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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-286d645aee2846f5b4cfba9c154358d8 | COc1ccccc1N.O=S(=O)(Cl)c1ccc(F)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(F)cc1 | COC=1C(=CC=CC1)N.FC1=CC=C(C=C1)S(=O)(=O)Cl>>FC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1 | COc1ccccc1N.O=S(=O)(Cl)c1ccc(F)cc1 | COc1ccccc1NS(=O)(=O)c1ccc(F)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 93.1 | [{"value": 93.1, "product": "FC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "FC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (1.0 ml, 8.55 mmol) and 4-fluorobenzenesulfonyl chloride (1.7 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.24 g (93.1%) of the title compound in the form of colorless prism crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1N.O=S(=O)(Cl)c1ccc(F)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df69311069264a20a142aa147b4fbb47 | COc1ccccc1N.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>>COc1ccccc1NS(=O)(=O)c1cccc([N+](=O)[O-])c1 | COC=1C(=CC=CC1)N.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl>>COC1=C(C=CC=C1)NS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1 | COc1ccccc1N.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | COc1ccccc1NS(=O)(=O)c1cccc([N+](=O)[O-])c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 89.5 | [{"value": 89.5, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (1.0 ml, 8.55 mmol) and 3-nitrobenzenesulfonyl chloride (1.95 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.36 g (89.5%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1N.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>>COc1ccccc1NS(=O)(=O)c1cccc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f25119feab274c18843fec44487e7f9a | COc1ccc(S(=O)(=O)Cl)cc1.COc1cccc(N)c1>>COc1ccc(S(=O)(=O)Nc2cccc(OC)c2)cc1 | COC1=CC(=CC=C1)N.COC1=CC=C(C=C1)S(=O)(=O)Cl>>COC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=CC=C1)OC | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1)(=[O:8])=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]2)[cH:19][cH:20]1 | COc1ccc(S(=O)(=O)Cl)cc1.COc1cccc(N)c1 | COc1ccc(S(=O)(=O)Nc2cccc(OC)c2)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 99.7 | [{"value": 99.7, "product": "COC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "COC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using m-anisidine (0.99 ml, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.50 g (99.7%) of the title compound in the form of light yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(S(=O)(=O)Cl)cc1.COc1cccc(N)c1>>COc1ccc(S(=O)(=O)Nc2cccc(OC)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-884108655568491b9b7065118f5c820d | COc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccccc1N>>COc1ccc(S(=O)(=O)Nc2ccccc2C#N)cc1 | NC1=C(C#N)C=CC=C1.COC1=CC=C(C=C1)S(=O)(=O)Cl>>C(#N)C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1)(=[O:8])=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]#[N:18])[cH:19][cH:20]1 | COc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccccc1N | COc1ccc(S(=O)(=O)Nc2ccccc2C#N)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 63.7 | [{"value": 63.7, "product": "C(#N)C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "C(#N)C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-aminobenzonitrile (1.03 g, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 1.57 g (63.7%) of the title compound in the form of colorless solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccccc1N>>COc1ccc(S(=O)(=O)Nc2ccccc2C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a203f03510c84376936109923b3e225b | COc1ccc(S(=O)(=O)Cl)cc1.Nc1ccccc1C(F)(F)F>>COc1ccc(S(=O)(=O)Nc2ccccc2C(F)(F)F)cc1 | FC(C1=C(N)C=CC=C1)(F)F.COC1=CC=C(C=C1)S(=O)(=O)Cl>>FC(C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC)(F)F | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]1)(=[O:8])=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[F:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1 | COc1ccc(S(=O)(=O)Cl)cc1.Nc1ccccc1C(F)(F)F | COc1ccc(S(=O)(=O)Nc2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 75.5 | [{"value": 75.5, "product": "FC(C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "FC(C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-trifluoromethylaniline (1.39 g, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.14 g (75.5%) of the title compound in the form of colorless solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(S(=O)(=O)Cl)cc1.Nc1ccccc1C(F)(F)F>>COc1ccc(S(=O)(=O)Nc2ccccc2C(F)(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcfcdbed56674c439cbfcd16edd11134 | COc1ccccc1N.O=C(O)c1ccc(S(=O)(=O)Cl)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1 | COC=1C(=CC=CC1)N.ClS(=O)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1 | COc1ccccc1N.O=C(O)c1ccc(S(=O)(=O)Cl)cc1 | COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 95.7 | [{"value": 95.5, "product": "COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (0.585 ml, 5.0 mmol) and 4-(chlorosulfonyl)benzoic acid (1.15 g, 5.0 mmol), the procedure of Reference Example 2 was repeated to obtain 1.47 g (95.5%) of the title compound in the form of pink powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1N.O=C(O)c1ccc(S(=O)(=O)Cl)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e35a3aec1e0643e09ded967995999b79 | COc1cccc(C(=O)Cl)c1.COc1ccccc1N>>COc1cccc(C(=O)Nc2ccccc2OC)c1 | COC=1C(=CC=CC1)N.C(C1=CC(=CC=C1)OC)(=O)Cl>>COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1 | Cl[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19]1 | COc1cccc(C(=O)Cl)c1.COc1ccccc1N | COc1cccc(C(=O)Nc2ccccc2OC)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (1.0 ml, 8.55 mmol) and m-anisoyl chloride (1.2 ml, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.2 g (100%) of the title compound in the form of brown oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1cccc(C(=O)Cl)c1.COc1ccccc1N>>COc1cccc(C(=O)Nc2ccccc2OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-942a079fe8694bdda867bffdec3990b6 | COc1ccccc1N.N#Cc1ccc(C(=O)O)cc1>>COc1ccccc1NC(=O)c1ccc(C#N)cc1 | S(=O)(Cl)Cl.C(#N)C1=CC=C(C(=O)O)C=C1.COC=1C(=CC=CC1)N.[OH-].[Na+]>>C(#N)C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1 | COc1ccccc1N.N#Cc1ccc(C(=O)O)cc1 | COc1ccccc1NC(=O)c1ccc(C#N)cc1 | null | null | CN(C)C=O.C1=CC=CC=C1.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 93.6 | [{"value": 93.6, "product": "C(#N)C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C(#N)C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In an atmosphere of dry air, 4-cyanobenzoic acid (1.5 g, 10 mmol) was dissolved in benzene (5 ml), and DMF (0.1 ml) and thionyl chloride (2.2 ml, 30 mmol) were added dropwise to the resulting solution at room temperature, followed by 30 minutes of heating under reflux. After removing the solvent by evaporation, the res... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C1=CC=CC=C1.C(Cl)Cl | null | 0.5 | COc1ccccc1N.N#Cc1ccc(C(=O)O)cc1>CN(C)C=O.C1=CC=CC=C1.C(Cl)Cl>COc1ccccc1NC(=O)c1ccc(C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a73df83aa26e46b6a84924990ae0f10f | COc1ccccc1N.O=C(O)c1ccncc1>>COc1ccccc1NC(=O)c1ccncc1 | COC=1C(=CC=CC1)N.C(=O)(O)C1=CC=NC=C1>>COC1=C(NC(=O)C2=CC=NC=C2)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | COc1ccccc1N.O=C(O)c1ccncc1 | COc1ccccc1NC(=O)c1ccncc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 97.3 | [{"value": 97.2, "product": "COC1=C(NC(=O)C2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "COC1=C(NC(=O)C2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (2.34 g, 19.0 mmol) and 4-carboxypyridine (2.29 g, 19.0 mmol), the procedure of Reference Example 11 was repeated to obtain 4.22 g (97.2%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | null | null | null | COc1ccccc1N.O=C(O)c1ccncc1>>COc1ccccc1NC(=O)c1ccncc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77cb8f49e98843759fa1c7777b2640d4 | COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1>>COc1ccccc1NC(=O)c1ccc(CCl)cc1 | COC=1C(=CC=CC1)N.[OH-].[Na+].ClCC1=CC=C(C(=O)Cl)C=C1>>ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][Cl:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][Cl:17])[cH:18][cH:19]1 | COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1 | COc1ccccc1NC(=O)c1ccc(CCl)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 94.3 | [{"value": 94.2, "product": "ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | o-Anisidine (0.69 ml, 6.0 mmol) was dissolved in methylene chloride (10 ml) and, with cooling in an ice bath, mixed with 20% sodium hydroxide (5 ml) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol). After 30 minutes of stirring at the same temperature, the reaction mixture was extracted with methylene chloride and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1>C(Cl)Cl>COc1ccccc1NC(=O)c1ccc(CCl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73cffb0515534384845ebf7bb0293e1c | COc1cccc(C(=O)Cl)c1.Nc1ccccn1>>COc1cccc(C(=O)Nc2ccccn2)c1 | NC1=NC=CC=C1.C(C1=CC(=CC=C1)OC)(=O)Cl>>COC=1C=C(C(=O)NC2=NC=CC=C2)C=CC1 | Cl[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[cH:17]1 | COc1cccc(C(=O)Cl)c1.Nc1ccccn1 | COc1cccc(C(=O)Nc2ccccn2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccn1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 21 | [{"value": 21.0, "product": "COC=1C=C(C(=O)NC2=NC=CC=C2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "COC=1C=C(C(=O)NC2=NC=CC=C2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-aminopyridine (670 mg, 7.12 mmol) and m-anisoyl chloride (1.2 ml, 8.55 mmol), the procedure of Reference Example 13 was repeated to obtain 341 mg (21.0%) of the title compound in the form of light yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | null | null | null | COc1cccc(C(=O)Cl)c1.Nc1ccccn1>>COc1cccc(C(=O)Nc2ccccn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc00450aae7f43bba3081ae919487779 | COc1cccc(CN)c1.O=C(Cl)c1ccc(CCl)cc1>>COc1cccc(CNC(=O)c2ccc(CCl)cc2)c1 | COC=1C=C(CN)C=CC1.ClCC1=CC=C(C(=O)Cl)C=C1>>ClCC1=CC=C(C(=O)NCC2=CC(=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:20]1.Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][Cl:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([CH2:16][Cl:17])[cH:18][cH:19]2)[cH:20]1 | COc1cccc(CN)c1.O=C(Cl)c1ccc(CCl)cc1 | COc1cccc(CNC(=O)c2ccc(CCl)cc2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 83.9 | [{"value": 83.9, "product": "ClCC1=CC=C(C(=O)NCC2=CC(=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "ClCC1=CC=C(C(=O)NCC2=CC(=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-methoxybenzylamine (754 mg, 5.39 mmol) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol), the procedure of Reference Example 13 was repeated to obtain 1.31 g (83.9%) of the title compound in the form of colorless crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1cccc(CN)c1.O=C(Cl)c1ccc(CCl)cc1>>COc1cccc(CNC(=O)c2ccc(CCl)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4ba4a81e15b4995a5093c01878efc4c | COc1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 | C([O-])(O)=O.[Na+].COC=1C(=CC=CC1)N.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1.Cl.CN(CCCN=C=NCC)C>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1 | COc1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1 | COc1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 87.5 | [{"value": 87.4, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | With cooling in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (630 mg, 3.29 mmol) was added to 15 ml of methylene chloride solution containing o-anisidine (368 mg, 2.99 mmol) and 4-nitrobenzoic acid (500 mg, 2.99 mmol). After 1 hour of stirring at the same temperature, the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 1 | COc1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1>C(Cl)Cl>COc1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b82805e2b34b4ecf82e3f2502d0befca | COc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | COC1=CC(=CC=C1)N.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2)[cH:20]1 | COc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | COc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 93.2 | [{"value": 93.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using m-anisidine (2.50 g, 15.0 mmol) and 4-nitrobenzoic acid (2.03 g, 16.5 mmol), the procedure of Reference Example 16 was repeated to obtain 3.80 g (93.2%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94cb357d0d594c1a9f47342a518b5646 | COc1ccc(OC)c(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1ccc(OC)c(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | COC1=C(N)C=C(C=C1)OC.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC(=C2)OC)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([NH2:10])[cH:22]1.O[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]2)[cH:22]1 | COc1ccc(OC)c(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | COc1ccc(OC)c(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 77.2 | [{"value": 77.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC(=C2)OC)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC(=C2)OC)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,5-dimethoxyaniline (2.53 g, 16.5 mmol) and 4-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.50 g (77.2%) of the title compound in the form of orange needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccc(OC)c(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1ccc(OC)c(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-328ffea84e8945bab5f2c5c05d92ed2e | COc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1>>COc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 | COC1=CC(=CC=C1)N.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)OC)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20]1 | COc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1 | COc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 91.3 | [{"value": 91.3, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using m-anisidine (2.03 g, 16.5 mmol) and 3-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.72 g (91.3%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1>>COc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5c35a8197eab49d69e7416ffbe7e9d87 | COc1ccc(N)c(OC)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c(OC)c1 | COC1=C(N)C=CC(=C1)OC.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=C(C=C2)OC)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:19]([O:20][CH3:21])[cH:22]1.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[c:19]([O:20][CH3:21])[cH:22]1 | COc1ccc(N)c(OC)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c(OC)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 91.3 | [{"value": 91.3, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=C(C=C2)OC)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=C(C=C2)OC)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,4-dimethoxyaniline (2.53 g, 16.0 mmol) and 4-nitrobenzoic acid (2.50 g, 14.8 mmol), the procedure of Reference Example 16 was repeated to obtain 3.72 g (91.3%) of the title compound in the form of yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccc(N)c(OC)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20a899a14e114ac08ae516cd5bce4b60 | Nc1ccccc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccccc1)c1ccc([N+](=O)[O-])cc1 | NC1=CC=CC=C1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1 | Nc1ccccc1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccccc1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 97.5 | [{"value": 97.5, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using aniline (1.50 ml, 16.5 mmol) and 4-nitrobenzoic acid (1.77 g, 10.5 mmol), the procedure of Reference Example 16 was repeated to obtain 2.48 g (97.5%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccccc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccccc1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bac4f35022814f6eaa0f9cad74b4ef8c | CSc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>CSc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | CSC=1C=C(N)C=CC1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)SC)C=C1 | [CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2)[cH:20]1 | CSc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | CSc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 85.3 | [{"value": 85.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)SC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)SC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-methylthioaniline (1.40 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.46 g (85.2%) of the title compound in the form of yellow powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CSc1cccc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>CSc1cccc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33162552f5a14903a0ce124e5d44dc3e | Nc1ccccc1C(F)(F)F.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccccc1C(F)(F)F)c1ccc([N+](=O)[O-])cc1 | FC(C1=C(N)C=CC=C1)(F)F.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(F)(F)F)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13].O[C:2](=[O:1])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1 | Nc1ccccc1C(F)(F)F.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccccc1C(F)(F)F)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 15.3 | [{"value": 15.3, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-trifluoromethylaniline (1.77 g, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 474 mg (15.3%) the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccccc1C(F)(F)F.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccccc1C(F)(F)F)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5184ffb1f92a40a8a3af5aec36316d41 | Nc1cccc(C(F)(F)F)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccc(C(F)(F)F)c1)c1ccc([N+](=O)[O-])cc1 | FC(C=1C=C(N)C=CC1)(F)F.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1.O[C:2](=[O:1])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1)[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1 | Nc1cccc(C(F)(F)F)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1cccc(C(F)(F)F)c1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 80 | [{"value": 80.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-trifluoromethylaniline (1.77 g, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.48 g (80.0%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1cccc(C(F)(F)F)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccc(C(F)(F)F)c1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9b80589636924c52a8e626d5bfe35bb7 | Nc1cccnc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1 | NC=1C=NC=CC1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1.O[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1 | Nc1cccnc1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccnc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11])-[c:3](:[c:4]):[c:5] | 49.6 | [{"value": 49.6, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-aminopyridine (1.55 g, 16.5 mmol) and 4-nitrobenzoic acid (2.5 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.81 g (49.6%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HO- | null | null | null | Nc1cccnc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfd5a32f672c46c19f0d787eab887512 | COc1cccc(N)c1.O=C(O)c1ccccc1[N+](=O)[O-]>>COc1cccc(NC(=O)c2ccccc2[N+](=O)[O-])c1 | COC1=CC(=CC=C1)N.[N+](=O)([O-])C1=C(C(=O)O)C=CC=C1>>[N+](=O)([O-])C1=C(C(=O)NC2=CC(=CC=C2)OC)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])[cH:20]1 | COc1cccc(N)c1.O=C(O)c1ccccc1[N+](=O)[O-] | COc1cccc(NC(=O)c2ccccc2[N+](=O)[O-])c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 85 | [{"value": 84.9, "product": "[N+](=O)([O-])C1=C(C(=O)NC2=CC(=CC=C2)OC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "[N+](=O)([O-])C1=C(C(=O)NC2=CC(=CC=C2)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using m-anisidine (2.03 g, 16.5 mmol) and 2-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.47 g (84.9%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cccc(N)c1.O=C(O)c1ccccc1[N+](=O)[O-]>>COc1cccc(NC(=O)c2ccccc2[N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-555bc4c8dfda4c9f9927d3dfcbc0d7ef | Nc1cccc([N+](=O)[O-])c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccc([N+](=O)[O-])c1)c1ccc([N+](=O)[O-])cc1 | [N+](=O)([O-])C=1C=C(N)C=CC1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1.O[C:2](=[O:1])[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1)[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1 | Nc1cccc([N+](=O)[O-])c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1cccc([N+](=O)[O-])c1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 83.2 | [{"value": 83.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-nitroaniline (2.76 g, 16.5 mmol) and 4-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.58 g (83.2%) of the title compound in the form of light yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1cccc([N+](=O)[O-])c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1cccc([N+](=O)[O-])c1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0da5c45fb1f94fe58e6de013c7b3d1b3 | COC(=O)c1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1>>COC(=O)c1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 | C(C=1C(N)=CC=CC1)(=O)OC.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1 | COC(=O)c1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1 | COC(=O)c1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 72.9 | [{"value": 72.9, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using methyl anthranilate (3.02 g, 20.0 mmol) and 4-nitrobenzoic acid (3.67 g, 22.0 mmol), the procedure of Reference Example 16 was repeated to obtain 4.20 g (72.9%) of the title compound in the form of light yellow prism crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1ccccc1N.O=C(O)c1ccc([N+](=O)[O-])cc1>>COC(=O)c1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ac9b042f4b28460bbb5f5ac06fb31c97 | COc1ccc(N)cc1.N#Cc1ccc(C(=O)O)cc1>>COc1ccc(NC(=O)c2ccc(C#N)cc2)cc1 | COC1=CC=C(C=C1)N.C(#N)C1=CC=C(C(=O)O)C=C1>>C(#N)C1=CC=C(C(=O)NC2=CC=C(C=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:18][cH:19]1.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | COc1ccc(N)cc1.N#Cc1ccc(C(=O)O)cc1 | COc1ccc(NC(=O)c2ccc(C#N)cc2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 91.7 | [{"value": 91.7, "product": "C(#N)C1=CC=C(C(=O)NC2=CC=C(C=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "C(#N)C1=CC=C(C(=O)NC2=CC=C(C=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using p-anisidine (1.35 g, 11.0 mmol) and 4-cyanobenzoic acid (1.47 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.31 g (91.7%) of the title compound in the form of colorless needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccc(N)cc1.N#Cc1ccc(C(=O)O)cc1>>COc1ccc(NC(=O)c2ccc(C#N)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0bbf02c3b9c74d45aad453e8f1838747 | COc1ccc(N)cc1.Cc1cc(C(=O)O)ccc1[N+](=O)[O-]>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(C)c2)cc1 | COC1=CC=C(C=C1)N.CC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>CC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:20][cH:21]1.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([CH3:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([CH3:18])[cH:19]2)[cH:20][cH:21]1 | COc1ccc(N)cc1.Cc1cc(C(=O)O)ccc1[N+](=O)[O-] | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(C)c2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 93 | [{"value": 93.0, "product": "CC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "CC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using p-anisidine (738 mg, 6.0 mmol) and 3-methyl-4-nitrobenzoic acid (906 mg, 5.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.33 g (93.0%) of the title compound in the form of yellow powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccc(N)cc1.Cc1cc(C(=O)O)ccc1[N+](=O)[O-]>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(C)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d6f0bef2d28347ca947ceb2e3c17a182 | COc1cc(C(=O)O)ccc1[N+](=O)[O-].COc1ccc(N)cc1>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(OC)c2)cc1 | COC1=CC=C(C=C1)N.COC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>COC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-] | O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([O:18][CH3:19])[cH:20]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([O:18][CH3:19])[cH:20]2)[cH:21][cH:22]1 | COc1cc(C(=O)O)ccc1[N+](=O)[O-].COc1ccc(N)cc1 | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(OC)c2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 92.7 | [{"value": 92.7, "product": "COC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "COC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using p-anisidine (738 mg, 6.0 mmol) and 3-methoxy-4-nitrobenzoic acid (986 mg, 5.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.40 g (92.7%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cc(C(=O)O)ccc1[N+](=O)[O-].COc1ccc(N)cc1>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(OC)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-225d5fd599ed478295e732ac8190f2ec | Cc1ccc(N)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1 | NC1=CC=C(C=C1)C.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)C)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:18][cH:19]1.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | Cc1ccc(N)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1 | Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 99.6 | [{"value": 99.6, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using p-toluidine (1.19 g, 11.0 mmol) and 4-nitrobenzoic acid (1.77 g, 10.5 mmol), the procedure of Reference Example 16 was repeated to obtain 2.68 g (99.6%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccc(N)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6dae5ade71d64ef5bed47b84c6e2b2bc | Nc1ccc(F)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc(F)cc1)c1ccc([N+](=O)[O-])cc1 | FC1=CC=C(N)C=C1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)F)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1 | Nc1ccc(F)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc(F)cc1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 65.8 | [{"value": 65.8, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-fluoroaniline (1.0 ml, 9.93 mmol) and 4-nitrobenzoic acid (1.58 g, 9.36 mmol), the procedure of Reference Example 16 was repeated to obtain 1.60 g (65.8%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccc(F)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc(F)cc1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5f8b75935a14742a17b9126f718e1bc | Nc1ccccc1.O=C(O)c1cccc([N+](=O)[O-])c1>>O=C(Nc1ccccc1)c1cccc([N+](=O)[O-])c1 | NC1=CC=CC=C1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O[C:2](=[O:1])[c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | Nc1ccccc1.O=C(O)c1cccc([N+](=O)[O-])c1 | O=C(Nc1ccccc1)c1cccc([N+](=O)[O-])c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 78.2 | [{"value": 78.2, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using aniline (1.50 ml, 16.5 mmol) and 3-nitrobenzoic acid (2.64 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.84 g (78.2%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccccc1.O=C(O)c1cccc([N+](=O)[O-])c1>>O=C(Nc1ccccc1)c1cccc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f1ead6dddb964cfda207e6e2ba7f29ba | Cc1ccc(N)cc1.O=C(O)c1cccc([N+](=O)[O-])c1>>Cc1ccc(NC(=O)c2cccc([N+](=O)[O-])c2)cc1 | NC1=CC=C(C=C1)C.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)C)C=CC1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:18][cH:19]1.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[cH:18][cH:19]1 | Cc1ccc(N)cc1.O=C(O)c1cccc([N+](=O)[O-])c1 | Cc1ccc(NC(=O)c2cccc([N+](=O)[O-])c2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 88.6 | [{"value": 88.3, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)C)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)C)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using p-toluidine (1.19 g, 11.0 mmol) and 3-nitrobenzoic acid (1.76 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.27 g (88.3%) of the title compound in the form of colorless needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccc(N)cc1.O=C(O)c1cccc([N+](=O)[O-])c1>>Cc1ccc(NC(=O)c2cccc([N+](=O)[O-])c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29a2732da3a948f4aae1ec2e95eeccf2 | Nc1ccc(F)cc1.O=C(O)c1cccc([N+](=O)[O-])c1>>O=C(Nc1ccc(F)cc1)c1cccc([N+](=O)[O-])c1 | FC1=CC=C(N)C=C1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)F)C=CC1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | Nc1ccc(F)cc1.O=C(O)c1cccc([N+](=O)[O-])c1 | O=C(Nc1ccc(F)cc1)c1cccc([N+](=O)[O-])c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 76.1 | [{"value": 76.0, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)F)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)F)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-fluoroaniline (1.1 ml, 10.9 mmol) and 3-nitrobenzoic acid (1.76 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.98 g (76.0%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccc(F)cc1.O=C(O)c1cccc([N+](=O)[O-])c1>>O=C(Nc1ccc(F)cc1)c1cccc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c16cf1c3e2df4892b6f3150e9b21bcaf | CSc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1>>CSc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 | CSC=1C=C(N)C=CC1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1>>[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)SC)C=CC1 | [CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20]1 | CSc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1 | CSc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 94.6 | [{"value": 94.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)SC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)SC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-methylthioaniline (2.1 ml, 16.5 mmol) and 3-nitrobenzoic acid (2.64 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 4.09 g (94.6%) of the title compound in the form of light yellow needle crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CSc1cccc(N)c1.O=C(O)c1cccc([N+](=O)[O-])c1>>CSc1cccc(NC(=O)c2cccc([N+](=O)[O-])c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f4298d191fb4ea180b3c22f289b3eb0 | Cc1ccc(N)cc1C.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1C | NC1=CC(=C(C=C1)C)C.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=C(C=C2)C)C)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:18][c:19]1[CH3:20].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[cH:18][c:19]1[CH3:20] | Cc1ccc(N)cc1C.O=C(O)c1ccc([N+](=O)[O-])cc1 | Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Using 3,4-xylidine (1.35 g, 11.0 mmol) and 4-nitrobenzoic acid (1.69 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.70 g (quantitative) of the title compound in the form of light yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccc(N)cc1C.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-faf03e3b2ef74ea6adbc16e6e6d66bc2 | Cc1cc(C)cc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1cc(C)cc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | NC1=CC(=CC(=C1)C)C.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC(=C2)C)C)C=C1 | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2)[cH:20]1 | Cc1cc(C)cc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1 | Cc1cc(C)cc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Using 3,5-xylidine (1.42 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.72 g (quantitative) of the title compound in the form of light yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1cc(C)cc(N)c1.O=C(O)c1ccc([N+](=O)[O-])cc1>>Cc1cc(C)cc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81108896a4f04eedb46c78483e919025 | Nc1ccc(Cl)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc(Cl)cc1)c1ccc([N+](=O)[O-])cc1 | ClC1=CC=C(N)C=C1.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)Cl)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1 | Nc1ccc(Cl)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc(Cl)cc1)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 98.7 | [{"value": 98.5, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-chloroaniline (1.42 g, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.84 g (98.5%) of the title compound in the form of yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccc(Cl)cc1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc(Cl)cc1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b04fe9c2f1da4526a30f3f2067ac49b1 | Nc1ccc2c(c1)OCO2.O=C(Cl)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc2c(c1)OCO2)c1ccc([N+](=O)[O-])cc1 | C1OC=2C=C(N)C=CC2O1.[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2.Cl[C:2](=[O:1])[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2)[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1 | Nc1ccc2c(c1)OCO2.O=C(Cl)c1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc2c(c1)OCO2)c1ccc([N+](=O)[O-])cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc2c(c1)OCO2)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 87.2 | [{"value": 87.2, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,4-methylenedioxyaniline (1.44 g, 10.5 mmol) and 4-nitrobenzoyl chloride (1.86 g, 10.0 mmol), the procedure of Reference Example 11 was repeated to obtain 2.49 g (87.2%) of the title compound in the form of yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)OCO2.c1ccccc1 | HCl | null | null | null | Nc1ccc2c(c1)OCO2.O=C(Cl)c1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc2c(c1)OCO2)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5fabbe4482ff451aa260f688512ff2dd | COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1 | C(C)N(CC)CC.ClC(=O)OCC.COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1.[BH4-].[Na+].Cl>>OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC | O=[C:17]([c:16]1[cH:15][cH:14][c:13]([S:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)(=[O:11])=[O:12])[cH:20][cH:19]1)[OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19][cH:20]1 | COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1 | COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1 | null | null | C1CCOC1.O | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 69.6 | [{"value": 69.6, "product": "OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In an atmosphere of argon and with cooling in an ice bath, 4-[(2-methoxyanilino)sulfonyl]benzoic acid (150 mg, 0.488 mmol) was dissolved in THF (5 ml), to which were subsequently added dropwise triethylamine (0.14 ml, 1.0 mmol) and ethyl chloroformate (50 μl, 0.509 mmol). After 30 minutes of stirring at the same temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1.O | null | 0.5 | COc1ccccc1NS(=O)(=O)c1ccc(C(=O)O)cc1>C1CCOC1.O>COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad335823cf4c4c7daba8d6b3227c7ced | CO.COc1ccccc1NC(=O)c1ccc(CCl)cc1>>COCc1ccc(C(=O)Nc2ccccc2OC)cc1 | ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1.CO.C1CCOC1.[OH-].[Na+]>>COCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1 | [CH3:1][OH:2].Cl[CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1 | CO.COc1ccccc1NC(=O)c1ccc(CCl)cc1 | COCc1ccc(C(=O)Nc2ccccc2OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | be62d176246b43d48f94f6bacb3beb02bd17fc7ee5c35751334f4a18453b201e | d4b2af534593ebf4ce27dc032f19c2f57b7f68624a1e46dd4bd7343947c883f4 | O=C(Nc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 92.9 | [{"value": 92.9, "product": "COCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 4-Chloromethyl-N-(2-methoxyphenyl)benzamide (138 mg, 0.50 mmol) was dissolved in a methanol-THF (1:1) mixture solution (6 ml) to which was subsequently added 10% sodium hydroxide aqueous solution (3 ml) at room temperature. After 14 hours of stirring at the same temperature, the reaction solution was subjected to 3 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Methanol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | 14 | CO.COc1ccccc1NC(=O)c1ccc(CCl)cc1>>COCc1ccc(C(=O)Nc2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9a7125374424a33a8c178a8e25b8efd | COc1ccccc1N.Cc1cccc(Cl)c1>>COc1ccccc1NC(=O)c1cccc(CO)c1 | BrN1C(CCC1=O)=O.C([O-])([O-])=O.[Ca+2].[BH4-].[Na+].[Cl-].[NH4+].C1(=CC(=CC=C1)Cl)C.COC=1C(=CC=CC1)N.[OH-].[Na+]>>OCC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[c:12]1[cH:13][cH:14][cH:15][c:16]([CH3:17])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19]1 | COc1ccccc1N.Cc1cccc(Cl)c1 | COc1ccccc1NC(=O)c1cccc(CO)c1 | null | CC(C)(C#N)N=NC(C)(C)C#N | C(Cl)(Cl)(Cl)Cl.C1CCOC1.CC(=O)C.O1CCOCC1.O.CO | Acylation | OtherReaction | 9bc8daa405087854496d46ded817289ecab7fa4d1598800179ede998ac92e467 | 6305b304df3b503730ed10ed2baa58ab1d596d05493d5cc5814ceee63ef2562c | O=C(Nc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](-[CH3;D1;+0:6]):[c:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:12]=[C:13](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[O;D1;H1:14]):[c:7]:1 | 66.1 | [{"value": 66.1, "product": "OCC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "OCC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | N-Bromosuccinimide (1.29 g, 7.2 mmol) and AIBN (50 mg, 0.30 mmol) were suspended in carbon tetrachloride (80 ml), mixed with m-toluyl chloride (0.8 ml, 6.0 mmol) and then heated under reflux for 4 hours while exposing to light. After concentrating the reaction solution to 1/3 volume, insoluble materials were removed by... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amide.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl.C1CCOC1.CC(=O)C.O1CCOCC1.O.CO | null | 0.333333 | COc1ccccc1N.Cc1cccc(Cl)c1>CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl.C1CCOC1.CC(=O)C.O1CCOCC1.O.CO>COc1ccccc1NC(=O)c1cccc(CO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-721576edcf544abdbf97d483a0968b14 | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O>>COc1ccccc1NC(=O)c1ccc(CO)cc1 | ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1.C([O-])([O-])=O.[Ca+2].O1CCOCC1.O>>OCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1 | Cl[CH2:16][c:15]1[cH:14][cH:13][c:12]([C:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)=[O:11])[cH:19][cH:18]1.[OH2:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][OH:17])[cH:18][cH:19]1 | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O | COc1ccccc1NC(=O)c1ccc(CO)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 231253c55c0f42174a17340b823c6702155eb165c3d2f7b555bb09f54b91b1a3 | e7141d94960d4874394ef66bcefdd72176a955fa44e71bb38bf7656b1bd4e11a | O=C(Nc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH2;D0;+0:5]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 88.3 | [{"value": 88.3, "product": "OCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.3, "product": "OCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 25 | HOUR | 4-Chloromethyl-N-(2-methoxyphenyl)benzamide (500 mg, 1.81 mmol) and precipitated calcium carbonate (970 mg, 9.7 mmol) were suspended in a dioxane-water (1:1) mixture solution (9 ml) and subjected to 25 hours of heating under reflux. After adding THF (25 ml) and filtering off the formed insoluble materials, the organic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 25 | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O>C1CCOC1>COc1ccccc1NC(=O)c1ccc(CO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-22c3de4c1b024e1b99af0b155d809e56 | C1=COCCC1.COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(COC2CCCCO2)cc1 | C([O-])(O)=O.[Na+].O1CCCC=C1.OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(CCCC1)OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC | [CH2:19]1[CH2:20][CH2:21][CH:22]=[CH:23][O:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH2:17][O:18][CH:19]2[CH2:... | C1=COCCC1.COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1 | COc1ccccc1NS(=O)(=O)c1ccc(COC2CCCCO2)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | O=S(=O)(Nc1ccccc1)c1ccc(COC2CCCCO2)cc1 | [#8:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[OH;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[O;H0;D2;+0:7]-[CH;D3;+0:2]1-[#8:1]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:4]-[C:3]-1 | 91.2 | [{"value": 91.2, "product": "O1C(CCCC1)OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "O1C(CCCC1)OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | 4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide (99.6 mg, 0.34 mmol) was dissolved in methylene chloride (3 ml) to which, with cooling in an ice bath, were subsequently added 3,4-dihydro-2H-pyrane (48 μl, 0.51 mmol) and a catalytically effective amount of p-toluenesulfonic acid monohydrate. After 90 minutes of st... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.c1ccccc1.C1CCOCC1 | null | C(Cl)Cl | null | 1.5 | C1=COCCC1.COc1ccccc1NS(=O)(=O)c1ccc(CO)cc1>C(Cl)Cl>COc1ccccc1NS(=O)(=O)c1ccc(COC2CCCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0629cd8f2ed34187aae991fef93b63da | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O=C1NC(=O)c2ccccc21>>COc1ccccc1NC(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | [I-].[Na+].[H-].[Na+].C1(C=2C(C(N1)=O)=CC=CC2)=O.ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1>>COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O | Cl[CH2:16][c:15]1[cH:14][cH:13][c:12]([C:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)=[O:11])[cH:29][cH:28]1.[NH:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]2[... | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O=C1NC(=O)c2ccccc21 | COc1ccccc1NC(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | null | null | CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C(Nc1ccccc1)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1>>[O;D1;H0:5]=[C:6]1-[c:11]:[c:10]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77.6 | [{"value": 77.6, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | In an atmosphere of argon, phthalimide (150 mg, 1.0 mmol) was dissolved in THF (10 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After 40 minutes of stirring at the same temperature, to this was added a DMF solution (5 ml) containing 4-chloromethyl-N-(2-methoxyphenyl)ben... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HCl | CN(C)C=O.C1CCOC1 | null | 0.666667 | COc1ccccc1NC(=O)c1ccc(CCl)cc1.O=C1NC(=O)c2ccccc21>CN(C)C=O.C1CCOC1>COc1ccccc1NC(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9314116e4867418e938602e89b4994f8 | C1COCCN1.COc1ccccc1NC(=O)c1ccc(CCl)cc1>>COc1ccccc1NC(=O)c1ccc(CN2CCOCC2)cc1 | C1CCOC1.C(CCC)[Li].N1CCOCC1.ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1>>COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1CCOCC1)=O | [NH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1.Cl[CH2:16][c:15]1[cH:14][cH:13][c:12]([C:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)=[O:11])[cH:24][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH... | C1COCCN1.COc1ccccc1NC(=O)c1ccc(CCl)cc1 | COc1ccccc1NC(=O)c1ccc(CN2CCOCC2)cc1 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(Nc1ccccc1)c1ccc(CN2CCOCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]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:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1):[c:4] | 39.2 | [{"value": 39.2, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.2, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | In an atmosphere of argon, morpholine (192 mg, 2.2 mmol) was dissolved in ether (5 ml) to which, with cooling in an ice bath, was subsequently added n-butyl lithium (1.45 ml, 1.52M, 2.2 mmol). After 5 minutes of stirring at room temperature, to this was added 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccccc1.C1COCC[NH]1 | HCl | CCOCC.O | null | 0.083333 | C1COCCN1.COc1ccccc1NC(=O)c1ccc(CCl)cc1>CCOCC.O>COc1ccccc1NC(=O)c1ccc(CN2CCOCC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6f09e6358c645c8a45e3f4af446ce3d | CNC.COc1ccccc1NC(=O)c1ccc(CCl)cc1>>COc1ccccc1NC(=O)c1ccc(CN(C)C)cc1 | ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1.CNC>>COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN(C)C)=O | [NH:17]([CH3:18])[CH3:19].Cl[CH2:16][c:15]1[cH:14][cH:13][c:12]([C:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)=[O:11])[cH:21][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CNC.COc1ccccc1NC(=O)c1ccc(CCl)cc1 | COc1ccccc1NC(=O)c1ccc(CN(C)C)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(Nc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2.5 | HOUR | In an atmosphere of argon, 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) was put into a 25 ml capacity eggplant type flask equipped with a cold finger and dissolved in dioxane (3 ml), followed by the addition of 50% dimethylamine aqueous solution (3 ml) at room temperature. After 2.5 hours of stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | HCl | O1CCOCC1 | 80 | 2.5 | CNC.COc1ccccc1NC(=O)c1ccc(CCl)cc1>O1CCOCC1>COc1ccccc1NC(=O)c1ccc(CN(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e483b3adf244fe28b89df6ce80d81bc | CN.COc1ccccc1NC(=O)c1ccc(CCl)cc1>>CNCc1ccc(C(=O)Nc2ccccc2OC)cc1 | ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1.CN>>COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CNC)=O | [CH3:1][NH2:2].Cl[CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1 | CN.COc1ccccc1NC(=O)c1ccc(CCl)cc1 | CNCc1ccc(C(=O)Nc2ccccc2OC)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(Nc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CNC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloromethyl-N-(2-methoxyphenyl)benzamide (400 mg, 1.45 mmol) was dissolved in dioxane (4 ml) and then mixed with 50% methylamine aqueous solution (4 ml) at room temperature. After 1 hour of stirring at the same temperature, dioxane was removed by evaporation, and the resulting residue was diluted with methylene chlo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HCl | O1CCOCC1 | null | null | CN.COc1ccccc1NC(=O)c1ccc(CCl)cc1>O1CCOCC1>CNCc1ccc(C(=O)Nc2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-15921a54043f4c95b9921819784b62d3 | BrCC1OCCO1.COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1>>COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CCl)cc1 | COC=1C(=CC=CC1)N.C(C)N(CC)CC.[OH-].[Na+].ClCC1=CC=C(C(=O)Cl)C=C1.BrCC1OCCO1>>ClCC1=CC=C(C(=O)N(CC2OCCO2)C2=C(C=CC=C2)OC)C=C1 | Br[CH2:10][CH:11]1[O:12][CH2:13][CH2:14][O:15]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH2:22][Cl:23])[cH:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH:11]1[O:12][CH2:13][CH2:14][O:15]1)[C:16](=[O:17])[c:18]1[cH:19][cH:20][c... | BrCC1OCCO1.COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1 | COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CCl)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 1602204b35b334a4ca067608433ad569a1c2ab239a2838907ec1876fac69c016 | 8b35e8410bcf3c8bdff4698b3ea59db09850817ec720e2e45b797eaef876f90e | O=C(c1ccccc1)N(CC1OCCO1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[C:5]-[#8:6]-1.Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[C:5]-[#8:6]-1)-[c:13](:[c:14]):[c:15])-[c:9](:[c:10]):[c:11] | 47.9 | [{"value": 47.9, "product": "ClCC1=CC=C(C(=O)N(CC2OCCO2)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "ClCC1=CC=C(C(=O)N(CC2OCCO2)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | DAY | In an atmosphere of argon, a mixture consisting of o-anisidine (500 mg, 4.06 mmol), triethylamine (1.6 ml, 11.5 mmol) and 2-bromomethyl-1,3-dioxolan (0.96 ml, 8.18 mmol) was stirred at 80° C. for 4 days, dissolved in methylene chloride (8 ml) and then, with cooling in an ice bath, mixed with 20% sodium hydroxide aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Primary amine | Tertiary amide | null | null | c1ccccc1.C1COCO1.c1ccccc1 | HCl.Br- | C(Cl)Cl | 80 | 96 | BrCC1OCCO1.COc1ccccc1N.O=C(Cl)c1ccc(CCl)cc1>C(Cl)Cl>COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CCl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2d3298a193f4e188fb14350c59014ca | O=C(c1ccc(F)cc1)C1CCNCC1.OCCBr>>O=C(c1ccc(F)cc1)C1CCN(CCO)CC1 | FC1=CC=C(C(=O)C2CCNCC2)C=C1.BrCCO>>FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12][NH:13][CH2:17][CH2:18]1.Br[CH2:14][CH2:15][OH:16]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][OH:16])[CH2:17][CH2:18]1 | O=C(c1ccc(F)cc1)C1CCNCC1.OCCBr | O=C(c1ccc(F)cc1)C1CCN(CCO)CC1 | null | null | C(C)N(CC)CC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(c1ccccc1)C1CCNCC1 | 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] | 78 | [{"value": 78.0, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In an atmosphere of argon, 4-(4-fluorobenzoyl)piperidine (2.07 g, 10 mmol) was dissolved in triethylamine (30 ml) to which was subsequently added dropwise 2-bromoethanol (1.1 ml, 14.7 mmol) at room temperature. After 1 hour of heating under reflux, triethylamine was removed by evaporation, and the resulting residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | C(C)N(CC)CC | null | null | O=C(c1ccc(F)cc1)C1CCNCC1.OCCBr>C(C)N(CC)CC>O=C(c1ccc(F)cc1)C1CCN(CCO)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-761b0c03342a44cd91f901367699772b | O=C(c1ccc(F)cc1)C1CCN(CCO)CC1.O=S(Cl)Cl>>Cl.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1 | FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1.CN(C)C=O.S(=O)(Cl)Cl>>Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O | O[CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][CH:11]([C:3](=[O:2])[c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[CH2:19][CH2:18]1.O=S([Cl:1])[Cl:17]>>[ClH:1].[O:2]=[C:3]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][Cl:17])[CH2:18][CH2:19]1 | O=C(c1ccc(F)cc1)C1CCN(CCO)CC1.O=S(Cl)Cl | Cl.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=C(c1ccccc1)C1CCNCC1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].O=S(-[Cl;H0;D1;+0:4])-[Cl;H0;D1;+0:5]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[Cl;H0;D1;+0:4].[ClH;D0;+0:5] | 96.3 | [{"value": 96.3, "product": "Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | In an atmosphere of dry air, 4-(4-fluorobenzoyl)-1-(2-hydroxyethyl)piperidine (1.96 g, 7.8 mmol) was dissolved in methylene chloride (10 ml) to which, with cooling in an ice bath, were subsequently added dropwise DMF (0.1 ml) and thionyl chloride (2.5 ml, 34.2 mmol). After 7 hours of stirring at room temperature, the s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.C1CC[NH]CC1 | Other | C(Cl)Cl | null | 7 | O=C(c1ccc(F)cc1)C1CCN(CCO)CC1.O=S(Cl)Cl>C(Cl)Cl>Cl.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ff4585334ae4e29b75a677785e6dfac | CCOC(CBr)OCC.O=C(c1ccc(F)cc1)C1CCNCC1>>CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC | FC1=CC=C(C(=O)C2CCNCC2)C=C1.C(C)OC(CBr)OCC.C(C)N(CC)CC>>C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:21][CH2:22][CH3:23].[NH:6]1[CH2:7][CH2:8][CH:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1)[O:2... | CCOC(CBr)OCC.O=C(c1ccc(F)cc1)C1CCNCC1 | CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(c1ccccc1)C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 25 | [{"value": 25.0, "product": "C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.0, "product": "C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(4-Fluorobenzoyl)piperidine (207 mg, 1.0 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added bromoacetoaldehyde diethylacetal (305 mg, 1.5 mmol) and triethylamine (0.5 ml). After 12 hours of heating under reflux, the solvent was removed by evaporation, and the resulting residue was purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HBr | C(Cl)Cl | null | null | CCOC(CBr)OCC.O=C(c1ccc(F)cc1)C1CCNCC1>C(Cl)Cl>CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-237b1973c5eb44b6bba25ecc54bfc269 | CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC.COc1ccccc1N>>COc1ccccc1NCCN1CCC(C(=O)c2ccc(F)cc2)CC1 | C(#N)[BH3-].[Na+].C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC.Cl.C([O-])([O-])=O.[Na+].[Na+].COC=1C(=CC=CC1)N>>FC1=CC=C(C(=O)C2CCN(CC2)CCNC2=C(C=CC=C2)OC)C=C1 | CCO[CH:10](OCC)[CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[c... | CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC.COc1ccccc1N | COc1ccccc1NCCN1CCC(C(=O)c2ccc(F)cc2)CC1 | null | null | C1CCOC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | 195459a3df13b9f6a3ac9e95fa34f12215bcc175daa16d824f73efce6c4f3922 | c773bdbff86697879727fed205b521624504ab38dc50d7c1d7232a521281a6bb | O=C(c1ccccc1)C1CCN(CCNc2ccccc2)CC1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[C:2]-[#7:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 66.2 | [{"value": 66.2, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCNC2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCNC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine (81 mg, 0.25 mmol) was dissolved in THF (3 ml) to which was subsequently added 10% hydrochloric acid (2 ml) at room temperature. After 1 hour of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | C1CCOC1.CO | null | 1 | CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC.COc1ccccc1N>C1CCOC1.CO>COc1ccccc1NCCN1CCC(C(=O)c2ccc(F)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ded3b8d2ed540a4b76f3f398d06c312 | BrCCOC1CCCCO1.COc1cccc(C(=O)Nc2ccccc2OC)c1>>COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1 | COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1.[H-].[Na+].O1C(CCCC1)OCCBr>>O1C(CCCC1)OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC | Br[CH2:11][CH2:12][O:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[O:26][CH3:27])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][O:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH... | BrCCOC1CCCCO1.COc1cccc(C(=O)Nc2ccccc2OC)c1 | COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(c1ccccc1)N(CCOC1CCCCO1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;D1;H0:4]=[C:5](-[c:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:5](=[O;D1;H0:4])-[c:6])-[c:8](:[c:9]):[c:10] | 67 | [{"value": 67.0, "product": "O1C(CCCC1)OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "O1C(CCCC1)OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In an atmosphere of argon, 3-methoxy-N-(2-methoxyphenyl) benzamide (500 mg, 1.94 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (85 mg, 60%, 2.13 mmol) at room temperature, followed by 20 minutes of stirring. After additional 5 minutes of stirring under an ultrasonic irradiation condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1.C1CCOCC1.c1ccccc1 | HBr | CN(C)C=O | null | 0.333333 | BrCCOC1CCCCO1.COc1cccc(C(=O)Nc2ccccc2OC)c1>CN(C)C=O>COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cbf5b75d0c184a8f8de856d128b7a42f | COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1>>COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1 | COC=1C=C(C(=O)N(CCOC2OCCCC2)C2=C(C=CC=C2)OC)C=CC1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C([O-])(O)=O.[Na+]>>OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC | C1CCC([O:13][CH2:12][CH2:11][N:10]([C:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22]2)=[O:9])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][CH3:21])OC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][OH:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][CH3:21])[cH:22]1 | COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1 | COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1 | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | O=C(Nc1ccccc1)c1ccccc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3] | 86.8 | [{"value": 86.8, "product": "OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide (501 mg, 1.30 mmol) was dissolved in methanol (4 ml) to which was subsequently added a catalytically effective amount of p-toluenesulfonic acid monohydrate and stirred for 3 hours at room temperature. The reaction solution was mixed with saturated s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1ccccc1.c1ccccc1 | HO- | CO | null | 3 | COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1>CO>COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18e129f85987443abf273cc4ec32d571 | COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1>>COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1 | OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC.C(C)N(CC)CC>>C(=O)CN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][OH:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][CH3:21])[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH:12]=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][CH3:21])[cH:22]1 | COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1 | COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C(Nc1ccccc1)c1ccccc1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-[OH;D1;+0:6]>>[O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH;D2;+0:5]=[O;H0;D1;+0:6] | 65.6 | [{"value": 65.6, "product": "C(=O)CN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "C(=O)CN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In an atmosphere of argon, N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide (339 mg, 1.12 mmol) was dissolved in DMSO (4 ml) to which were subsequently added dropwise triethylamine (0.724 ml, 5.20 mmol) and a DMSO solution (8 ml) of a sulfur trioxide-pyridine complex (844 mg, 5.20 mmol) at room temperature. Af... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | CS(=O)C | null | 0.333333 | COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1>CS(=O)C>COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f48f4894ab44bc5ac2137804fdccac1 | COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>>COc1ccccc1N(CC=O)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | COC1=C(C=CC=C1)N(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)CC2OCCO2.Cl>>C(=O)CN(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)C2=C(C=CC=C2)OC | C1C[O:12][CH:11]([CH2:10][N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([CH2:19][N:20]3[C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[C:29]3=[O:30])[cH:31][cH:32]2)O1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH:11]=[O:12])[C:13](=[O:... | COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | COc1ccccc1N(CC=O)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C(Nc1ccccc1)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH;D3;+0:5]1-O-C-C-[O;H0;D2;+0:6]-1>>[O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH;D2;+0:5]=[O;H0;D1;+0:6] | 73.5 | [{"value": 73.5, "product": "C(=O)CN(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)C2=C(C=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "C(=O)CN(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)C2=C(C=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | N-(2-Methoxyphenyl)-N-(1,3-dioxolan-2-yl)methyl-4-phthalimidomethylbenzamide (450 mg, 0.953 mmol) was dissolved in THF (6 ml) to which was subsequently added 10% hydrochloric acid (4 ml) at room temperature. After 2 hours of stirring at 60° C., the resulting reaction solution was extracted with chloroform and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | 60 | 2 | COc1ccccc1N(CC1OCCO1)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>C1CCOC1>COc1ccccc1N(CC=O)C(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8b481bd661041d298e29f0d4a578067 | COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1.O=C(c1ccc(F)cc1)C1CCNCC1>>COc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)c1 | C(#N)[BH3-].[Na+].C(=O)CN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC.FC1=CC=C(C(=O)C2CCNCC2)C=C1.CC(=O)C>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1 | O=[CH:12][CH2:11][N:10]([C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36]1)=[O:9])[c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[O:34][CH3:35].[NH:13]1[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N... | COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1.O=C(c1ccc(F)cc1)C1CCNCC1 | COc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)c1 | null | null | CCOCC.CO | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | O=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5])-[C:9]-[C:10] | 46.1 | [{"value": 46.1, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)-benzamide (141 mg, 0.473 mmol), and 4-(4-fluorobenzoyl)piperidine (125 mg, 0.60 mmol) were dissolved in methanol (4.5 ml) to which was subsequently added molecular sieve 4A (300 mg) at room temperature. After 1 hour of stirring at the same temperature, sodium cyanoborohydrid... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | CCOCC.CO | null | 0.75 | COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1.O=C(c1ccc(F)cc1)C1CCNCC1>CCOCC.CO>COc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b3fc71d9b19b4a1fa85aa8e5ceb7054c | COc1ccc(S(=O)(=O)N(CCO)c2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCNCC1>>COc1ccc(S(=O)(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | FC1=CC=C(C(=O)C2CCNCC2)C=C1.C(#N)[BH3-].[Na+].C(C)N(CC)CC.[OH-].[Na+].OCCN(S(=O)(=O)C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)OC)C=C1 | O[CH2:12][CH2:11][N:10]([S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]1)(=[O:8])=[O:9])[c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[O:34][CH3:35].[NH:13]1[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8]... | COc1ccc(S(=O)(=O)N(CCO)c2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCNCC1 | COc1ccc(S(=O)(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | null | null | CS(=O)C.CCOCC.CO.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 511913fc601efdcc18555347fcfe0c2354215793b65f509995496ee3f61c9425 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 20.7 | [{"value": 15.4, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In an atmosphere of argon at room temperature, N-hydroxyethyl-4-methoxy-N-(2-methoxyphenyl)benzene sulfonamide (235 mg, 0.697 mmol) was dissolved in DMSO (3 ml) to which were subsequently added dropwise triethylamine (0.48 ml, 3.44 mmol) and sulfur trioxide-pyridine complex (558 mg, 3.44 mmol) which has been dissolved ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | CS(=O)C.CCOCC.CO.CC(=O)C | null | 0.5 | COc1ccc(S(=O)(=O)N(CCO)c2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCNCC1>CS(=O)C.CCOCC.CO.CC(=O)C>COc1ccc(S(=O)(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1362f36b27ab4a15833b7044edb1e473 | COCc1ccc(C(=O)Nc2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1>>COCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | [H-].[Na+].COCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1.Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O.[I-].[Na+]>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)COC)=O)C2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[O:34][CH3:35])[cH:36][cH:37]1.Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=... | COCc1ccc(C(=O)Nc2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1 | COCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[O;D1;H0:4]=[C:5](-[c:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:5](=[O;D1;H0:4])-[c:6])-[c:8](:[c:9]):[c:10] | 54.7 | [{"value": 54.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)COC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)COC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | In an atmosphere of argon, 4-methoxymethyl-N-(2-methoxyphenyl)benzamide (126 mg, 0.464 mmol), 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (157 mg, 0.511 mmol) and sodium iodide (154 mg, 1.02 mmol) were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (40 mg, 60%, 1.0 mmol) at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 0.166667 | COCc1ccc(C(=O)Nc2ccccc2OC)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1>CN(C)C=O>COCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7e6ae5c11c3c403ba17edba9a968e45c | COc1ccccc1NS(=O)(=O)c1ccc(C)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C)cc1 | ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O.COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C.[I-].[Na+].[H-].[Na+]>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C)C2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([CH3:34])[cH:35][cH:36]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([... | COc1ccccc1NS(=O)(=O)c1ccc(C)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[O;D1;H0:4]=[#16:5](=[O;D1;H0:6])(-[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[#16:5](=[O;D1;H0:4])(=[O;D1;H0:6])-[c:7] | 91.5 | [{"value": 91.5, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In an atmosphere of argon, N-(2-methoxyphenyl)-p-toluenesulfonamide (277 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After stirring at the same temperature for 30 minutes and t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 0.5 | COc1ccccc1NS(=O)(=O)c1ccc(C)cc1.O=C(c1ccc(F)cc1)C1CCN(CCCl)CC1>CN(C)C=O>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d1b23c0b5a4476792e51a44f8a8659a | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(COC2CCCCO2)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1 | FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)COC2OCCCC2)C2=C(C=CC=C2)OC)C=C1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C([O-])(O)=O.[Na+]>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1 | C1CCC([O:35][CH2:34][c:33]2[cH:32][cH:31][c:30]([S:27]([N:9]([c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]4[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]4)[CH2:25][CH2:26]3)(=[O:28])=[O:29])[cH:37][cH:36]2)OC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(COC2CCCCO2)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1 | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | [c:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[OH;D1;+0:3]-[C:2]-[c:1] | 100.1 | [{"value": 100.0, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzene sulfonamide (101 mg, 0.165 mmol) was dissolved in methanol (5 ml) to which was subsequently added p-toluenesulfonic acid monohydrate (35 mg, 0.18 mmol) at room temperature. After 2 hour of stirring at the same temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | CO | null | null | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(COC2CCCCO2)cc1>CO>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6642989d69874a4bb62b90deed971d65 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1 | FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([CH2:34][OH:35])[cH:36][cH:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 81.7 | [{"value": 81.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Activated manganese dioxide (870 mg, 10.0 mmol) was suspended in methylene chloride (10 ml), and N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzene sulfonamide (259 mg, 0.492 mmol) dissolved in methylene chloride (3 ml) was added to the suspension. After 30 minutes of stirring at room... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | 0.5 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CO)cc1>[O-2].[O-2].[Mn+4].C(Cl)Cl>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4df58d28e9e34965aa240b18daf00714 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1.NO>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)C1=CCC(=NO)C=C1 | O.FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1.Cl.ON.C([O-])([O-])=O.[Na+].[Na+]>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1 | O=C[c:33]1[cH:32][cH:31][c:30]([S:27]([N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)(=[O:28])=[O:29])[cH:37][cH:36]1.[NH2:34][OH:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1.NO | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)C1=CCC(=NO)C=C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1800e5dd6fdabfd02faf94fedebc1c5dfd0ef9672feec59181be7f48b943c2f9 | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | N=C1C=CC(S(=O)(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2ccccc2)=CC1 | O=C-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[#16:5](-[#7:6])(=[O;D1;H0:7])=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.[NH2;D1;+0:11]-[O;D1;H1:12]>>[#7:6]-[#16:5](=[O;D1;H0:7])(=[O;D1;H0:8])-[C;H0;D3;+0:4]1=[CH;D2;+0:3]-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[O;D1;H1:12])-[CH;D2;+0:10]=[CH;D2;+0:... | 102.7 | [{"value": 100.0, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-formyl-N-(2-methoxyphenyl)benzenesulfonamide (63 mg, 0.12 mmol) and hydroxyamine hydrochloride (9.5 mg, 0.132 mmol) were dissolved in ethanol (2 ml) to which were subsequently added anhydrous sodium carbonate (14 mg, 0.132 mmol) and water (1 ml). After 1.5 hours of stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | c1ccccc1 | C1=CCCC=C1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.C1=CCCC=C1 | HO- | C(C)O | null | 1.5 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1.NO>C(C)O>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)C1=CCC(=NO)C=C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b00834c08920492095e2fbe7b5a3d02d | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(=O)O)cc1.N>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(N)=O)cc1 | CN1CCOCC1.ClC(=O)OCC(C)C.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C2=C(C=CC=C2)OC)S(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=C1.N>>C(N)(=O)C1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O | O[C:34]([c:33]1[cH:32][cH:31][c:30]([S:27]([N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)(=[O:28])=[O:29])[cH:38][cH:37]1)=[O:36].[NH3:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(=O)O)cc1.N | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(N)=O)cc1 | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 50.9 | [{"value": 50.9, "product": "C(N)(=O)C1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "C(N)(=O)C1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 15 | MINUTE | In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 0.25 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(=O)O)cc1.N>C1CCOC1>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C(N)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92d7b0faebcf42cd917c0eec104efa76 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CO)cc1.O=C1CCC(=O)N1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN2C(=O)CCC2=O)cc1 | N(=NC(=O)OCC)C(=O)OCC.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CO)=O)C2=C(C=CC=C2)OC)C=C1.C1(CCC(N1)=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CN2C(CCC2=O)=O)=O)C2=C(C=CC=C2)OC)C=C1 | O[CH2:33][c:32]1[cH:31][cH:30][c:29]([C:27]([N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)=[O:28])[cH:42][cH:41]1.[NH:34]1[C:35](=[O:36])[CH2:37][CH2:38][C:39]1=[O:40]>>[CH3:1][O... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CO)cc1.O=C1CCC(=O)N1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN2C(=O)CCC2=O)cc1 | null | null | C1CCOC1.O | Heteroatom Alkylation and Arylation | Mitsunobu_imide | 903824a0afb8c2e133e09288818f267e150c1b9486232a0ca9327396f16febc9 | 8a66434962da2945c8a8685e3bd4f60c7955241df224c95aa14ead6db9d240f9 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc(CN3C(=O)CCC3=O)cc2)c2ccccc2)CC1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 66.8 | [{"value": 66.8, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CN2C(CCC2=O)=O)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.8, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CN2C(CCC2=O)=O)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 30 | MINUTE | In an atmosphere of argon, N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzamide (54 mg, 0.11 mmol), succinimide (13 mg, 0.132 mmol) and triphenylphosphine (34.6 mg, 0.132 mmol) were dissolved in THF (1 ml) to which was subsequently added dropwise diethyl azodicarboxylate (21 μl, 0.132... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Substituted dicarboximide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | HO- | C1CCOC1.O | null | 0.5 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CO)cc1.O=C1CCC(=O)N1>C1CCOC1.O>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN2C(=O)CCC2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f45ef41d64f43759ade38b0eb4ac1d1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN)cc1 | FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CN2C(C=3C(C2=O)=CC=CC3)=O)C3=C(C=CC=C3)OC)C=C1.O.NN.C([O-])(O)=O.[Na+]>>NCC1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O | O=C1c2ccccc2C(=O)[N:35]1[CH2:34][c:33]1[cH:32][cH:31][c:30]([S:27]([N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)(=[O:28])=[O:29])[cH:37][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN)cc1 | null | null | C(C)(=O)OCC.CO.C1CCOC1 | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(c1ccccc1)C1CCN(CCN(c2ccccc2)S(=O)(=O)c2ccccc2)CC1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3])-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:1]-[C:2]-[c:3] | 76.4 | [{"value": 76.4, "product": "NCC1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "NCC1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide (77 mg, 0.117 mmol) was dissolved in a methanol-THF (3:2) mixture solution (2.5 ml) to which was subsequently added hydrazine hydrate (1 ml) while cooling in an ice bath. After 15 minutes of stirring at the same tempera... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OCC.CO.C1CCOC1 | null | 0.25 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>C(C)(=O)OCC.CO.C1CCOC1>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(CN)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-06bcb6d3c8c846a7a6b2788898b644c4 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc([N+](=O)[O-])cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | [OH-].[Na+].Cl.[Sn].[N+](=O)([O-])C1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1>>NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | O=[N+:33]([O-])[c:32]1[cH:31][cH:30][c:29]([C:27]([N:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)=[O:28])[cH:35][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc([N+](=O)[O-])cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | null | null | C(Cl)(Cl)Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98.3 | [{"value": 97.9, "product": "NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-Nitro-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (264.0 mg, 0.52 mmol) was dissolved in methanol (5 ml) to which were subsequently added concentrated hydrochloric acid (2.0 ml) and tin (powder, 186.0 mg, 1.57 mmol) while cooling in an ice bath. After 1 hour of stirring at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)Cl.CO | null | 1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc([N+](=O)[O-])cc1>C(Cl)(Cl)Cl.CO>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-418d73d6c7d54b44966aa6f680a9e3c2 | CC(=O)OC(C)=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:34]([CH3:35])=[O:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([NH2:33])[cH:37][cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6... | CC(=O)OC(C)=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 84.5 | [{"value": 84.3, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (2.65 g, 5.58 mmol) and acetic anhydride (0.79 ml, 8.37 mmol), the procedure of Inventive Example 94 was repeated to obtain 2.44 g (84.3%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23cc6cf96ac3449ba9386436d694eaeb | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:33]([CH3:34])=[O:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[cH:36][cH:37]2)[cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH... | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 78.3 | [{"value": 78.3, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (1.00 g, 2.10 mmol) and acetic anhydride (0.24 ml, 2.54 mmol), the procedure of Inventive Example 94 was repeated to obtain 851.0 mg (78.3%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7adcc4760c8a42a8978a2bdf56ac6adb | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1 | NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:32]([CH3:33])=[O:34].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]2)[C:25](=[O:26])[c:27]2[cH:28][cH:29][c:30]([NH2:31])[cH:35][cH:36]2)[cH:37][cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:... | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1 | COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 78.7 | [{"value": 78.7, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (556.9 mg, 1.17 mmol) and acetic anhydride (0.13 ml, 1.41 mmol), the procedure of Inventive Example 94 was repeated to obtain 476.8 mg (78.7%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77091d57cc5f408ca23282c7137e6852 | CC(=O)OC(C)=O.COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:35]([CH3:36])=[O:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([N:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[CH2:26][CH2:27]2)[C:28](=[O:29])[c:30]2[cH:31][cH:32][c:33]([NH2:34])[cH:38][cH:39]2)[cH:40]1>>[CH3:1][O:2][c:3]1... | CC(=O)OC(C)=O.COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 71.5 | [{"value": 71.5, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2,5-dimethoxyphenyl)benzamide (170.0 mg, 0.34 mmol) and acetic anhydride (0.16 ml, 1.70 mmol), the procedure of Inventive Example 94 was repeated to obtain 132.0 mg (71.5%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1ccc(OC)c(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c92fd9fd8e544ca88d8b4695eacd281 | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 | NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1 | CC(=O)O[C:34]([CH3:35])=[O:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][c:32]([NH2:33])[cH:37]2)[cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH... | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 84.9 | [{"value": 84.9, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (216.0 mg, 0.45 mmol) and acetic anhydride (0.051 ml, 0.54 mmol), the procedure of Inventive Example 97 was repeated to obtain 197.5 mg (84.9%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-587ef0d326c74c95a3b01efcf8ff42fd | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c(OC)c1>>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c(OC)c1 | NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:32]([CH3:33])=[O:34].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]2)[C:25](=[O:26])[c:27]2[cH:28][cH:29][c:30]([NH2:31])[cH:35][cH:36]2)[c:37]([O:38][CH3:39])[cH:40]1>>[CH3:1][O:2][c:3]1... | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c(OC)c1 | COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c(OC)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 73.6 | [{"value": 73.6, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2,4-dimethoxyphenyl)benzamide (203.4 mg, 0.40 mmol) and acetic anhydride (0.046 ml, 0.49 mmol), the procedure of Inventive Example 94 was repeated to obtain 161.2 mg (73.6%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c(OC)c1>>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47a428a9721e4a74a1f659ae73f83499 | CC(=O)OC(C)=O.Cc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][cH:32][c:33]([CH3:34])[cH:35]2)[cH:36][cH:37]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][... | CC(=O)OC(C)=O.Cc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C)c2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 100.3 | [{"value": 99.9, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methylphenyl)benzamide (285.0 mg, 0.62 mmol) and acetic anhydride (0.071 ml, 0.74 mmol), the procedure of Inventive Example 94 was repeated to obtain 311.8 mg (99.9%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b464a797a3914e7b8c2b1401d223bc36 | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1 | NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8... | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 71 | [{"value": 71.0, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(phenyl)benzamide (503.8 mg, 1.13 mmol) and acetic anhydride (0.128 ml, 1.36 mmol), the procedure of Inventive Example 94 was repeated to obtain 309.9 mg (71.0%) of the title compound in a light brown amorphous form.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51ccabd8e1604910a2824d56424dda2c | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[C:35]([F:36])([F:37])[F:38])[cH:39][cH:40]1>>[CH3:1][C:2](=[O:3])[... | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-trifluoromethylphenyl)benzamide (243.0 mg, 0.474 mmol) and acetic anhydride (0.13 ml, 1.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 265.0 mg quantitative) of the title compound in a colorless amorphous form.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c83589f7df44030bbb9d6f308f640b9 | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38]2)[cH:39][cH:40]1>>[CH3:1][C:2](=[O:3]... | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 101.4 | [{"value": 96.2, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_de... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-trifluoromethylphenyl)benzamide (256.0 mg, 0.474 mmol) and acetic anhydride (0.13 ml, 1.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 267.0 mg (96.2%) of the title compound in a colorless amorphous form.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(C(F)(F)F)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84265045acc04ccbaee0286fe298b5e3 | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][cH:32][n:33][cH:34]2)[cH:35][cH:36]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]... | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 95.6 | [{"value": 95.6, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (150.0 mg, 0.335 mmol) and acetic anhydride (0.038 ml, 0.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 151.0 mg (95.6%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf8e0ae8899349c9bf22fff5e2ff09a3 | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2N)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2NC(C)=O)c1 | NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1 | CC(=O)O[C:35]([CH3:36])=[O:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[NH2:34])[cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6... | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2N)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2NC(C)=O)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:10] | 65.9 | [{"value": 65.9, "product": "C(C)(=O)NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "C(C)(=O)NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 2-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 170.4 mg (65.9%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2N)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccccc2NC(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-151f51647e9c4cf08e2d101eb56a9b8b | CC(=O)OC(C)=O.COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:36]([CH3:37])=[O:38].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[N:11]([CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1)[C:29](=[O:30])[c:31]1[cH:32][cH:33][c:34]([NH2:35])[cH:39][cH:40]1>>[CH3:1][O:2][C:3](=[... | CC(=O)OC(C)=O.COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 96 | [{"value": 96.0, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxycarbonylphenyl)benzamide (291.0 mg, 0.58 mmol) and acetic anhydride (0.11 ml, 1.16 mmol), the procedure of Inventive Example 94 was repeated to obtain 303.0 mg (96.0%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COC(=O)c1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(C)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7176200d5bd54428a5b4fbfba85f6255 | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(C)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(C)c2)c1 | NC1=C(C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C.C(C)(=O)OC(C)=O>>CC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O | CC(=O)O[C:33]([CH3:34])=[O:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[c:36]([CH3:37])[cH:38]2)[cH:39]1>>[CH3:1][O:2][c:3]1[cH:4]... | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(C)c2)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(C)c2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 89.3 | [{"value": 89.3, "product": "CC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "CC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-amino-3-methyl-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(3-methoxyphenyl)benzamide (489.0 mg, 1.00 mmol) and acetic anhydride (0.19 ml, 2.00 mmol), the procedure of Inventive Example 94 was repeated to obtain 474.0 mg (89.3%) of the title compound in a colorless amorphous form.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(C)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(C)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36584347913d4b168f2b2a55aee4be5c | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(OC)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(OC)c2)c1 | NC1=C(C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)OC.C(C)(=O)OC(C)=O>>COC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O | CC(=O)O[C:33]([CH3:34])=[O:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[c:36]([O:37][CH3:38])[cH:39]2)[cH:40]1>>[CH3:1][O:2][c:3]1... | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(OC)c2)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(OC)c2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 77.9 | [{"value": 77.9, "product": "COC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "COC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 4-amino-3-methoxy-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (253.0 mg, 0.50 mmol) and acetic anhydride (0.095 ml, 1.00 mmol), the procedure of inventive Example 94 was repeated to obtain 213.0 mg (77.9%) of the title compound in a yellow amorphous form.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)c(OC)c2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)c(OC)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55df25e97ace40dfac201fefc1def505 | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)cc1 | NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][c:32]([CH3:33])[cH:34][cH:35]2)[cH:36][cH:37]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][... | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 95.4 | [{"value": 95.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methylphenyl)benzamide (452.7 mg, 0.99 mmol) and acetic anhydride (0.122 ml, 1.19 mmol), the procedure of Inventive Example 94 was repeated to obtain 473.6 mg (95.4%) of the title compound in a light brown amorphous form.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-000ec81bde38468aaccb0d7eb96f7ed1 | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1 | NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[cH:36]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:... | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1 | CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 74.1 | [{"value": 73.1, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(phenyl)benzamide (126.4 mg, 0.28 mmol) and acetic anhydride (0.03 ml, 0.32 mmol), the procedure of Inventive Example 94 was repeated to obtain 101.1 mg (73.1%) of the title compound in a colorless powder form.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93813b22fa694a3887830185b57555d2 | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)cc1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)c1 | NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][c:33]([CH3:34])[cH:35][cH:36]2)[cH:37]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][... | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)cc1 | CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 97.8 | [{"value": 97.8, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methylphenyl)benzamide (230.1 mg, 0.50 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 245.2 mg (97.8%) of the title compound in a light yellow amorphous form.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)cc1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93729f963acf4e478d221e694bd673f8 | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1 | NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]2)[cH:37]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH... | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1 | CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 98.3 | [{"value": 98.3, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-fluorophenyl)benzamide (223.2 mg, 0.48 mmol) and acetic anhydride (0.055 ml, 0.58 mmol), the procedure of inventive Example 94 was repeated to obtain 238.6 mg (98.3%) of the title compound in a light yellow amorphous form.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1>>CC(=O)Nc1cccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(F)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fbefbfc24389469fbc5d75415f5a85ff | CC(=O)OC(C)=O.CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1>>CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 | NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1 | CC(=O)O[C:34]([CH3:35])=[O:36].[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][c:32]([NH2:33])[cH:37]2)[cH:38]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH... | CC(=O)OC(C)=O.CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1 | CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 80.7 | [{"value": 80.7, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methylthiophenyl)benzamide (196.7 mg, 0.40 mmol) and acetic anhydride (0.046 ml, 0.48 mmol), the procedure of Inventive Example 94 was repeated to obtain 172.2 mg (80.7%) of the title compound in a light brown amorphous form.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(N)c2)c1>>CSc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2cccc(NC(C)=O)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5d00c7efd69469a9294ced4892fbbb5 | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1C>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)c(C)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][c:32]([CH3:33])[c:34]([CH3:35])[cH:36]2)[cH:37][cH:38]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5... | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1C | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)c(C)c2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99.7 | [{"value": 99.7, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,4-dimethylphenyl)benzamide (333.1 mg, 0.70 mmol) and acetic anhydride (0.080 ml, 0.85 mmol), the procedure of Inventive Example 94 was repeated to obtain 359.9 mg (99.7%) of the title compound in a light brown amorphous form.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1C>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(C)c(C)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ff506a4a1d54dc184980c1e28e6f79c | CC(=O)OC(C)=O.Cc1cc(C)cc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cc(C)cc(C)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][c:31]([CH3:32])[cH:33][c:34]([CH3:35])[cH:36]2)[cH:37][cH:38]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5... | CC(=O)OC(C)=O.Cc1cc(C)cc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cc(C)cc(C)c2)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 86.4 | [{"value": 86.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,5-dimethylphenyl)benzamide (382.8 mg, 0.81 mmol) and acetic anhydride (0.092 ml, 0.99 mmol), the procedure of Inventive Example 94 was repeated to obtain 360.9 mg (86.4%) of the title compound in a light brown amorphous form.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1cc(C)cc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cc(C)cc(C)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-74b6e25d44754f5c854a4d8a691736f2 | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1 | NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:29]2[cH:30][cH:31][c:32]3[c:33]([cH:34]2)[O:35][CH2:36][O:37]3)[cH:38][cH:39]1>>[CH3:1][C:2](=[O:3])[NH:4]... | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccc3c(c2)OCO3)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 79 | [{"value": 79.0, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,4-methylenedioxyphenyl)benzamide (245.0 mg, 0.501 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 210.3 mg (79.0%) of the title compound in a colorless amorphous form.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)OCO2 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc3c(c2)OCO3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0a82c402a4540cdb23dc731ebf18155 | CC(=O)OC(C)=O.COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CC(=O)O[C:34]([CH3:35])=[O:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]2)[C:27](=[O:28])[c:29]2[cH:30][cH:31][c:32]([NH2:33])[cH:37][cH:38]2)[cH:39]1>>[CH3:1][O:2][c:3]1[cH:4][... | CC(=O)OC(C)=O.COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(c1ccccc1)C1CCN(CCCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 96.5 | [{"value": 96.5, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.4, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | Using 4-amino-N-{3-[4-(4-fluorobenzoyl)piperidino]propyl}-N-(3-methoxyphenyl)benzamide (300.0 mg, 0.61 mmol) and acetic anhydride (0.069 ml, 0.73 mmol), the procedure of inventive Example 94 was repeated to obtain 312.6 mg (96.5%) of the title compound in a light yellow amorphous form.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a132e45c439f4a42bf67f0c0f2f018a2 | CCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(CC)(=O)Cl>>C(CC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][cH:33][c:34]([O:35][CH3:36])[cH:37]2)[cH:38][cH:39]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH... | CCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 90.4 | [{"value": 90.4, "product": "C(CC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "C(CC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and propionyl chloride (0.077 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 240.0 mg (90.4%) of the title compound in a yellow amorphous form.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-168d47d80cce4a7580c8b6a29d6630e9 | CCCCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(CCCC)(=O)Cl>>C(CCCC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([C:21](=[O:22])[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[CH2:30][CH2:31]2)[c:32]2[cH:33][cH:34][cH:35][c:36]([O:37][CH3:38])[cH:39]2)[cH:40][cH:41]1>>[CH3:1][CH2:2]... | CCCCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 83 | [{"value": 83.0, "product": "C(CCCC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "C(CCCC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and valeryl chloride (0.071 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 232.0 mg (83.0%) of the title compound in a yellow amorphous form.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCCCC(=O)Cl.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(OC)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c4227a76df44fad9548989db9d0be2a | CC(C)(C)C(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)C(C)(C)C)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C(C)(C)C)(=O)Cl>>C(C(C)(C)C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | Cl[C:34](=[O:35])[C:36]([CH3:37])([CH3:38])[CH3:39].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([NH2:33])[cH:40][cH:41]1>>[CH3:1][O:2][c... | CC(C)(C)C(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)C(C)(C)C)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 91.3 | [{"value": 91.2, "product": "C(C(C)(C)C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "C(C(C)(C)C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (200.0 mg, 0.42 mmol) and pivaloyl chloride (0.062 ml, 0.51 mmol), the procedure of Inventive Example 94 was repeated to obtain 214.6 mg (91.2%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)C(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)C(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19a9af2199cc4a38989a98f4ca8a5f8d | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.CS(=O)(=O)Cl>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNS(C)(=O)=O)cc1 | NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)Cl>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([CH2:33][NH2:34])[cH:39][cH:40]1.Cl[S:35]([CH3:36])(=[O:37])=[O:38]>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.CS(=O)(=O)Cl | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNS(C)(=O)=O)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 57.5 | [{"value": 57.5, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Using 4-aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(2-methoxyphenyl)benzamide (60 mg, 0.123 mmol) and methanesulfonyl chloride (11 μl, 0.142 mmol), the procedure of Inventive Example 94 was repeated to obtain 40 mg (57.5%) of the title compound in a colorless amorphous form.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.CS(=O)(=O)Cl>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNS(C)(=O)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88d2038d3eab43a0904c4e3aa426feda | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NS(C)(=O)=O)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)Cl>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([NH2:33])[cH:38][cH:39]1.Cl[S:34]([CH3:35])(=[O:36])=[O:37]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1.CS(=O)(=O)Cl | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NS(C)(=O)=O)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 50.7 | [{"value": 50.7, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (50.0 mg, 0.11 mmol) and methanesulfonyl chloride (0.025 ml, 0.316 mmol), the procedure of Inventive Example 94 was repeated to obtain 29.5 mg (50.7%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NS(C)(=O)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cec41e879094d138e4a40b6eea1b5f3 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.CS(=O)(=O)Cl>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NS(C)(=O)=O)cc2)c1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)Cl>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=CC(=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[cH:37][cH:38]2)[cH:39]1.Cl[S:33]([CH3:34])(=[O:35])=[O:36]>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.CS(=O)(=O)Cl | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NS(C)(=O)=O)cc2)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 95.4 | [{"value": 95.4, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=CC(=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=CC(=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (475.0mg, 1.00 mmol) and methanesulfonyl chloride (0.12 ml, 1.50 mmol), the procedure of inventive Example 94 was repeated to obtain 527.8 mg (95.4%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.CS(=O)(=O)Cl>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NS(C)(=O)=O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-04858e3c86474c34819e6545cb9b7d88 | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1>>CCOC(=O)NCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.ClC(=O)OCC>>C(C)OC(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([C:21](=[O:22])[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[CH2:30][CH2:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]2[O:38][CH3:39])[cH:40][cH:41]1>>[CH3:1][CH2:2][O:3... | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1 | CCOC(=O)NCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | null | null | null | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 72.7 | [{"value": 72.7, "product": "C(C)OC(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "C(C)OC(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Using 4-aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (60 mg, 0.123 mmol) and ethyl chloroformate (13 μl, 0.136 mmol), the procedure of Inventive Example 94 was repeated to obtain 50 mg (72.7%) of the title compound in a colorless amorphous form.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1>>CCOC(=O)NCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b7f3a20729a4b3bb98778a8a7a4c4e0 | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.ClC(=O)OCC>>C(C)OC(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:20](=[O:21])[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:29][CH2:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]2[O:37][CH3:38])[cH:39][cH:40]1>>[CH3:1][CH2:2][O:3][C:4](=... | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | null | null | null | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 37.5 | [{"value": 37.5, "product": "C(C)OC(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.5, "product": "C(C)OC(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (185.0 mg, 0.39 mmol) and ethyl chloroformate (0.11 ml, 1.17 mmol), the procedure of Inventive Example 94 was repeated to obtain 80.0 mg (37.5%) of the title compound in a colorless oily form.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)Cl.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-455b69c6551746be8a9a9cf6a7695e89 | COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)cc1 | C([O-])(O)=O.[Na+].C(=O)(OC(C)(C)C)N[C@@H](C)C(=O)O.NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CCN=C=NCCCN(C)C.Cl>>C(C)(C)(C)OC(=O)N[C@H](C(=O)NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C | [CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1)[C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([CH2:29][NH2:30])[cH:43][cH:44]1.O[C:31](=[O:32])[C@H:33]([CH3:34])[NH:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:4... | COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O | COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)cc1 | null | null | C(Cl)Cl.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCC(C(=O)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[NH2;D1;+0:13]-[C:14]-[c:15]>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:14]-[c:... | 72.6 | [{"value": 68.9, "product": "C(C)(C)(C)OC(=O)N[C@H](C(=O)NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "C(C)(C)(C)OC(=O)N[C@H](C(=O)NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C", "details": "CALCULATEDPERCENTYIE... | null | null | 4 | HOUR | 4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamide (120 mg, 0.245 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added Boc-L-alanine (46.4 mg, 0.245 mmol) and EDC hydrochloride (52 mg, 0.270 mmol) while cooling in an ice bath. After 4 hours of stirring at t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.O | null | 4 | COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN)cc1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O>C(Cl)Cl.O>COCCN(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CNC(=O)[C@H](C)NC(=O)OC(C)(C)C)cc1 |
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