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-01dbb772c5e249108f0b191ed17a2c0c | ord-2914492a9d1346ff9a2310b39c27edd6 | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.CC1CCNCC1>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1 | [CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:24][CH2:25]1.O=[C:6]1[NH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]32>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20]... | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 98d409ed27efd2986317a1caf6aa32bc5bb9b6fd20baa673c7140c501309393d | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCCCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9])-[C:13]-[C:14] | 83 | [{"value": 83.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.73 g (0.0150 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 14.9 g (0.150 mole) of 4-methylpiperidine, followed by 8.54 g (0.045 mole) of titanium tetrachloride.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CCNCC1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-89f7b1fe33fd41fd9d2f66dd79fef021 | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | N1CCOCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCOCC2)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:22]2[c:21]3[c:16]1[cH:17][cH:18][cH:19][c:20]3[CH2:24][CH2:23]2>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1... | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 77cbbfcb360cf8ffc4d29995320470770d66e3cc49d169b2f4a9c075c5bb0e49 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1 | null | [] | null | null | null | null | A mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 21.8 g (0.250 mole) of morpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1COCCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1COCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1COCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a604d29521f746d8809c9c1e6fc19b43 | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | N1CCSCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][S:13][CH2:14][CH2:15]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:22]2[c:21]3[c:16]1[cH:17][cH:18][cH:19][c:20]3[CH2:24][CH2:23]2>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][S:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1... | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 373ab209369d29aee2a31639c43788945ab59f851be2e4dc663048335aff1fdf | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#16:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#16:10]-[C:15]-[C:14]-1 | 88 | [{"value": 88.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7.88 g (0.025 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 25.8 g (0.250 mole) of thiomorpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CSCCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CSCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CSCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-366e5f5f05d44e1db595573b5e37fedd | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21>>CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 | BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12>>BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1 | O=[C:4]([N:2]([CH3:1])[CH3:3])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[N:13]2[CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][c:20]1[c:21]32 | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | C1=Nc2ccccc2N2CCc3cccc1c32 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C;D1;H3:14])-[C;D1;H3:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C;D1;H3:14])-[C;D1;H3:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 48 | [{"value": 48.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10.8 g (0.030 mole) of N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea and 110 ml of phosphorus oxychloride, under nitrogen, was heated under reflux for 6 hours, with stirring, and then cooled to room temperature. The excess phosphorus oxychloride was removed under vacuum with gentle war... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21>P(=O)(Cl)(Cl)Cl>CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1a0b2efa16a04e6f9b9dd632b5d51a5a | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2>>Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1>>CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1 | O=[N+:8]([O-])[c:6]1[c:5]2[c:4]([cH:3][c:2]([CH3:1])[cH:7]1)[CH2:19][CH2:18][N:17]2[c:16]1[c:11]([C:9](O)=[O:10])[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([cH:7]1)[NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N:17]3[CH2:18][CH2:19]2 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | null | Cl.[Pd] | C(C)O | Functional Group Interconversion | OtherReaction | 94a1cafe2daeec29b33699cad8b97c79501dab2e65aa6ba6ba0ea111a1bd36c4 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Nc2cccc3c2N(CC3)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8](-[N+;H0;D3:9](=O)-[O-]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-[#7:6]-[c:5]:[c:3]-1:[c:4] | 66.6 | [{"value": 66.0, "product": "CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | To a solution of 2-(5-methyl-7-nitroindolin-1-yl)benzoic acid (9 g, 0.03 mole), conc. hydrochloric acid (several drops) and ethanol (200 ml) was added 5% palladium-charcoal (1.5 gm). The mixture was shaked under hydrogen (58 psi) for 30 hours. The solvent was removed and the residue was loaded onto a silica gel flash c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CNc1cccc3c1N2CC3 | c1ccc2c(c1)CNc1cccc3c1N2CC3 | Other | Cl.[Pd].C(C)O | null | 30 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2>Cl.[Pd].C(C)O>Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bdf54aa101ac42ae9c74e2e30e8f117d | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21>>CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | C([O-])(O)=O.[Na+].CN(C(=O)Cl)C.Cl.NC1=C(C=CC(=C1)Br)N1CCC2=CC=CC=C12.C([O-])(O)=O.[Na+].CN(C(=O)Cl)C.O.C([O-])(O)=O.[Na+].CN(C(=O)Cl)C>>BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12 | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21 | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | c1ccc(N2CCc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 40.3 | [{"value": 40.0, "product": "BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.3, "product": "BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a stirred mixture, under nitrogen, of 28.9 g (0.10 mole) of 1-(2-amino-4-bromophenyl)indoline hydrochloride and 16.8 g (0.20 mole) of anhydrous powdered sodium bicarbonate in 500 ml of chloroform was added a solution of 21.5 g (0.20 mole) of dimethylcarbamyl chloride in 25 ml of chloroform, over a 10 minute period. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)(Cl)Cl | null | 0.166667 | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21>C(Cl)(Cl)Cl>CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5d5026eae7df4acdbb2617c4f3ddf508 | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 | ClCCl.BrC=1C=C2CCNC2=CC1.N1=C(C=C(C=C1C)C)C.FC1=C(C=CC=C1)[N+](=O)[O-]>>BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-] | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21 | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F | O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | 55 | [{"value": 55.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Bromoindoline (4.0 g, 0.02 mole), collidine (3.6 g, 0.03 mole), and o-fluoronitrobenzene (2.8 g, 0.02 mole) in xylene (25 ml) were heated at 185° C. (oil bath temperature) for 24 hours. The mixture was cooled to room temperature and poured into dichloromethane. The dichloromethane solution was washed with 1N hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | C=1(C(=CC=CC1)C)C | null | null | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F>C=1(C(=CC=CC1)C)C>O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c00a9480d9f0457d8175dcbd5a9b8e1d | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-]>>Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | [OH-].[K+].C(CO)O.CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C#N)C=CC=C1.ClCCl>>CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1 | N#[C:18][c:17]1[c:12]([N:11]2[c:5]3[c:4]([cH:3][c:2]([CH3:1])[cH:10][c:6]3[N+:7](=[O:8])[O-:9])[CH2:22][CH2:21]2)[cH:13][cH:14][cH:15][cH:16]1.OCC[OH:19].[OH-:20]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([N+:7](=[O:8])[O-:9])[cH:10]1)[N:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18](=[O:19])[OH:20])[CH2:21][CH2:22]2 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-] | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | null | null | O | Acylation | OtherReaction | 5e76f9eb1645dffa65f7e1b9c084dfced9f3cb65f8b76df935c174c7208ba236 | 3746af5ef2d46561e999a498fd7e2fe230c1b687b933f9146ccf2b5206980b7a | c1ccc(N2CCc3ccccc32)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C-C-[OH;D1;+0:5].[OH-;D0:6]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:2](:[c:3]):[c:4] | 32 | [{"value": 32.0, "product": "CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 175 | CELSIUS | null | null | A stirred solution under nitrogen of potassium hydroxide (30 g, 0.53 mole) in ethylene glycol (250 ml) and water (35 ml) was heated to 175° C., at which temperature there was added 2-(5-methyl-7-nitroindolin-1-yl)benzonitrile (26 g, 0.093 mole). After heating at 175° C. for 3 hours, the reaction mixture was cooled to r... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol.Primary alcohol | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | O | 175 | null | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-]>O>Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9668d0e9fda4468fbca2ca68f0b03c0f | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F>>Cc1ccc2c(c1)CCN2c1ccccc1C#N | O.FC1=C(C#N)C=CC=C1.CC=1C=C2CCNC2=CC1.[H-].[Na+]>>CC=1C=C2CCN(C2=CC1)C1=C(C#N)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][NH:10]2.F[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][N:10]2[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18] | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F | Cc1ccc2c(c1)CCN2c1ccccc1C#N | null | null | ClCCl.CS(=O)C.CCCCCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[c:8]:[c:9]1:[c:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[c:10]:[c:9]-1:[c:8]):[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | A slurry of 5-methylindoline (31 g, 0.23 mole), sodium hydride (11.3 g, 60% in oil) and dimethylsulfoxide (120 ml) was stirred at room temperature for 1 hour. A solution of o-fluorobenzonitrile (31 gm, 0.25 mole) in dimethylsulfoxide (25 ml) was added dropwise at a temperature below 20° C. Upon completion of the additi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | HF | ClCCl.CS(=O)C.CCCCCC | null | 2 | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F>ClCCl.CS(=O)C.CCCCCC>Cc1ccc2c(c1)CCN2c1ccccc1C#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e951f8226fdd416ab3c1a1366fab07a4 | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21>>CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)N(C([O-])=O)C1=CC=CC=C1.CN1CCNCC1>>BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.[O-][C:6](=[O:7])[N:8](c1ccccc1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:1... | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | null | null | CCOCC | Acylation | OtherReaction | 496a5327138afc6b4ae1864000645ab6e93b3f844fab5c88cb790c49ef142972 | 81c44ebb5d5e93adc64259393ae8569fe75b140c0973e872fa8c9e9e1eafe33f | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O-]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-c1:c:c:c:c:c:1>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 90 | [{"value": 90.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate (11.5 g, 28.5 mmoles), N-methylpiperazine (15 ml) and ether (50 ml) was stirred at room temperature for 2 hours. The ether was evaporated. The mixture was filtered through a silica gel column (150 g), packed with dichloromethaane, and the column was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CCOCC | null | null | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21>CCOCC>CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f25e64ba06b24bfdb0ae4125221bcb0b | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F>>Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] | CC=1C=C2CCCNC2=CC1.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.FC1=C(C=CC=C1)[N+](=O)[O-]>>CC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-].NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)C.CC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1 | O=[C:8]([N:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1)[NH:16][c:17]1[c:22]([N:23]2[c:5]3[cH:4][cH:26][cH:19][cH:7][c:6]3[CH2:25][CH2:24]2)[cH:21][cH:20][c:28](F)[cH:33]1.[CH3:45][c:46]1[cH:47][cH:48][c:49]2[c:50]([cH:51]1)[CH2:52][CH2:53][CH2:54][NH:55]2.O=[C:1](O)/[CH:18]=[CH:3]\[C:2](=O)O.F[c:56]1[cH:57][cH... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F | Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6ca60e38e39dc88a021e139cfa12c405adbfe51666b70740d648bd3aae2b090e | 16420b30599f384e4953986cb91d4be65adeef1dc89e6bf44daf7e8a6def4af3 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].F-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c:9]:[c:10](-[#7:11]2-[C:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:14]3:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[c:19]:3-2):[c;H0;D3;+0:20](-[NH;D2;+0:21]-[C;H0;D3;+0:22](=O)-[#7:23](-[C:24])-[C:25]):[cH;D2;+0:26]:1.O-[C;H0;D3;+0... | null | [] | null | null | null | null | Starting with 6-methyl-1,2,3,4-tetrahydroquinoline and 2-fluoronitrobenzene and following steps 1a to 1f of Example 2, one may obtain, in sequence, 6-methyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-aminophenyl)-6-methyl-1,2,3,4-tetrahydroquinoline, N-[2-(6-methyl-1-phenyl)-1,2,3,4-tetrahydroquinolin-1-yl]-4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Primary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccc2c(c1)CCCN2.c1ccccc1 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F>>Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0823a69713da42928339c4f36c660f9c | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.BrC=1C=CC(=C(C1)[N+](=O)[O-])F>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12.BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[c:14]([N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:21][cH:22][cH:23][c:24]32)[cH:13][cH:32][c:30](F)[cH:29]1.O=[C:12](O)/[CH:37]=[CH:53]\[C:52](=O)O.F[c:34]1[c:28]([N+:27](=[O:45])[O-:47])[cH:49][c:10]([Br:11])[cH:9][cH:33]1.[NH:55]1[CH2:56][CH2:57][C... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | eaab8a83f2efcd21169149c49e508483a800d994959b618d733698350034b565 | 9e6d5d764f8c19082eefcd2319c75b4e9b2c9ac0a73bd7ddf3d30cc2416a7660 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH;D2;+0:4]-[C;H0;D3;+0:5](=O)-[#7:6](-[C:7])-[C:8]):[c:9](-[#7:10]2-[C:11]-[C:12]-[c;H0;D3;+0:13]3:[cH;D2;+0:14]:[cH;D2;+0:15]:[c:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18]:3-2):[cH;D2;+0:19]:[cH;D2;+0:20]:1.F-[c;H0;D3;+0:21]1:[cH;D2;+0:22]:[cH;D2;+0:23]:[c;H0;D3;+0:24](-[Br;D1;H... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 5-bromo-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-bromophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-bromophenyl)-1,2,3,4-tetrahydroquinolin-1-yl}... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Nitro group.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Nitro group.Primary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6a47530caf27464e9ee5adb12b91d28b | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.ClC=1C=CC(=C(C1)[N+](=O)[O-])F>>ClC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)Cl)N1CCCC2=CC=CC=C12.ClC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10](F)[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:39]2[c:24]1[cH:43][cH:42][cH:41][cH:40]2.O=[C:18](O)/[CH:37]=[CH:33]\[C:32](=O)O.F[c:54]1[c:48]([N+:46](=[O:45])[O-:47])[cH:49][c:50]([Cl:11])[cH:52][cH:53]1.[NH:27]1[CH2:56][CH2:57][CH2... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2 | CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ac579b59724da5233aaa883b67f65306d5e022a843e2d4b7e900b46ba351ab53 | a2640ca05bc62a3cfd99a450eeb71d3465e1453d6bb0da848a76659e73bcaf93 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[Cl;H0;D1;+0:5]):[c:6]:[c:7]:1-[#7;+:8].F-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[#7:13]2-[C:14]-[CH2;D2;+0:15]-[c;H0;D3;+0:16]3:[c:17]:[c:18]:[c:19]:[cH;D2;+0:20]:[c;H0;D3;+0:21]:3-2):[c:22](-[NH;D2;+0:23]-[C;H0;D3;+0:24](=O)-[#7:25](-[C:26])-[C:27]):[c:28]:1.O-[C;H0;D3;+0:... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 5-chloro-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-chloro-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-chlorophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-chlorophenyl)-1,2,3,4-tetrahydroquinolin-1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine.Tertiary amine.Tertiary amine | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccc2c(c1)CCCN2 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-50db5f899137486aaab10e21f98eedfe | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2>>Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.FC1=C(C=C(C=C1)C)[N+](=O)[O-]>>CC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)C)N1CCCC2=CC=CC=C12.CC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:33]([NH:17][c:16]1[c:5]([N:6]2[CH2:7][CH2:8][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[cH:4][cH:3][c:2](F)[cH:18]1)[N:24]1[CH2:49][CH2:50][N:51]([CH3:52])[CH2:53][CH2:54]1.F[c:23]1[cH:22][cH:21][c:20]([CH3:19])[cH:38][c:34]1[N+:35](=[O:36])[O-:37].O=[C:1](O)/[CH:9]=[CH:39]\[C:40](=O)O.[CH2:25]1[NH:46][c:44]2[cH:... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2 | Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4387834540f1429daf07b17756144e2cbab865128a22f11dcca80dafe41cb1a6 | 691748feafd0861bf6396f8cf88bef6c995c57f8467567eff885149cff33e35a | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].F-[c;H0;D3;+0:7]1:[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:11](=O)-[N;H0;D3;+0:12]2-[CH2;D2;+0:13]-[C:14]-[#7:15](-[C;D1;H3:16])-[C:17]-[CH2;D2;+0:18]-2):[c:19](-[#7:20]2-[C:21]-[CH2;D2;+0:22]-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]-2:[c:27]):[c:28]:[c:29]:1.O-[C;H0;D3... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 2-fluoro-5-methylnitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinone, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinoline,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2>>Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-37c06d96b5ee4ba3aa341faa5c166ae9 | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2>>O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | FC1=C(C=CC=C1)[N+](=O)[O-].N1CCCC2=CC=CC=C12.N1=C(C=C(C=C1C)C)C>>[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12 | F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1.[NH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2 | O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | null | null | CC1=C(C(=CC=C1)C)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | de606d160ccc80ef355eabdb340e2f4f96955660dd0088ab61ab49bbb46dfbde | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 22.2 | [{"value": 22.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.2, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture, under nitrogen of 70.6 g (0.50 mole) of 1-fluoro-2-nitrobenzene, 133.2 g (1.00 mole) of 1,2,3,4-tetrahydroquinoline and 121.2 g (1.00 mole) of symmetrical collidine in 500 ml of 1,2,3-trimethylbenzene was refluxed (bp 178°) for 5 days. The mixture was concentrated in vacuo. The residue was taken up i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | CC1=C(C(=CC=C1)C)C | null | null | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2>CC1=C(C(=CC=C1)C)C>O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cbb4808b692a4f609145ab6de26bd51d | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)C)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1 | O=[C:9]([NH:8][c:6]1[c:5]([N:24]2[c:23]3[cH:17][cH:18][c:19]([Br:20])[cH:21][c:22]3[CH2:26][CH2:25]2)[cH:4][cH:3][c:2]([CH3:1])[cH:7]1)[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18... | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:14]-[#7:13](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12])-[C:15] | 53.9 | [{"value": 53.9, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.8, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide (3.3 g, 7.68 mmoles) and phosphorus oxychloride (30 ml) was heated at reflux for 25 minutes under nitrogen. The solution was cooled and excess phosphorus oxychloride was removed at 55°-60° C. under vacuum. Ice-chilled 2N-sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1>P(=O)(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c6cdf19ab61f40fc890ba6f32e88d976 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>>Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 | BrN1C(CCC1=O)=O.CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC(=C2)C.ClCCl>>BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[N:9]1[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]31)[C:18]([N:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1)=[N:26]2.O=C1CCC(=O)N1[Br:8]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[N:9]1[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]31... | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br | Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 48755bf12d8d10c717a9c5a6c9ffd950e176b302684d6c5c7e94778ebdccddd5 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[#7:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[C;D1;H3:7]):[c:8] | 11.6 | [{"value": 11.6, "product": "BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.6, "product": "BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of N-bromosuccinimide (0.91 g, 5.1 mmoles) in dimethylformamide (3 ml) was added dropwise to a solution of 6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (1.6 g, 4.8 mmoles) in dimethylformamide (30 ml) at 0°-3° C. The reaction mixture was stirred for 30 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1=Nc2ccccc2N2CCc3cccc1c32.C1CCNC1 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | CN(C=O)C | null | 0.5 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>CN(C=O)C>Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d63ac06d4b64e4ca99b120a96de594c | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 | BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1>>BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]3[c:26]1[N:25]2[CH2:24][CH2:23]3>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][c... | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]1:[c:3]2:[c:4]-[C:5]=[#7:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[N;H0;D3;+0:12]-2-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1>>[c:1]:[c:2]1:[cH;D2;+0:14]:[cH;D2;+0:13]:[n;H0;D3;+0:12]2:[c:3]:1:[c:4]-[C:5]=[#7:6]-[c:7](:[c:8]):[c;H0;D3;+0:9]-2:[c:10]:[c:11] | 42.7 | [{"value": 42.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.7, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (5.7 g, 13.8 mmoles) in chloroform (540 ml) was added manganese dioxide (25 gm), and the mixture was heated under reflux for 4 days. The mixture was filtered, and the filter cake washed with dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9a65ccb0ddb418c83d873e96b8bd48d | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl>>Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)C)[N+](=O)[O-].ClCCl>>Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC(=CC=C12)Br | O=[N+:17]([O-])[c:16]1[c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]32)[cH:4][cH:3][c:2]([CH3:1])[cH:18]1.ClC[Cl:19]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]32)[c:16]([NH2:17])[cH:18]1.[ClH:19] | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl | Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl | null | [Pt] | C(C)O | Miscellaneous | OtherReaction | c17f7e044bc060a97225c6ab4003d36cc5b3c62b420a125a65d55de2f342fd7a | 0910f6290f48bbc37d9ffbe0f747096afada90a5ba51c082c83c032e14c970e2 | c1ccc(N2CCc3ccccc32)cc1 | Cl-C-[Cl;H0;D1;+0:1].O=[N+;H0;D3:2](-[O-])-[c:3](:[c:4]):[c:5]>>[ClH;D0;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5] | 39 | [{"value": 39.0, "product": "Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a warm solution of 4-(5-bromo-1-indolinyl)-3-nitrotoluene (10 g, 0.03 mole) in dichloromethane (40 ml) and ethanol (160 ml) was added 1% platinum-on-carbon (2.0 gm). The mixture was shaken under hydrogen (57 psi) for 3.5 hours. The mixture was filtered and concentrated. The residue was dried under vacuum at 55° C. P... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | [Pt].C(C)O | null | 3.5 | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl>[Pt].C(C)O>Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5f9dfecb7ead4899b6fe668fa8962cab | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21>>O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 | [N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC=CC=C12.BrN1C(CCC1=O)=O.O>>[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br | O=C1CCC(=O)N1[Br:17].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21 | O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(N2CCc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 68 | [{"value": 68.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a solution of 1-(2-nitro-4-bromophenyl)indoline (15 g, 0.047 moles) in dimethylformamide (150 ml) at -10° C. was added dropwise a solution of N-bromosuccinimide (9.4 g, 0.054 mole) in dimethylformamide (50 ml) over 10 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. The solution was added slowly to... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C | 0 | 0.25 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21>CN(C=O)C>O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53391d34fae14644b538478e4ff63a6d | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | BrN1C(CCC1=O)=O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C.ClCCl>>BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:23][cH:24][c:25]32)[CH2:26][CH2:27]1.O=C1CCC(=O)N1[Br:22]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 84 | [{"value": 84.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 15 | MINUTE | N-Bromosuccinimide (2.6 g, 14.5 mmoles) was added to a solution of N-[2-(indolin-1-yl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide (5.0 g, 12.0 mmoles) in dimethylformamide (50 ml). The solution was stirred at room temperature for 15 minutes and at 60° C. for 15 minutes. The solution was cooled and poured into dich... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CC[NH]2.C1CCNC1 | c1ccc2c(c1)CC[NH]2 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C | 60 | 0.25 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br>CN(C=O)C>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c129258517f04833a6b4a09dc7b58560 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19]... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 70.3 | [{"value": 70.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of N-[2-(5-bromo-1-indolinyl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide (12.3 g, 24.8 mmoles) and phosphorus oxychloride (250 ml) was heated under reflux for 1 hour. The reaction mixture was cooled and then concentrated at 50°-60° C. under vacuum. Ice-chilled sodium hydroxide solution (15%, 500 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | 0.333333 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a336759d16894dc48e61e823dcf0ae71 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 | BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1>>BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][c:20]([Br:21])[cH:22][c:23]2[c:24]43)[CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3-[n:15]3[cH:16][cH:17][c:18]4[cH:19][c:2... | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11])-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[N;H0;D3;+0:14]-2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[n;H0;D3;+0:14]:2-1 | 75.2 | [{"value": 75.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture 4,9-dibromo-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]-benzodiazepine (4.5 g, 9.45 mmoles) and manganese(IV) dioxide (7.0 g) in chloroform (150 ml) was heated under reflux for 3.5 hours. An additional 4.5 g of manganese dioxide was added. The reaction mixture was stirred overnight at... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | 8 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c2f682b48eea413db9b847972f11227f | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21>>O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | [N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12.BrN1C(CCC1=O)=O.[OH-].[Na+]>>BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-] | O=C1CCC(=O)N1[Br:17].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 6a871f64bbdddc1ef7b40779396401fbf01bbad117bf7136b596038af1a81e74 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(N2CCCc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 82.7 | [{"value": 82.0, "product": "BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.7, "product": "BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution, under nitrogen, of 1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (76.3 g, 0.30 mole) in dimethylformamide (1000 ml) was cooled to -10° C. A solution of of N-bromosuccinimide (58.7 g, 0.33 mole) in dimethylformamide (250 ml) was added dropwise at such a rate as to keep the reaction temperature below ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C=O)C | null | null | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21>CN(C=O)C>O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2b04d48d5e5a4e3d9c091e3fa05cb57e | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21>>Nc1ccccc1N1CCCc2cc(Br)ccc21 | BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-].C1=CC=CC=C1.C(C)O.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]21>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]21 | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | Nc1ccccc1N1CCCc2cc(Br)ccc21 | null | [Pt] | CCOCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 55 | [{"value": 55.0, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A Parr hydrogenation bottle was charged with 6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (16.7 g, 0.050 mole), 1% platinum-on-carbon (1 g), benzene (100 ml) and ethanol (100 ml). The mixture was shaken under an initial hydrogen pressure of 58 psi until uptake ceased. The mixture was then filtered to remove the ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pt].CCOCC | null | null | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21>[Pt].CCOCC>Nc1ccccc1N1CCCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8adb78538964131b53b10b97ff7a357 | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | C(\C=C/C(=O)O)(=O)O.CN1CCNCC1.CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br.C(C)N(CC)CC>>C(\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:26][CH2:27]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2... | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | null | null | ClCCl.C(C)O.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 61 | [{"value": 61.0, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A stirred solution, under nitrogen, of 1-(2-aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline (21.2 g, 0.070 mole) and triethylamine (10.1 g, 0.10 mole) in dichloromethane (200 ml) was cooled to 0° C. Then there was added dropwise phenylchloroformate (15.7 g, 0.10 mole) at such a rate as to keep the reaction temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.C(C)O.O | null | 0.5 | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1>ClCCl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-240ef7a4906440f9b2865b52b530e7fc | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 | CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br>>BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][CH2:17][c:18]4[cH:19]... | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | cb9ebe4be98e2ad3a66f5dbc95abbc6d189782ed4aae6aab9e7485070f90ad10 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 79 | [{"value": 79.0, "product": "BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide (14.2 g, 0.0330 mole) in phosphorus oxychloride (250 ml) was heated under reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature and excess phosphorous oxychloride was removed at asp... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CCC[NH]2 | C1=Nc2ccccc2N2CCCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-16910464cc86414581b08344acd38357 | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2>>O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | BrC1=C(C=C(C=C1)Br)[N+](=O)[O-].N1CCCC2=CC=CC=C12.N1=C(C=C(C=C1C)C)C>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-] | Br[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Br:7])[cH:8][cH:9]1.[NH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | null | null | CC1=C(C(=CC=C1)C)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | de606d160ccc80ef355eabdb340e2f4f96955660dd0088ab61ab49bbb46dfbde | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 18 | [{"value": 18.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture, under nitrogen, of 2,5-dibromonitrobenzene (140.5 g, 0.50 mole), 1,2,3,4-tetrahydroquinoline (133.2 g, 1.00 mole) and symmetrical collidine (121.2 g, 1.00 mole) in 1,2,3-trimethylbenzene (500 ml) as solvent was heated at 160°-165° C. for 7 days. The mixture was cooled to room temperature, filtered, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CC1=C(C(=CC=C1)C)C | null | null | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2>CC1=C(C(=CC=C1)C)C>O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-be31b5d785ad45829427ebbf59eaec37 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21>>Nc1cc(Br)ccc1N1CCCc2ccccc21 | BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].C(C)O>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | Nc1cc(Br)ccc1N1CCCc2ccccc21 | null | [Pt] | C1=CC=CC=C1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6.5 | HOUR | 1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (11.6 g, 0.035 mole) was dissolved in benzene (125 ml), and ethanol added (75 ml), followed by 1% platinum-on-charcoal (0.40 g). The mixture was shaken under an initial pressure of 56 psi for 6.5 hours. The mixture was filtered and the filtrate was evaporated at 50°... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pt].C1=CC=CC=C1 | null | 6.5 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21>[Pt].C1=CC=CC=C1>Nc1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4793acac75d84b23abda4b52e9f8c0da | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl.C1(=CC=CC=C1)OC(=O)Cl.BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N.C(C)N(CC)CC>>CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:26][CH2:27]1.[NH2:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[N:16]1[CH2:17][CH2:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2... | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | null | null | ClCCl.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 61.2 | [{"value": 61.0, "product": "CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1-(4-Bromo-2-aminophenyl)-1,2,3,4-tetrahydroquinoline (10.6 g, 0.035 mole) was dissolved on a steam bath in dichloromethane (150 ml). The solution was cooled to -5° C. in ice/methanol and triethylamine (5.01 g, 0.050 mole) was added in one portion, followed by a solution of phenylchloroformate (7.85 g, 0.050 mole) diss... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.O | null | 2 | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>ClCCl.O>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-249a436bedba4ee9a623de6abab0c274 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 | CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12>>BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][CH2:18][c:19]... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | cb9ebe4be98e2ad3a66f5dbc95abbc6d189782ed4aae6aab9e7485070f90ad10 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 56 | [{"value": 56.0, "product": "BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A stirred solution of 4-methyl-N-[5-bromo-2-(1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide (8.6 g, 0.020 mole) in phosphorus oxychloride (200 ml) was heated under reflux under nitrogen for 6 hours. The reaction mixture was cooled to room temperature and excess phosphorus oxychloride was removed at aspira... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CCC[NH]2 | C1=Nc2ccccc2N2CCCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | 0.25 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-58bb8be7bc7c4cb280e7586c11800968 | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 | CN1CCNCC1.NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12.C(C)N(CC)CC.C(\C=C/C(=O)O)(=O)O.CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl>>C(\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][CH2... | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 | null | null | ClCCl.C(C)O.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 65.4 | [{"value": 65.0, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A stirred solution, under nitrogen of 1-(2-aminophenyl)-1,2,3,4-tetrahydroquinoline (4.50 g, 0.020 mole), and triethylamine (3.04 g, 0.030 mole) in dichloromethane (50 ml) was cooled to 0° C. and phenylchloroformate (4.70 g, 0.030 mole) was added dropwise at such a rate such as to keep the reaction temperature below 5°... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.C(C)O.O | null | 0.166667 | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>ClCCl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-50974b72a97646e5b2e5616160666f39 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>>NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 | FC1=C(C(=O)N)C=CC=C1.ClC=1C=C2CCNC2=CC1.[H-].[Na+]>>ClC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]21 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F | NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8].[c:9]:[c:10]1:[c:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[c:11]:[c:10]-1:[c:9]):[c:2]:[c:3] | 43.3 | [{"value": 43.3, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A slurry was prepared comprising 5-chloroindoline (15.3 gm, 0.1 mole), dimethylsulfoxide (DMSO) [50 ml] and sodium hydride (5.28 gm, 50% in oil, washed with hexane). The slurry was permitted to stir at room temperature for 1 hour. To this a solution of o-fluorobenzamide (15.2 gm, 1.1 eq.) in DMSO (20 ml) was added drop... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | CS(=O)C | null | 1 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>CS(=O)C>NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-95a7be5599144175bfe972f11741a8b3 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21>>NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | ClC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)N)C=CC=C1>>ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1 | O=[N+:19]([O-])[c:18]1[cH:17][c:15]([Cl:16])[cH:14][c:13]2[c:20]1[N:10]([c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1)[CH2:11][CH2:12]2>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][c:18]([NH2:19])[c:20]21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | null | null | CN(C=O)C.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]>>[#7:5]-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 119.3 | [{"value": 119.3, "product": "ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To the solution of 2-(5-chloro-7-nitroindolin-1-yl)benzamide of Example 1b (10 gm, 26.5 mmoles) in dimethylformamide (DMF) [100 ml] and ethanol (100 ml) was added 1% Pt/carbon (2.0 gm). The mixture was shaken under hydrogen (59 psi) for 41/2 hours. The mixture was then filtered under nitrogen and concentrated to remove... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | CN(C=O)C.C(C)O | null | 2 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21>CN(C=O)C.C(C)O>NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f89196dda9834a2ab9a49b6b2bc34888 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21>>O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 | ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1>>ClC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1 | N[C:2](=[O:1])[c:19]1[c:14]([N:11]2[c:10]3[c:4]([NH2:3])[cH:5][c:6]([Cl:7])[cH:8][c:9]3[CH2:13][CH2:12]2)[cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]3[c:10]2[N:11]([CH2:12][CH2:13]3)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 | null | null | CO.ClCCl | Miscellaneous | OtherReaction | 699e7bfbbd46d2067058ea48bc645fe6abf364bea853a0751c83a61ba7a46d64 | f24c9f1ec9fd5abfe6f68cf1415b34cc6e64faf9d608cbf5712660ea976e20b3 | O=C1Nc2cccc3c2N(CC3)c2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-[#7:6]-[c:5]:[c:3]-1:[c:4] | null | [] | null | null | 2 | HOUR | 2-(5-chloro-7-aminoindolin-1-yl)benzamide of Example 1c (28.7 g, 0.10 mole) was dissolved in methanol/dichloromethane (DCM) solution (1:9 v/v) at 35° C. Silica gel (510 gm) was added to absorb the starting material, then the solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Secondary amide | null | c1ccc2c(c1)CNc1cccc3c1N2CC3 | c1ccc2c(c1)CNc1cccc3c1N2CC3 | Other | CO.ClCCl | null | 2 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21>CO.ClCCl>O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f438735f89784c17b8bc9f86333be2b6 | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F>>CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | C(\C=C/C(=O)O)(=O)O.NC=1C=C(C=CC1F)N1CCC2=CC=CC=C12.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl.C(C)N(CC)CC.C(=O)(Cl)Cl>>C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)=[O:7].[NH2:8][c:9]1[cH:10][c:15]([N:16]2[CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]32)[cH:14][cH:13][c:11]1[F:12]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19]3... | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | null | null | C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl | Acylation | OtherReaction | e2d29a6723220f7540ade03be1350afcc1e105044dd661555a27f5f3b0755993 | aad7770ec49cc1fbb0c48907b32832faee613a05b9b63a5a2c921d89bf7e8d07 | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[#7:7](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[F;D1;H0:12]):[c;H0;D3;+0:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:1)-[c:16]>>[C:6]-[#7:7](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[F;D1;H0:12]):[cH;D2;+0:15]:[c;H0;D3;+0:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](... | null | [] | null | null | 15 | MINUTE | To a stirred solution under nitrogen, of 50.2 g (0.22 mole) of 1-(3-amino-4-fluorophenyl)indoline of Example 2b, and 66.7 g (0.66 mole) of triethylamine in 900 ml of chloroform was added 65.7 g (0.33 mole) of 4-methyl-1-piperazine carbonyl chloride hydrochloride in portions over 5 minutes. The reaction was refluxed for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Tertiary amide.Primary amine | Aromatic halide.Urea | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F>C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl>CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-18bf4299586b4424bad0163395810e9c | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 | N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C>>FC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 20.8 | [{"value": 20.8, "product": "FC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 10.6 g (0.030 mole) of N-[2-(2,3-dihydro-1H-indol-1-yl)-5-fluorophenyl]-4-methyl-1-piperazine carboxamide of Example 2c in 250 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure w... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-335b2707800d4740ab2dc3e70b9aa8ae | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | C(\C=C/C(=O)O)(=O)O.BrC1=CC(=C(C=C1)N1CCC2=CC=CC=C12)N.C([O-])([O-])=O.[K+].[K+].Cl.CN1CCN(CC1)C(=O)Cl.C([O-])([O-])=O.[K+].[K+].C(=O)(Cl)Cl>>C(\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12 | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)=[O:7].[NH2:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[N:16]1[CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19... | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | null | null | C(C)O.C(Cl)(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 39.8 | [{"value": 16.0, "product": "C(\\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "C(\\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen of 43.5 g (0.15 mole) of 1-(4-bromo-2-aminophenyl)indoline of Example 3b and 82.8 g (0.60 mole) of milled potassium carbonate in 1000 ml of chloroform was added 44.7 g (0.225 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over 10 minutes. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)O.C(Cl)(Cl)Cl.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21>C(C)O.C(Cl)(Cl)Cl.O>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c9be424df61a4d4180fb5f79d589d8d6 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 29.7 | [{"value": 29.7, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 9.14 g (0.022 mole) of N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 3c in 250 ml of phosphorus oxychloride was refluxed for 7 hours under nitrogen then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure with... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a070677bb7a34268aa9e3cb9e14d0546 | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2>>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 | ClC1=C(C=C(C=C1)Cl)[N+](=O)[O-].N1CCC2=CC=CC=C12>>ClC1=CC(=C(C=C1)N1CCC2=CC=CC=C12)[N+](=O)[O-] | Cl[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Cl:7])[cH:8][cH:9]1.[NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | null | [] | null | null | null | null | A stirred solution of 38.4 g (0.20 mole) of 1,4-dichloro-2-nitrobenzene and 59.6 g (0.50 mole) of indoline in 400 ml of dimethylformamide (DMF) was heated under nitrogen at 140°-145° C. overnight (23 hours). The DMF solvent was then removed in vacuo and the residue was dissolved in 500 ml of dichloromethane. This solut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C=O)C | null | null | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2>CN(C=O)C>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ae31c543661a4d11b2d7f1f9829b2104 | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 | ClC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][... | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 37 | [{"value": 37.0, "product": "ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 6.30 g (0.017 mole) of N-[5-chloro-2-(2,3-dihydro-1H-indol-1-yl)-phenyl]-4-methyl-1piperazinecarboxamide of Example 4b in 100 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure w... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e183824526644da2a8afab71bf2cdfe4 | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1>>Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | C(\C=C/C(=O)O)(=O)O.C([O-])([O-])=O.[K+].[K+].C(=O)(Cl)Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].Cl.CN1CCN(CC1)C(=O)Cl>>C(\C=C/C(=O)O)(=O)O.CC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12 | Cl[C:17](=[O:18])[N:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[c:15]([NH2:16])[cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[c:15]([NH:16][C:17](=[O:18])[N:... | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1 | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | null | null | ClCCl.C(Cl)(Cl)Cl.CO.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen of 43.0 g (0.190 mole) of 1-(2-amino-4-methylphenyl)indoline of Example 5b and 105 g (0.76 mole) of milled potassium carbonate in 1000 ml of chloroform was added 56.7 (0.285 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over 10 minutes. The reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2.C1C[NH]CC[NH]1 | HCl | ClCCl.C(Cl)(Cl)Cl.CO.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1>ClCCl.C(Cl)(Cl)Cl.CO.O>Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a5ce352d39dd40c585d35d1aac501dc7 | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 | CC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>CC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:9]([NH:8][c:6]1[c:5]([N:23]2[c:22]3[cH:17][cH:18][cH:19][cH:20][c:21]3[CH2:25][CH2:24]2)[cH:4][cH:3][c:2]([CH3:1])[cH:7]1)[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19]... | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:14]-[#7:13](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12])-[C:15] | 41 | [{"value": 41.0, "product": "CC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 35.1 (0.10 mole) of N-[5-methyl-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 5c in 500 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure with ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1>P(=O)(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ce491d289a224f31850e1c7889598975 | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21>>CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | NC1=C(C=CC=C1)N1CCC2=CC=CC=C12.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl.C(\C=C/C(=O)O)(=O)O.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl>>C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20]... | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21 | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | null | null | C(Cl)(Cl)Cl.C(C)O.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 53 | [{"value": 53.0, "product": "C(\\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.9, "product": "C(\\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen, of 21.0 g (0.10 mole) of 1-(2-aminophenyl)indoline and 30.4 g (0.30 mole) of triethylamine in 400 ml of chloroform was added 29.9 g (0.15 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over about 5 minutes. The reaction was refluxed for 6 hours when an a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)(Cl)Cl.C(C)O.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21>C(Cl)(Cl)Cl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fbcb141eb3f341e5a4ef7c25626213c6 | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 | N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C>>CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:24][CH2:23]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][c:21]2[c:... | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 10 | [{"value": 10.0, "product": "CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.0, "product": "CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 21.1 g (0.0627 mole) of N-[2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 7a was added 500 ml of phosphorus oxychloride and this was refluxed under nitrogen overnight. The excess POCl3 was then removed at aspirator pressure with warming. The residue was boiled and triturated on the ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8616870cff044e7d82aec6c73d00f16b | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl>>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | ClC=1C=C2CCNC2=CC1.ClC1=C(C=C(C=C1)Cl)[N+](=O)[O-].N1=C(C=C(C=C1C)C)C>>ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-] | [NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]21.Cl[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Cl:7])[cH:8][cH:9]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]21 | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | 40 | [{"value": 40.0, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 123 g (0.80 mole) of 5-chloroindoline, 134 g (0.70 mole) of 1,4-dichloronitrobenzene and 97 g (0.80 mole) of collidine in 1000 ml of dimethylformamide was heated under nitrogen at 150° C. for 48 hours. The mixture was then cooled, filtered from some insolubles, and the solvent was removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C=O)C | null | null | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl>CN(C=O)C>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-045e2fa84c854fe2b6a46ce09d53e1c2 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21>>CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-].C1=CC=CC=C1>>C(C)[O-].Cl.NC1=C(C=CC(=C1)Cl)N1CCC2=CC(=CC=C12)Cl | [O-][N+:5](=[O:3])[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][c:18]([Cl:4])[cH:20][cH:21][c:22]21>>[CH3:1][CH2:2][O-:3].[ClH:4].[NH2:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:22]21 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | null | [Pt] | C(C)O | Functional Group Interconversion | Reduction of nitro groups to amines | 7d8327c707810ad9bf9cab994013125d90d07022ab441f2f6714198d54f0463b | 33553c41c42ab392a899ed959afa486593c8da248b31b16bda6197a51e957d22 | c1ccc(N2CCc3ccccc32)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[O-]-[N+;H0;D3:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:12]-[C:13]-[O-;H0;D1:8].[Cl;D1;H0:14]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:9](:[c:10]):[c:11].[ClH;D0;+0:1] | null | [] | null | null | null | null | A Parr bottle, charged with 12.4 g (0.040 mole) of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline of Example 8a, 100 ml of benzene, 100 ml of absolute ethanol and 0.5 g of 1% Pt/C was shaken under an initial hydrogen pressure of 57 psig until uptake ceased. The catalyst was then removed by filtration and the filtrate was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Aromatic halide.Primary amine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | [Pt].C(C)O | null | null | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21>[Pt].C(C)O>CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81091ad136594f5ebb09a525d78f5e7e | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>>NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 | BrC=1C=C2CCNC2=CC1.[H-].[Na+].FC1=C(C(=O)N)C=CC=C1>>BrC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21 | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F | NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8].[c:9]:[c:10]1:[c:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[c:11]:[c:10]-1:[c:9]):[c:2]:[c:3] | null | [] | 55 | CELSIUS | 30 | MINUTE | A slurry was prepared from 5-bromoindoline (9.85 g, 50 mmoles) dimethylsulfoxide (DMSO) (35 ml), sodium hydride (2.6 g, 50% in oil, washed with hexane, 1.1 eq). The slurry was stirred for 30 minutes. To this a solution of o-fluorobenzamide (7.9 g, 1.1 eq) in DMSO (15 ml) was added dropwise with temperature between 12°-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | CS(=O)C | 55 | 0.5 | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>CS(=O)C>NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5f08fd378dbe4e63866b0a1299019a73 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][c:19]([Br:20])[cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Br:20])[... | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 57 | [{"value": 57.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (11.5 g, 27.5 mmoles) and 750 ml of phosphorus oxychloride was stirred until a solution was obtained and then heated under reflux for 40 minutes. The reaction mixture was cooled. Excess phosphorus oxychloride was removed by evaporation at 5... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-47b8b78671e24d5398bda6a120b7d060 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | ClC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C.ClCCCl>>ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Cl:20])[... | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 29.5 | [{"value": 28.0, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.5, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 15 | MINUTE | To N-[2-(5-chloro-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (13.5 g, 36.5 mmoles) was added a solution of polyphosphoric acid ethyl ester and 1,2-dichloroethane (250 ml). The solution was heated at 75° C. for 4 hours with exclusion of moisture. The solution was cooled and poured into a mixture of ice-sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | ClCCl | 75 | 0.25 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1>ClCCl>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0ba9868a4412467886ba230e311bf0b1 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1>>Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 | C1(=CC=CC=C1)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1 | O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:28]2[c:27]3[c:22]1[cH:23][cH:24][cH:25][c:26]3[CH2:30][CH2:29]2.[NH:10]1[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([c:14]3[cH:15]... | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1 | Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Protection | OtherReaction | 98711646775885568a342f905905ff5ba0e597f682ac14122a128c5434eecc65 | cc3066bc8728393c812617a52db29f0bb6fceaa1e59ff8a41efec6544d2cffe9 | c1ccc(N2CCN(C3=Nc4ccccc4N4CCc5cccc3c54)CC2)cc1 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | 68 | [{"value": 68.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 40.6 g (0.250 mole) of N-phenylpiperazine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | c1cc2c3c(c1)CNc1ccccc1N3CC2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.c1ccccc1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93613dc9f48943e2bff8d01f1f002984 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1>>Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 | C(C1=CC=CC=C1)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CC2=CC=CC=C2)C=CC=C4CC3)C=C1 | O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:29]2[c:28]3[c:23]1[cH:24][cH:25][cH:26][c:27]3[CH2:31][CH2:30]2.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH2:1... | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1 | Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Protection | OtherReaction | 98711646775885568a342f905905ff5ba0e597f682ac14122a128c5434eecc65 | cc3066bc8728393c812617a52db29f0bb6fceaa1e59ff8a41efec6544d2cffe9 | c1ccc(CN2CCN(C3=Nc4ccccc4N4CCc5cccc3c54)CC2)cc1 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 44.1 g (0.250 mole) of N-benzylpiperazine, followed by 14.2 g (0.0750 mole) of titanium tetrachloride. The m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | c1cc2c3c(c1)CNc1ccccc1N3CC2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.c1ccccc1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e14a8dbd106648d2905843dffce31170 | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | C(CC)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1 | [CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:26][CH2:27]1.O=[C:8]1[NH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[N:17]2[CH2:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][c:24]1[c:25]32>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:8]2=[N:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[N:17]3[CH2:18... | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 237f558d3d4dc4c7b9112e11c22321b33ed2e8f12d9e26cb655dd9b67be9c0e9 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:4]:[c:3]1:[c:5]-[#7:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2)=[N;H0;D2;+0:2]-1 | 30.1 | [{"value": 30.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.1, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated until a solution resulted. Then there was added 32.1 g (0.25 mole) of N-propylpiperazine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1ad10de5b78b4bdf9211708118c4d309 | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | CCOC(=O)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C(=O)OCC)C=CC=C4CC3)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:28][CH2:29]1.O=[C:10]1[NH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]2[N:19]2[CH2:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][c:26]1[c:27]32>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10]2=[N:11][c:12]3[cH:13][c:14]([Br:15])[cH:16][c... | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 237f558d3d4dc4c7b9112e11c22321b33ed2e8f12d9e26cb655dd9b67be9c0e9 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:4]:[c:3]1:[c:5]-[#7:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2)=[N;H0;D2;+0:2]-1 | null | [] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.025 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml toluene was heated under nitrogen until a solution resulted. Then there was added 39.6 g (0.250 mole) of ethyl N-piperazinocarboxylate followed by 14.2 g (0.075 mole) of titanium tetrachloride. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e9900028a3e64abb947a008cb915a7e1 | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1>>CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 | ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1>>ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Cl:20])[cH:21][c:22]2[c:23]43)[CH2:24][CH2:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[n:14]3[cH:15][cH:16][c:17]4[cH:18][c:19]([Cl:20])[cH:2... | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11])-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[N;H0;D3;+0:14]-2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[n;H0;D3;+0:14]:2-1 | 63.7 | [{"value": 63.0, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (6 g, 17 mmoles), in chloroform (150 ml) was added manganese dioxide (10.5 g). The mixture was heated under reflux for 24 hours. The mixture was cooled, filtered and the solid was washed with dichloromethane (20... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-436f9d4d56d4444ca9533632a7256525 | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2>>Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 | CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1.CN1CCNCC1>>CC=1C=C2C=3N(C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4)CCC3C1 | [NH:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1.O=[C:9]1[NH:8][c:6]2[c:5]3[c:4]([cH:3][c:2]([CH3:1])[cH:7]2)[CH2:25][CH2:24][N:23]3[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19... | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ebdcff6ea69ef8e3f8b8452dbdc2ecd5ea17480cbfbc99d1fe4894ddf896c9e5 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1cc2c3c(c1)N=C(N1CCNCC1)c1ccccc1N3CC2 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | null | null | 30 | MINUTE | A solution of 4-methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one (3.6 g, 14.3 mmoles), N-methylpiperazine (16 ml) and toluene (350 ml) was heated to 110° C. Titanium tetrachloride (4.3 ml) was added in three portions in two minute intervals. The mixture was heated under reflux for two hours and coole... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2c(c1)CNc1cccc3c1N2CC3 | C1C[NH]CC[NH]1.C1=Nc2cccc3c2N(CC3)c2ccccc21 | C1C[NH]CC[NH]1.C1=Nc2cccc3c2N(CC3)c2ccccc21 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.5 | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f7516339756740c0a28c8861e84e7229 | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3>>Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 | CC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.CC1CCNCC1>>CC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][CH2:16]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[cH:7]2)[N:23]2[c:22]3[c:17]1[cH:18][cH:19][cH:20][c:21]3[CH2:25][CH2:24]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:... | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3 | Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 98d409ed27efd2986317a1caf6aa32bc5bb9b6fd20baa673c7140c501309393d | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCCCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9])-[C:13]-[C:14] | null | [] | null | null | 15 | MINUTE | A stirred mixture of 6.26 g (0.0250 mole) of 9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 24.8 g (0.250 mole) of 4-methylpiperidine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CCNCC1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fe13066693e84f94b9653cbc3fa3240f | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.CC1CCNCC1>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1 | [CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:24][CH2:25]1.O=[C:6]1[NH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]32>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20]... | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 98d409ed27efd2986317a1caf6aa32bc5bb9b6fd20baa673c7140c501309393d | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCCCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9])-[C:13]-[C:14] | 83 | [{"value": 83.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.73 g (0.0150 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 14.9 g (0.150 mole) of 4-methylpiperidine, followed by 8.54 g (0.045 mole) of titanium tetrachloride.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CCNCC1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | CC1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CC1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-da5ab91eda8345f9b310bc45ebd51614 | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | N1CCOCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCOCC2)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:22]2[c:21]3[c:16]1[cH:17][cH:18][cH:19][c:20]3[CH2:24][CH2:23]2>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1... | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 77cbbfcb360cf8ffc4d29995320470770d66e3cc49d169b2f4a9c075c5bb0e49 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1 | null | [] | null | null | null | null | A mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 21.8 g (0.250 mole) of morpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1COCCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1COCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1COCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | C1COCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCOCC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2e1e3cb5253b4e03a6ca1c4e3a64197f | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | N1CCSCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][S:13][CH2:14][CH2:15]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:22]2[c:21]3[c:16]1[cH:17][cH:18][cH:19][c:20]3[CH2:24][CH2:23]2>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][S:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1... | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 373ab209369d29aee2a31639c43788945ab59f851be2e4dc663048335aff1fdf | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#16:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#16:10]-[C:15]-[C:14]-1 | 88 | [{"value": 88.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCSCC2)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7.88 g (0.025 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 25.8 g (0.250 mole) of thiomorpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CSCCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CSCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CSCC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | C1CSCCN1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCSCC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-87bc5f6c4d4c476f8fd2af4fd4073b48 | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21>>CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 | BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12>>BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1 | O=[C:4]([N:2]([CH3:1])[CH3:3])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[N:13]2[CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][c:20]1[c:21]32 | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | C1=Nc2ccccc2N2CCc3cccc1c32 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C;D1;H3:14])-[C;D1;H3:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C;D1;H3:14])-[C;D1;H3:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 48 | [{"value": 48.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N(C)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10.8 g (0.030 mole) of N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea and 110 ml of phosphorus oxychloride, under nitrogen, was heated under reflux for 6 hours, with stirring, and then cooled to room temperature. The excess phosphorus oxychloride was removed under vacuum with gentle war... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21>P(=O)(Cl)(Cl)Cl>CN(C)C1=Nc2cc(Br)ccc2N2CCc3cccc1c32 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9f90a1beae2d4c59a31e373ad0b02378 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2>>Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1>>CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1 | O=[N+:8]([O-])[c:6]1[c:5]2[c:4]([cH:3][c:2]([CH3:1])[cH:7]1)[CH2:19][CH2:18][N:17]2[c:16]1[c:11]([C:9](O)=[O:10])[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([cH:7]1)[NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N:17]3[CH2:18][CH2:19]2 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | null | Cl.[Pd] | C(C)O | Functional Group Interconversion | OtherReaction | 94a1cafe2daeec29b33699cad8b97c79501dab2e65aa6ba6ba0ea111a1bd36c4 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Nc2cccc3c2N(CC3)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8](-[N+;H0;D3:9](=O)-[O-]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-[#7:6]-[c:5]:[c:3]-1:[c:4] | 66.6 | [{"value": 66.0, "product": "CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | To a solution of 2-(5-methyl-7-nitroindolin-1-yl)benzoic acid (9 g, 0.03 mole), conc. hydrochloric acid (several drops) and ethanol (200 ml) was added 5% palladium-charcoal (1.5 gm). The mixture was shaked under hydrogen (58 psi) for 30 hours. The solvent was removed and the residue was loaded onto a silica gel flash c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CNc1cccc3c1N2CC3 | c1ccc2c(c1)CNc1cccc3c1N2CC3 | Other | Cl.[Pd].C(C)O | null | 30 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2>Cl.[Pd].C(C)O>Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-48a037212ff84f66a30fe0afce7b08b4 | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21>>CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | C([O-])(O)=O.[Na+].CN(C(=O)Cl)C.Cl.NC1=C(C=CC(=C1)Br)N1CCC2=CC=CC=C12.C([O-])(O)=O.[Na+].CN(C(=O)Cl)C.O.C([O-])(O)=O.[Na+].CN(C(=O)Cl)C>>BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12 | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21 | CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | c1ccc(N2CCc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 40.3 | [{"value": 40.0, "product": "BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.3, "product": "BrC=1C=CC(=C(C1)NC(=O)N(C)C)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a stirred mixture, under nitrogen, of 28.9 g (0.10 mole) of 1-(2-amino-4-bromophenyl)indoline hydrochloride and 16.8 g (0.20 mole) of anhydrous powdered sodium bicarbonate in 500 ml of chloroform was added a solution of 21.5 g (0.20 mole) of dimethylcarbamyl chloride in 25 ml of chloroform, over a 10 minute period. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)(Cl)Cl | null | 0.166667 | CN(C)C(=O)Cl.Nc1cc(Br)ccc1N1CCc2ccccc21>C(Cl)(Cl)Cl>CN(C)C(=O)Nc1cc(Br)ccc1N1CCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29f5254ffce34974b22ac7032000c5f7 | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 | ClCCl.BrC=1C=C2CCNC2=CC1.N1=C(C=C(C=C1C)C)C.FC1=C(C=CC=C1)[N+](=O)[O-]>>BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-] | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21 | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F | O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | 55 | [{"value": 55.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Bromoindoline (4.0 g, 0.02 mole), collidine (3.6 g, 0.03 mole), and o-fluoronitrobenzene (2.8 g, 0.02 mole) in xylene (25 ml) were heated at 185° C. (oil bath temperature) for 24 hours. The mixture was cooled to room temperature and poured into dichloromethane. The dichloromethane solution was washed with 1N hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | C=1(C(=CC=CC1)C)C | null | null | Brc1ccc2c(c1)CCN2.O=[N+]([O-])c1ccccc1F>C=1(C(=CC=CC1)C)C>O=[N+]([O-])c1ccccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a49a0ffb48db4738a1beaed2e1be1dd6 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-]>>Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | [OH-].[K+].C(CO)O.CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C#N)C=CC=C1.ClCCl>>CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1 | N#[C:18][c:17]1[c:12]([N:11]2[c:5]3[c:4]([cH:3][c:2]([CH3:1])[cH:10][c:6]3[N+:7](=[O:8])[O-:9])[CH2:22][CH2:21]2)[cH:13][cH:14][cH:15][cH:16]1.OCC[OH:19].[OH-:20]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([N+:7](=[O:8])[O-:9])[cH:10]1)[N:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18](=[O:19])[OH:20])[CH2:21][CH2:22]2 | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-] | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 | null | null | O | Acylation | OtherReaction | 5e76f9eb1645dffa65f7e1b9c084dfced9f3cb65f8b76df935c174c7208ba236 | 3746af5ef2d46561e999a498fd7e2fe230c1b687b933f9146ccf2b5206980b7a | c1ccc(N2CCc3ccccc32)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C-C-[OH;D1;+0:5].[OH-;D0:6]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:2](:[c:3]):[c:4] | 32 | [{"value": 32.0, "product": "CC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 175 | CELSIUS | null | null | A stirred solution under nitrogen of potassium hydroxide (30 g, 0.53 mole) in ethylene glycol (250 ml) and water (35 ml) was heated to 175° C., at which temperature there was added 2-(5-methyl-7-nitroindolin-1-yl)benzonitrile (26 g, 0.093 mole). After heating at 175° C. for 3 hours, the reaction mixture was cooled to r... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol.Primary alcohol | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | O | 175 | null | Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C#N)CC2.OCCO.[OH-]>O>Cc1cc2c(c([N+](=O)[O-])c1)N(c1ccccc1C(=O)O)CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9a20ead3ca914bdeaf8bbce1eb40aca9 | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F>>Cc1ccc2c(c1)CCN2c1ccccc1C#N | O.FC1=C(C#N)C=CC=C1.CC=1C=C2CCNC2=CC1.[H-].[Na+]>>CC=1C=C2CCN(C2=CC1)C1=C(C#N)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][NH:10]2.F[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][N:10]2[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18] | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F | Cc1ccc2c(c1)CCN2c1ccccc1C#N | null | null | ClCCl.CS(=O)C.CCCCCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[c:8]:[c:9]1:[c:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[c:10]:[c:9]-1:[c:8]):[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | A slurry of 5-methylindoline (31 g, 0.23 mole), sodium hydride (11.3 g, 60% in oil) and dimethylsulfoxide (120 ml) was stirred at room temperature for 1 hour. A solution of o-fluorobenzonitrile (31 gm, 0.25 mole) in dimethylsulfoxide (25 ml) was added dropwise at a temperature below 20° C. Upon completion of the additi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | HF | ClCCl.CS(=O)C.CCCCCC | null | 2 | Cc1ccc2c(c1)CCN2.N#Cc1ccccc1F>ClCCl.CS(=O)C.CCCCCC>Cc1ccc2c(c1)CCN2c1ccccc1C#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-acd7ac4d5a5744caa39dbf8193533fd0 | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21>>CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)N(C([O-])=O)C1=CC=CC=C1.CN1CCNCC1>>BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.[O-][C:6](=[O:7])[N:8](c1ccccc1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:1... | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | null | null | CCOCC | Acylation | OtherReaction | 496a5327138afc6b4ae1864000645ab6e93b3f844fab5c88cb790c49ef142972 | 81c44ebb5d5e93adc64259393ae8569fe75b140c0973e872fa8c9e9e1eafe33f | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O-]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-c1:c:c:c:c:c:1>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 90 | [{"value": 90.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate (11.5 g, 28.5 mmoles), N-methylpiperazine (15 ml) and ether (50 ml) was stirred at room temperature for 2 hours. The ether was evaporated. The mixture was filtered through a silica gel column (150 g), packed with dichloromethaane, and the column was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CCOCC | null | null | CN1CCNCC1.O=C([O-])N(c1ccccc1)c1ccccc1N1CCc2cc(Br)ccc21>CCOCC>CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-804949ae43174ef7bf8cecd9db4b4a69 | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F>>Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] | CC=1C=C2CCCNC2=CC1.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.FC1=C(C=CC=C1)[N+](=O)[O-]>>CC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-].NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)C.CC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1 | O=[C:8]([N:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1)[NH:16][c:17]1[c:22]([N:23]2[c:5]3[cH:4][cH:26][cH:19][cH:7][c:6]3[CH2:25][CH2:24]2)[cH:21][cH:20][c:28](F)[cH:33]1.[CH3:45][c:46]1[cH:47][cH:48][c:49]2[c:50]([cH:51]1)[CH2:52][CH2:53][CH2:54][NH:55]2.O=[C:1](O)/[CH:18]=[CH:3]\[C:2](=O)O.F[c:56]1[cH:57][cH... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F | Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6ca60e38e39dc88a021e139cfa12c405adbfe51666b70740d648bd3aae2b090e | 16420b30599f384e4953986cb91d4be65adeef1dc89e6bf44daf7e8a6def4af3 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].F-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c:9]:[c:10](-[#7:11]2-[C:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:14]3:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[c:19]:3-2):[c;H0;D3;+0:20](-[NH;D2;+0:21]-[C;H0;D3;+0:22](=O)-[#7:23](-[C:24])-[C:25]):[cH;D2;+0:26]:1.O-[C;H0;D3;+0... | null | [] | null | null | null | null | Starting with 6-methyl-1,2,3,4-tetrahydroquinoline and 2-fluoronitrobenzene and following steps 1a to 1f of Example 2, one may obtain, in sequence, 6-methyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-aminophenyl)-6-methyl-1,2,3,4-tetrahydroquinoline, N-[2-(6-methyl-1-phenyl)-1,2,3,4-tetrahydroquinolin-1-yl]-4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Primary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccc2c(c1)CCCN2.c1ccccc1 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc2c(c1)CCCN2.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1ccccc1F>>Cc1cc2c3c(c1)C(N1CCN(C)CC1)=Nc1ccccc1N3CCC2.Cc1ccc2c(c1)CCCN2c1ccccc1N.Cc1ccc2c(c1)CCCN2c1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f25e2397d0e44ac98f1fbbc579c59523 | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.BrC=1C=CC(=C(C1)[N+](=O)[O-])F>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12.BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[c:14]([N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:21][cH:22][cH:23][c:24]32)[cH:13][cH:32][c:30](F)[cH:29]1.O=[C:12](O)/[CH:37]=[CH:53]\[C:52](=O)O.F[c:34]1[c:28]([N+:27](=[O:45])[O-:47])[cH:49][c:10]([Br:11])[cH:9][cH:33]1.[NH:55]1[CH2:56][CH2:57][C... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | eaab8a83f2efcd21169149c49e508483a800d994959b618d733698350034b565 | 9e6d5d764f8c19082eefcd2319c75b4e9b2c9ac0a73bd7ddf3d30cc2416a7660 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH;D2;+0:4]-[C;H0;D3;+0:5](=O)-[#7:6](-[C:7])-[C:8]):[c:9](-[#7:10]2-[C:11]-[C:12]-[c;H0;D3;+0:13]3:[cH;D2;+0:14]:[cH;D2;+0:15]:[c:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18]:3-2):[cH;D2;+0:19]:[cH;D2;+0:20]:1.F-[c;H0;D3;+0:21]1:[cH;D2;+0:22]:[cH;D2;+0:23]:[c;H0;D3;+0:24](-[Br;D1;H... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 5-bromo-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-bromophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-bromophenyl)-1,2,3,4-tetrahydroquinolin-1-yl}... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Nitro group.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Nitro group.Primary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Br)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29477431647d4931a2f3595675113023 | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.ClC=1C=CC(=C(C1)[N+](=O)[O-])F>>ClC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)Cl)N1CCCC2=CC=CC=C12.ClC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10](F)[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:39]2[c:24]1[cH:43][cH:42][cH:41][cH:40]2.O=[C:18](O)/[CH:37]=[CH:33]\[C:32](=O)O.F[c:54]1[c:48]([N+:46](=[O:45])[O-:47])[cH:49][c:50]([Cl:11])[cH:52][cH:53]1.[NH:27]1[CH2:56][CH2:57][CH2... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2 | CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ac579b59724da5233aaa883b67f65306d5e022a843e2d4b7e900b46ba351ab53 | a2640ca05bc62a3cfd99a450eeb71d3465e1453d6bb0da848a76659e73bcaf93 | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[Cl;H0;D1;+0:5]):[c:6]:[c:7]:1-[#7;+:8].F-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[#7:13]2-[C:14]-[CH2;D2;+0:15]-[c;H0;D3;+0:16]3:[c:17]:[c:18]:[c:19]:[cH;D2;+0:20]:[c;H0;D3;+0:21]:3-2):[c:22](-[NH;D2;+0:23]-[C;H0;D3;+0:24](=O)-[#7:25](-[C:26])-[C:27]):[c:28]:1.O-[C;H0;D3;+0:... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 5-chloro-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-chloro-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-chlorophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-chlorophenyl)-1,2,3,4-tetrahydroquinolin-1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine.Tertiary amine.Tertiary amine | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccc2c(c1)CCCN2 | C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.O=C(O)/C=C\C(=O)O.O=[N+]([O-])c1cc(Cl)ccc1F.c1ccc2c(c1)CCCN2>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCCc4cccc2c43)CC1.Nc1cc(Cl)ccc1N1CCCc2ccccc21.O=[N+]([O-])c1cc(Cl)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3262cb51b9624327bd0dd8061914aac7 | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2>>Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 | N1CCCC2=CC=CC=C12.C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C.FC1=C(C=C(C=C1)C)[N+](=O)[O-]>>CC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].NC1=C(C=CC(=C1)C)N1CCCC2=CC=CC=C12.CC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:33]([NH:17][c:16]1[c:5]([N:6]2[CH2:7][CH2:8][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[cH:4][cH:3][c:2](F)[cH:18]1)[N:24]1[CH2:49][CH2:50][N:51]([CH3:52])[CH2:53][CH2:54]1.F[c:23]1[cH:22][cH:21][c:20]([CH3:19])[cH:38][c:34]1[N+:35](=[O:36])[O-:37].O=[C:1](O)/[CH:9]=[CH:39]\[C:40](=O)O.[CH2:25]1[NH:46][c:44]2[cH:... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2 | Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4387834540f1429daf07b17756144e2cbab865128a22f11dcca80dafe41cb1a6 | 691748feafd0861bf6396f8cf88bef6c995c57f8467567eff885149cff33e35a | c1ccc(N2CCCc3ccccc32)cc1.c1ccc(N2CCCc3ccccc32)cc1.c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].F-[c;H0;D3;+0:7]1:[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:11](=O)-[N;H0;D3;+0:12]2-[CH2;D2;+0:13]-[C:14]-[#7:15](-[C;D1;H3:16])-[C:17]-[CH2;D2;+0:18]-2):[c:19](-[#7:20]2-[C:21]-[CH2;D2;+0:22]-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]-2:[c:27]):[c:28]:[c:29]:1.O-[C;H0;D3... | null | [] | null | null | null | null | Starting with 1,2,3,4-tetrahydroquinoline and 2-fluoro-5-methylnitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinone, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinoline,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Urea.Secondary amine | Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2c(c1)CCC[NH]2.C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | null | null | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1.Cc1ccc(F)c([N+](=O)[O-])c1.O=C(O)/C=C\C(=O)O.c1ccc2c(c1)CCCN2>>Cc1ccc(N2CCCc3ccccc32)c(N)c1.Cc1ccc(N2CCCc3ccccc32)c([N+](=O)[O-])c1.Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CCC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1d615a0854084fa8ba74a799183ea8a6 | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2>>O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | FC1=C(C=CC=C1)[N+](=O)[O-].N1CCCC2=CC=CC=C12.N1=C(C=C(C=C1C)C)C>>[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12 | F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1.[NH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2 | O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | null | null | CC1=C(C(=CC=C1)C)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | de606d160ccc80ef355eabdb340e2f4f96955660dd0088ab61ab49bbb46dfbde | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 22.2 | [{"value": 22.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.2, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture, under nitrogen of 70.6 g (0.50 mole) of 1-fluoro-2-nitrobenzene, 133.2 g (1.00 mole) of 1,2,3,4-tetrahydroquinoline and 121.2 g (1.00 mole) of symmetrical collidine in 500 ml of 1,2,3-trimethylbenzene was refluxed (bp 178°) for 5 days. The mixture was concentrated in vacuo. The residue was taken up i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | CC1=C(C(=CC=C1)C)C | null | null | O=[N+]([O-])c1ccccc1F.c1ccc2c(c1)CCCN2>CC1=C(C(=CC=C1)C)C>O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4882086860284a1fbde1dfc444e2b6de | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)C)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1 | O=[C:9]([NH:8][c:6]1[c:5]([N:24]2[c:23]3[cH:17][cH:18][c:19]([Br:20])[cH:21][c:22]3[CH2:26][CH2:25]2)[cH:4][cH:3][c:2]([CH3:1])[cH:7]1)[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18... | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:14]-[#7:13](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12])-[C:15] | 53.9 | [{"value": 53.9, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.8, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide (3.3 g, 7.68 mmoles) and phosphorus oxychloride (30 ml) was heated at reflux for 25 minutes under nitrogen. The solution was cooled and excess phosphorus oxychloride was removed at 55°-60° C. under vacuum. Ice-chilled 2N-sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | Cc1ccc(N2CCc3cc(Br)ccc32)c(NC(=O)N2CCN(C)CC2)c1>P(=O)(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e6ad3859c7e94e6f8543e4cfc32c0e25 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>>Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 | BrN1C(CCC1=O)=O.CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC(=C2)C.ClCCl>>BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[N:9]1[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]31)[C:18]([N:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1)=[N:26]2.O=C1CCC(=O)N1[Br:8]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[N:9]1[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]31... | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br | Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 48755bf12d8d10c717a9c5a6c9ffd950e176b302684d6c5c7e94778ebdccddd5 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[#7:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[C;D1;H3:7]):[c:8] | 11.6 | [{"value": 11.6, "product": "BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.6, "product": "BrC=1C(=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of N-bromosuccinimide (0.91 g, 5.1 mmoles) in dimethylformamide (3 ml) was added dropwise to a solution of 6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (1.6 g, 4.8 mmoles) in dimethylformamide (30 ml) at 0°-3° C. The reaction mixture was stirred for 30 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1=Nc2ccccc2N2CCc3cccc1c32.C1CCNC1 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | CN(C=O)C | null | 0.5 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>CN(C=O)C>Cc1cc2c(cc1Br)N1CCc3cccc(c31)C(N1CCN(C)CC1)=N2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-74e05c2c9854445a8e4145015077fa4c | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 | BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)C)N4CCN(CC4)C)C1>>BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]3[c:26]1[N:25]2[CH2:24][CH2:23]3>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][c... | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]1:[c:3]2:[c:4]-[C:5]=[#7:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[N;H0;D3;+0:12]-2-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1>>[c:1]:[c:2]1:[cH;D2;+0:14]:[cH;D2;+0:13]:[n;H0;D3;+0:12]2:[c:3]:1:[c:4]-[C:5]=[#7:6]-[c:7](:[c:8]):[c;H0;D3;+0:9]-2:[c:10]:[c:11] | 42.7 | [{"value": 42.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.7, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)C)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (5.7 g, 13.8 mmoles) in chloroform (540 ml) was added manganese dioxide (25 gm), and the mixture was heated under reflux for 4 days. The mixture was filtered, and the filter cake washed with dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3c1N2CC3>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cc(Br)cc3ccn-2c13 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-86c94ea8aedb41b7a1f5fa8f5d4e6e4a | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl>>Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)C)[N+](=O)[O-].ClCCl>>Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC(=CC=C12)Br | O=[N+:17]([O-])[c:16]1[c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]32)[cH:4][cH:3][c:2]([CH3:1])[cH:18]1.ClC[Cl:19]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]32)[c:16]([NH2:17])[cH:18]1.[ClH:19] | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl | Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl | null | [Pt] | C(C)O | Miscellaneous | OtherReaction | c17f7e044bc060a97225c6ab4003d36cc5b3c62b420a125a65d55de2f342fd7a | 0910f6290f48bbc37d9ffbe0f747096afada90a5ba51c082c83c032e14c970e2 | c1ccc(N2CCc3ccccc32)cc1 | Cl-C-[Cl;H0;D1;+0:1].O=[N+;H0;D3:2](-[O-])-[c:3](:[c:4]):[c:5]>>[ClH;D0;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5] | 39 | [{"value": 39.0, "product": "Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a warm solution of 4-(5-bromo-1-indolinyl)-3-nitrotoluene (10 g, 0.03 mole) in dichloromethane (40 ml) and ethanol (160 ml) was added 1% platinum-on-carbon (2.0 gm). The mixture was shaken under hydrogen (57 psi) for 3.5 hours. The mixture was filtered and concentrated. The residue was dried under vacuum at 55° C. P... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | [Pt].C(C)O | null | 3.5 | Cc1ccc(N2CCc3cc(Br)ccc32)c([N+](=O)[O-])c1.ClCCl>[Pt].C(C)O>Cc1ccc(N2CCc3cc(Br)ccc32)c(N)c1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e608e546edba4941a2b95b36e8acb710 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21>>O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 | [N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC=CC=C12.BrN1C(CCC1=O)=O.O>>[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br | O=C1CCC(=O)N1[Br:17].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21 | O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(N2CCc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 68 | [{"value": 68.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)Br)N1CCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a solution of 1-(2-nitro-4-bromophenyl)indoline (15 g, 0.047 moles) in dimethylformamide (150 ml) at -10° C. was added dropwise a solution of N-bromosuccinimide (9.4 g, 0.054 mole) in dimethylformamide (50 ml) over 10 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. The solution was added slowly to... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C | 0 | 0.25 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1cc(Br)ccc1N1CCc2ccccc21>CN(C=O)C>O=[N+]([O-])c1cc(Br)ccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2ce819aca6f04395bd35af5077e02462 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | BrN1C(CCC1=O)=O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C.ClCCl>>BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:23][cH:24][c:25]32)[CH2:26][CH2:27]1.O=C1CCC(=O)N1[Br:22]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 84 | [{"value": 84.0, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 15 | MINUTE | N-Bromosuccinimide (2.6 g, 14.5 mmoles) was added to a solution of N-[2-(indolin-1-yl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide (5.0 g, 12.0 mmoles) in dimethylformamide (50 ml). The solution was stirred at room temperature for 15 minutes and at 60° C. for 15 minutes. The solution was cooled and poured into dich... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CC[NH]2.C1CCNC1 | c1ccc2c(c1)CC[NH]2 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C | 60 | 0.25 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1.O=C1CCC(=O)N1Br>CN(C=O)C>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1577a09d549645cab8527ad89e92fb7a | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Br)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19]... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 70.3 | [{"value": 70.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of N-[2-(5-bromo-1-indolinyl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide (12.3 g, 24.8 mmoles) and phosphorus oxychloride (250 ml) was heated under reflux for 1 hour. The reaction mixture was cooled and then concentrated at 50°-60° C. under vacuum. Ice-chilled sodium hydroxide solution (15%, 500 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | 0.333333 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a557c01681f3427aae102bfc86f521ce | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 | BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC(=C4)Br)N4CCN(CC4)C)C1>>BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][c:20]([Br:21])[cH:22][c:23]2[c:24]43)[CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3-[n:15]3[cH:16][cH:17][c:18]4[cH:19][c:2... | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11])-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[N;H0;D3;+0:14]-2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[n;H0;D3;+0:14]:2-1 | 75.2 | [{"value": 75.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC(=C4)Br)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture 4,9-dibromo-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]-benzodiazepine (4.5 g, 9.45 mmoles) and manganese(IV) dioxide (7.0 g) in chloroform (150 ml) was heated under reflux for 3.5 hours. An additional 4.5 g of manganese dioxide was added. The reaction mixture was stirred overnight at... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | 8 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cc(Br)cc2c43)CC1>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3-n3ccc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ab03dcd7288f4d6ab044db4a533c6a88 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21>>O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | [N+](=O)([O-])C1=C(C=CC=C1)N1CCCC2=CC=CC=C12.BrN1C(CCC1=O)=O.[OH-].[Na+]>>BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-] | O=C1CCC(=O)N1[Br:17].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21 | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 6a871f64bbdddc1ef7b40779396401fbf01bbad117bf7136b596038af1a81e74 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(N2CCCc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 82.7 | [{"value": 82.0, "product": "BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.7, "product": "BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution, under nitrogen, of 1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (76.3 g, 0.30 mole) in dimethylformamide (1000 ml) was cooled to -10° C. A solution of of N-bromosuccinimide (58.7 g, 0.33 mole) in dimethylformamide (250 ml) was added dropwise at such a rate as to keep the reaction temperature below ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C=O)C | null | null | O=C1CCC(=O)N1Br.O=[N+]([O-])c1ccccc1N1CCCc2ccccc21>CN(C=O)C>O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ecac07d9339d401fa8667c978f48221a | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21>>Nc1ccccc1N1CCCc2cc(Br)ccc21 | BrC=1C=C2CCCN(C2=CC1)C1=C(C=CC=C1)[N+](=O)[O-].C1=CC=CC=C1.C(C)O.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]21>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]21 | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21 | Nc1ccccc1N1CCCc2cc(Br)ccc21 | null | [Pt] | CCOCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 55 | [{"value": 55.0, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A Parr hydrogenation bottle was charged with 6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (16.7 g, 0.050 mole), 1% platinum-on-carbon (1 g), benzene (100 ml) and ethanol (100 ml). The mixture was shaken under an initial hydrogen pressure of 58 psi until uptake ceased. The mixture was then filtered to remove the ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pt].CCOCC | null | null | O=[N+]([O-])c1ccccc1N1CCCc2cc(Br)ccc21>[Pt].CCOCC>Nc1ccccc1N1CCCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c8d324b564d0491d91020d54c175f9db | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | C(\C=C/C(=O)O)(=O)O.CN1CCNCC1.CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl.NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br.C(C)N(CC)CC>>C(\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:26][CH2:27]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2... | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | null | null | ClCCl.C(C)O.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 61 | [{"value": 61.0, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A stirred solution, under nitrogen, of 1-(2-aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline (21.2 g, 0.070 mole) and triethylamine (10.1 g, 0.10 mole) in dichloromethane (200 ml) was cooled to 0° C. Then there was added dropwise phenylchloroformate (15.7 g, 0.10 mole) at such a rate as to keep the reaction temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.C(C)O.O | null | 0.5 | CN1CCNCC1.Nc1ccccc1N1CCCc2cc(Br)ccc21.O=C(Cl)Oc1ccccc1>ClCCl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4aa0b3c2bfd344ab8cd45f0cf5194902 | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 | CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC(=CC=C12)Br>>BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][CH2:17][c:18]4[cH:19]... | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | cb9ebe4be98e2ad3a66f5dbc95abbc6d189782ed4aae6aab9e7485070f90ad10 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 79 | [{"value": 79.0, "product": "BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "BrC=1C=C2CCCN3C2=C(C(=NC2=C3C=CC=C2)N2CCN(CC2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide (14.2 g, 0.0330 mole) in phosphorus oxychloride (250 ml) was heated under reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature and excess phosphorous oxychloride was removed at asp... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CCC[NH]2 | C1=Nc2ccccc2N2CCCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e4d5655a3184459db8a25be7ea081d4a | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2>>O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | BrC1=C(C=C(C=C1)Br)[N+](=O)[O-].N1CCCC2=CC=CC=C12.N1=C(C=C(C=C1C)C)C>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-] | Br[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Br:7])[cH:8][cH:9]1.[NH:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | null | null | CC1=C(C(=CC=C1)C)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | de606d160ccc80ef355eabdb340e2f4f96955660dd0088ab61ab49bbb46dfbde | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 18 | [{"value": 18.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture, under nitrogen, of 2,5-dibromonitrobenzene (140.5 g, 0.50 mole), 1,2,3,4-tetrahydroquinoline (133.2 g, 1.00 mole) and symmetrical collidine (121.2 g, 1.00 mole) in 1,2,3-trimethylbenzene (500 ml) as solvent was heated at 160°-165° C. for 7 days. The mixture was cooled to room temperature, filtered, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CC1=C(C(=CC=C1)C)C | null | null | O=[N+]([O-])c1cc(Br)ccc1Br.c1ccc2c(c1)CCCN2>CC1=C(C(=CC=C1)C)C>O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3ebfa7b3c5cb47f9828c4e52f9823e21 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21>>Nc1cc(Br)ccc1N1CCCc2ccccc21 | BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)[N+](=O)[O-].C(C)O>>BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21 | Nc1cc(Br)ccc1N1CCCc2ccccc21 | null | [Pt] | C1=CC=CC=C1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6.5 | HOUR | 1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (11.6 g, 0.035 mole) was dissolved in benzene (125 ml), and ethanol added (75 ml), followed by 1% platinum-on-charcoal (0.40 g). The mixture was shaken under an initial pressure of 56 psi for 6.5 hours. The mixture was filtered and the filtrate was evaporated at 50°... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pt].C1=CC=CC=C1 | null | 6.5 | O=[N+]([O-])c1cc(Br)ccc1N1CCCc2ccccc21>[Pt].C1=CC=CC=C1>Nc1cc(Br)ccc1N1CCCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c5fcc801525f4ce79084810a6244bdb8 | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl.C1(=CC=CC=C1)OC(=O)Cl.BrC1=CC(=C(C=C1)N1CCCC2=CC=CC=C12)N.C(C)N(CC)CC>>CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:26][CH2:27]1.[NH2:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[N:16]1[CH2:17][CH2:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2... | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | null | null | ClCCl.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 61.2 | [{"value": 61.0, "product": "CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1-(4-Bromo-2-aminophenyl)-1,2,3,4-tetrahydroquinoline (10.6 g, 0.035 mole) was dissolved on a steam bath in dichloromethane (150 ml). The solution was cooled to -5° C. in ice/methanol and triethylamine (5.01 g, 0.050 mole) was added in one portion, followed by a solution of phenylchloroformate (7.85 g, 0.050 mole) diss... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.O | null | 2 | CN1CCNCC1.Nc1cc(Br)ccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>ClCCl.O>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c02c5b01a8b142b7bc373ce591917ce7 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 | CN1CCN(CC1)C(=O)NC1=C(C=CC(=C1)Br)N1CCCC2=CC=CC=C12>>BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][CH2:18][c:19]... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | cb9ebe4be98e2ad3a66f5dbc95abbc6d189782ed4aae6aab9e7485070f90ad10 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CCC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 56 | [{"value": 56.0, "product": "BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "BrC=1C=CC2=C(N=C(C3=C4N2CCCC4=CC=C3)N3CCN(CC3)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A stirred solution of 4-methyl-N-[5-bromo-2-(1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide (8.6 g, 0.020 mole) in phosphorus oxychloride (200 ml) was heated under reflux under nitrogen for 6 hours. The reaction mixture was cooled to room temperature and excess phosphorus oxychloride was removed at aspira... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CCC[NH]2 | C1=Nc2ccccc2N2CCCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | 0.25 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bcb545cdbfe545d6b82f26fc5e2f0e56 | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>>CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 | CN1CCNCC1.NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12.C(C)N(CC)CC.C(\C=C/C(=O)O)(=O)O.CN1CCNCC1.C1(=CC=CC=C1)OC(=O)Cl>>C(\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21.Cl[C:6](Oc1ccccc1)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][CH2... | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1 | CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 | null | null | ClCCl.C(C)O.O | Acylation | OtherReaction | b6821e3ed8a606a69f9047f0f0c14a83254e5b692012114470ccd0e454afa8d3 | 8917b8ef2b26b2272c946143c570a5b9d9ca0dbc9a2daf393c5b57d5362fafc2 | O=C(Nc1ccccc1N1CCCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1 | 65.4 | [{"value": 65.0, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "C(\\C=C/C(=O)O)(=O)O.CN1CCN(CC1)C(=O)NC1=C(C=CC=C1)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A stirred solution, under nitrogen of 1-(2-aminophenyl)-1,2,3,4-tetrahydroquinoline (4.50 g, 0.020 mole), and triethylamine (3.04 g, 0.030 mole) in dichloromethane (50 ml) was cooled to 0° C. and phenylchloroformate (4.70 g, 0.030 mole) was added dropwise at such a rate such as to keep the reaction temperature below 5°... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Secondary amine | Urea | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl.C(C)O.O | null | 0.166667 | CN1CCNCC1.Nc1ccccc1N1CCCc2ccccc21.O=C(Cl)Oc1ccccc1>ClCCl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-da936a24b5e443619348b1d75c279850 | BrCc1ccccc1.O=c1cc(CO)occ1O>>O=c1cc(CO)occ1OCc1ccccc1 | OC=1C(C=C(OC1)CO)=O.[Na].C(C1=CC=CC=C1)Br>>OCC=1OC=C(C(C1)=O)OCC1=CC=CC=C1 | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[c:2]1[cH:3][c:4]([CH2:5][OH:6])[o:7][cH:8][c:9]1[OH:10]>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][OH:6])[o:7][cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrCc1ccccc1.O=c1cc(CO)occ1O | O=c1cc(CO)occ1OCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=c1ccocc1OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#8;a:9]:[c:10]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#8;a:9]:[c:10]):[c:4] | null | [] | 30 | CELSIUS | 8 | HOUR | 69 g (3 mmol) of sodium were dissolved in 5 l of methanol. Subsequently 425.3 g (3 mol) of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one was added and stirred at 30° C. until a clear solution was obtained. 595 g (3.5 mol) of benzyl bromide was then added and stirred for 1 hour under reflux. The warm, dark colored solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccocc1.c1ccccc1 | HBr | CO | 30 | 8 | BrCc1ccccc1.O=c1cc(CO)occ1O>CO>O=c1cc(CO)occ1OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4f60e5d4a7d141feb6cb2275775489e2 | O=c1cc(CO)occ1OCc1ccccc1>>O=C(O)c1cc(=O)c(OCc2ccccc2)co1 | OCC=1OC=C(C(C1)=O)OCC1=CC=CC=C1.CC(=O)C.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>O=C1C=C(OC=C1OCC1=CC=CC=C1)C(=O)O | [CH2:2]([OH:3])[c:4]1[cH:5][c:6](=[O:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][o:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](=[O:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][o:18]1 | O=c1cc(CO)occ1OCc1ccccc1 | O=C(O)c1cc(=O)c(OCc2ccccc2)co1 | null | null | O | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | O=c1ccocc1OCc1ccccc1 | [O;D1;H1:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[O;D1;H0:7]=[C;H0;D3;+0:2](-[O;D1;H1:1])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 5 | [{"value": 5.0, "product": "O=C1C=C(OC=C1OCC1=CC=CC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 232 g (1 mol) of 2-(hydroxymethyl)-5-(phenylmethoxy)-4H-pyran-4-one was put into a 10 l stirring flask containing 6.6 l of acetone and 400 ml of water. The clear solution was cooled to +5° C. by means of an ice bath. While maintaining the temperature at +5° C. to 10° C., 640 ml of Jones reagent (202 g CrO3, 600 ml wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | c1ccocc1.c1ccccc1 | Other | O | null | 2 | O=c1cc(CO)occ1OCc1ccccc1>O>O=C(O)c1cc(=O)c(OCc2ccccc2)co1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ee518e2f571a476b881d464d821846ae | O=C(O)c1cc(=O)c(OCc2ccccc2)co1.[NH4+]>>O=C(O)c1cc(=O)c(OCc2ccccc2)c[nH]1 | Cl.O=C1C=C(OC=C1OCC1=CC=CC=C1)C(=O)O.[OH-].[NH4+].[OH-].[NH4+]>>O=C1C=C(NC=C1OCC1=CC=CC=C1)C(=O)O | o1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6](=[O:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1.[NH4+:18]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](=[O:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][nH:18]1 | O=C(O)c1cc(=O)c(OCc2ccccc2)co1.[NH4+] | O=C(O)c1cc(=O)c(OCc2ccccc2)c[nH]1 | null | null | null | Functional Group Interconversion | OtherReaction | e7c486df1791b1a0991ac397f50e05e23945cbaabf714b0407c28e0bee45c8f6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=c1cc[nH]cc1OCc1ccccc1 | [#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):o:[cH;D2;+0:9]:1.[NH4+;D0:10]>>[#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[nH;D2;+0:10]:[cH;D2;+0:9]:1 | null | [] | null | null | 3 | HOUR | 300 g (1.22 mol) of 4-oxo-5-(phenylmethoxy)-4H-pyran-2-carboxylic acid was put into a flask and 5 l of 33% ammonium hydroxide was carefully added with stirring. The reaction mixture was then stirred under reflux. After 3 hours, one additional liter of 33% ammonium hydroxide was added slowly. Stirring was continued for ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HO- | null | null | 3 | O=C(O)c1cc(=O)c(OCc2ccccc2)co1.[NH4+]>>O=C(O)c1cc(=O)c(OCc2ccccc2)c[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1ae072769e534869ae592e459a10025e | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1>>O=C(O)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1 | C1(=CC=CC=C1)COC1=CC(=NC=C1OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1.[OH-].[K+].Cl>>C1(=CC=CC=C1)COC1=CC(=NC=C1OCC1=CC=CC=C1)C(=O)O | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15]([O:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][n:25]2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH... | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1 | O=C(O)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1 | null | null | O.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccncc2OCc2ccccc2)cc1 | [#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5] | 94.9 | [{"value": 94.9, "product": "C1(=CC=CC=C1)COC1=CC(=NC=C1OCC1=CC=CC=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid, phenylmethyl ester (1.60 g, 3.76 mmole) in 15 ml of tetrahydrofuran and 2.2 ml of water was added 4 ml of 1N aqueous potassium hydroxide. The mixture was stirred at room temperature overnight. Water (15 ml) was added and 1N hydrochloric acid was added s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | O.O1CCCC1 | null | 8 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1>O.O1CCCC1>O=C(O)c1cc(OCc2ccccc2)c(OCc2ccccc2)cn1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ddaa86d81d414c41b26b1fb192d4a590 | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1>>C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1 | FC(C(=O)O)(F)F.OC=1C(C=C(NC1)C(COP(=O)(N1[C@H]([C@@H](C1=O)NC(OC(C)(C)C)=O)C)O)=O)=O.[K].C1(=CC=CC=C1)OC>>FC(C(=O)O)(F)F.N[C@H]1[C@@H](N(C1=O)P(O)(=O)OCC(=O)C=1NC=C(C(C1)=O)O)C | CC(C)(C)OC(=O)[NH:4][C@H:3]1[C@H:2]([CH3:1])[N:7]([P:8](=[O:9])([OH:10])[O:11][CH2:12][C:13](=[O:14])[c:15]2[cH:16][c:17](=[O:18])[c:19]([OH:20])[cH:21][nH:22]2)[C:5]1=[O:6]>>[CH3:1][C@H:2]1[C@H:3]([NH2:4])[C:5](=[O:6])[N:7]1[P:8](=[O:9])([OH:10])[O:11][CH2:12][C:13](=[O:14])[c:15]1[cH:16][c:17](=[O:18])[c:19]([OH:20])... | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1 | C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1 | null | null | ClCCl.C1(=CC=CC=C1)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CO[PH](=O)N1CCC1=O)c1cc(=O)cc[nH]1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[#7:4](-[#15:5])-[C:6]-1=[O;D1;H0:7]>>[#15:5]-[#7:4]1-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:6]-1=[O;D1;H0:7] | null | [] | null | null | 3 | MINUTE | Trifluoroacetic acid (3 ml) was added to a 5° C. stirred suspension of (2S-trans)-[1-[[2-(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester, monopotassium salt (375 mg) in 4 ml of dry dichloromethane containing 1 ml of anisole. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1C[NH]C1.c1ccncc1 | HO- | ClCCl.C1(=CC=CC=C1)C | null | 0.05 | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1>ClCCl.C1(=CC=CC=C1)C>C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1cc(=O)c(O)c[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5ddfe65b2c3c413f8c72b9a144125d66 | NCc1ccccc1.O=c1cc(CO)occ1OCc1ccccc1>>O=c1cc(CO)n(Cc2ccccc2)cc1OCc1ccccc1 | OCC=1OC=C(C(C1)=O)OCC1=CC=CC=C1.C(C1=CC=CC=C1)N>>OCC=1N(C=C(C(C1)=O)OCC1=CC=CC=C1)CC1=CC=CC=C1 | [NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.o1[c:4]([CH2:5][OH:6])[cH:3][c:2](=[O:1])[c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:15]1>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][OH:6])[n:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:... | NCc1ccccc1.O=c1cc(CO)occ1OCc1ccccc1 | O=c1cc(CO)n(Cc2ccccc2)cc1OCc1ccccc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(Cc2ccccc2)cc1OCc1ccccc1 | [#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):o:[cH;D2;+0:8]:1.[NH2;D1;+0:9]-[C:10]-[c:11]>>[#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):[n;H0;D3;+0:9](-[C:10]-[c:11]):[cH;D2;+0:8]:1 | null | [] | null | null | 8 | HOUR | A solution of 2-(hydroxymethyl)-5-(phenylmethoxy)-4H-pyran-4-one (10.5 g, 45.3 mmol) in benzylamine (40 ml) and water (60 ml) was refluxed for four hours and then stirred overnight at room temperature. The resulting precipitate was collected and washed thoroughly with water to give 9.17 g (28.6 mmol) of 2-(hydroxymethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | O | null | 8 | NCc1ccccc1.O=c1cc(CO)occ1OCc1ccccc1>O>O=c1cc(CO)n(Cc2ccccc2)cc1OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9d7e217a7e7454187283988eab03121 | Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.O=C(Cl)CCl>>O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | ClCC(=O)Cl.C([O-])(O)=O.[K+].C(C1=CC=CC=C1)OC=1C=C(N)C=CC1OCC1=CC=CC=C1.ClCC(=O)Cl>>ClCC(=O)NC1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1 | [NH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([O:19]... | Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.O=C(Cl)CCl | O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | null | null | C(C)#N.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(COc2ccccc2OCc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 15 | MINUTE | To 7.7 g (25 mmol) of 3,4-dibenzyloxyaniline in 50 ml of 1:1 acetonitrile/water at 0° C. was added chloroacetyl chloride (3.0 ml) while keeping the pH at 6.5 with saturated aqueous potassium bicarbonate. When the pH remained constant for 15 minutes, an additional 3 ml of chloroacetyl chloride was added in small portion... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(C)#N.O | null | 0.25 | Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.O=C(Cl)CCl>C(C)#N.O>O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b6175eeac55148129b4ba8d24ceb3f10 | O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.[I-]>>O=C(CI)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | ClCC(=O)NC1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1.[I-].[Na+]>>ICC(=O)NC1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1 | Cl[CH2:3][C:2](=[O:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27]1.[I-:4]>>[O:1]=[C:2]([CH2:3][I:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([O:19][C... | O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.[I-] | O=C(CI)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccc(COc2ccccc2OCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[I-;H0;D0:6]>>[I;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | 60.4 | [{"value": 60.4, "product": "ICC(=O)NC1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide (8.98 g, 23.5 mmol) and sodium iodide (3.53 g, 23.5 mmol) in acetone (75 ml) was refluxed for two hours and allowed to stand overnight at room temperature. The reaction was filtered hot to remove the sodium iodide and a precipitate formed in the cold filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | CC(=O)C | null | 8 | O=C(CCl)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1.[I-]>CC(=O)C>O=C(CI)Nc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c98143d1d5664d11907a5d25e56ab78d | O=C(CCl)c1ccc(O)c(O)c1.O=S(=O)(O)O>>CC(=O)Oc1ccc(C(=O)CCl)cc1OC(C)=O | ClCC(=O)C1=CC(=C(C=C1)O)O.S(O)(O)(=O)=O>>ClCC(=O)C1=CC(=C(C=C1)OC(C)=O)OC(C)=O | [cH:1]1[cH:6][c:5]([OH:4])[c:14]([OH:15])[cH:13][c:8]1[C:9](=[O:10])[CH2:11][Cl:12].O=S(O)(=[O:3])[OH:18]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][Cl:12])[cH:13][c:14]1[O:15][C:16]([CH3:17])=[O:18] | O=C(CCl)c1ccc(O)c(O)c1.O=S(=O)(O)O | CC(=O)Oc1ccc(C(=O)CCl)cc1OC(C)=O | null | null | C(C)(=O)OC(C)=O | Acylation | OtherReaction | e6b75bad79b7942b597d0fe73c8de588d070768227b8cd5bb2afa4318810727b | 365b7cd484773b14f22600514702de9192a4215628a7fd006d20a290abddebd0 | c1ccccc1 | O-S(=O)(=[O;H0;D1;+0:1])-[OH;D1;+0:2].[C:3]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10](-[OH;D1;+0:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[C:3]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8](-[O;H0;D2;+0:9]-[C:14](-[C;D1;H3:15])=[O;H0;D1;+0:2]):[c:10](-[O;H0;D2;+0:11]-[C:16](-[CH3;D1;+0:13])=[O;... | null | [] | null | null | 1.5 | HOUR | A suspension of α-chloro-3',4'-dihydroxyacetophenone (9.33 g, 0.05 mole) in 78 ml of acetic anhydride was treated with 0.1 ml of concentrated sulfuric acid and stirred for 1.5 hours under an argon atmosphere. Initially, the reaction temperature rose to 40° C. and the starting material completely dissolved yielding a cl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol.Aromatic alcohol | Ketone.Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(C)(=O)OC(C)=O | null | 1.5 | O=C(CCl)c1ccc(O)c(O)c1.O=S(=O)(O)O>C(C)(=O)OC(C)=O>CC(=O)Oc1ccc(C(=O)CCl)cc1OC(C)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7b463b2c4b634287ae0797a585b376de | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1>>C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1 | FC(C(=O)O)(F)F.OC=1C=C(C=CC1O)C(COP(=O)(N1[C@H]([C@@H](C1=O)NC(OC(C)(C)C)=O)C)O)=O.[K].C1(=CC=CC=C1)OC>>FC(C(=O)O)(F)F.N[C@H]1[C@@H](N(C1=O)P(OCC(=O)C1=CC(=C(C=C1)O)O)(O)=O)C | CC(C)(C)OC(=O)[NH:4][C@H:3]1[C@H:2]([CH3:1])[N:7]([P:8](=[O:9])([OH:10])[O:11][CH2:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([OH:19])[c:20]([OH:21])[cH:22]2)[C:5]1=[O:6]>>[CH3:1][C@H:2]1[C@H:3]([NH2:4])[C:5](=[O:6])[N:7]1[P:8](=[O:9])([OH:10])[O:11][CH2:12][C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([OH:19])[c:20]([... | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1 | C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1 | null | null | ClCCl.C1(=CC=CC=C1)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CO[PH](=O)N1CCC1=O)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[#7:4](-[#15:5])-[C:6]-1=[O;D1;H0:7]>>[#15:5]-[#7:4]1-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:6]-1=[O;D1;H0:7] | null | [] | 0 | CELSIUS | 2 | HOUR | To a suspension of (2S-trans)-[1-[[2-(3,4-dihydroxyphenyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester, monopotassium salt (117 mg, 0.25 mmol) in 2.5 ml of dry dichloromethane was added 100 μl of anisole and the mixture was then cooled to 0° C. in an ice bath under ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1C[NH]C1.c1ccccc1 | HO- | ClCCl.C1(=CC=CC=C1)C | 0 | 2 | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1>ClCCl.C1(=CC=CC=C1)C>C[C@H]1[C@H](N)C(=O)N1P(=O)(O)OCC(=O)c1ccc(O)c(O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-412af217645140608f36a96b6d5ec195 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.COC(O)c1cc(=O)c(OCc2ccccc2)c[nH]1>>CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=C(C=C1)S(=O)(=O)O)C.O=C1C=C(NC=C1OCC1=CC=CC=C1)C(OC)O.C(C)OC(C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O>>O=C1C=C(NC=C1OCC1=CC=CC=C1)/C=C/C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[P:24]([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)([c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1.CO[CH:7]([c:8]1[cH:9][c:10](=[O:11])[c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][nH:22]1)[OH:23]>>[CH3:1][CH2:2][... | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.COC(O)c1cc(=O)c(OCc2ccccc2)c[nH]1 | CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | dc2bf74eb91f5ec6340caab7b789fd45bf85ac1ad21e11aa46bf35e19a64a278 | 8061c1ff870280a1885e4cffc5aa0ba5da0b35197945fe71cf719bb40e632df9 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=c1cc[nH]cc1OCc1ccccc1 | C-O-[CH;D3;+0:1](-[OH;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[P;H0;D4;+0:12](-[c:13](:[c:14]):[c:15])(-[c:16](:[c:17]):[c:18])-[c:19](:[c:20]):[c:21]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])/[CH;D2;+0:11]=[CH;D2;+0:1]/[c:3](:[c:4]):[#7;a:5]:[c:6].[O;H0;D1;+0:2]=[P;H0;D4;+0:12](... | null | [] | null | null | null | null | p-Toluenesulfonic acid (0.5 g), 6.26 g of 1,4-dihydro-4-oxo-2-[(hydroxy)(methoxy)methyl]-5-(phenylmethoxy)pyridine and 8.35 g of (triphenylphosphoranylidene)acetic acid ethyl ester were stirred for three hours at 70° C. A clear dark solution was formed. Evaporation of the solvent in vacuo yielded an oily residue of the... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary alcohol | Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.COC(O)c1cc(=O)c(OCc2ccccc2)c[nH]1>>CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1.O=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
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