C1CCNCC1.C=O.Cc1cc2ccccc2c(=O)[nH]1>C(C)(=O)O>Cc1[nH]c(=O)c2ccccc2c1CN1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-208a136c94274b2092f67b3ffbd33b59 | C=O.CC(C)c1cc2ccccc2c(=O)[nH]1.CNC>>CC(C)c1[nH]c(=O)c2ccccc2c1CN(C)C | C(C)(C)C=1NC(C2=CC=CC=C2C1)=O.Cl.CNC.C=O.C(C)(=O)OC(C)=O>>CN(C)CC1=C(NC(C2=CC=CC=C12)=O)C(C)C | O=[CH2:15].[CH3:1][CH:2]([CH3:3])[c:4]1[nH:5][c:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1.[NH:16]([CH3:17])[CH3:18]>>[CH3:1][CH:2]([CH3:3])[c:4]1[nH:5][c:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[CH2:15][N:16]([CH3:17])[CH3:18] | C=O.CC(C)c1cc2ccccc2c(=O)[nH]1.CNC | CC(C)c1[nH]c(=O)c2ccccc2c1CN(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a95056b7e52de2aad1489fd29451c1e6efb1e65e834a8038c1e4587dacdef7b | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]ccc2ccccc12 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](:[c:11]):[cH;D2;+0:12]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](:[c:11]):[c;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:3](-[C;D1;H3:2])-[C;D1;H3:4] | null | [] | 60 | CELSIUS | null | null | While heating a mixture of dimethylamine hydrochloride (2.45 g) and 37% aqueous formalin solution (2.43 g) to 50° C., acetic anhydride (9.4 mL) was added dropwise thereto slowly. After the completion of the dropwise addition, the mixture was heated at 60° C. for 30 min. 3-Isopropyl-2H-isoquinolin-1-one (1.87 g) was add... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1cc2ccccc2cn1 | c1cc2ccccc2cn1 | c1cc2ccccc2cn1 | HO- | null | 60 | null | C=O.CC(C)c1cc2ccccc2c(=O)[nH]1.CNC>>CC(C)c1[nH]c(=O)c2ccccc2c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b3ca704589bc463f87fa7c77d7e5fcbd | C1CCNCC1.COCOc1nc2c(c(CBr)nn2C)c2ccc(F)cc12>>Cn1nc(CN2CCCC2)c2c3ccc(F)cc3c(=O)[nH]c21 | BrCC1=NN(C=2N=C(C=3C=C(C=CC3C21)F)OCOC)C.N1CCCCC1.C([O-])([O-])=O.[K+].[K+].O>>FC=1C=CC=2C3=C(NC(C2C1)=O)N(N=C3CN3CCCC3)C | C1[CH2:7][NH:6][CH2:10][CH2:9][CH2:8]1.COC[O:20][c:19]1[c:18]2[c:12]([c:11]3[c:4]([CH2:5]Br)[n:3][n:2]([CH3:1])[c:22]3[n:21]1)[cH:13][cH:14][c:15]([F:16])[cH:17]2>>[CH3:1][n:2]1[n:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[c:11]2[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]3[c:19](=[O:20])[nH:21][c:22]12 | C1CCNCC1.COCOc1nc2c(c(CBr)nn2C)c2ccc(F)cc12 | Cn1nc(CN2CCCC2)c2c3ccc(F)cc3c(=O)[nH]c21 | null | null | C(C)#N | Acylation | OtherReaction | b61550aeb3e8182a827e65861ba2d45dd70f8b19550172ec19c16ccae6e9b358 | 714a4e6e45f4072a308f627479ca1cf83f014283e415427338a100b5074567f4 | O=c1[nH]c2[nH]nc(CN3CCCC3)c2c2ccccc12 | Br-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[O;H0;D2;+0:9]-C-O-C):[c:10](:[c:11]):[c:12]:[c:13]:2:1.C1-[CH2;D2;+0:14]-[NH;D2;+0:15]-[C:16]-[C:17]-[CH2;D2;+0:18]-1>>[C;D1;H3:5]-[#7;a:4]1:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15]2-[C:16]-[C:17]-[CH2;D2;+0:18]-[CH2;D2;... | null | [] | null | null | 2 | DAY | After the completion of the reaction, the reaction solution was allowed to cool to room temperature, and the precipitated solid was removed by filtration. The filtrate was concentrated, and the residue was filtrated using silica gel (hexane:ethyl acetate=2:1). The filtrate was concentrated to give 1-bromomethyl-7-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2c(cnc3n[nH]cc32)c1 | C1CC[NH]C1.c1ccc2c(c1)cnc1[nH]ncc12 | C1CC[NH]C1.c1ccc2c(c1)cnc1[nH]ncc12 | HBr | C(C)#N | null | 48 | C1CCNCC1.COCOc1nc2c(c(CBr)nn2C)c2ccc(F)cc12>C(C)#N>Cn1nc(CN2CCCC2)c2c3ccc(F)cc3c(=O)[nH]c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a243f2132184c8ea3a0e69cc8445a07 | O=c1[nH]cc(-c2cc[n+](Cc3ccccc3)cc2)c2ccccc12>>O=c1[nH]cc(C2=CCN(Cc3ccccc3)CC2)c2ccccc12 | [Br-].C(C1=CC=CC=C1)[N+]1=CC=C(C=C1)C1=CNC(C2=CC=CC=C12)=O.[BH4-].[Na+]>>C(C1=CC=CC=C1)N1CCC(=CC1)C1=CNC(C2=CC=CC=C12)=O | [O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n+:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][N:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[c:19]2[cH:20][cH:21][cH:... | O=c1[nH]cc(-c2cc[n+](Cc3ccccc3)cc2)c2ccccc12 | O=c1[nH]cc(C2=CCN(Cc3ccccc3)CC2)c2ccccc12 | null | null | CO | Oxidation | OtherReaction | e081af41b1b117f306f65cdf7f3ba0a0eafacd590ae90c42b0242eb6cd826e86 | 8f4b2fdd46ea6ea671fc39222cd3ec27819c44f61f7e3fc49b31ceb24f59ce12 | O=c1[nH]cc(C2=CCN(Cc3ccccc3)CC2)c2ccccc12 | [c:1]-[C:2]-[n+;H0;D3:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:2:[c:13]):[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[c:1]-[C:2]-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:2:[c:13])=[CH;D2;+0:14]-[CH2;D2;+0:... | 89.8 | [{"value": 89.8, "product": "C(C1=CC=CC=C1)N1CCC(=CC1)C1=CNC(C2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-4-(1-oxo-2H-isoquinolin-4-yl)pyridinium bromide (9.0 g) was dissolved in methanol (100 mL), and sodium borohydride (3.7 g) was added in small portions with stirring at room temperature. After the completion of the reaction, the solvent was evaporated. Water was added to the obtained residue, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1=CC=[NH+]C=C1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1cncc2ccccc12 | null | CO | null | null | O=c1[nH]cc(-c2cc[n+](Cc3ccccc3)cc2)c2ccccc12>CO>O=c1[nH]cc(C2=CCN(Cc3ccccc3)CC2)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f29c37076ab4202b31983e93ade142b | CC(C)I.O=c1[nH]cc(C2=CCNCC2)c2ccccc12>>CC(C)N1CC=C(c2c[nH]c(=O)c3ccccc23)CC1 | C(C)(C)I.N1CCC(=CC1)C1=CNC(C2=CC=CC=C12)=O.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)N1CCC(=CC1)C1=CNC(C2=CC=CC=C12)=O | I[CH:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH:6]=[C:7]([c:8]2[cH:9][nH:10][c:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH:6]=[C:7]([c:8]2[cH:9][nH:10][c:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | CC(C)I.O=c1[nH]cc(C2=CCNCC2)c2ccccc12 | CC(C)N1CC=C(c2c[nH]c(=O)c3ccccc23)CC1 | null | null | C(C)#N.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6b6286b31d61c20684d99950edaf50898a4ce902605b1a75f62ec46d7177141e | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=c1[nH]cc(C2=CCNCC2)c2ccccc12 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7;a:4]:[c:5]:[c:6]-[C:7]1=[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:4]:[c:5]:[c:6]-[C:7]1=[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:11]-[C:12]-1 | null | [] | 40 | CELSIUS | null | null | 4-(1,2,3,6-Tetrahydropyridin-4-yl)-2H-isoquinolin-1-one (0.4 g) obtained in Example 205 and potassium carbonate (1 g) were suspended in acetonitrile (10 mL) and water (1 mL), and isopropyl iodide (0.35 mL) was added at room temperature. The mixture was stirred under heating overnight at 40° C. After the completion of t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1cncc2ccccc12 | HI | C(C)#N.O | 40 | null | CC(C)I.O=c1[nH]cc(C2=CCNCC2)c2ccccc12>C(C)#N.O>CC(C)N1CC=C(c2c[nH]c(=O)c3ccccc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1b8d7b8362444ac879111cc04c7b82c | C=O.Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21>>CN1CCC(c2nn(C)c3[nH]c(=O)c4ccccc4c23)CC1 | Cl.N1CCC(CC1)C1=NN(C=2NC(C=3C=CC=CC3C21)=O)C.C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CN1CCC(CC1)C1=NN(C=2NC(C=3C=CC=CC3C21)=O)C | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][n:8]([CH3:9])[c:10]3[nH:11][c:12](=[O:13])[c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]4[c:20]23)[CH2:21][CH2:22]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][n:8]([CH3:9])[c:10]3[nH:11][c:12](=[O:13])[c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]4[c:20]23)[CH2:21][CH2:22]1 | C=O.Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21 | CN1CCC(c2nn(C)c3[nH]c(=O)c4ccccc4c23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]c2[nH]nc(C3CCNCC3)c2c2ccccc12 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 54.9 | [{"value": 54.9, "product": "CN1CCC(CC1)C1=NN(C=2NC(C=3C=CC=CC3C21)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-(Piperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5(4H)-one hydrochloride (1.0 g) obtained in Example 227 and 35% aqueous formalin solution (0.53 g) were suspended in water (20 mL), and sodium triacetoxyborohydride (1.3 g) was added at room temperature, and the mixture was stirred for 1 hr. After the completion of... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)cnc1n[nH]cc12 | Other | O | null | 1 | C=O.Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21>O>CN1CCC(c2nn(C)c3[nH]c(=O)c4ccccc4c23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9fca6ad6373e43cc9b3bee6b8366157a | CCOC(=O)N1CCC(c2nn(C)c3c2c2ccccc2c(=O)n3C(=O)OCC)CC1>>Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21 | ClC(=O)OCC.Cl.[Cl-].[Al+3].[Cl-].[Cl-].C([O-])([O-])=O.[K+].[K+].C(C)OC(=O)N1CCC(CC1)C1=NN(C=2NC(C=3C=CC=CC3C21)=O)C.C(C)OC(=O)N1C(C=2C=CC=CC2C2=C1N(N=C2C2CCN(CC2)C(=O)OCC)C)=O>>Cl.N1CCC(CC1)C1=NN(C=2NC(C=3C=CC=CC3C21)=O)C | CCOC(=O)[N:9]1[CH2:8][CH2:7][CH:6]([c:5]2[n:4][n:3]([CH3:2])[c:22]3[c:12]2[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[c:19](=[O:20])[n:21]3C(=O)OCC)[CH2:11][CH2:10]1>>[CH3:2][n:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]2[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19](=[O:20])[nH:21][c:22]12 | CCOC(=O)N1CCC(c2nn(C)c3c2c2ccccc2c(=O)n3C(=O)OCC)CC1 | Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21 | null | null | C(C)(=O)O | Reduction | OtherReaction | 65a5849213d52035b8d82ffaf283add598594465027147af065fbe837e5dc7c0 | d3d6a130d74aabb30468d26aa60800f736e1a49de91299f2a34ef882a7641931 | O=c1[nH]c2[nH]nc(C3CCNCC3)c2c2ccccc12 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].C-C-O-C(=O)-[n;H0;D3;+0:6](:[c:7](=[O;D1;H0:8]):[c:9]):[c:10]1:[c:11]:[c:12]:[#7;a:13]:[#7;a:14]:1-[C;D1;H3:15]>>[C;D1;H3:15]-[#7;a:14]1:[#7;a:13]:[c:12]:[c:11]:[c:10]:1:[nH;D2;+0:6]:[c:7](=[O;D1;H0:8]):[c:9].[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | 4 | HOUR | After the completion of the dropwise addition, the mixture was stirred at room temperature for 4 hrs and ice-cooled. Aluminum chloride (13.6 g) was added to the reaction mixture, and the mixture was stirred overnight at room temperature. After the completion of the reaction, the reaction mixture was poured into ice-wat... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether | Secondary amine | C1CC[NH]CC1.c1nc2n[nH]cc2c2ccccc12 | C1CCNCC1.c1ccc2c(c1)cnc1[nH]ncc12 | C1CCNCC1.c1ccc2c(c1)cnc1[nH]ncc12 | HO- | C(C)(=O)O | null | 4 | CCOC(=O)N1CCC(c2nn(C)c3c2c2ccccc2c(=O)n3C(=O)OCC)CC1>C(C)(=O)O>Cn1nc(C2CCNCC2)c2c3ccccc3c(=O)[nH]c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6d41f9e20934b8ea0055f3cf62db671 | CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1.NO>>CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1 | C(C)(=O)[O-].[Na+].C(C)OC(=O)N1CCC(CC1)C(=O)C(C#N)C1=CC=CC=C1.COC(=O)N1CCC(CC1)C(=O)C(C#N)C1=CC=CC=C1.Cl.NO>>NC1=C(C(=NO1)C1CCN(CC1)C(=O)OCC)C1=CC=CC=C1 | O=[C:10]([CH:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:23][CH2:22]1)[CH:15]([C:13]#[N:14])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]([NH2:14])[c:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2... | CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1.NO | CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | a8d4cc880726ca831e942d4cfcbe4c771bf0338e900283b4b37180663c2a8323 | cba055f16bb6d8902fe3b7ee13bd8e7822896a26eeb51828f22dbf1978e995c7 | c1ccc(-c2conc2C2CCNCC2)cc1 | O=[C;H0;D3;+0:1](-[C:2](-[C:3])-[C:4])-[CH;D3;+0:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[NH2;D1;+0:13]-[OH;D1;+0:14]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[o;H0;D2;+0:14]:[c;H0;D3;+0:6](-[NH2;D1;+0:7]):[c;H0;D3;+0:5]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[C:4] | 38.2 | [{"value": 38.2, "product": "NC1=C(C(=NO1)C1CCN(CC1)C(=O)OCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture (1:1, 17.5 g) of α-(1-ethoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile and α-(1-methoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile, hydroxylamine hydrochloride (5.63 g) and sodium acetate (13.1 g) were suspended in water (20 mL) and ethanol (160 mL), and the suspension was heated under reflux for... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine | Primary amine | null | c1cnoc1 | C1CC[NH]CC1.c1cnoc1.c1ccccc1 | HO- | O.C(C)O | null | null | CCOC(=O)N1CCC(C(=O)C(C#N)c2ccccc2)CC1.NO>O.C(C)O>CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b21e90475f348b6afa0c3c727bba012 | CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1 | C([O-])([O-])=O.[K+].[K+].ClC(=O)OCC.NC1=C(C(=NO1)C1CCN(CC1)C(=O)OCC)C1=CC=CC=C1.NC1=C(C(=NO1)C1CCN(CC1)C(=O)OC)C1=CC=CC=C1.[Cl-].[Al+3].[Cl-].[Cl-].ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>C(C)OC(=O)N1CCC(CC1)C1=NOC=2NC(C=3C=CC=CC3C21)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]([NH2:14])[c:23]2-[c:22]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:24][CH2:25]1.ClC(Cl)(Cl)O[C:15](OC(Cl)(Cl)Cl)=[O:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]3[nH:14][c:15](=[O:16])[c:17]4[... | CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1 | null | null | N1=CC=CC=C1.C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | a6a1a1f06ed4a4f9f62a87c0f6a5deb296c96157b52f5bab59f40ad9cd43f245 | 85b4bf2087a5481ace7d95ffc08f83fb4764d9f3312671f9f9fd96f76b74e60a | O=c1[nH]c2onc(C3CCNCC3)c2c2ccccc12 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[c:4]1:[#7;a:5]:[#8;a:6]:[c:7](-[NH2;D1;+0:8]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[C:3]-[c:4]1:[#7;a:5]:[#8;a:6]:[c:7]2:[nH;D2;+0:8]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:15]3:[c:14]:[c:13]:[c:12]:[c:11]:... | 130.2 | [{"value": 130.2, "product": "C(C)OC(=O)N1CCC(CC1)C1=NOC=2NC(C=3C=CC=CC3C21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6.5 | HOUR | Triphosgene (1.83 g) was dissolved in methylene chloride (20 mL), a solution (30 mL) of a mixture (1:1, 5.57 g) of 5-amino-3-(1-ethoxycarbonylpiperidin-4-yl)-4-phenylisoxazole and 5-amino-3-(1-methoxycarbonylpiperidin-4-yl)-4-phenylisoxazole, and pyridine (3.50 g) in methylene chloride was added dropwise under ice-cool... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | null | c1cnoc1.c1ccccc1 | c1nc2oncc2c2ccccc12 | C1CC[NH]CC1.c1nc2oncc2c2ccccc12 | HCl | N1=CC=CC=C1.C(Cl)Cl | null | 6.5 | CCOC(=O)N1CCC(c2noc(N)c2-c2ccccc2)CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>N1=CC=CC=C1.C(Cl)Cl>CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2775f69bc99495c85e29758b94f9ac0 | CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1>>O=c1[nH]c2onc(C3CCNCC3)c2c2ccccc12 | C(C)OC(=O)N1CCC(CC1)C1=NOC=2NC(C=3C=CC=CC3C21)=O.COC(=O)N1CCC(CC1)C1=NOC=2NC(C=3C=CC=CC3C21)=O.Cl>>Cl.N1CCC(CC1)C1=NOC=2NC(C=3C=CC=CC3C21)=O | CCOC(=O)[N:12]1[CH2:11][CH2:10][CH:9]([c:8]2[n:7][o:6][c:5]3[nH:4][c:3](=[O:2])[c:21]4[c:16]([c:15]32)[cH:17][cH:18][cH:19][cH:20]4)[CH2:14][CH2:13]1>>[O:2]=[c:3]1[nH:4][c:5]2[o:6][n:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[c:15]2[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1 | O=c1[nH]c2onc(C3CCNCC3)c2c2ccccc12 | null | null | C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | 6dc5c07be2bf2a2ccc4ff166fd44281ea50e6dda805f74758334dcde1ad7a582 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=c1[nH]c2onc(C3CCNCC3)c2c2ccccc12 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | A mixture (1:1, 2.74 g) of 1-(1-ethoxycarbonylpiperidin-4-yl)-isoxazolo[5,4-c]isoquinolin-5(4H)-one and 1-(1-methoxycarbonylpiperidin-4-yl)-isoxazolo[5,4-c]isoquinolin-5(4H)-one was suspended in acetic acid (15 mL) and concentrated hydrochloric acid (15 mL), and the suspension was heated under reflux for 18 hrs. After ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1nc2oncc2c2ccccc12 | HO- | C(C)(=O)O | null | null | CCOC(=O)N1CCC(c2noc3[nH]c(=O)c4ccccc4c23)CC1>C(C)(=O)O>O=c1[nH]c2onc(C3CCNCC3)c2c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8829e2560fe14f9bb7ca3bc6075cc1ad | CCOC(=O)CC(=O)OCC.N=C(N)c1ccccc1>>Oc1cc(O)nc(-c2ccccc2)n1 | Cl.C(C1=CC=CC=C1)(=N)N.C(CC(=O)OCC)(=O)OCC.C1CCC2=NCCCN2CC1>>C1(=CC=CC=C1)C1=NC(=CC(=N1)O)O | CCO[C:2](=[O:1])[CH2:3][C:4](OCC)=[O:5].[NH2:6][C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[NH:14]>>[OH:1][c:2]1[cH:3][c:4]([OH:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1 | CCOC(=O)CC(=O)OCC.N=C(N)c1ccccc1 | Oc1cc(O)nc(-c2ccccc2)n1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C.[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[NH;D1;+0:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]... | 73.1 | [{"value": 73.0, "product": "C1(=CC=CC=C1)C1=NC(=CC(=N1)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "C1(=CC=CC=C1)C1=NC(=CC(=N1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzamidine hydrochloride (44.41 g; 0.284 mol), diethyl malonate (45.51 g; 0.284 mol) and DBU (86.40 g; 0.568 mol) in DMF (250 mL) was heated at 85° C. for 20 h. After cooling to room temperature, the flask was placed in a refrigerator overnight. The crystalline product was collected by filtration and was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CCOC(=O)CC(=O)OCC.N=C(N)c1ccccc1>CN(C)C=O>Oc1cc(O)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a15c2862730942d099ef8aa5d1f73e13 | Clc1cc(Cl)nc(-c2ccccc2)n1.N>>Nc1cc(Cl)nc(-c2ccccc2)n1 | O.ClC1=NC(=NC(=C1)Cl)C1=CC=CC=C1.N>>ClC1=CC(=NC(=N1)C1=CC=CC=C1)N | Cl[c:2]1[cH:3][c:4]([Cl:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1.[NH3:1]>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1 | Clc1cc(Cl)nc(-c2ccccc2)n1.N | Nc1cc(Cl)nc(-c2ccccc2)n1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 90f3138935f3ad06434c84a4ac47f6a17b2b61711b0b3fffea5d29513d5b1a76 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(-c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[NH3;D0;+0:9]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:9]):[c:8]:1 | null | [] | null | null | 24 | HOUR | An ice-cold suspension of pyrimidine 3 (44.34 g; 0.197 mol) in DMSO (366 mL) was saturated with ammonia, during which time a solution formed. After 24 h at rt, water (710 mL) was added dropwise. The suspension was cooled in an ice bath for 1 h then collected by filtration and washed with water (500 mL), yielding a ligh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CS(=O)C | null | 24 | Clc1cc(Cl)nc(-c2ccccc2)n1.N>CS(=O)C>Nc1cc(Cl)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43391e59d7e94d0b8f75ac45ed0b5da4 | CC(=O)NCCN.Nc1cc(Cl)nc(-c2ccccc2)n1>>CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1 | ClC1=CC(=NC(=N1)C1=CC=CC=C1)N.NCCNC(C)=O>>NC1=CC(=NC(=N1)C1=CC=CC=C1)NCCNC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH2:7].Cl[c:8]1[cH:9][c:10]([NH2:11])[n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH2:11])[n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1 | CC(=O)NCCN.Nc1cc(Cl)nc(-c2ccccc2)n1 | CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1 | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1 | null | [] | null | null | 4 | HOUR | A solution of chloroarene 4 (20.57 g; 0.100 mol) in N-(2-aminoethyl)-acetamide (71.05 g; 0.696 mol) was heated from 60 to 120° C. over 20 min then kept at 120° C. for 4.0 h. After cooling to rt, the reaction was diluted with EtOAc (500 mL) then washed with water (1×150 mL). The aq phase was extracted with EtOAc (3×25 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CCOC(=O)C | null | 4 | CC(=O)NCCN.Nc1cc(Cl)nc(-c2ccccc2)n1>CCOC(=O)C>CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a477ea60466643d2a089ed85061e832e | CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1.O=C(Cl)CCl>>CC(=O)NCCNc1cc(NC(=O)CCl)nc(-c2ccccc2)n1 | NC1=CC(=NC(=N1)C1=CC=CC=C1)NCCNC(C)=O.NC1=CC(=NC(=N1)C1=CC=CC=C1)NCCNC(C)=O.N1=C(C=CC=C1C)C.CO.ClCC(=O)Cl.ClCC(=O)Cl.ClCC(=O)Cl>>C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CCl)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH2:11])[n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1.Cl[C:12](=[O:13])[CH2:14][Cl:15]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][Cl:15])[n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][... | CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1.O=C(Cl)CCl | CC(=O)NCCNc1cc(NC(=O)CCl)nc(-c2ccccc2)n1 | null | null | CN(C)C=O.C(Cl)Cl.CCOC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | null | [] | null | null | 0.5 | HOUR | A solution of amine 5 was titrated with chloroacetyl chloride with monitoring by TLC (SiO2/8:1 and 14:1 DCM:MeOH) as follows: Neat chloroacetyl chloride (0.45 mL; 5.7 mmol) was slowly added down the side of a flask immersed in an ice-water bath into a solution of aminopyrimidine 5 (1.531 g; 5.64 mmol) and 2,6-lutidine ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cncnc1.c1ccccc1 | HCl | CN(C)C=O.C(Cl)Cl.CCOC(=O)C | null | 0.5 | CC(=O)NCCNc1cc(N)nc(-c2ccccc2)n1.O=C(Cl)CCl>CN(C)C=O.C(Cl)Cl.CCOC(=O)C>CC(=O)NCCNc1cc(NC(=O)CCl)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c82bb2c21d64f9d9787abb9f1b3766d | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCC(Oc2ccccc2Cl)CC1.Oc1ccccc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1ccc(C=C2CCN(Cc3ccccc3)CC2)cc1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C=CC=C1)Cl.C(C)(C)(C)OC(=O)N1CCC(CC1)O.ClC1=C(C=CC=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>C(C1=CC=CC=C1)N1CCC(CC1)=CC1=CC=C(C=C1)OC | CC(C)(C)O[C:1](=O)N1CCC(O)CC1.CC(C)(C)O[C:12](=O)[N:11]1[CH2:10][CH2:9][CH:8](O[c:7]2ccccc2Cl)[CH2:20][CH2:19]1.Cl[c:22]1[c:3]([OH:2])[cH:4][cH:5][cH:6][cH:21]1.c1ccc(P(c2ccccc2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14]... | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCC(Oc2ccccc2Cl)CC1.Oc1ccccc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1ccc(C=C2CCN(Cc3ccccc3)CC2)cc1 | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6f316f73a676f3e2733fb0c4bb9c8c214b23f684d6baa23ba7ff4eb8da150e08 | d50a79b6732e9cbd1d44436093f13cf20df12234b7411c05a8b89728d772a5dc | C(=C1CCN(Cc2ccccc2)CC1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-N1-C-C-C(-O)-C-C-1.C-C(-C)(-C)-O-[C;H0;D3;+0:2](=O)-[#7:3]1-[C:4]-[C:5]-[CH;D3;+0:6](-O-[c;H0;D3;+0:7]2:c:c:c:c:c:2-Cl)-[C:8]-[C:9]-1.Cl-[c;H0;D3;+0:10]1:[c:11]:[cH;D2;+0:12]:[c:13]:[c:14]:[c:15]:1-[OH;D1;+0:16].[c:17]:[c:18]:[c;H0;D3;+0:19](-P(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:20]:[c... | null | [] | null | null | 8 | DAY | 4-(2-Chlorophenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10.6) This compound was prepared from 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (9) (3.505 g; 17.4 mmol), 2-chloro-phenol (3.375 g; 26.3 mmol), triphenylphosphine (6.002 g; 22.9 mmol) and DIAD (4.30 mL; 21.8 mmol) in a manner analogous to 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Carbamic ester.Ether.Ether.Ether.Secondary alcohol.Aromatic alcohol.Boc.Boc | Ether | C1CCNCC1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | CCOC(=O)C | null | 192 | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCC(Oc2ccccc2Cl)CC1.Oc1ccccc1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>CCOC(=O)C>COc1ccc(C=C2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edec8b233e194fceafd64bb58625aa2e | CC(C)(C)OC(=O)N1CCC(Oc2cccc(Cl)c2)CC1>>CC(C)(C)OC(=O)N1CCC(O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=CC(=CC=C1)Cl>>C(C)(C)(C)OC(=O)N1CCC(CC1)O | Clc1cccc([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:14][CH2:13]2)c1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)N1CCC(Oc2cccc(Cl)c2)CC1 | CC(C)(C)OC(=O)N1CCC(O)CC1 | null | null | FC(C(=O)O)(F)F | Deprotection | OtherReaction | 42b6fce52a2a7b1764e08be5630337fff31a2f44663b859da9821eaf5991296a | c17636d1f30ad0d310124eaad244dab59d754c3fc002ac1288afcb2d562b945b | C1CCNCC1 | Cl-c1:c:c:c:c(-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | null | [] | null | null | 15 | MINUTE | Trifluoroacetic acid (40 mL) was added to crude carbamate 10.5 (18.6 g; 59.7 mmol) cooled in an ice-water bath. After 1 min the reaction was stirred at rt for 15 min, then concentrated on a rotary evaporator. Ether (200 mL) was added and this washed with 3 M NaOH (3×50 mL) and water (50 mL). The product was extracted i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Secondary alcohol | c1ccccc1 | null | C1CC[NH]CC1 | HCl | FC(C(=O)O)(F)F | null | 0.25 | CC(C)(C)OC(=O)N1CCC(Oc2cccc(Cl)c2)CC1>FC(C(=O)O)(F)F>CC(C)(C)OC(=O)N1CCC(O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a0e1ba5626842d9a0e913e15b5f3977 | CC(C)(C)OC(=O)N1CCNCC1.O=Cc1cccc(Cl)c1>>CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1 | [OH-].[Na+].C(C)(C)(C)OC(=O)N1CCNCC1.ClC=1C=C(C=O)C=CC1.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=CC=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:20][CH2:21]1.O=[CH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]2)[CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCNCC1.O=Cc1cccc(Cl)c1 | CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1 | null | null | ClC(C)Cl.CCOC(=O)C | Heteroatom Alkylation and Arylation | reductive amination | 66e6667395903ee1c54d8aecc784ece1bccbdcbc9661ebcae0e6a980f9380640 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCNCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1):[c:4] | 87.4 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of piperazine-1-carboxylic acid tert-butyl ester (4.00 g, 21.5 mmol) in dry dichloroethane (70 mL) are added 3-chlorobenzaldehyde (2.49 mL, 3.08 g, 21.9 mmol), HOAc (2.58 mL, 2.71 g, 45.1 mmol) and NaBH(OAc)3 (5.46 g, 25.8 mmol) at ambient temperature. After stirring at ambient temperature for 3d, 2N NaOH... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Other | ClC(C)Cl.CCOC(=O)C | null | null | CC(C)(C)OC(=O)N1CCNCC1.O=Cc1cccc(Cl)c1>ClC(C)Cl.CCOC(=O)C>CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d33f0fe59b9f4c7fb9bb1a4030d09d4b | CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1>>Clc1cccc(CN2CCNCC2)c1 | C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=CC=C1)Cl.C(=O)(C(F)(F)F)O>>ClC=1C=C(CN2CCNCC2)C=CC1 | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:14]2)[CH2:13][CH2:12]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14]1 | CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1 | Clc1cccc(CN2CCNCC2)c1 | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CN2CCNCC2)cc1 | 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:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | To 4-(3-chlorobenzyl)-piperazine-1-carboxylic acid tert-butyl ester (20.24) (8.82 g, 28.4 mmol) is added TFA (45 mL) at ambient temperature over 5 min. After 1 h 50 min, TFA is evaporated, the residue is dissolved in 2N HCl (45 mL) and extracted with ether (2×45 mL). The aqueous layer is basified to pH 13 with 2N NaOH ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(Cc2cccc(Cl)c2)CC1>>Clc1cccc(CN2CCNCC2)c1 |
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