dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3dfcab9abe244c0b588d9f74b10f0ea | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccccc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)C1 | CN1CC(CCC1)COC1=CC=C(C=C1)N.OC=C1C(NC2=CC=CC=C12)=O>>CN1CC(CCC1)COC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:25][cH:26]2)[CH2:27]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]3[C:16](=[O:17])[NH:1... | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccccc2C1=CO | CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 81.2 | [{"value": 81.0, "product": "CN1CC(CCC1)COC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "CN1CC(CCC1)COC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine (656 mg, 1.2 equiv.) and 3-hydroxymethylene-1,3-dihydro-indol-2-one (400 mg, 2.48 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (732 mg, 81%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccccc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b854c689cfc4eab8446db253b93ae8f | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cccc(F)c2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cccc(F)c43)cc2)C1 | CN1CC(CCC1)COC1=CC=C(C=C1)N.FC1=C2C(C(NC2=CC=C1)=O)=CO>>FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]2)[CH2:28]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[c:25]21>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]3[C:16](=[O:17... | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cccc(F)c2C1=CO | CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cccc(F)c43)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 68 | [{"value": 68.0, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine (590 mg, 1.2 equiv.) and 4-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (400 mg, 2.23 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (576 mg, 68%).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cccc(F)c2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cccc(F)c43)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f938834d6b24fafa5b503cac5b7493d | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(F)cc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(F)cc43)cc2)C1 | Cl.CN1CC(CCC1)COC1=CC=C(C=C1)N.FC=1C=C2C(C(NC2=CC1)=O)=CO.CCN(CC)CC>>FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]2)[CH2:28]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]21>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]3[C:16](=[O:17... | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(F)cc2C1=CO | CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(F)cc43)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 77.2 | [{"value": 77.0, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine hydrochloride (688 mg, 1.2 equiv.) and 5-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (400 mg, 2.23 mmol, 1 equiv.) with the addition of anhydrous Et3N (2.25 equiv.) are reacted to give the named compound as a yell... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(F)cc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(F)cc43)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8edf77683bd44a118525e22bcc9d8585 | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(Cl)cc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(Cl)cc43)cc2)C1 | Cl.CN1CC(CCC1)COC1=CC=C(C=C1)N.ClC=1C=C2C(C(NC2=CC1)=O)=CO.CCN(CC)CC>>ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]2)[CH2:28]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]21>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]3[C:16](=[O:1... | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(Cl)cc2C1=CO | CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(Cl)cc43)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 49.3 | [{"value": 49.0, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.3, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine hydrochloride (158 mg, 1.2 equiv.) and 5-chloro-3-hydroxymethylene-1,3-dihydro-indol-2-one (100 mg, 0.51 mmol, 1 equiv.) with the addition of anhydrous Et3N (2.11 equiv.) are reacted to give the named compound as a yell... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2ccc(Cl)cc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4ccc(Cl)cc43)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05ec8b81a6074b43aabbd230172ff7a9 | C1CCNCC1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>>O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCCCC1 | C([O-])(O)=O.[Na+].[N+](=O)([O-])C1=CC=C(C=C1)CC(=O)O.N1CCCCC1>>[N+](=O)([O-])C1=CC=C(C=C1)CC(=O)N1CCCCC1 | [NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | C1CCNCC1.O=C(O)Cc1ccc([N+](=O)[O-])cc1 | O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCCCC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4])-[C:8]-[C:9] | null | [] | null | null | 8 | HOUR | A room temperature solution of 2.53 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (10 mL) is treated with 2.44 gms. 1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath. The reaction mixture is stirred in the ice bath for 30 minutes then it is allowed to warm to room temperature. Once at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | O1CCCC1 | null | 8 | C1CCNCC1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>O1CCCC1>O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-330fa2a41eb648ecb7a397e4c790b955 | O=[N+]([O-])c1ccc(CCN2CCCCC2)cc1>>Nc1ccc(CCN2CCCCC2)cc1 | [OH-].[Na+].[N+](=O)([O-])C1=CC=C(C=C1)CCN1CCCCC1.C(C)(=O)O.Cl>>N1(CCCCC1)CCC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | O=[N+]([O-])c1ccc(CCN2CCCCC2)cc1 | Nc1ccc(CCN2CCCCC2)cc1 | null | null | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCN2CCCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 58.4 | [{"value": 58.4, "product": "N1(CCCCC1)CCC1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | 1-[2-(4-Nitro-phenyl)-ethyl]-piperidine (0.1178 gms.) is suspended in 4.5 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then immersed in a 65° C. oil bath and treated in dropwise fashion with 9 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl. Over the course of the addition a color chan... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | Other | O | 65 | null | O=[N+]([O-])c1ccc(CCN2CCCCC2)cc1>O>Nc1ccc(CCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e9e9595f9b24f91af653c3b48e4f759 | Cc1cccc2c1CC(=O)N2.Nc1ccc(NCCCN2CCOCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(NCCCN3CCOCC3)cc1)C(=O)N2 | NC1=CC=CC=C1.CC1=C2CC(NC2=CC=C1)=O.N1C(CC2=CC=CC=C12)=O.N1(CCOCC1)CCCNC1=CC=C(C=C1)N>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)NCCCN1CCOCC1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][C:27](=[O:28])[NH:29]2.[NH2:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH2:16][CH2:17][... | Cc1cccc2c1CC(=O)N2.Nc1ccc(NCCCN2CCOCC2)cc1 | Cc1cccc2c1C(=CNc1ccc(NCCCN3CCOCC3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f758903f83045820aa2796f0613e9efc40596c9df4963f018a1708e6363b1ea6 | 7cfdda6b313596a2c22c8b14542e800c357c71515516e6891ac9e4b2afd7445f | O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCOCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[C:12]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The named compound is prepared by substituting 4-methyl-1,3-dihydro-indol-2-one for the 1,3-dihydro-indol-2-one and N-(3-morpholin-4-yl-propyl)-benzene-1,4-diamine (used for the preparation of Example 290) for aniline in the reaction of Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: The named comp... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Enamine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.C1COCC[NH]1.c1ccc2c(c1)CCN2 | Other | null | null | null | Cc1cccc2c1CC(=O)N2.Nc1ccc(NCCCN2CCOCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(NCCCN3CCOCC3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5e621a7e85043d59505c128388c60b9 | O=[N+]([O-])c1ccc(NCCCN2CCOCC2)cc1>>Nc1ccc(NCCCN2CCOCC2)cc1 | N1(CCOCC1)CCCNC1=CC=C(C=C1)[N+](=O)[O-].O.NN>>N1(CCOCC1)CCCNC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:16][cH:17]1 | O=[N+]([O-])c1ccc(NCCCN2CCOCC2)cc1 | Nc1ccc(NCCCN2CCOCC2)cc1 | null | [Ni].[Ni].[Ni] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCCCN2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | null | null | A suspension of 5.00 gms. of (3-morpholin-4-yl-propyl)-(4-nitro-phenyl)-amine in 110 mL of ethanol is heated to 50° C. Once dissolution is achieved 5.49 mL hydrazine monohydrate is added to the solution. A Raney nickel slurry in water is added to the 50° C. solution dropwise, waiting after each addition for the bubblin... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Ni].[Ni].[Ni].O.C(C)O | 50 | null | O=[N+]([O-])c1ccc(NCCCN2CCOCC2)cc1>[Ni].[Ni].[Ni].O.C(C)O>Nc1ccc(NCCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ade4ba1e0e814d698861e81744a019a2 | Nc1ccc(NCCCN2CCOCC2)cc1.Nc1ccccc1.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCOCC2)cc1 | NC1=CC=CC=C1.N1C(CC2=CC=CC=C12)=O.N1(CCOCC1)CCCNC1=CC=C(C=C1)N>>N1(CCOCC1)CCCNC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[cH:27][cH:28]1.Nc1cccc[cH:11]1.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([NH:1... | Nc1ccc(NCCCN2CCOCC2)cc1.Nc1ccccc1.O=C1Cc2ccccc2N1 | O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCOCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 614736c6452b49792a9cfef0c47c1bbcfeb2e44995a7e43fa6798fd677ee6ad9 | cb38d990d25d6ca3504b5351083a2f2348c4fe81dc23cc421367015ba77adfa5 | O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCOCC2)cc1 | N-c1:[cH;D2;+0:1]:c:c:c:c:1.[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Example 298–301 are prepared by substituting the appropriate 6′-fluoro or 5′-chloro or 5′-fluoro or 4′-fluoro substituted 1,3-dihydro-indol-2-one for the 1,3-dihydro-indol-2-one and N-(3-morpholin-4-yl-propyl)-benzene-1,4-diamine (used in the preparation of Example 297) for aniline in the reaction of Example 1.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Enamine | c1ccccc1.c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.C1COCC[NH]1 | Other | null | null | null | Nc1ccc(NCCCN2CCOCC2)cc1.Nc1ccccc1.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd5c83c4a79a42c4a343217e1748191c | CN1CCN(CCCN)CC1.O=[N+]([O-])c1ccc(F)cc1>>CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1 | FC1=CC=C(C=C1)[N+](=O)[O-].CN1CCN(CC1)CCCN.C(C)(C)NC(C)C>>CN1CCN(CC1)CCCNC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH2:9])[CH2:19][CH2:20]1.F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | CN1CCN(CCCN)CC1.O=[N+]([O-])c1ccc(F)cc1 | CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCCN2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | A mixture of 4.44 mL of p-fluoronitrobenzene, 6 gms. 3-(4-methyl-piperazin-1-yl)-propylamine and 6.65 mL N,N-diisopropylamine in 19 mL dioxane is heated at 105° C. for 2 days. The reaction mixture is cooled to room temperature, evaporated to dryness, and recrystallized from hot isopropanol yielding [3-(4-methyl-piperaz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HF | O1CCOCC1 | null | null | CN1CCN(CCCN)CC1.O=[N+]([O-])c1ccc(F)cc1>O1CCOCC1>CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb1ff254344f4230a9d813e4b5254294 | CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1>>CN1CCN(CCCNc2ccc(N)cc2)CC1 | CN1CCN(CC1)CCCNC1=CC=C(C=C1)[N+](=O)[O-].O.NN>>CN1CCN(CC1)CCCNC1=CC=C(C=C1)N | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([NH:9][CH2:8][CH2:7][CH2:6][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:18][CH2:17]2)[cH:16][cH:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1 | CN1CCN(CCCNc2ccc(N)cc2)CC1 | null | [Ni].[Ni].[Ni] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCCCN2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | null | null | A suspension of 0.1385 gms. of [3-(4-methyl-piperazin-1-yl)-propyl]-(4-nitro-phenyl)-amine in 3 mL of ethanol is heated to 50° C. Once dissolution is achieved 0.144 mL hydrazine monohydrate is addded to the solution. A Raney nickel slurry in water is added to the 50° C. solution dropwise, waiting after each addition fo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Ni].[Ni].[Ni].O.C(C)O | 50 | null | CN1CCN(CCCNc2ccc([N+](=O)[O-])cc2)CC1>[Ni].[Ni].[Ni].O.C(C)O>CN1CCN(CCCNc2ccc(N)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c6fcb32e13c4d3a9d0af936d845a880 | CN1CCN(CCCNc2ccc(N)cc2)CC1.Cc1cccc2c1CC(=O)N2>>Cc1cccc2c1C(=CNc1ccc(NCCCN3CCN(C)CC3)cc1)C(=O)N2 | NC1=CC=CC=C1.CC1=C2CC(NC2=CC=C1)=O.N1C(CC2=CC=CC=C12)=O.CN1CCN(CC1)CCCNC1=CC=C(C=C1)N>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)NCCCN1CCN(CC1)C | [NH2:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]2)[cH:26][cH:27]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][C:28](=[O:29])[NH:30]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH2:16... | CN1CCN(CCCNc2ccc(N)cc2)CC1.Cc1cccc2c1CC(=O)N2 | Cc1cccc2c1C(=CNc1ccc(NCCCN3CCN(C)CC3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f758903f83045820aa2796f0613e9efc40596c9df4963f018a1708e6363b1ea6 | 7cfdda6b313596a2c22c8b14542e800c357c71515516e6891ac9e4b2afd7445f | O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[C:12]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The named compound is prepared by substituting 4-methyl-1,3-dihydro-indol-2-one for the 1,3-dihydro-indol-2-one and N-[3-(4-methyl-piperazin-1-yl)-propyl]-benzene-1,4-diamine (used for the preparation of Example 302) for aniline in the reaction of Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: The... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Enamine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2c(c1)CCN2 | Other | null | null | null | CN1CCN(CCCNc2ccc(N)cc2)CC1.Cc1cccc2c1CC(=O)N2>>Cc1cccc2c1C(=CNc1ccc(NCCCN3CCN(C)CC3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0fe886e64964a629a4f35c8f12e3ce0 | CN1CCN(CCCNc2ccc(N)cc2)CC1.O=C1Cc2ccc(F)cc2N1>>CN1CCN(CCCNc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)CC1 | NC1=CC=CC=C1.FC1=CC=C2CC(NC2=C1)=O.N1C(CC2=CC=CC=C12)=O.CN1CCN(CC1)CCCNC1=CC=C(C=C1)N>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)NCCCN1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:27][cH:28]2)[CH2:29][CH2:30]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:... | CN1CCN(CCCNc2ccc(N)cc2)CC1.O=C1Cc2ccc(F)cc2N1 | CN1CCN(CCCNc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f758903f83045820aa2796f0613e9efc40596c9df4963f018a1708e6363b1ea6 | 7cfdda6b313596a2c22c8b14542e800c357c71515516e6891ac9e4b2afd7445f | O=C1Nc2ccccc2C1=CNc1ccc(NCCCN2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[C:12]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The named compound is prepared by substituting 6-fluoro-1,3-dihydro-indol-2-one for the 1,3-dihydro-indol-2-one and N-[3-(4-methyl-piperazin-1-yl)-propyl]-benzene-1,4-diamine (used for the preparation of Example 302) for aniline in the reaction of Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: The... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Enamine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCN2 | Other | null | null | null | CN1CCN(CCCNc2ccc(N)cc2)CC1.O=C1Cc2ccc(F)cc2N1>>CN1CCN(CCCNc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2c660de81c34d78b9d027c0b0d05515 | FC1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCC(F)C2)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.Cl.FC1CNCC1>>FC1CN(CC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:21]1[CH2:22][CH2:23][CH:24]([F:25])[CH2:26]1.I[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:28][cH:27]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:1... | FC1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCC(F)C2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and 3-fluoro-pyrrolidine hydrochloride (226 mg, 1.2 equiv.) (prepared by the method of Giardina, G et al, Synlett (1995), (1), 55–7) are converted to the named compound as a slightly brownish yel... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HI | null | null | null | FC1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCC(F)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f62c3c18b80740c0b6b9fd0839671267 | C1COCCN1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>>O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCOCC1 | [N+](=O)([O-])C1=CC=C(C=C1)CC(=O)O.N1CCOCC1.C([O-])(O)=O.[Na+]>>N1(CCOCC1)C(CC1=CC=C(C=C1)[N+](=O)[O-])=O | [NH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | C1COCCN1.O=C(O)Cc1ccc([N+](=O)[O-])cc1 | O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCOCC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | null | [] | 35 | CELSIUS | 1 | HOUR | A room temperature solution of 1.8839 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (5 mL) is treated with 1.8069 gms. 1′,1′-carbonyl-diimidizole. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 1.0 mL morpholine. The reaction is heated overnight at 35° C. The reaction is then ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | O1CCCC1 | 35 | 1 | C1COCCN1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>O1CCCC1>O=C(Cc1ccc([N+](=O)[O-])cc1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a49e417045f44d7a0b79b55aee7f367 | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1>>O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCOCC1 | [N+](=O)([O-])C1=CC=C(C=C1)CCCC(=O)O.N1CCOCC1.C([O-])(O)=O.[Na+]>>N1(CCOCC1)C(CCCC1=CC=C(C=C1)[N+](=O)[O-])=O | [NH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1)[N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1 | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1 | O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCOCC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCCc1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | null | [] | 35 | CELSIUS | 1 | HOUR | A room temperature solution of 1.1180 gms. 4-(4-nitro-phenyl)-butyric acid in tetrahydrofuran (3 mL) is treated with 0.9052 gms. 1′,1′-carbonyl-diimidizole using an ice bath to attenuate the intensity of the reaction. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 0.5 mL morpholine. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | O1CCCC1 | 35 | 1 | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1>O1CCCC1>O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f164a86a1ed0474fb9451ef746bcacbf | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1>>O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCCCC1 | C([O-])(O)=O.[Na+].[N+](=O)([O-])C1=CC=C(C=C1)CCCC(=O)O.N1CCOCC1>>[N+](=O)([O-])C1=CC=C(C=C1)CCCC(=O)N1CCCCC1 | O1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1.O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1)[N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1 | O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCCCC1 | null | null | O1CCCC1 | Acylation | OtherReaction | a96d25d999a7e3c312b77c7e0e3a251b11b05f4e7f9892abbe6806618e604717 | face37508b08df202202ccc41ac58b51abeb084067a6e34d8ef463ce96851537 | O=C(CCCc1ccccc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].O1-[CH2;D2;+0:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[CH2;D2;+0:9]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7]1-[C:6]-[CH2;D2;+0:5]-[C:10]-[CH2;D2;+0:9]-[C:8]-1 | null | [] | 35 | CELSIUS | null | null | A room temperature solution of 1.1220 gms. 4-(4-nitro-phenyl)-butyric acid in tetrahydrofuran (3 mL) is treated with 0.8978 gms. 1′,1′-carbonyl-diimidizole using an ice bath to attenuate the intensity of the reaction. The reaction mixture is stirred for 30 minutes in the ice bath and 30 minutes at room temperature. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Secondary amine | Tertiary amide | C1COCCN1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | O1CCCC1 | 35 | null | C1COCCN1.O=C(O)CCCc1ccc([N+](=O)[O-])cc1>O1CCCC1>O=C(CCCc1ccc([N+](=O)[O-])cc1)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fe46712cd1942958efdafa5a636c66d | CC(C)(C)OC(=O)Nc1ccccc1N.N#Cc1ccc(C(=O)O)cn1>>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1 | C(=O)(OC(C)(C)C)NC1=C(C=CC=C1)N.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(#N)C1=NC=C(C(=O)O)C=C1.CN1CCOCC1.ClC(=O)OCC(C)C>>C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1C=NC(=CC1)C#N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH2:15].O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22]#[N:23])[n:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:2... | CC(C)(C)OC(=O)Nc1ccccc1N.N#Cc1ccc(C(=O)O)cn1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 78.3 | [{"value": 78.3, "product": "C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1C=NC(=CC1)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | To a solution of 444 mg (3.0 mmol) 6-cyano-nicotinic acid and 354 mg (3.5 mmol) N-methylmorpholine in 7 ml DMF at −20° C. was added 450 mg (3.3 mmol) isobutyl chloroformate. The reaction mixture was warmed to 5° C., and 625 mg (3.0 mmol) mono-boc-ortho-phenylenediamine was added. The reaction mixture was warmed to rt o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C)C=O | 5 | null | CC(C)(C)OC(=O)Nc1ccccc1N.N#Cc1ccc(C(=O)O)cn1>CN(C)C=O>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d0d19c1f38d4ac39a2931cfcb53fdfb | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1>>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)nc1 | C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1C=NC(=CC1)C#N)=O.C1CCOC1>>C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1C=NC(=CC1)CN)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22]#[N:23])[n:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21](... | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)nc1 | null | [Pd] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(Nc1ccccc1)c1cccnc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 87.2 | [{"value": 87.2, "product": "C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1C=NC(=CC1)CN)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | In a flask, 2920 mg (8.72 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester and 1000 mg Pd (10% on carbon) were placed under nitrogen and 10 ml THF and 120 ml methanol were added. The starting material was hydrogenated under atmospheric pressure and at rt for 3.5 h. The catalyst was fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccncc1 | null | [Pd].CO | null | 3.5 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C#N)nc1>[Pd].CO>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b17ff0364e5a47e0aa4d2f4b50d032a6 | C=CCN(CC=C)Cc1ccc(C(=O)OC)s1>>C=CCN(CC=C)Cc1ccc(C(=O)O)s1 | COC(=O)C=1SC(=CC1)CN(CC=C)CC=C.[OH-].[K+]>>C(C=C)N(CC=C)CC1=CC=C(S1)C(=O)O | C[O:15][C:13]([c:12]1[cH:11][cH:10][c:9]([CH2:8][N:4]([CH2:3][CH:2]=[CH2:1])[CH2:5][CH:6]=[CH2:7])[s:16]1)=[O:14]>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[s:16]1 | C=CCN(CC=C)Cc1ccc(C(=O)OC)s1 | C=CCN(CC=C)Cc1ccc(C(=O)O)s1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccsc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 95.3 | [{"value": 95.3, "product": "C(C=C)N(CC=C)CC1=CC=C(S1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | To a solution of 4.5 g (17.9 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid methyl ester in 45 ml methanol were added to 17.9 ml of a 1 N aqueous solution of KOH (17.9 mmol). The reaction mixture was stirred at 50° C. for 16 h and 1 h at reflux. The solvent was evaporated, 20 ml water was added to the residue a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1 | Other | CO | 50 | 1 | C=CCN(CC=C)Cc1ccc(C(=O)OC)s1>CO>C=CCN(CC=C)Cc1ccc(C(=O)O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8e9914bc2ed46f08901e363f3b422c0 | C=CCN(CC=C)Cc1ccc(C(=O)O)s1.CC(C)(C)OC(=O)Nc1ccccc1N>>C=CCN(CC=C)Cc1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | C(=O)(OC(C)(C)C)NC1=C(C=CC=C1)N.C(C=C)N(CC=C)CC1=CC=C(S1)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CN(CC=C)CC=C)=O | O[C:13]([c:12]1[cH:11][cH:10][c:9]([CH2:8][N:4]([CH2:3][CH:2]=[CH2:1])[CH2:5][CH:6]=[CH2:7])[s:30]1)=[O:14].[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])... | C=CCN(CC=C)Cc1ccc(C(=O)O)s1.CC(C)(C)OC(=O)Nc1ccccc1N | C=CCN(CC=C)Cc1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 84.3 | [{"value": 84.3, "product": "C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CN(CC=C)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 2.70 g (11.38 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid in 50 ml THF was added 2.03 g (12.51 mmol) carbonyldiimidazol. After 45 min at rt, 2.48 g (11.95 mmol) mono-boc-ortho-phenylenediamine were added to the reaction mixture, and it was stirred for 3 h at rt. The solvent was evaporated an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | null | 0.75 | C=CCN(CC=C)Cc1ccc(C(=O)O)s1.CC(C)(C)OC(=O)Nc1ccccc1N>C1CCOC1>C=CCN(CC=C)Cc1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fde35acb794e44f89d09261016546ce8 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.CCC(C)CC(=O)O>>CCC(C)CC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 | CC(CC(=O)O)CC.C(=O)(N1C=NC=C1)N1C=NC=C1.FC(C(=O)O)(F)F.C(=O)(O)[O-].[Na+].C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CN)=O>>NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CNC(CC(CC)C)=O | CC(C)(C)OC(=O)[NH:23][c:22]1[c:17]([NH:16][C:14]([c:13]2[cH:12][cH:11][c:10]([CH2:9][NH2:8])[s:24]2)=[O:15])[cH:18][cH:19][cH:20][cH:21]1.O[C:6]([CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4])=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:... | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.CCC(C)CC(=O)O | CCC(C)CC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 | null | null | C1CCOC1 | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(Nc1ccccc1)c1cccs1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#16;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12]>>[#16;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12].[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 59.4 | [{"value": 59.4, "product": "NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CNC(CC(CC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 33.43 mg (0.288 mmol) 3-methylpentanoic acid in 1 ml THF were added 46.67 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 3 h at rt. 1.7 m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | null | 3 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.CCC(C)CC(=O)O>C1CCOC1>CCC(C)CC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e05e980ae8ac4510ba2589fcb4989b89 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.O=C(n1ccnc1)n1ccnc1>>C#CCNC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 | C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CN)=O.FC(C(=O)O)(F)F.C(=O)(O)[O-].[Na+]>>NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)CNC(=O)NCC#C | C[C:2](C)(O[C:5](=[O:6])[NH:22][c:21]1[c:16]([NH:15][C:13]([c:12]2[cH:11][cH:10][c:9]([CH2:8][NH2:7])[s:23]2)=[O:14])[cH:17][cH:18][cH:19][cH:20]1)[CH3:1].O=C(n1ccnc1)n1cc[n:4][cH:3]1>>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20]... | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.O=C(n1ccnc1)n1ccnc1 | C#CCNC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 | null | null | C1CCOC1 | Acylation | OtherReaction | 196c848380cb989baef99af6daf345ce72cf1e7cc10cef1e65e85edd91b8e7f6 | 0f36a742e3b3789f6d9b6dd0e635f3401096f12ad61afd9387b414e7c3f77b3a | O=C(Nc1ccccc1)c1cccs1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8].[#16;a:9]:[c:10]-[C:11]-[NH2;D1;+0:12].O=C(-n1:[cH;D2;+0:13]:[n;H0;D2;+0:14]:c:c:1)-n1:c:c:n:c:1>>[#16;a:9]:[c:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:14]-[CH2;D2;+0:13]-[C;H0;D2;+0:1]#[CH;D1;+0:... | null | [] | null | null | 1 | HOUR | To a solution of 15.8 mg (0.288 mmol) in 1 ml THF were added 46.7 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 1 h at rt. 1.7 ml trifluoroacetic acid we... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine.Boc | Urea.Primary amine.Alkyne | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(CN)s1.O=C(n1ccnc1)n1ccnc1>C1CCOC1>C#CCNC(=O)NCc1ccc(C(=O)Nc2ccccc2N)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f049805b02c647ba9683e13a05b400db | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc([N+](=O)[O-])c1CBr>>CCOC(=O)C(Cc1c(OC)cccc1[N+](=O)[O-])(NC(C)=O)C(=O)OCC | COC1=C(CBr)C(=CC=C1)[N+](=O)[O-].[Na].C(C)(=O)NC(C(=O)OCC)C(=O)OCC>>C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)CC1=C(C=CC=C1[N+](=O)[O-])OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:19][C:20]([CH3:21])=[O:22])[C:23](=[O:24])[O:25][CH2:26][CH3:27].Br[CH2:7][c:8]1[c:9]([O:10][CH3:11])[cH:12][cH:13][cH:14][c:15]1[N+:16](=[O:17])[O-:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][c:8]1[c:9]([O:10][CH3:11])[cH:12][cH:13][cH:14][c:15]1[N+:16](=[O:17])[O-:18]... | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc([N+](=O)[O-])c1CBr | CCOC(=O)C(Cc1c(OC)cccc1[N+](=O)[O-])(NC(C)=O)C(=O)OCC | null | null | O1CCCC1.C(C)O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[#7:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[#7:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14](=[O;D1;H0:15])-[#8... | 80.8 | [{"value": 80.8, "product": "C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)CC1=C(C=CC=C1[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Sodium metal (1.15 g) was dissolved in absolute ethanol (500 mL), and to the resulting solution was added diethyl 2-acetylaminomalonate (9.1 g). After 15 min at room temperature, a solution of 2-methoxy-6-nitrobenzyl bromide (J. Med. Chem. 1977, 20, 190–196) (8.6 g) in tetrahydrofuran (25 mL) was added over 2 min. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1 | HBr | O1CCCC1.C(C)O | null | 0.25 | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc([N+](=O)[O-])c1CBr>O1CCCC1.C(C)O>CCOC(=O)C(Cc1c(OC)cccc1[N+](=O)[O-])(NC(C)=O)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b8f64453b0740288fbfa5f4cd0e66e6 | CCOC(=O)C1(NNC(C)=O)Cc2c(cccc2OC)NC1=O>>COc1cccc2c1CC(N)C(=O)N2 | C(C)(=O)NNC1(C(NC2=CC=CC(=C2C1)OC)=O)C(=O)OCC.Cl>>Cl.NC1C(NC2=CC=CC(=C2C1)OC)=O | CCOC(=O)[C:10]1([NH:11]NC(C)=O)[CH2:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]2[NH:14][C:12]1=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][CH:10]([NH2:11])[C:12](=[O:13])[NH:14]2 | CCOC(=O)C1(NNC(C)=O)Cc2c(cccc2OC)NC1=O | COc1cccc2c1CC(N)C(=O)N2 | null | null | null | Reduction | OtherReaction | 2c338b3fc2cd663fdeee6d151fc6977eb4ab6d56c1ee0f9a83292028af3cb257 | e1ff1c0fc834910ed4e0ca9feef7d4e05e8e69a52715b51aaad0c2f8843bdde1 | O=C1CCc2ccccc2N1 | C-C-O-C(=O)-[C;H0;D4;+0:1]1(-[NH;D2;+0:2]-N-C(-C)=O)-[C:3]-[c:4]:[c:5]-[#7:6]-[C:7]-1=[O;D1;H0:8]>>[NH2;D1;+0:2]-[CH;D3;+0:1]1-[C:3]-[c:4]:[c:5]-[#7:6]-[C:7]-1=[O;D1;H0:8] | null | [] | null | null | null | null | A mixture of 3-acetamidoamino-3-carboethoxy-5-methoxy-3,4-dihydrocarbostyril (5.7 g) and 6 M aqueous hydrochloric acid (75 mL) was refluxed for 6 h. This mixture was evaporated to a solid which was triturated with acetonitrile. Filtration provided 3-amino-5-methoxy-3,4-dihydrocarbostyril hydrochloride (3.8 g, mp 301–30... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ester | Primary amine | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | HO- | null | null | null | CCOC(=O)C1(NNC(C)=O)Cc2c(cccc2OC)NC1=O>>COc1cccc2c1CC(N)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-882c13e9df2048968dbb8b5b49176140 | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O>>N[C@@H]1Cc2ccccc2NC1=O | C(C)(C)(C)OC(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.Cl>>Cl.N[C@H]1C(NC2=CC=CC=C2C1)=O | CC(C)(C)OC(=O)[NH:2][C@@H:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11][C:12]1=[O:13]>>[NH2:2][C@@H:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11][C:12]1=[O:13] | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O | N[C@@H]1Cc2ccccc2NC1=O | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7] | null | [] | null | null | null | null | (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (178 mg) was dissolved in 4 M hydrogen chloride in 1,4-dioxane solution (10 mL) at 0° C. After 1 h the solution was slowly warmed to room temperature over 2 h. The solvent was evaporated under vacuum, and the residue was twice taken up in toluene (10 mL) and evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCCN2 | HO- | O1CCOCC1 | null | null | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O>O1CCOCC1>N[C@@H]1Cc2ccccc2NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f9378c9da544df4bb857bb8e09642db | N[C@@H]1Cc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | C(C)(C)N(CC)C(C)C.Cl.N[C@H]1C(NC2=CC=CC=C2C1)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O | [NH2:3][C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14].O[C:2](=[O:1])[c:15]1[cH:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]2[nH:24]1>>[O:1]=[C:2]([NH:3][C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:2... | N[C@@H]1Cc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13] | 81.2 | [{"value": 81.2, "product": "ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Alternatively, (R)-3-amino-3,4-dihydrocarbostyril hydrochloride (95 mg) was added to a mixture of tetrahydrofuran (10 mL), 5-chloroindole-2-carboxylic acid (103 mg), 1-hydroxy-7-azabenzotriazole (85 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (120 mg) at room temperature. Diisopropylethylamin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCN2.c1ccc2[nH]ccc2c1 | HO- | C(C)(=O)OCC.O1CCCC1 | null | 2 | N[C@@H]1Cc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>C(C)(=O)OCC.O1CCCC1>O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2512700fc8144e54b4578077e1a943bc | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.C(C)(C)(C)OC(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(NC2=CC=CC=C2C1)=O | [O:1]=[C:2]([NH:3][C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]2[nH:24]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:22][c... | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (prepared in Example 5) by the procedures described for the preparation of (R)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 5) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. HPLC/MS [M+H]+, 340; [... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CCCN2.c1ccc2[nH]ccc2c1 | null | null | null | null | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d12725ce188849a28139487c1b120a88 | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O.COC(=O)CBr>>COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21 | C(C)(C)(C)OC(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.BrCC(=O)OC.C(C)(=O)OCC.C[O-].[Na+]>>C(C)(C)(C)OC(=O)N[C@H]1C(N(C2=CC=CC=C2C1)CC(=O)OC)=O | [NH:6]1[C:7](=[O:8])[C@H:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21.Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@H:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][c:19]2[cH:... | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O.COC(=O)CBr | COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21 | null | null | O.O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 00bdf42034ad419e8a7421c967f14ba303b548b011e99dd40ab321f2309531bf | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1CCc2ccccc2N1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:10](:[c:11]):[c:12] | 72.4 | [{"value": 72.4, "product": "C(C)(C)(C)OC(=O)N[C@H]1C(N(C2=CC=CC=C2C1)CC(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (26 mg), as prepared in Example 5, was dissolved in tetrahydrofuran (5 mL) at room temperature under argon. To the stirring solution was added methyl bromoacetate (31 mg), followed by sodium methoxide (26 mg). The resulting suspension was stirred for 30 min before di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HBr | O.O1CCCC1 | null | null | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O.COC(=O)CBr>O.O1CCCC1>COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78cfe89bac18470c801689497e4e731f | COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21>>COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21 | C(C)(C)(C)OC(=O)N[C@H]1C(N(C2=CC=CC=C2C1)CC(=O)OC)=O.Cl>>Cl.N[C@H]1C(N(C2=CC=CC=C2C1)CC(=O)OC)=O | CC(C)(C)OC(=O)[NH:10][C@H:9]1[C:7](=[O:8])[N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:17]2[c:12]([cH:13][cH:14][cH:15][cH:16]2)[CH2:11]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@H:9]([NH2:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21 | COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10])-[c:11]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6](-[c:11])-[C:4](=[O;D1;H0:5])-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | null | null | (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril (20 mg) was dissolved in 4 M hydrogen chloride in 1,4-dioxane solution (5 mL) at room temperature. After 1 h the solvent was evaporated under vacuum, and the residue was twice taken up in toluene (10 mL) and evaporated under vacuum to provide (R)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCC[NH]2 | HO- | O1CCOCC1 | null | null | COC(=O)CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21>O1CCOCC1>COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c28c8a5e0d064f24bb8eb2c35c7f7138 | COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(C)(C)N(CC)C(C)C.Cl.N[C@H]1C(N(C2=CC=CC=C2C1)CC(=O)OC)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C>>C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | [CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@H:9]([NH2:10])[CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21.O[C:11](=[O:12])[c:13]1[cH:14][c:15]2[cH:16][c:17]([Cl:18])[cH:19][cH:20][c:21]2[nH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@H:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][... | COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#7:11](-[c:12])-[C:13](=[O;D1;H0:14])-[C:15](-[NH2;D1;+0:16])-[C:17]>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#7:11](-[c:12])-[C:13](=[O;D1;H0:14])-[C:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[... | 26.3 | [{"value": 26.3, "product": "C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Alternatively, (R)-3-amino-1-carbomethoxymethyl-3,4-dihydrocarbostyril hydrochloride (19 mg) was added to a mixture of tetrahydrofuran (10 mL), 5-chloroindole-2-carboxylic acid (15 mg), 1-hydroxy-7-azabenzotriazole (12 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (16 mg) at room temperature. D... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HO- | C(C)(=O)OCC.O1CCCC1 | null | 16 | COC(=O)CN1C(=O)[C@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1>C(C)(=O)OCC.O1CCCC1>COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6b32ea6655540abb07919434d96aeb2 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.C(C)(C)(C)OC(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O>>C(=O)(OC)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | [CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@H:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([Cl:18])[cH:19][cH:20][c:21]3[nH:22]2)[CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:... | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (prepared in Example 5) by the procedures described for the preparation of (R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 7) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-813d8b6b01f04099a39edd6df9f74699 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.O.[OH-].[Li+].Cl>>C(=O)(O)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | C[O:3][C:2](=[O:1])[CH2:4][N:5]1[C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]3[nH:21]2)[CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]1[C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[cH... | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | CO.O.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 95.6 | [{"value": 95.6, "product": "C(=O)(O)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 7) (13 mg) was dissolved in a 2:2:1 mixture of tetrahydrofuran, methanol, and water (5 mL). Lithium hydroxide monohydrate (3 mg) was added, and the resulting mixture was stirred at room temperature for 2 h. Addition of 1.0 M aqu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | Other | CO.O.O1CCCC1 | null | 2 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>CO.O.O1CCCC1>O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e27a544e111c468b84bfc09d15cd05db | O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(=O)(O)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.C(=O)(OC)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl>>C(=O)(O)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | [O:1]=[C:2]([OH:3])[CH2:4][N:5]1[C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]3[nH:21]2)[CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]1[C:6](=[O:7])[C@@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[c... | O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (S)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 8) by the procedures described for the preparation of (R)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 9) from (R)-1-carbomethoxymethyl-3-(5-chloroindole... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | O=C(O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-53c7f65f8f8a484284f4f588533f0f5f | O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>O=C(N[C@H]1Cc2ccccc2N(CCO)C1=O)c1cc2cc(Cl)ccc2[nH]1 | C(=O)(O)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.Cl.C(C)(=O)OCC>>OCCN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | O=[C:14]([CH2:13][N:12]1[c:11]2[c:6]([cH:7][cH:8][cH:9][cH:10]2)[CH2:5][C@H:4]([NH:3][C:2](=[O:1])[c:18]2[cH:19][c:20]3[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]3[nH:27]2)[C:16]1=[O:17])[OH:15]>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[N:12]([CH2:13][CH2:14][OH:15])[C:16]1=[O:17])[c:18]1[... | O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | O=C(N[C@H]1Cc2ccccc2N(CCO)C1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | O1CCCC1.B | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]-[#7:4]-[C:3]-[CH2;D2;+0:1]-[O;D1;H1:2] | 19 | [{"value": 19.0, "product": "OCCN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | 3 | HOUR | A mixture of (S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 10) (6 mg) in 1.0 M borane in tetrahydrofuran solution (2 mL) under argon was stirred at 35° C. for 3 h. After cooling to room temperature, 1.0 M aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)CCC[NH]2.c1ccc2[nH]ccc2c1 | Other | O1CCCC1.B | 35 | 3 | O=C(O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>O1CCCC1.B>O=C(N[C@H]1Cc2ccccc2N(CCO)C1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a3dd76371664609a5344ed600f823e0 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N>>NC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(=O)(OC)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.N>>NC(=O)CN1C(=O)[C@@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | CO[C:2](=[O:3])[CH2:4][N:5]1[C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]3[nH:21]2)[CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21.[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17... | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N | NC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | CO.O1CCCC1 | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | 16 | HOUR | (R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 7) (5.6 mg) was dissolved in a mixture of tetrahydrofuran (2 mL) and 2 M ammonia in methanol solution (2 mL). After stirring for 16 h at room temperature, the solvent was evaporated under vacuum and the residue was coevaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HO- | CO.O1CCCC1 | null | 16 | COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N>CO.O1CCCC1>NC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f50d546389dc4eed91959315280729a1 | COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N>>NC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | C(=O)(OC)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl.N>>NC(=O)CN1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | CO[C:2](=[O:3])[CH2:4][N:5]1[C:6](=[O:7])[C@@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]3[nH:21]2)[CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21.[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[C:6](=[O:7])[C@@H:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([Cl:... | COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N | NC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | CO.O1CCCC1 | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | 16 | HOUR | (S)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 8) (5 mg) was dissolved in a mixture of tetrahydrofuran (1 mL) and 2 M ammonia in methanol solution (2 mL). After stirring for 16 h at room temperature, the solvent was evaporated and the residue was coevaporated with methanol (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HO- | CO.O1CCCC1 | null | 16 | COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21.N>CO.O1CCCC1>NC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ac6fa017fd64b0fbef0e360df747472 | CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21>>CN1C(=O)[C@H](N)Cc2ccccc21 | C(C)(C)(C)OC(=O)N[C@H]1C(N(C2=CC=CC=C2C1)C)=O.Cl>>Cl.N[C@H]1C(N(C2=CC=CC=C2C1)C)=O | CC(C)(C)OC(=O)[NH:6][C@H:5]1[C:3](=[O:4])[N:2]([CH3:1])[c:13]2[c:8]([cH:9][cH:10][cH:11][cH:12]2)[CH2:7]1>>[CH3:1][N:2]1[C:3](=[O:4])[C@H:5]([NH2:6])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21 | CN1C(=O)[C@H](N)Cc2ccccc21 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C;D1;H3:7])-[c:8]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6](-[C;D1;H3:7])-[c:8] | null | [] | null | null | null | null | (R)-3-t-butyloxycarbonylamino-1-methyl-3,4-dihydrocarbostyril (20 mg) was dissolved in 4 M hydrogen chloride in 1,4-dioxane solution (5 mL) at room temperature. After 1 h the solvent was evaporated under vacuum, and the residue was twice taken up in toluene (5 mL) and evaporated under vacuum to provide (R)-3-amino-1-me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCC[NH]2 | HO- | O1CCOCC1 | null | null | CN1C(=O)[C@H](NC(=O)OC(C)(C)C)Cc2ccccc21>O1CCOCC1>CN1C(=O)[C@H](N)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9013a076f6747788b58534bb7b45797 | CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(N(C2=CC=CC=C2C1)C)=O.C(C)(C)(C)OC(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(N(C2=CC=CC=C2C1)C)=O | [CH3:1][N:2]1[C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[nH:18]2)[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][N:2]1[C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[nH:18]2)[CH2:19][c:20]2[... | CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (prepared in Example 5) by the procedures described for the preparation of (R)-3-(5-chloroindole-2-carbonylamino)-1-methyl-3,4-dihydrocarbostyril (Example 14) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. HPLC/MS [M+H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5adcca477c254be6a192106fe55a0014 | C=CCN1C(=O)[C@@H](NC(=O)OC(C)(C)C)Cc2ccccc21>>C=CCN1C(=O)[C@@H](N)Cc2ccccc21 | C(C=C)N1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)OC(C)(C)C.Cl>>Cl.C(C=C)N1C(=O)[C@H](CC2=CC=CC=C12)N | CC(C)(C)OC(=O)[NH:8][C@@H:7]1[C:5](=[O:6])[N:4]([CH2:3][CH:2]=[CH2:1])[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[CH2:9]1>>[CH2:1]=[CH:2][CH2:3][N:4]1[C:5](=[O:6])[C@@H:7]([NH2:8])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | C=CCN1C(=O)[C@@H](NC(=O)OC(C)(C)C)Cc2ccccc21 | C=CCN1C(=O)[C@@H](N)Cc2ccccc21 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7]-[C:8]=[C;D1;H2:9])-[c:10]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7]-[C:8]=[C;D1;H2:9])-[c:10] | null | [] | null | null | null | null | (S)-1-allyl-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (9.7 mg) was dissolved in 4 M hydrogen chloride in 1,4-dioxane solution (2 mL) at room temperature, and a white precipitate soon formed. After 30 min the solvent was evaporated under vacuum, and the residue was twice taken up in toluene (5 mL) and evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCC[NH]2 | HO- | O1CCOCC1 | null | null | C=CCN1C(=O)[C@@H](NC(=O)OC(C)(C)C)Cc2ccccc21>O1CCOCC1>C=CCN1C(=O)[C@@H](N)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-516d5b56df98453cafe3dd8cb1f58999 | C=CCN1C(=O)[C@@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>C=CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | Cl.C(C=C)N1C(=O)[C@H](CC2=CC=CC=C12)N.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C.C(C)(C)N(CC)C(C)C>>C(C=C)N1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | [CH2:1]=[CH:2][CH2:3][N:4]1[C:5](=[O:6])[C@@H:7]([NH2:8])[CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.O[C:9](=[O:10])[c:11]1[cH:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]2[nH:20]1>>[CH2:1]=[CH:2][CH2:3][N:4]1[C:5](=[O:6])[C@@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([Cl:16])[cH:17][cH... | C=CCN1C(=O)[C@@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | C=CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13]-[C:14]=[C;D1;H2:15])-[c:16]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13]-[C:14]=[C;D1;H2:15])-[c:16] | 53.7 | [{"value": 53.7, "product": "C(C=C)N1C(=O)[C@H](CC2=CC=CC=C12)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | (S)-1-allyl-3-amino-3,4-dihydrocarbostyril hydrochloride (7.6 mg) was added to a mixture of tetrahydrofuran (4 mL), 5-chloroindole-2-carboxylic acid (6.9 mg), 1-hydroxy-7-azabenzotriazole (5.5 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.7 mg) at room temperature. Diisopropylethylamine (12 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HO- | O1CCCC1 | null | 16 | C=CCN1C(=O)[C@@H](N)Cc2ccccc21.O=C(O)c1cc2cc(Cl)ccc2[nH]1>O1CCCC1>C=CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79c37683c1aa4634b0c0d6974cfb87dd | N#CCBr.O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>>N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | Cl.C[O-].[Na+].ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(NC2=CC=CC=C2C1)=O.BrCC#N>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(N(C2=CC=CC=C2C1)CC#N)=O | Br[CH2:3][C:2]#[N:1].[NH:4]1[C:5](=[O:6])[C@@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]3[nH:20]2)[CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21>>[N:1]#[C:2][CH2:3][N:4]1[C:5](=[O:6])[C@@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([Cl:16])[cH:17][cH:18][... | N#CCBr.O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | O.C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e7b4b186b3651fd15b60671427dc34c5cd6cb02aa0116a7c1fd6c1cf6f406256 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[c:8](:[c:9]):[c:10] | 26.8 | [{"value": 26.8, "product": "ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(N(C2=CC=CC=C2C1)CC#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 4, 13.4 mg) was dissolved in tetrahydrofuran (5 mL) at room temperature under argon with stirring. After cooing to 0° C., sodium methoxide (4.3 mg) was added, followed 2 h later by bromoacetonitrile (7.2 mg). This was warmed to room temperature over... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HBr | O.C(C)(=O)OCC.O1CCCC1 | null | null | N#CCBr.O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>O.C(C)(=O)OCC.O1CCCC1>N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b00a7ed4fdea484c9fcb5f3121dbfe6d | N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>N#CCN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(N(C2=CC=CC=C2C1)CC#N)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(NC2=CC=CC=C2C1)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NC2=CC=CC=C2C1)=O>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(N(C2=CC=CC=C2C1)CC#N)=O | [N:1]#[C:2][CH2:3][N:4]1[C:5](=[O:6])[C@@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]3[nH:20]2)[CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21>>[N:1]#[C:2][CH2:3][N:4]1[C:5](=[O:6])[C@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]... | N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | N#CCN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (R)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 3) by the procedures described for the preparation of (S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril (Example 17) from (S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril. H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | N#CCN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21>>N#CCN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d639b90ca6dd451282aa8ebb8b743be1 | N[C@H]1COc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | Cl.N[C@H]1COC2=C(NC1=O)C=CC=C2.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C.C(C)(C)N(CC)C(C)C>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1COC2=C(NC1=O)C=CC=C2 | [NH2:3][C@H:4]1[CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14]1=[O:15].O[C:2](=[O:1])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]2[nH:25]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14]1=[O:15])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[c... | N[C@H]1COc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#8:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]>>[#8:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14] | 88.8 | [{"value": 88.8, "product": "ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1COC2=C(NC1=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Alternatively, to a mixture of (S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt (54 mg) (prepared in Itoh, et al., Chem. Pharm. Bull. 1986, 34, 1128–1147), tetrahydrofuran (10 mL), 5-chloroindole-2-carboxylic acid (39 mg), 1-hydroxy-7-azabenzotriazole (31 mg), and 1-[3-(dimethylamino)propyl]-3-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)NCCCO2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | null | N[C@H]1COc2ccccc2NC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>O1CCCC1>O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c264e9779284e15bdd86025c4faf7dd | N[C@H]1COc2ccccc2NC1=O>>N[C@@H]1COc2ccccc2NC1=O | Cl.N[C@H]1COC2=C(NC1=O)C=CC=C2.C(C)(C)(C)OC(=O)N[C@@H](CO)C(=O)O.C(C)(C)(C)OC(=O)N[C@H](CO)C(=O)O>>Cl.N[C@@H]1COC2=C(NC1=O)C=CC=C2 | [NH2:2][C@H:3]1[CH2:4][O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14]>>[NH2:2][C@@H:3]1[CH2:4][O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14] | N[C@H]1COc2ccccc2NC1=O | N[C@@H]1COc2ccccc2NC1=O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCOc2ccccc2N1 | null | null | [] | null | null | null | null | (R)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt was prepared from N-t-butyloxycarbonyl-D-serine by the procedures described in Itoh, et al., Chem. Pharm. Bull. 1986, 34, 1128–1147 for the preparation of (S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt from N-t-butyloxycarbonyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)NCCCO2 | null | null | null | null | N[C@H]1COc2ccccc2NC1=O>>N[C@@H]1COc2ccccc2NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5487c0c5805446b1b2432f0aff196960 | O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1COC2=C(NC1=O)C=CC=C2.Cl.N[C@H]1COC2=C(NC1=O)C=CC=C2.Cl.N[C@@H]1COC2=C(NC1=O)C=CC=C2>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1COC2=C(NC1=O)C=CC=C2 | [O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14]1=[O:15])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]2[nH:25]1>>[O:1]=[C:2]([NH:3][C@@H:4]1[CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14]1=[O:15])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[cH:... | O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@@H]1COc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (R)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt by the procedures described for the preparation of (S)-3-(5-chloroindole-2-carbonylamino)-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Example 20) from (S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride s... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)NCCCO2.c1ccc2[nH]ccc2c1 | null | null | null | null | O=C(N[C@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@@H]1COc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bce1a18b501744319de4def70546e546 | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)OC(C)(C)C>>C[C@@H]1Oc2ccccc2NC(=O)[C@H]1N | C(C)(C)(C)OC(=O)N[C@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C.FC(C(=O)O)(F)F.ClCCl.O1CCCC1>>FC(C(=O)O)(F)F.N[C@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C | CC(C)(C)OC(=O)[NH:14][C@H:13]1[C@H:2]([CH3:1])[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][C@@H:2]1[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11](=[O:12])[C@H:13]1[NH2:14] | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)OC(C)(C)C | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1N | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCOc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[#8:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]>>[#8:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8] | null | [] | null | null | null | null | (2S,3S)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt was prepared from (2S,3S)-3-t-butyloxycarbonylamino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Rob, et al., Bioorg. & Med. Chem. Lett. 1994, 4, 1789–1794) by treatment with a solution of trifluoroacetic acid-dichloromethane-tetr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)NCCCO2 | HO- | null | null | null | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)OC(C)(C)C>>C[C@@H]1Oc2ccccc2NC(=O)[C@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef2594d9793d4786b45c3fc9f7b648ba | C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)OC(C)(C)C>>C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1N | C(C)(C)(C)OC(=O)N[C@@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C.FC(C(=O)O)(F)F.ClCCl.O1CCCC1>>FC(C(=O)O)(F)F.N[C@@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C | CC(C)(C)OC(=O)[NH:14][C@@H:13]1[C@H:2]([CH3:1])[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][C@@H:2]1[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11](=[O:12])[C@@H:13]1[NH2:14] | C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)OC(C)(C)C | C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1N | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCOc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[#8:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]>>[#8:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8] | null | [] | null | null | null | null | (2S,3R)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt was prepared from (2S,3R)-3-t-butyloxycarbonylamino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Robl, et al., Bioorg. & Med. Chem. Lett. 1994, 4, 1789–1794) by treatment with a solution of trifluoroacetic acid-dichloromethane-tet... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)NCCCO2 | HO- | null | null | null | C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)OC(C)(C)C>>C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-659e4f7223dd4a359a81bd1f34cd5b0f | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1>>C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 | ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C.FC(C(=O)O)(F)F.N[C@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C.FC(C(=O)O)(F)F.N[C@@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1[C@@H](OC2=C(NC1=O)C=CC=C2)C | [CH3:1][C@@H:2]1[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11](=[O:12])[C@H:13]1[NH:14][C:15](=[O:16])[c:17]1[cH:18][c:19]2[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]2[nH:26]1>>[CH3:1][C@@H:2]1[O:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11](=[O:12])[C@@H:13]1[NH:14][C:15](=[O:16])[c:17]1[cH:18][c:19]2[cH:... | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 | C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(N[C@@H]1COc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | [] | null | null | null | null | The title compound was prepared from (2S,3R)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt by the procedures described for the preparation of (2S,3S)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Example 22) from (2S,3S)-3-amino-2-methyl-2,3-dihydro-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)NCCCO2.c1ccc2[nH]ccc2c1 | null | null | null | null | C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1>>C[C@@H]1Oc2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4ab1160d8704717bff53901854961c7 | N[C@@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 | C(C)(C)N(CC)C(C)C.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C.Cl.N[C@H]1C(NCC2=C(C1)C=CC=C2)=O>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NCC2=C(C1)C=CC=C2)=O | [NH2:3][C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][NH:13][C:14]1=[O:15].O[C:2](=[O:1])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]2[nH:25]1>>[O:1]=[C:2]([NH:3][C@@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][NH:13][C:14]1=[O:15])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:... | N[C@@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H]1Cc2ccccc2CNC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:13] | 44 | [{"value": 44.0, "product": "ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]1C(NCC2=C(C1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | (R)-4-amino-2, 3,4,5-tetrahydro-2-benzazepin-3 (1H)-one hydrochloride salt (387 mg) (amine free base prepared in U.S. Pat. No. 5,545,735) was added to a mixture of tetrahydrofuran (40 mL), 5-chloroindole-2-carboxylic acid (356 mg), 1-hydroxy-7-azabenzotriazole (272 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCNC2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | 16 | N[C@@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>O1CCCC1>O=C(N[C@@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94d114d92fa5432ab753cd58d55d0023 | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1C#N>>C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN | C(C)(C)(C)OC(=O)N([C@@H](C)C(=O)O)C1=C(C=CC=C1)C#N>>C(C)(C)(C)OC(=O)N([C@@H](C)C(=O)O)C1=C(C=CC=C1)CN | [CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[C:20]#[N:21]>>[CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20][NH2:21] | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1C#N | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN | null | [Ni] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 40 | [{"value": 40.0, "product": "C(C)(C)(C)OC(=O)N([C@@H](C)C(=O)O)C1=C(C=CC=C1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | A mixture of (S)—N-t-butyloxycarbonyl(2-cyanophenyl)alanine (1.0 g), Raney® Nickel (1.0 g), and methanol (20 mL) was hydrogenated in a Parr apparatus at 50 psi for 60 h at room temperature. The catalyst was filtered and rinsed with methanol (20 mL three times). The combined filtrate and rinses were evaporated under vac... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | [Ni].CO | null | 60 | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1C#N>[Ni].CO>C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca029937102741169ab21ba3db64bf5e | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN>>CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O | C(C)(C)(C)OC(=O)N([C@@H](C)C(=O)O)C1=C(C=CC=C1)CN.CN(C=O)C.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C>>C(C)(C)(C)OC(=O)N[C@@H]1C(NCC2=C(C1)C=CC=C2)=O | O[C:19]([C@@H:9]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[CH2:17][NH2:18])[CH3:10])=[O:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][NH:18][C:19]1=[O:20] | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN | CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 5d30c0390c44183b097b5657eb2c4ee943c1eb6c4c46da809f138024ee5031ac | 0db3a89fcba8d0e75060638a126c5d84ec832d585668e18e59a622c723c2f731 | O=C1CCc2ccccc2CN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[CH3;D1;+0:4])-[N;H0;D3;+0:5](-[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;+0:13](:[c:14]:[c:15]):[c:16](-[C:17]-[NH2;D1;+0:18]):[c:19]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:5]-[C:3]1-[CH2;D2... | null | [] | null | null | 1 | HOUR | A mixture of (S)—N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine (353 mg), N,N-dimethylformamide (10 mL), dichloromethane (50 mL), 1-hydroxy-7-azabenzotriazole (252 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (180 mg) was stirred at room temperature for 1 h. The solvent was removed under vac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Primary amine | Carbamic ester.Secondary amide | c1ccccc1 | c1ccc2c(c1)CCCNC2 | c1ccc2c(c1)CCCNC2 | HO- | ClCCl | null | 1 | C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)c1ccccc1CN>ClCCl>CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da942735b7e648a3ac69568f23773259 | CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O>>N[C@H]1Cc2ccccc2CNC1=O | C(C)(C)(C)OC(=O)N[C@@H]1C(NCC2=C(C1)C=CC=C2)=O.Cl>>Cl.N[C@@H]1C(NCC2=C(C1)C=CC=C2)=O | CC(C)(C)OC(=O)[NH:2][C@H:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][NH:12][C:13]1=[O:14]>>[NH2:2][C@H:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][NH:12][C:13]1=[O:14] | CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O | N[C@H]1Cc2ccccc2CNC1=O | null | null | C(C)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCc2ccccc2CN1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | 16 | HOUR | (S)-4-(t-butyloxycarbonylamino)-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one (276 mg) was dissolved in 2 M hydrogen chloride in diethyl ether solution (25 mL) at room temperature. A precipitate slowly formed. After 16 h stirring the solvent was evaporated under vacuum. The residue was twice taken up in toluene (10 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCCNC2 | HO- | C(C)OCC | null | 16 | CC(C)(C)OC(=O)N[C@H]1Cc2ccccc2CNC1=O>C(C)OCC>N[C@H]1Cc2ccccc2CNC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f80ff37dc2a4555bcb5ef06034a0b77 | N[C@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>O=C(N[C@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 | Cl.N[C@@H]1C(NCC2=C(C1)C=CC=C2)=O.ClC=1C=C2C=C(NC2=CC1)C(=O)O.ON1N=NC2=C1N=CC=C2.Cl.CN(CCCN=C=NCC)C.C(C)(C)N(CC)C(C)C>>ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@@H]1C(NCC2=C(C1)C=CC=C2)=O | [NH2:3][C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][NH:13][C:14]1=[O:15].O[C:2](=[O:1])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]2[nH:25]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][NH:13][C:14]1=[O:15])[c:16]1[cH:17][c:18]2[cH:19][c:20]([Cl:21... | N[C@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | O=C(N[C@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H]1Cc2ccccc2CNC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:13] | null | [] | null | null | null | null | A mixture of (S)-4-amino-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one hydrochloride (all of that prepared above), tetrahydrofuran (25 mL), 5-chloroindole-2-carboxylic acid (198 mg), 1-hydroxy-7-azabenzotriazole (150 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (210 mg) was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCNC2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | null | N[C@H]1Cc2ccccc2CNC1=O.O=C(O)c1cc2cc(Cl)ccc2[nH]1>O1CCCC1>O=C(N[C@H]1Cc2ccccc2CNC1=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0855fb1c75354af99d14871d375e7943 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1cccnc1Cl>>CC(C)(C)OC(=O)N[C@@H](COc1ncccc1[N+](=O)[O-])C(=O)O | O.C(C)(C)(C)OC(=O)N[C@@H](CO)C(=O)O.[H-].[Na+].ClC1=NC=CC=C1[N+](=O)[O-]>>C(C)(C)(C)OC(=O)N[C@@H](COC1=NC=CC=C1[N+](=O)[O-])C(=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][OH:11])[C:21](=[O:22])[OH:23].Cl[c:12]1[n:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][O:11][c:12]1[n:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20])[C:21](=... | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1cccnc1Cl | CC(C)(C)OC(=O)N[C@@H](COc1ncccc1[N+](=O)[O-])C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]-[C:8](=[O;D1;H0:7])-[O;D1;H1:9]):[#7;a:2]:[c:3] | 74.5 | [{"value": 74.5, "product": "C(C)(C)(C)OC(=O)N[C@@H](COC1=NC=CC=C1[N+](=O)[O-])C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a stirring solution of N-t-butyloxycarbonyl-L-serine (2.26 g) in N,N-dimethylformamide (15 mL) under argon at −20° C. was slowly added sodium hydride (60% oil dispersion, 0.88 g gross weight). The resulting mixture was warmed to 0° C. for 1 h, then recooled to −20° C. before a solution of 2-chloro-3-nitropyridine (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | 0 | 1 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1cccnc1Cl>CN(C=O)C>CC(C)(C)OC(=O)N[C@@H](COc1ncccc1[N+](=O)[O-])C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b68b01f24c048a9abcf80baf3ff1997 | NC1Cc2ccccc2NC1=O.O=C(O)c1cc2ccccc2[nH]1>>O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | Cl.NC1C(NC2=CC=CC=C2C1)=O.N1C(=CC2=CC=CC=C12)C(=O)O>>N1C(=CC2=CC=CC=C12)C(=O)NC1C(NC2=CC=CC=C2C1)=O | [NH2:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14].O[C:2](=[O:1])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1 | NC1Cc2ccccc2NC1=O.O=C(O)c1cc2ccccc2[nH]1 | O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13] | null | [] | null | null | null | null | The title compound was prepared by the methods of Example 5 using 3-amino-3,4-dihydrocarbostyril hydrochloride in place of (R)-3-amino-3,4-dihydrocarbostyril hydrochloride and indole-2-carboxylic acid in place of 5-chloroindole-2-carboxylic acid. HPLC/MS [M+H]+, 306; [M+Na]+, 328.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCN2.c1ccc2[nH]ccc2c1 | HO- | null | null | null | NC1Cc2ccccc2NC1=O.O=C(O)c1cc2ccccc2[nH]1>>O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61481d47f7f540eabd244280fdc4ba8c | COC(=O)C[C@@H]1c2ccccc2NC(=O)[C@H]1N.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>COC(=O)C[C@H]1c2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 | FC(C(=O)O)(F)F.N[C@@H]1C(NC2=CC=CC=C2[C@H]1CC(=O)OC)=O.Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1N=CC=C2.ClC=1C=C2C=C(NC2=CC1)C(=O)O.C(C)(C)N(CC)C(C)C>>C(=O)(OC)C[C@@H]1[C@H](C(NC2=CC=CC=C12)=O)NC(=O)C=1NC2=CC=C(C=C2C1)Cl | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]1[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14](=[O:15])[C@H:16]1[NH2:17].O[C:18](=[O:19])[c:20]1[cH:21][c:22]2[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]2[nH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]1[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14](=[O:15])[C@@H:16]... | COC(=O)C[C@@H]1c2ccccc2NC(=O)[C@H]1N.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | COC(=O)C[C@H]1c2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | CO.O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13] | 56 | [{"value": 56.0, "product": "C(=O)(OC)C[C@@H]1[C@H](C(NC2=CC=CC=C12)=O)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "C(=O)(OC)C[C@@H]1[C@H](C(NC2=CC=CC=C12)=O)NC(=O)C=1NC2=CC=C(C=C2C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1 mL reaction vessel was charged with trans 3-amino-4-carbomethoxymethyl-3,4-dihydrocarbostyril trifluoroacetic acid salt (13 mg, 0.04 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (9 mg, 0.05 mmol), 1-hydroxy-7-azabenzotriazole (7 mg, 0.05 mmol), 5-chloroindole-2-carboxylic acid (8 mg, 0.04 mm... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCN2.c1ccc2[nH]ccc2c1 | HO- | CO.O.CN(C=O)C | null | null | COC(=O)C[C@@H]1c2ccccc2NC(=O)[C@H]1N.O=C(O)c1cc2cc(Cl)ccc2[nH]1>CO.O.CN(C=O)C>COC(=O)C[C@H]1c2ccccc2NC(=O)[C@@H]1NC(=O)c1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06705e7a1e0948f294c7e03ad98290a8 | COC(=O)[C@H](C)N.O=Cc1ccc(F)cc1>>COC(=O)[C@H](C)NCc1ccc(F)cc1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+].Cl.COC([C@H](C)N)=O.FC1=CC=C(C=O)C=C1.C(C)N(CC)CC>>COC([C@H](C)NCC1=CC=C(C=C1)F)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH2:7].O=[CH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1 | COC(=O)[C@H](C)N.O=Cc1ccc(F)cc1 | COC(=O)[C@H](C)NCc1ccc(F)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "COC([C@H](C)NCC1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (S)-2-amino-propionic acid methyl ester hydrochloride (25 g, 179 mmol) and 4-fluorobenzaldehyde (23 mL, 215 mmol) in 1,2-dichloroethane (200 mL) was added triethylamine (25 mL, 179 mmol). The resulting mixture was stirred for two hours at ambient temperature followed by addition of sodium triacetoxybor... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | ClCCCl | null | 2 | COC(=O)[C@H](C)N.O=Cc1ccc(F)cc1>ClCCCl>COC(=O)[C@H](C)NCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3814d07017d476faad65d26565c6cf8 | COC(=O)[C@H](C)NCc1ccc(F)cc1.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O>>COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C | COC([C@H](C)NCC1=CC=C(C=C1)F)=O.C(C(C)C)OC(=O)Cl.C(C)(C)(C)OC(=O)N[C@@H](C(=O)O)C.CN1CCOCC1>>COC([C@H](C)N(CC1=CC=C(C=C1)F)C([C@@H](C)NC(=O)OC(C)(C)C)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1.O[C:16](=[O:17])[C@@H:18]([CH3:19])[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[C:16](=[O:17... | COC(=O)[C@H](C)NCc1ccc(F)cc1.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O | COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | 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].[C;D1;H3:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17](-[C;D1;H3:18])-[NH;D2;+0:19]-[C:20]-[c:21]>>[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;... | 69.7 | [{"value": 69.7, "product": "COC([C@H](C)N(CC1=CC=C(C=C1)F)C([C@@H](C)NC(=O)OC(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (R)-2-tert-butoxycarbonylamino-propionic acid (37 g, 195 mmol) in dry tetrahydrofuran (250 mL) at 0° C. was added 4-methyl morpholine (21.5 mL, 195 mmol) followed by isobutylchloroformate (25.3 mL, 195 mmol). The reaction was allowed to warm to ambient temperature and stirred for two hours. This was fo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 2 | COC(=O)[C@H](C)NCc1ccc(F)cc1.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O>O1CCCC1>COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c843a15b5d714641a5db49ffbd9018c2 | COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C>>C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O | COC([C@H](C)N(CC1=CC=C(C=C1)F)C([C@@H](C)NC(=O)OC(C)(C)C)=O)=O.FC(C(=O)O)(F)F>>FC1=CC=C(CN2C([C@H](NC([C@@H]2C)=O)C)=O)C=C1 | COC(=O)[C@H:6]([CH3:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1)[C:17]([C@@H:2]([CH3:1])[NH:3][C:4](OC(C)(C)C)=[O:5])=[O:18]>>[CH3:1][C@H:2]1[NH:3][C:4](=[O:5])[C@H:6]([CH3:7])[N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[C:17]1=[O:18] | COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C | C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O | null | null | ClCCl | C-C Coupling | OtherReaction | 39ffc0aec208184cbe5c4ca2a02565c0e43f84f147cd00817fd9f8a86be7f3ec | 068cd5629b3d99840ebb2991cb3eaa14690fdac6ebf4c6b53047fbd6cceb4255 | O=C1CN(Cc2ccccc2)C(=O)CN1 | C-O-C(=O)-[C@H;D3;+0:1](-[C;D1;H3:2])-[#7:3](-[C:4])-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-O-C(-C)(-C)-C>>[C:4]-[#7:3]1-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C@@H;D3;+0:1]-1-[C;D1;H3:2] | 23 | [{"value": 23.0, "product": "FC1=CC=C(CN2C([C@H](NC([C@@H]2C)=O)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (2S)-2-[(2R)-(2-tert-butoxycarbonylamino-propionyl)-(4-fluoro-benzyl)-amino]-propionic acid methyl ester (43 g, 382 mmol) in dichloromethane (120 mL) at 0° C. was added trifluoroacetic acid (60 mL). The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction was cooled... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Secondary amide | null | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccccc1 | HO- | ClCCl | null | 2 | COC(=O)[C@H](C)N(Cc1ccc(F)cc1)C(=O)[C@@H](C)NC(=O)OC(C)(C)C>ClCCl>C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b9d9636867a430cb92018a7cec32039 | C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O>>C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1 | FC1=CC=C(CN2C([C@H](NC([C@@H]2C)=O)C)=O)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>FC1=CC=C(CN2[C@@H](CN[C@H](C2)C)C)C=C1 | O=[C:3]1[C@H:2]([CH3:1])[N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[C:7](=O)[C@@H:5]([CH3:6])[NH:4]1>>[CH3:1][C@@H:2]1[CH2:3][NH:4][C@@H:5]([CH3:6])[CH2:7][N:8]1[CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1 | null | null | O1CCCC1 | Reduction | OtherReaction | 2222693cbc80ef6a16c214c8222fe58dea489881251dfa212831bf000001d833 | 1e111e1677c741c445104f499dde4d06874c64781551b41f18ee18795c631ec3 | c1ccc(CN2CCNCC2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=O)-[#7:6](-[C:7])-[C:8]-1-[C;D1;H3:9]>>[C:7]-[#7:6]1-[CH2;D2;+0:5]-[C:3](-[C;D1;H3:4])-[#7:2]-[CH2;D2;+0:1]-[C:8]-1-[C;D1;H3:9] | 90.6 | [{"value": 90.6, "product": "FC1=CC=C(CN2[C@@H](CN[C@H](C2)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (3R,6S)-1-(4-fluoro-benzyl)-3,6-dimethyl-piperazine-2,5-dione (22 g, 87.9 mmol) in dry tetrahydrofuran (160 mL) at 0° C. was added a solution of lithium aluminum hydride (1M in tetrahydrofuran, 373 mL, 373 mmol) dropwise over 40 minutes. The reaction mixture was then refluxed for 4 hours, cooled to amb... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide | null | C1CNCC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccccc1 | Other | O1CCCC1 | null | null | C[C@H]1NC(=O)[C@H](C)N(Cc2ccc(F)cc2)C1=O>O1CCCC1>C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-60ca7772c831497391bbb6d09424b31d | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.Cc1ccc2c(c1)OC(=O)CC2>>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1 | FC1=CC=C(CN2[C@@H](CN[C@H](C2)C)C)C=C1.CC1=CC=C2CCC(OC2=C1)=O>>FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(C=C(C=C2)C)O)=O)C)C=C1 | [NH:10]1[CH2:11][C@@H:12]([CH3:13])[N:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[CH2:23][C@@H:24]1[CH3:25].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:26]([cH:28]1)[O:27][C:8](=[O:9])[CH2:7][CH2:6]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C:8](=[O:9])[N:10]2[CH2:11][C@H:12]([CH3:13])[N:14]([CH2:15][c:... | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.Cc1ccc2c(c1)OC(=O)CC2 | Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | dc21ff2b157e54c9886fd241d9fd249bb6a60abdcf01f136b737377190871de0 | f44eeb513838e5dc505e102b5199fe85d83755bec10694d688dc5fa8c8eea5db | O=C(CCc1ccccc1)N1CCN(Cc2ccccc2)CC1 | [C;D1;H3:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1.[O;D1;H0:8]=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[c:12]:[c:13](:[c:14])-[O;H0;D2;+0:15]-1>>[C;D1;H3:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[N;H0;D3;+0:7]-1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[C:10]-[C:11]-[c:12]:[c:13](-[OH;D1;+0:15]):[c:14] | 79 | [{"value": 79.0, "product": "FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(C=C(C=C2)C)O)=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2R,5S)-1-(4-fluoro-benzyl)-2,5-dimethyl-piperazine (0.25 g, 1.12 mmol) in toluene (10 mL) was added 7-methyl-chroman-2-one (0.25 g, 1.54 mmol) and the resulting solution was heated to reflux for 48 hours. The reaction was cooled, concentrated in vacuo and purified via chromatography on silica gel to g... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide.Aromatic alcohol | C1CNCC[NH]1.c1ccc2c(c1)CCCO2 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.Cc1ccc2c(c1)OC(=O)CC2>C1(=CC=CC=C1)C>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f8f1f63cfdc4540b5a25b5d637eae2a | COC(=O)CBr.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1>>COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | COC(CBr)=O.FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(C=C(C=C2)C)O)=O)C)C=C1.[H-].[Na+]>>COC(COC1=C(C=CC(=C1)C)CCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][cH:12][c:13]1[CH2:14][CH2:15][C:16](=[O:17])[N:18]1[CH2:19][C@H:20]([CH3:21])[N:22]([CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][C@H:32]1[CH3:33]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][cH... | COC(=O)CBr.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1 | COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(CCc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 103.8 | [{"value": 103.8, "product": "COC(COC1=C(C=CC(=C1)C)CCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-(2-hydroxy-4-methyl-phenyl)-propan-1-one, (0.15 g, 0.38 mmol) in tetrahydrofuran (2 mL) at 0° C. was added sodium hydride (0.023 g, 0.57 mmol). The reaction was stirred for 5 minutes, then bromoacetic acid methyl ester (0.043 mL, 0.45 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | O1CCCC1 | null | 0.083333 | COC(=O)CBr.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(O)c1>O1CCCC1>COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87154cd5bc314ab29bbd3e6f8b4b4c8f | COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1 | COC(COC1=C(C=CC(=C1)C)CCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.O1CCCC1.CO.O.[OH-].[Li+]>>FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(OCC(=O)O)C=C(C=C2)C)=O)C)C=C1 | C[O:31][C:29]([CH2:28][O:27][c:26]1[c:5]([CH2:6][CH2:7][C:8](=[O:9])[N:10]2[CH2:11][C@H:12]([CH3:13])[N:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][C@H:24]2[CH3:25])[cH:4][cH:3][c:2]([CH3:1])[cH:32]1)=[O:30]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C:8](=[O:9])[N:10]2[CH2:11][C@H:12]([... | COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1 | null | null | O.Cl | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CCc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 90.4 | [{"value": 90.4, "product": "FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(OCC(=O)O)C=C(C=C2)C)=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (2-{3-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic acid methyl ester (0.18 g, 0.40 mmol) in 2:2:1 tetrahydrofuran:methanol:water (5 mL) was added lithium hydroxide hydrate (0.026 g, 0.62 mmol) and the reaction was stirred at ambient temperature for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | O.Cl | null | 2 | COC(=O)COc1cc(C)ccc1CCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>O.Cl>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c1427aeb6c74cd89a227305147d78b4 | CS(N)(=O)=O.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1>>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)NS(C)(=O)=O)c1 | FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(OCC(=O)O)C=C(C=C2)C)=O)C)C=C1.Cl.CN(CCCN=C=NCC)C.CS(=O)(=O)N.C(C)N(CC)CC>>FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(OCC(=O)NS(=O)(=O)C)C=C(C=C2)C)=O)C)C=C1 | [NH2:31][S:32]([CH3:33])(=[O:34])=[O:35].O[C:29]([CH2:28][O:27][c:26]1[c:5]([CH2:6][CH2:7][C:8](=[O:9])[N:10]2[CH2:11][C@H:12]([CH3:13])[N:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][C@H:24]2[CH3:25])[cH:4][cH:3][c:2]([CH3:1])[cH:36]1)=[O:30]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C:... | CS(N)(=O)=O.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1 | Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)NS(C)(=O)=O)c1 | null | CN(C1=CC=NC=C1)C | ClCCl.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(CCc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[#16:6](-[NH2;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[#16:6](-[C;D1;H3:5])(=[O;D1;H0:8])=[O;D1;H0:9] | 80.2 | [{"value": 80.2, "product": "FC1=CC=C(CN2C[C@H](N(C[C@@H]2C)C(CCC2=C(OCC(=O)NS(=O)(=O)C)C=C(C=C2)C)=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of (2-{3-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic acid (0.052 g, 0.12 mmol) in methylene chloride (1 mL) was added 4-dimethylaminopyridine (0.022 g, 0.18 mmol), (3-(dimethylamino)propyl)ethyl carbodiimide hydrochloride (0.032 g, 0.17 mmol), methanesu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.C(Cl)Cl | null | 18 | CS(N)(=O)=O.Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)O)c1>CN(C1=CC=NC=C1)C.ClCCl.C(Cl)Cl>Cc1ccc(CCC(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(OCC(=O)NS(C)(=O)=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b437499df33d48f784286683f8fd74db | COc1cc(Cl)ccc1O.O=C(O)CCl>>COc1cc(Cl)ccc1OCC(=O)O | Cl.[OH-].[Na+].ClC1=CC(=C(C=C1)O)OC.ClCC(=O)O>>ClC1=CC(=C(OCC(=O)O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[OH:10].Cl[CH2:11][C:12](=[O:13])[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][C:12](=[O:13])[OH:14] | COc1cc(Cl)ccc1O.O=C(O)CCl | COc1cc(Cl)ccc1OCC(=O)O | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 120 | [{"value": 120.0, "product": "ClC1=CC(=C(OCC(=O)O)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3 | HOUR | To a solution of sodium hydroxide (6.6 g, 160 mmol) in water (45 mL) was added 4-chloro-2-methoxy-phenol (2.0 mL, 16 mmol) and chloroacetic acid (7.7 g, 81 mmol). The resulting mixture was heated to 95° C. and stirred for three hours. The reaction was allowed to cool to ambient temperature and slowly acidified with con... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | O | 95 | 3 | COc1cc(Cl)ccc1O.O=C(O)CCl>O>COc1cc(Cl)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a62f0d2dcbcb40f2a0c77212a8c65747 | COc1cc(Cl)ccc1OCC(=O)O>>O=C(O)COc1ccc(Cl)cc1O | [Br-].ClC1=CC(=C(OCC(=O)O)C=C1)OC>>ClC1=CC(=C(OCC(=O)O)C=C1)O | C[O:13][c:12]1[c:6]([O:5][CH2:4][C:2](=[O:1])[OH:3])[cH:7][cH:8][c:9]([Cl:10])[cH:11]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[OH:13] | COc1cc(Cl)ccc1OCC(=O)O | O=C(O)COc1ccc(Cl)cc1O | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 48% aqueous hyrdrogen bromide (20 mL) was added (4-chloro-2-methoxy-phenoxy)-acetic acid (2.1 g, 9.7 mmol). The resulting mixture was heated to reflux overnight. The mixture was cooled to ambient temperature, diluted with water and extracted with diethyl ether. The organic layer was dried over magnesiu... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | O | null | null | COc1cc(Cl)ccc1OCC(=O)O>O>O=C(O)COc1ccc(Cl)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fa15cbc844647a681a1b88e23376cc0 | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C1COc2ccc(Cl)cc2O1>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O | ClC=1C=CC2=C(OC(CO2)=O)C1.FC1=CC=C(CN2[C@@H](CN[C@H](C2)C)C)C=C1>>ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)O | [CH3:1][C@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@H:13]([CH3:14])[CH2:15][NH:16]1.[C:17]1(=[O:18])[CH2:19][O:20][c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]2[O:28]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15][N:1... | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C1COc2ccc(Cl)cc2O1 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 6c0900bd46f51c9090197774b1f18e79f46c457766aa8aebe292b16c1b938f4f | f44eeb513838e5dc505e102b5199fe85d83755bec10694d688dc5fa8c8eea5db | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | [C;D1;H3:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1.[O;D1;H0:8]=[C;H0;D3;+0:9]1-[C:10]-[#8:11]-[c:12]:[c:13](:[c:14])-[O;H0;D2;+0:15]-1>>[C;D1;H3:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[N;H0;D3;+0:7]-1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[C:10]-[#8:11]-[c:12]:[c:13](-[OH;D1;+0:15]):[c:14] | 63.3 | [{"value": 63.3, "product": "ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | To a solution of 7-chloro-benzo[1,4]dioxin-2-one (0.48 g, 2.6 mmol) in toluene (5 mL) was added 1-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazine (0.59 g, 2.6 mmol). The resulting mixture was heated to 95° C. overnight. The reaction was cooled to ambient temperature and concentrated in vacuo. Chromatography on silica... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide.Aromatic alcohol | C1CNCC[NH]1.c1ccc2c(c1)OCCO2 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | 95 | null | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C1COc2ccc(Cl)cc2O1>C1(=CC=CC=C1)C>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-828f525a56584702a50c7b8b62725b8b | COC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O>>COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)O.COC(CBr)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>COC(COC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]1[O:14][CH2:15][C:16](=[O:17])[N:18]1[CH2:19][C@H:20]([CH3:21])[N:22]([CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][C@H:32]1[CH3:33]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12]... | COC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O | COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 169.8 | [{"value": 169.8, "product": "COC(COC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.30 g, 0.75 mmol) and bromo-acetic acid methyl ester (0.14 mL, 1.5 mmol) in dioxane (3 mL) was added cesium carbonate (0.50 g, 1.5 mmol). The resulting mixture was stirred at ambient temperature overni... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | O1CCOCC1 | null | 8 | COC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O>O1CCOCC1>COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ad60219dd484f4eafc9f52d082067ec | COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O | Cl.COC(COC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.O.[OH-].[Li+]>>ClC=1C=CC(=C(OCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | C[O:32][C:30]([CH2:29][O:28][c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1)=[O:31]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)... | COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O | null | null | CO.O.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 74.8 | [{"value": 74.8, "product": "ClC=1C=CC(=C(OCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-acetic acid methyl ester (0.21 g, 0.46 mmol) in methanol (2 mL), tetrahydrofuran (2 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.039 g, 0.93 mmol). The resulting mixture was stirred at amb... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | CO.O.O1CCCC1 | null | 3 | COC(=O)COc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>CO.O.O1CCCC1>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f44ef485b6494d718fea161cc4781aaa | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)NS(C)(=O)=O | ClC=1C=CC(=C(OCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.Cl.CN(CCCN=C=NCC)C.CS(=O)(=O)N.C(C)N(CC)CC>>ClC=1C=CC(=C(OCC(=O)NS(=O)(=O)C)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | [NH2:32][S:33]([CH3:34])(=[O:35])=[O:36].O[C:30]([CH2:29][O:28][c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1)=[O:31]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7]... | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)NS(C)(=O)=O | null | CN(C1=CC=NC=C1)C | ClCCl.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[#16:6](-[NH2;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[#16:6](-[C;D1;H3:5])(=[O;D1;H0:8])=[O;D1;H0:9] | null | [] | null | null | 3 | DAY | To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-acetic acid (0.051 g, 0.10 mmol) in methylene chloride (1 mL) was added 4-dimethylaminopyridine (0.022 g, 0.18 mmol), (3-(dimethylamino)propyl)ethyl carbodiimide hydrochloride (0.033 g, 0.17 mmol), methanesu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.C(Cl)Cl | null | 72 | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)O>CN(C1=CC=NC=C1)C.ClCCl.C(Cl)Cl>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1OCC(=O)NS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b2b8380db7e41eda5472024bba50d5f | CCOC(=O)[C@H](C)O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O>>CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OC([C@H](C)O)=O.C(C)OC(=O)N=NC(=O)OCC>>C(C)OC(C(C)OC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | O[C@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[OH:8][c:9]1[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18](=[O:19])[N:20]1[CH2:21][C@H:22]([CH3:23])[N:24]([CH2:25][c:26]2[cH:27][cH:28][c:29]([F:30])[cH:31][cH:32]2)[CH2:33][C@H:34]1[CH3:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[O:8][c:9]1[c... | CCOC(=O)[C@H](C)O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O | CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | dcfcc873dea6ee5e165c0ecd29b721f7fe5378b92b644a66f7b493dd677cb7f9 | 23ac5fc1d8cc7460c5f165241138db5f1d60f846b59bf6c4b239ddd29d58ddda | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 85.5 | [{"value": 85.5, "product": "C(C)OC(C(C)OC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.076 g, 0.18 mmol), triphenylphosphine (0.076 g, 0.29 mmol) and (2S)-2-hydroxy-propionic acid ethyl ester (0.036 g, 0.31 mmol) in tetrahydrofuran (1 mL) was added diethyl-azodicarboxylate (0.049 g, 0.2... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O1CCCC1 | null | 8 | CCOC(=O)[C@H](C)O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1O>O1CCCC1>CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1df5b5df44fb43f082eaff3a52802315 | CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>>CC(Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)C(=O)O | Cl.C(C)OC(C(C)OC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.O.[OH-].[Li+]>>ClC=1C=CC(=C(OC(C(=O)O)C)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | CC[O:33][C:31]([CH:2]([CH3:1])[O:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][C:13](=[O:14])[N:15]1[CH2:16][C@H:17]([CH3:18])[N:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]2)[CH2:28][C@H:29]1[CH3:30])=[O:32]>>[CH3:1][CH:2]([O:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][... | CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | CC(Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)C(=O)O | null | null | CO.O.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 91.9 | [{"value": 91.9, "product": "ClC=1C=CC(=C(OC(C(=O)O)C)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-propionic acid ethyl ester (0.075 g, 0.15 mmol) in methanol (0.4 mL), tetrahydrofuran (0.4 mL) and water (0.2 mL) was added lithium hydroxide monohydrate (0.010 g, 0.24 mmol). The resulting mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | CO.O.O1CCCC1 | null | 3 | CCOC(=O)C(C)Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>CO.O.O1CCCC1>CC(Oc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44dafea2b06842acb7dacd01a2391aa6 | CCO.O=C(O)CCC(=O)c1cc(Cl)ccc1O>>CCOC(=O)CCC(=O)c1cc(Cl)ccc1O | ClC=1C=CC(=C(C1)C(CCC(=O)O)=O)O.Cl.C(C)O>>C(C)OC(CCC(=O)C1=C(C=CC(=C1)Cl)O)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[OH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[OH:17] | CCO.O=C(O)CCC(=O)c1cc(Cl)ccc1O | CCOC(=O)CCC(=O)c1cc(Cl)ccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6].[C;D1;H3:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | null | null | A solution of 4-(5-chloro-2-hydroxy-phenyl)-4-oxo-butyric acid (0.25 g, 1.09 mmol) in ethanol (10 mL) saturated with hydrogen chloride (g) was stirred at ambient temperature for 12 hours. The reaction was concentrated in vacuo, dissolved in diethyl ether and washed with saturated aqueous sodium bicarbonate. The organic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)CCC(=O)c1cc(Cl)ccc1O>>CCOC(=O)CCC(=O)c1cc(Cl)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe8e31829e854627b42103dff1a859eb | CCOC(=O)CCC(=O)c1cc(Cl)ccc1O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl>>CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.C(C)OC(CCC(=O)C1=C(C=CC(=C1)Cl)O)=O.C1CNC2=NCCCN2C1>>C(C)OC(CCC(=O)C1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[OH:17].Cl[CH2:18][C:19](=[O:20])[N:21]1[CH2:22][C@H:23]([CH3:24])[N:25]([CH2:26][c:27]2[cH:28][cH:29][c:30]([F:31])[cH:32][cH:33]2)[CH2:34][C@H:35]1[CH3:36]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8](... | CCOC(=O)CCC(=O)c1cc(Cl)ccc1O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl | CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[O;D1;H0:7]=[C:8]-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:9]-[C:8]=[O;D1;H0:7])-[C:6] | 45 | [{"value": 45.0, "product": "C(C)OC(CCC(=O)C1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.11 g, 0.36 mmol), 4-(5-chloro-2-hydroxy-phenyl)-4-oxo-butyric acid ethyl ester (0.11 g, 0.43 mmol) and 1,5,7-triazabicyclo[4,4,0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (0.21 g, 0.54 mmol) in acetonitrile (1.8 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)#N | null | 12 | CCOC(=O)CCC(=O)c1cc(Cl)ccc1O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl>C(C)#N>CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a03833925d5e4fcc95b698c04ab760a1 | CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C(=O)CCC(=O)O | C(C)OC(CCC(=O)C1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.O1CCCC1.CO.O.[OH-].[Li+]>>ClC=1C=CC(=C(C1)C(CCC(=O)O)=O)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | CC[O:34][C:32]([CH2:31][CH2:30][C:28]([c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1)=[O:29])=[O:33]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10... | CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C(=O)CCC(=O)O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 91.7 | [{"value": 91.7, "product": "ClC=1C=CC(=C(C1)C(CCC(=O)O)=O)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyric acid ethyl ester (0.082 g, 0.16 mmol) in 2:2:1 tetrahydrofuran:methanol:water(1.5 mL) was added lithium hydroxide monohydrate (0.34 g, 0.79 mmol). The resulting solution was stirred 12 hours a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | O | null | 12 | CCOC(=O)CCC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>O>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C(=O)CCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47c853a443844d0ebba44d6152144a8d | C[C@@H]1CNCCN1.Fc1ccc(CCl)cc1>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1 | C[C@H]1NCCNC1.FC1=CC=C(CCl)C=C1.C(O)([O-])=O.[Na+]>>FC1=CC=C(CN2C[C@H](NCC2)C)C=C1 | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:13][CH2:14][NH:15]1.Cl[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1 | C[C@@H]1CNCCN1.Fc1ccc(CCl)cc1 | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f302e0798768754bbc60184db743cc667f2eb421e32357dcb3b8d027a535a203 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 53.3 | [{"value": 53.3, "product": "FC1=CC=C(CN2C[C@H](NCC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2R)-2-methyl-piperizine (4.5 g, 45 mmol) in ethanol (80 mL) was added 4-fluorobenzyl chloride (5.38 mL, 45.0 mmol) and sodium hydrogen carbonate (11.3 g, 135 mmol). The reaction was refluxed overnight, cooled and concentrated. The remaining residue was diluted with dichloromethane and washed with wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1CNCC[NH]1 | C1CNCC[NH]1.c1ccccc1 | HCl | C(C)O | null | null | C[C@@H]1CNCCN1.Fc1ccc(CCl)cc1>C(C)O>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03d958e6728f4420bdfbc1d54303f87c | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1.O=C(Cl)CCl>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl | ClCC(=O)Cl.FC1=CC=C(CN2C[C@H](NCC2)C)C=C1.C(C)N(CC)CC>>ClCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1.Cl[C:16](=[O:17])[CH2:18][Cl:19]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[CH2:18][Cl:19] | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1.O=C(Cl)CCl | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 6dd420fad17fb719b6bd840e8952a8d7b2fb24721f86f8b8f9c697a36eb97ec3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(CN2CCNCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C;D1;H3:5]-[C:6]1-[C:7]-[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:5]-[C:6]1-[C:7]-[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4] | null | [] | 0 | CELSIUS | 2 | HOUR | To a solution of (3R)-1-(4-fluoro-benzyl)-3-methyl-piperazine (3 g, 14.4 mmol) in dichloromethane (40 mL) was added triethylamine (2.0 mL, 14.4 mmol). The reaction was cooled to 0° C. and chloroacetyl chloride was added (1.1 mL, 14.4 mmol). The reaction was allowed to warm to ambient temperature and stirred for 2 hours... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | ClCCl | 0 | 2 | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1.O=C(Cl)CCl>ClCCl>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12b92824c8e24178912e292742904661 | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | ClCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C.ClC1=CC(=C(C=C1)O)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>ClC1=CC(=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-] | Cl[CH2:18][C:16]([N:15]1[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14]1)=[O:17].[OH:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]1[N+:27](=[O:28])[O-:29]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][N:15]... | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | 94.8 | [{"value": 94.8, "product": "ClC1=CC(=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.40 g, 1.4 mmol) in 2-butanone (14 mL) was added 4-chloro-2-nitro-phenol (0.25 g, 1.4 mmol), potassium carbonate (0.39 g, 2.8 mmol) and potassium iodide (233 mg, 1.4 mmol). The reaction was refluxed overnight, cooled and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | CC(CC)=O | null | null | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O>CC(CC)=O>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72a368a4f648413cbbab05cee7b6819b | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N | ClC1=CC(=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-].[H][H]>>NC1=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl | O=[N+:27]([O-])[c:26]1[c:20]([O:19][CH2:18][C:16]([N:15]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[CH2:13][CH2:14]2)=[O:17])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[... | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N | null | [Pt](=O)=O | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 82.4 | [{"value": 82.4, "product": "NC1=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.55 g, 1.3 mmol) in ethanol (25 mL) was added platinum dioxide on carbon (0.50 g, 5% on carbon). The reaction was subject to 35 psi hydrogen gas for 20 minutes. The reaction was then filtered through celite and... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | [Pt](=O)=O.C(C)O | null | null | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]>[Pt](=O)=O.C(C)O>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cfd19eb5d2bc4c8bbfbf484c02e6d7bb | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1 | NC1=C(OCC(=O)N2[C@@H](CN(CC2)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl.N1=CC=CC=C1.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C1=CC=C(C=C1)OC(NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O | [CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[CH2:18][O:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]1[NH2:27].Cl[C:28](=[O:29])[O:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:... | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1 | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccccc1OCC(=O)N1CCN(Cc2ccccc2)CC1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#8:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 99.7 | [{"value": 99.7, "product": "[N+](=O)([O-])C1=CC=C(C=C1)OC(NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.14 g, 0.36 mmol) in dichloromethane (5 mL) was added pyridine (0.032 mL, 0.39 mmol) and 4-nitrophenyl chloroformate (0.079 g, 0.39 mmol). The reaction was stirred at ambient temperature for one hour and concen... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 1 | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1N.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>ClCCl>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f71fd0844e740eab34efa62eff663d6 | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1>>COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C | [N+](=O)([O-])C1=CC=C(C=C1)OC(NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O.Cl.COC(CCN)=O.C(C)N(CC)CC>>COC(CCNC(=O)NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH2:7].O=[N+]([O-])c1ccc(O[C:8](=[O:9])[NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[O:18][CH2:19][C:20](=[O:21])[N:22]2[CH2:23][CH2:24][N:25]([CH2:26][c:27]3[cH:28][cH:29][c:30]([F:31])[cH:32][cH:33]3)[CH2:34][C@H:35]2[CH3:36])cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH... | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1 | COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C | null | null | CO | Acylation | OtherReaction | dd3b9a4695237168f6d34c716b0d8ecc0b7dab5f3656c298943f9410474c8d9b | 5fa2a2a7e6cfabf5985397b87c657557cf5ccf660b3e3b63891b8b721891cd49 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4]):c:c:1.[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 80 | [{"value": 80.0, "product": "COC(CCNC(=O)NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-carbamic acid 4-nitro-phenyl ester (0.10 g, 0.18 mmol) in methanol was added β-alanine methyl ester hydrochloride (0.038 g, 0.27 mmol) and triethylamine (0.038 mL, 0.27 mmol). The reaction was stirred at ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Primary amine | Urea | c1ccccc1 | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CO | null | 8 | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)Oc1ccc([N+](=O)[O-])cc1>CO>COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f75693f6867e4644b7b4bb511c63c3fc | COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C>>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)NCCC(=O)O | COC(CCNC(=O)NC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C)=O.O.[OH-].[Li+]>>ClC=1C=CC(=C(C1)NC(NCCC(=O)O)=O)OCC(=O)N1[C@@H](CN(CC1)CC1=CC=C(C=C1)F)C | C[O:35][C:33]([CH2:32][CH2:31][NH:30][C:28]([NH:27][c:26]1[c:20]([O:19][CH2:18][C:16]([N:15]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[CH2:13][CH2:14]2)=[O:17])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1)=[O:29])=[O:34]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:... | COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C | C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)NCCC(=O)O | null | null | CO.O.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of 3-[3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-ureido]-propionic acid methyl ester (0.057 g, 0.11 mmol) in tetrahydrofuran (3 mL), methanol (3 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.023 g, 0.55 mmol). The reaction was stirred at amb... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | CO.O.O1CCCC1 | null | 8 | COC(=O)CCNC(=O)Nc1cc(Cl)ccc1OCC(=O)N1CCN(Cc2ccc(F)cc2)C[C@H]1C>CO.O.O1CCCC1>C[C@@H]1CN(Cc2ccc(F)cc2)CCN1C(=O)COc1ccc(Cl)cc1NC(=O)NCCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-560be2081f054067815e1cc2c2faf8c2 | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C(Cl)CCl>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl | ClCC(=O)Cl.FC1=CC=C(CN2[C@@H](CN[C@H](C2)C)C)C=C1.C(C)N(CC)CC>>ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | [CH3:1][C@@H:2]1[CH2:3][NH:16][C@@H:13]([CH3:14])[CH2:15][N:4]1[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.Cl[C:17](=[O:18])[CH2:19][Cl:20]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15][N:16]1[C:17](=[O:18])[CH2:19][Cl:20] | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C(Cl)CCl | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 949c19544298d3876f7b0458b2280abace43b4774b9d92cfdfa0edf7e77056ba | 33bbcee2d30fd19070312c9da89cbcd21bc5c4bdf302b8e5117d0cbfbe912965 | c1ccc(CN2CCNCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C;D1;H3:5]-[C@H;D3;+0:6]1-[CH2;D2;+0:7]-[N;H0;D3;+0:8](-[C:9]-[c:10])-[C@H;D3;+0:11](-[C;D1;H3:12])-[CH2;D2;+0:13]-[NH;D2;+0:14]-1>>[C;D1;H3:5]-[C@H;D3;+0:6]1-[CH2;D2;+0:7]-[N;H0;D3;+0:14](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[C@H;D3;+0:11](-[C;D1;H3:12])... | 84.9 | [{"value": 84.9, "product": "ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (2R,5S)-1-(4-fluoro-benzyl)-2,5-dimethyl-piperazine (2.5 g, 11.2 mmol) in dry dichloromethane (11 mL) at 0° C. was added triethylamine (1.57 mL, 11.2 mmol) followed by chloroacetyl chloride (0.86 mL, 11.2 mmol). The resulting reaction mixture was stirred for 30 minutes. The reaction was then filtered t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine.Tertiary amine | Tertiary amide.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | ClCCl | null | 0.5 | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1.O=C(Cl)CCl>ClCCl>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25061445411d408e8604d629580259c9 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.[N+](=O)([O-])C1=C(C=CC(=C1)Cl)O.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-] | Cl[CH2:19][C:17]([N:16]1[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15]1)=[O:18].[OH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[N+:28](=[O:29])[O-:30]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | null | null | CC(CC)=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | 92.5 | [{"value": 92.5, "product": "ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (1.0 g, 3.35 mmol) in butanone (35 mL) was added 2-nitro-4-chlorophenol (0.64 g, 3.69 mmol), potassium carbonate (0.93 g, 6.7mmol) and potassium iodide (0.56 g, 3.35 mmol). The reaction mixture was heated at reflux overnight.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | CC(CC)=O.O | null | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=[N+]([O-])c1cc(Cl)ccc1O>CC(CC)=O.O>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2050dd585794dadb81d98c2170cc5a9 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N | ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)[N+](=O)[O-].[H][H]>>NC1=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl | O=[N+:28]([O-])[c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[C... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N | null | [Pt] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 69.3 | [{"value": 69.3, "product": "NC1=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (2.2 g, 5.05 mmol) in ethanol (50 mL) in a par bottle was added 5% platinum on carbon (2.2 g). The reaction mixture was subjected to hydrogen gas (35 psi) for 30 minutes. The reaction mixture was filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | [Pt].C(C)O | null | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]>[Pt].C(C)O>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51ce9bb9875247e18ea225cd6ad21a82 | CCOC(=O)CS(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1NS(=O)(=O)CC(=O)O | O.[OH-].[Li+].NC1=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl.C([O-])([O-])=O.[K+].[K+].C(C)OC(CS(=O)(=O)Cl)=O.CN(C)C1=NC=CC=C1>>ClC=1C=CC(=C(C1)NS(=O)(=O)CC(=O)O)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | CC[O:35][C:33]([CH2:32][S:29](Cl)(=[O:30])=[O:31])=[O:34].[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15][N:16]1[C:17](=[O:18])[CH2:19][O:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[NH2:28]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c... | CCOC(=O)CS(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1NS(=O)(=O)CC(=O)O | null | null | CN(C=O)C.O.C(C)(=O)OCC | Acylation | OtherReaction | cbfd6f28b9d0b9d94f7e4648596955340b078b671cf962c5f2f1350eb0523981 | 856cd572bbc6c063d7e2e7d418946e4ec910f62888e2087856bb7fd393157377 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[S;H0;D4;+0:5](-Cl)(=[O;D1;H0:6])=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[S;H0;D4;+0:5](=[O;D1;H0:7])(-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | To a solution of 2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.030 g, 0.074 mmol) in dimethylformamide (0.5 ml) was added potassium carbonate (0.030 g, 0.239 mmol), chlorosulfonyl-acetic acid ethyl ester (0.02 g, 0.12 mmol) (for preparation, see: Helv. Chim. Acta.,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Sulfonyl halide | Sulfonamide.Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.O.C(C)(=O)OCC | null | null | CCOC(=O)CS(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1N>CN(C=O)C.O.C(C)(=O)OCC>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1NS(=O)(=O)CC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-505cb70f068b4b7f89454fbc2fbe49c7 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=Cc1cc(Cl)ccc1O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O | ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.ClC1=CC=C(C(C=O)=C1)O.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>ClC=1C=CC(=C(C=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | Cl[CH2:19][C:17]([N:16]1[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15]1)=[O:18].[OH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[CH:28]=[O:29]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=Cc1cc(Cl)ccc1O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O | null | null | CN(C=O)C.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[O;D1;H0:7]=[C:8]-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:9]-[C:8]=[O;D1;H0:7])-[C:6] | 84.5 | [{"value": 84.5, "product": "ClC=1C=CC(=C(C=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (2.87 g, 9.6 mmol) in dimethylformamide (20 mL) was added 5-chlorosalicylaldehyde (1.65 g, 10.5 mmol), potassium carbonate (2.64 g, 19.2 mmol) and potassium iodide (1.59 g, 9.6 mmol). The resulting mixture was heated to 100° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.[Cl-].[Na+].O | 100 | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=Cc1cc(Cl)ccc1O>CN(C=O)C.[Cl-].[Na+].O>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc7c522e78254b1bac83549a81ef66f7 | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O>>COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C(#N)[BH3-].[Na+].ClC=1C=CC(=C(C=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.Cl.COC(CCN)=O>>COC(CCNCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH2:7].O=[CH:8][c:9]1[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18](=[O:19])[N:20]1[CH2:21][C@H:22]([CH3:23])[N:24]([CH2:25][c:26]2[cH:27][cH:28][c:29]([F:30])[cH:31][cH:32]2)[CH2:33][C@H:34]1[CH3:35]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][CH2:8][c:9]1[cH... | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O | COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | C(C)(=O)O.CO.C(C)(=O)OCC.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 38.4 | [{"value": 38.4, "product": "COC(CCNCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.075 g, 0.18 mmol) in methanol (2 mL) was added 3-amino-propionic acid methyl ester hydrochloride salt (0.063 g, 0.45 mmol) and the pH of the solution was adjusted to 5–6 with triethylamine and acetic a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C(C)(=O)O.CO.C(C)(=O)OCC.C(C)N(CC)CC | null | 1 | COC(=O)CCN.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O>C(C)(=O)O.CO.C(C)(=O)OCC.C(C)N(CC)CC>COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-622432d3bf8e4e35b4337c9306449914 | COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CNCCC(=O)O | COC(CCNCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.O.[OH-].[Li+]>>ClC=1C=CC(=C(CNCCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | C[O:34][C:32]([CH2:31][CH2:30][NH:29][CH2:28][c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1)=[O:33]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10]... | COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CNCCC(=O)O | null | null | CO.O.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamino)-propionic acid methyl ester (0.035 g, 0.069 mmol) in tetrahydrofuran (0.2 mL), methanol (0.2 mL) and water (0.1 mL) was added lithium hydroxide monohydrate (0.015 g, 0.35 mmol). The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | CO.O.O1CCCC1 | null | 8 | COC(=O)CCNCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C>CO.O.O1CCCC1>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CNCCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e670c84d8b25493984d67a7d7e5b877b | NC(=O)c1cccc(CCl)c1C(N)=O.Oc1ccc(Cl)cc1>>O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O | ClC1=CC=C(C=C1)O.ClCC1=C(C(C(=O)N)=CC=C1)C(=O)N.CO>>ClC=1C=CC(=C(CN2C(C3=CC=CC=C3C2=O)=O)C1)O | N[C:9]([c:8]1[c:3]([C:2](=[O:1])[NH2:11])[c:4]([CH2:12]Cl)[cH:5][cH:6][cH:7]1)=[O:10].[cH:13]1[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]1[OH:20]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][c:13]1[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]1[OH:20] | NC(=O)c1cccc(CCl)c1C(N)=O.Oc1ccc(Cl)cc1 | O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O | null | [Cl-].[Zn+2].[Cl-] | null | Acylation | OtherReaction | 73e4de8720adaa306cfce637e1b8579a9dd4dd28c86d9933455a9545c9033513 | d409ff325fafc88481d814a49cb90e56150b5ec0f94fa64b291dbf1c8c89c364 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](-N)=[O;D1;H0:8]):[c:9]:1-[C:10](-[NH2;D1;+0:11])=[O;D1;H0:12].[O;D1;H1:13]-[c:14](:[c:15]):[cH;D2;+0:16]:[c:17]:[c:18]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:14](-[O;D1;H1:13]):[c:15])-[C:10]... | null | [] | 90 | CELSIUS | 48 | HOUR | To 4-chlorophenol (2.0 g, 15.5 mmol) and chloromethylphthalamide (2.62 g, 13.4 mmol) was added zinc chloride (3 mL, 0.5 M in tetrahydrofuran, 1.5 mmol). The reaction was stirred at 90° C. for 48 hours. After cooling the reaction was diluted with methanol (15 mL) and brought to reflux. After 30 minutes the hot suspensio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amide.Primary amide | Substituted dicarboximide | c1ccccc1.c1ccccc1 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | [Cl-].[Zn+2].[Cl-] | 90 | 48 | NC(=O)c1cccc(CCl)c1C(N)=O.Oc1ccc(Cl)cc1>[Cl-].[Zn+2].[Cl-]>O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48c9e93d53b0453aa0a8c08da1bd324d | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O | ClCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.[I-].[K+].ClC=1C=CC(=C(CN2C(C3=CC=CC=C3C2=O)=O)C1)O.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=CC(=C(CN2C(C3=CC=CC=C3C2=O)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | Cl[CH2:19][C:17]([N:16]1[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15]1)=[O:18].[OH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[CH2:28][N:29]1[C:30](=[O:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]2[C:38]1=[O:39]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccccc1CN1C(=O)c2ccccc2C1=O)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | 63.3 | [{"value": 63.3, "product": "ClC=1C=CC(=C(CN2C(C3=CC=CC=C3C2=O)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.75 g, 2.50 mmol) in dry dimethylformamide (25 mL) was added potassium iodide (0.40 g, 2.39 mmol), 2-(5-chloro-2-hydroxy-benzyl)-isoindole-1,3-dione (0.80 g, 2.76 mmol) and potassium carbonate (0.70 g, 5.10 mmol). The resul... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HCl | O.CN(C=O)C | 70 | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl.O=C1c2ccccc2C(=O)N1Cc1cc(Cl)ccc1O>O.CN(C=O)C>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e772f25c01b4b32b32b3bd235b01aab | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN | ClC=1C=CC(=C(CN2C(C3=CC=CC=C3C2=O)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.NN>>NCC1=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl | O=C1c2ccccc2C(=O)[N:29]1[CH2:28][c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)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] | null | [] | null | null | 17 | HOUR | To 2-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-isoindole-1,3-dione (0.87 g, 1.59 mmol) in ethanol (20 mL) was added 35% hydrazine (3 mL, 33.1 mmol). After 17 hours, the reaction was filtered and concentrated to a tan solid. This solid was triturated with methylene ch... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HO- | C(C)O | null | 17 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN1C(=O)c2ccccc2C1=O>C(C)O>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23074664ee454d3abe3137f8c295aaf7 | CCOC(=O)C(C)S(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN>>CC(C(=O)O)S(=O)(=O)NCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C(C)OC(C(C)S(=O)(=O)Cl)=O.NCC1=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=CC(=C1)Cl.C(C)N(CC)CC.CN(C)C1=NC=CC=C1>>ClC=1C=CC(=C(CNS(=O)(=O)C(C(=O)O)C)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | CC[O:5][C:3]([CH:2]([CH3:1])[S:6](Cl)(=[O:7])=[O:8])=[O:4].[NH2:9][CH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[O:18][CH2:19][C:20](=[O:21])[N:22]1[CH2:23][C@H:24]([CH3:25])[N:26]([CH2:27][c:28]2[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]2)[CH2:35][C@H:36]1[CH3:37]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[S:6](=... | CCOC(=O)C(C)S(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN | CC(C(=O)O)S(=O)(=O)NCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | null | C(C)(=O)OCC.O1CCCC1 | Miscellaneous | OtherReaction | 4d74724bc142da1113df2b4e9399f96e02619849034a54fbdd3d6c71934c1f8a | f29ac8585382f8298a9dbb9cc996a0739a952f5223b9c6de8b120b7811c408d9 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[S;H0;D4;+0:6](-Cl)(=[O;D1;H0:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[C;D1;H3:5]-[C:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[S;H0;D4;+0:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10]-[c:11] | null | [] | null | null | null | null | To a solution of 2-(2-aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.05 g, 0.119 mmol) in tetrahydrofuran (1 ml) at −40° C. was added triethylamine (0.021 ml, 0.151 mmol), catalytic dimethylaminopyridine and finally a solution of 2-chlorosulfonyl-propionic acid eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Sulfonyl halide | Sulfonamide.Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)(=O)OCC.O1CCCC1 | null | null | CCOC(=O)C(C)S(=O)(=O)Cl.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CN>C(C)(=O)OCC.O1CCCC1>CC(C(=O)O)S(=O)(=O)NCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a56750f9d5d440e2bf22ef0d9a46e092 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO | [OH-].[Na+].Cl.ClC=1C=CC(=C(C=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.[BH4-].[Na+]>>ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)CO | [CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15][N:16]1[C:17](=[O:18])[CH2:19][O:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[CH:28]=[O:29]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:1... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 98.7 | [{"value": 98.7, "product": "ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.99 g, 2.36 mmol) in dry methanol (25 mL) was added sodium borohydride (0.19 g, 4.92 mmol). After 1 hour the reaction was acidified to pH 2 by the addition of 1N hydrochloric acid. After 5 minutes the r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | null | CO | null | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1C=O>CO>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97b235d71bf44205a4006c9047c4a223 | CC(C)(C)OC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C | [H-].[Na+].ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)CO.BrCC(=O)OC(C)(C)C>>C(C)(C)(C)OC(COCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O | Br[CH2:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37].[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C@@H:13]([CH3:14])[CH2:15][N:16]1[C:17](=[O:18])[CH2:19][O:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[CH2:28][OH:29]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]... | CC(C)(C)OC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4541d644834c1bca555c4310180b1edadd2271c26488a32c314314a2e4f9c76f | 1858e49e1dc71f5ec31a1f9e719a3d52cdbfbbd98e3e0f8a48e0f56789173453 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[C:10]-[c:11]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C:10]-[c:11] | 65.4 | [{"value": 65.4, "product": "C(C)(C)(C)OC(COCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 0° C. solution of sodium hydride (0.025 g, 60% dispersion, 1.0 mmol) in tetrahydrofuran (2 mL) was added a solution of 2-(4-chloro-2-hydroxymethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.17 g, 0.40 mmol) and tert-butyl bromoacetate (0.23 g, 3.0 mmol) in tetrahydrofuran (2 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester.Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | null | CC(C)(C)OC(=O)CBr.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO>O1CCCC1>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc2428fcedcd452c91dbdc8ef927468e | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C>>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O | Cl.C(C)(C)(C)OC(COCC1=C(C=CC(=C1)Cl)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C)=O.FC(C(=O)O)(F)F>>ClC=1C=CC(=C(COCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | CC(C)(C)[O:33][C:31]([CH2:30][O:29][CH2:28][c:27]1[c:21]([O:20][CH2:19][C:17]([N:16]2[C@H:2]([CH3:1])[CH2:3][N:4]([CH2:5][c:6]3[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]3)[C@@H:13]([CH3:14])[CH2:15]2)=[O:18])[cH:22][cH:23][c:24]([Cl:25])[cH:26]1)=[O:32]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([F:10])[... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic acid tert-butyl ester (0.14 g, 0.25 mmol) in dichloromethane (5.0 mL) was added trifluoroacetic acid (0.5 mL). The resulting mixture was stirred at ambient temperature overnight, diluted with dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | ClCCl | null | 8 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)OC(C)(C)C>ClCCl>C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19342639db9b4a3ba8c49da68878b3f5 | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O>>CC(=O)C(OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)S(N)(=O)=O | ClC=1C=CC(=C(COCC(=O)O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C.C1(CCCCC1)N=C=NC1CCCCC1.CS(=O)(=O)N>>ClC=1C=CC(=C(COC(S(=O)(=O)N)C(C)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | [CH3:1][S:34]([NH2:35])(=[O:36])=[O:37].O[C:2](=[O:3])[CH2:4][O:5][CH2:6][c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]1[O:14][CH2:15][C:16](=[O:17])[N:18]1[CH2:19][C@H:20]([CH3:21])[N:22]([CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][C@H:32]1[CH3:33]>>[CH3:1][C:2](=[O:3])[CH:4]([O:5][CH2:6][c:7]1... | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O | CC(=O)C(OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)S(N)(=O)=O | null | CN(C1=CC=NC=C1)C | ClCCl | C-C Coupling | OtherReaction | ef4c24c8618fb05ddb9f753c03d5ae07a6f763c9b659b2d73d681b8edc5ed76d | 297ed2948e8a04d00e87d7fa50440f162f825b8d3e3b2ae92283e866a3596c29 | O=C(COc1ccccc1)N1CCN(Cc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[#8:4]-[C:5].[CH3;D1;+0:6]-[S;H0;D4;+0:7](-[N;D1;H2:8])(=[O;D1;H0:9])=[O;D1;H0:10]>>[C:5]-[#8:4]-[CH;D3;+0:3](-[C;H0;D3;+0:1](-[CH3;D1;+0:6])=[O;D1;H0:2])-[S;H0;D4;+0:7](-[N;D1;H2:8])(=[O;D1;H0:9])=[O;D1;H0:10] | 36.8 | [{"value": 36.8, "product": "ClC=1C=CC(=C(COC(S(=O)(=O)N)C(C)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic acid (0.11 g, 0.22 mmol) in dichloromethane (10 mL) was added 4-dimethylaminopyridine (0.04 g, 0.33 mmol) and 1,3-dicyclohexylcarbodiimide (0.049 g, 0.24 mmol). The resulting reaction mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid.Ether | Sulfonamide.Ketone | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 0.333333 | CS(N)(=O)=O.C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1COCC(=O)O>CN(C1=CC=NC=C1)C.ClCCl>CC(=O)C(OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c0eb05c8a254cc7ada9c39c6c9c73e0 | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO.Cc1ccccc1S(=O)(=O)N=C=O>>Cc1ccccc1S(=O)(=O)NC(=O)OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | C=1(C(=CC=CC1)S(=O)(=O)N=C=O)C.ClC1=CC(=C(OCC(=O)N2[C@@H](CN([C@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)CO.C(C)N(CC)CC>>ClC=1C=CC(=C(COC(NS(=O)(=O)C2=C(C=CC=C2)C)=O)C1)OCC(=O)N1[C@@H](CN([C@H](C1)C)CC1=CC=C(C=C1)F)C | [OH:14][CH2:15][c:16]1[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:22]1[O:23][CH2:24][C:25](=[O:26])[N:27]1[CH2:28][C@H:29]([CH3:30])[N:31]([CH2:32][c:33]2[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]2)[CH2:40][C@H:41]1[CH3:42].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[N:11]=[C:12]=[O:13]>>[CH3:1][c:2]1[... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO.Cc1ccccc1S(=O)(=O)N=C=O | Cc1ccccc1S(=O)(=O)NC(=O)OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | null | CN(C1=CC=NC=C1)C | C1(=CC=CC=C1)C | Protection | OtherReaction | 5903472f7fde872c0e2c01c89ed6188579dca0b618d750fc8f4727ce6f8df9e4 | 9b07b5c64086b5fa83ceb215f711b596c3e070d0d9c870e61dc7f6592ff6725e | O=C(NS(=O)(=O)c1ccccc1)OCc1ccccc1OCC(=O)N1CCN(Cc2ccccc2)CC1 | [O;D1;H0:1]=[#16:2](=[O;D1;H0:3])(-[c:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:1]=[#16:2](=[O;D1;H0:3])(-[c:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C:9]-[c:10] | null | [] | 55 | CELSIUS | null | null | To a solution of 2-(4-chloro-2-hydroxymethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.050 g, 0.12 mmol) in dry toluene (2 mL) was added triethylamine (0.05 mL, 0.36 mmol) followed by o-toluenesulfonylisocyanate (0.05 mL, 0.36 mmol) and catalytic 4-dimethylaminopyridine. After 23 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Sulfonamide.Carbamic ester | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C | 55 | null | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1CO.Cc1ccccc1S(=O)(=O)N=C=O>CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C>Cc1ccccc1S(=O)(=O)NC(=O)OCc1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf5034813b064e95bf4b078c69cd9ad9 | COC(=O)c1cc(Cl)ccc1OC>>COc1ccc(Cl)cc1CO | COC(C1=C(C=CC(=C1)Cl)OC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClC=1C=CC(=C(C1)CO)OC | CO[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Cl:7])[cH:8]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[CH2:10][OH:11] | COC(=O)c1cc(Cl)ccc1OC | COc1ccc(Cl)cc1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 999.5 | [{"value": 999.5, "product": "ClC=1C=CC(=C(C1)CO)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of 5-chloro-2-methoxy-benzoic acid methyl ester (20 g, 9.97 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of lithium aluminum hydride (210 mL, 210 mmol, 1M soln. in THF). The solution was then warmed to reflux for 2 hours. The reaction was cooled to 0° C. and carefully quenched by the addit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | 0 | null | COC(=O)c1cc(Cl)ccc1OC>C1CCOC1>COc1ccc(Cl)cc1CO |
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