dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-414b3cd795ae4514b86cda581bc75930 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>>O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | Cl.[OH-].[Na+].O1CCCC1.N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)OCC>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[n:17][c:18]1[O:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[n:17][c:18]1[O:19][CH2:20... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:7]:[#7;a:8] | 101.1 | [{"value": 100.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.1, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinecarboxylate (5.0 g, 13 mmol) in ethanol (25 mL) were added 10% aqueous sodium hydroxide solution (15 mL) and tetrahydrofuran (15 mL) and the mixture was heated under reflux for 30 min. The reaction mixture was allowed to cool to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>C(C)O>O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a86ffa6c30744c3a9d4d59f0fa7c72b0 | CC(C)(C)NCC(=O)O.O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>>CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | C(C)N(CC)CC.N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)O.C(C)(C)(C)NCC(=O)O.Cl.C(C)N=C=NCCCN(C)C>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[NH:9][CH2:8][C:6]([OH:5])=[O:7].O[C:10](=[O:11])[c:12]1[cH:13][n:14][c:15]([N:16]2[CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]32)[n:25][c:26]1[O:27][CH2:28][c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][NH:9][C:10](... | CC(C)(C)NCC(=O)O.O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | null | null | ClCCl.O.C(C)(=O)OCC | Acylation | OtherReaction | c54f479ffc9b41b0ea2c6a4101b6abf50916253f0008c07a4235fa679957b6cf | e12782c1b1214506ec032a591df2d8d697da45a1a2e11f536931ef1aa62d5cae | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#8:9].[C;D1;H3:10]-[C;H0;D4;+0:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[NH;D2;+0:14]-[C:15]-[C:16](=[O;D1;H0:17])-[OH;D1;+0:18]>>[#8:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:15]-[C:16](=[O;D1;H0:1... | 88 | [{"value": 88.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a suspension of ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinecarboxylate (5.0 g, 13 mmol) in ethanol (25 mL) were added 10% aqueous sodium hydroxide solution (15 mL) and tetrahydrofuran (15 mL) and the mixture was heated under reflux for 30 min. The reaction mixture was allowed to cool to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Secondary amine | Ester.Secondary amide | null | null | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO- | ClCCl.O.C(C)(=O)OCC | null | 18 | CC(C)(C)NCC(=O)O.O=C(O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>ClCCl.O.C(C)(=O)OCC>CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6eb1dbf01ab84dcea7514ad8fd9f045f | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1>>COc1ccc(COc2nc(N3CCc4ccccc43)ncc2C(=O)O)cc1 | Cl.[OH-].[Na+].O1CCCC1.N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)OCC>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)O | CC[O:26][C:24]([c:23]1[c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]2)[n:10][c:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[n:21][cH:22]1)=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[n:10][c:11]([N:12]3[CH2:13][CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:1... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1 | COc1ccc(COc2nc(N3CCc4ccccc43)ncc2C(=O)O)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:5]:[#7;a:6] | 96 | [{"value": 96.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-methoxybenzyl)oxy]-5-pyrimidinecarboxylate (5.5 g, 13.6 mmol) in ethanol (50 mL) were added 10% aqueous sodium hydroxide solution (30 mL) and tetrahydrofuran (30 mL) and the mixture was heated under reflux for 30 min. The reaction mixture was allowed to cool ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccc2c(c1)CC[NH]2 | Other | C(C)O | null | null | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1>C(C)O>COc1ccc(COc2nc(N3CCc4ccccc43)ncc2C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6f742a697e84fcea25f99e5bc06f882 | CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>>O=C(O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)OC(C)(C)C>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)O | CC(C)(C)[O:3][C:2](=[O:1])[CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][c:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[n:21][c:22]1[O:23][CH2:24][c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][c:11]([N:12]2[CH2:13][CH2:14][c:1... | CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | O=C(O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | null | null | FC(C(=O)O)(F)F.ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 82.9 | [{"value": 70.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)NCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | t-Butyl 2-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetate (210 mg, 0.4 mmol) was dissolved in trifluoroacetic acid-dichloromethane (4:1, 2 mL) and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure and the pr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | Other | FC(C(=O)O)(F)F.ClCCl | null | 0.25 | CC(C)(C)OC(=O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1>FC(C(=O)O)(F)F.ClCCl>O=C(O)CNC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f6a0eda9df54bc286584a94be20d1da | OC1CN(CCOCCc2ccc3sccc3c2)C1>>OC1CN(CCOCCc2ccc3sccc3c2)C1 | S1C=CC2=C1C=CC(=C2)CCOCCN2CC(C2)O.C(C)(=O)OCC.Cl>>Cl.S1C=CC2=C1C=CC(=C2)CCOCCN2CC(C2)O | [OH:2][CH:3]1[CH2:4][N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[s:15][cH:16][cH:17][c:18]3[cH:19]2)[CH2:20]1>>[OH:2][CH:3]1[CH2:4][N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[s:15][cH:16][cH:17][c:18]3[cH:19]2)[CH2:20]1 | OC1CN(CCOCCc2ccc3sccc3c2)C1 | OC1CN(CCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2cc(CCOCCN3CCC3)ccc2s1 | null | null | [] | null | null | 1 | HOUR | In 4.2 mL of ethyl acetate was dissolved 1.03 g of 1-{2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl}-3-azetidinol, and to the solution was added 0.86 mL of a 4.76 mol/L dried hydrogen chloride-ethyl acetate solution. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 hour. The crystals p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | null | 1 | OC1CN(CCOCCc2ccc3sccc3c2)C1>C(C)(=O)OCC>OC1CN(CCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c37f61942b04b9e986f75c9bbc72dab | ClCCCOCCc1ccc2ccsc2c1.OC1CNC1>>OC1CN(CCCOCCc2ccc3ccsc3c2)C1 | Cl.ClCCCOCCC1=CC2=C(C=CS2)C=C1.Cl.N1CC(C1)O.C([O-])([O-])=O.[K+].[K+]>>S1C=CC2=C1C=C(C=C2)CCOCCCN2CC(C2)O | Cl[CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][s:17][c:18]2[cH:19]1.[OH:1][CH:2]1[CH2:3][NH:4][CH2:20]1>>[OH:1][CH:2]1[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][s:17][c:18]3[cH:19]2)[CH2:20]1 | ClCCCOCCc1ccc2ccsc2c1.OC1CNC1 | OC1CN(CCCOCCc2ccc3ccsc3c2)C1 | null | null | CS(=O)C.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2ccc(CCOCCCN3CCC3)cc2s1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:4]-[C:5]-[C:6]-1 | 24.5 | [{"value": 24.5, "product": "S1C=CC2=C1C=C(C=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 2.5 | HOUR | In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 6-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the solution. The resulting mixture was stirred at 75° C. for 2.5 hours and then at 95° C. for 1.5 hours. After the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1 | HCl | CS(=O)C.O.C(C)(=O)OCC | 75 | 2.5 | ClCCCOCCc1ccc2ccsc2c1.OC1CNC1>CS(=O)C.O.C(C)(=O)OCC>OC1CN(CCCOCCc2ccc3ccsc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8299922f87304667a70416c850fe5f40 | OC1CN(CCCOCCc2ccc3ccsc3c2)C1>>OC1CN(CCCOCCc2ccc3ccsc3c2)C1 | S1C=CC2=C1C=C(C=C2)CCOCCCN2CC(C2)O.C(C)(=O)OCC.Cl>>Cl.S1C=CC2=C1C=C(C=C2)CCOCCCN2CC(C2)O | [OH:2][CH:3]1[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][s:18][c:19]3[cH:20]2)[CH2:21]1>>[OH:2][CH:3]1[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][s:18][c:19]3[cH:20]2)[CH2:21]1 | OC1CN(CCCOCCc2ccc3ccsc3c2)C1 | OC1CN(CCCOCCc2ccc3ccsc3c2)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2ccc(CCOCCCN3CCC3)cc2s1 | null | null | [] | null | null | 1 | HOUR | In 3.0 mL of ethyl acetate was dissolved 0.28 g of 1-{3-[2-(1-benzothiophen-6-yl)ethoxy]propyl}-3-azetidinol, and to the solution was added 0.35 mL of a 3.25 mol/L dried hydrogen chloride-ethyl acetate solution, after which the resulting mixture was stirred at room temperature for 1 hour. Then, the solvent was distille... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | null | 1 | OC1CN(CCCOCCc2ccc3ccsc3c2)C1>C(C)(=O)OCC>OC1CN(CCCOCCc2ccc3ccsc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecef0c41657b40eb8c5d05201a090f57 | ClCCCOCCc1ccc2sccc2c1.OC1CNC1>>OC1CN(CCCOCCc2ccc3sccc3c2)C1 | Cl.ClCCCOCCC=1C=CC2=C(C=CS2)C1.Cl.N1CC(C1)O.[OH-].[Na+]>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O | Cl[CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]2[s:15][cH:16][cH:17][c:18]2[cH:19]1.[OH:1][CH:2]1[CH2:3][NH:4][CH2:20]1>>[OH:1][CH:2]1[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[s:15][cH:16][cH:17][c:18]3[cH:19]2)[CH2:20]1 | ClCCCOCCc1ccc2sccc2c1.OC1CNC1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | CS(=O)C.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:4]-[C:5]-[C:6]-1 | 64.2 | [{"value": 64.2, "product": "S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 3.5 | HOUR | In 30 mL of dimethyl sulfoxide was dissolved 6.50 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and to the solution were added 5.60 g of 3-azetidinol hydrochloride and 15.3 mL of a 5.mol/L aqueous sodium hydroxide solution, after which the resulting mixture was stirred at 65° C. for 3.5 hours. After the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1 | HCl | CS(=O)C.O.C(C)(=O)OCC | 65 | 3.5 | ClCCCOCCc1ccc2sccc2c1.OC1CNC1>CS(=O)C.O.C(C)(=O)OCC>OC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29de0b52a98a445486f5088690f37733 | ClCCCOCCc1csc2ccccc12.OC1CNC1>>OC1CN(CCCOCCc2csc3ccccc23)C1 | Cl.ClCCCOCCC1=CSC2=C1C=CC=C2.FC(C(=O)O)(F)F.N1CC(C1)O.C([O-])([O-])=O.[K+].[K+]>>S1C=C(C2=C1C=CC=C2)CCOCCCN2CC(C2)O | Cl[CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]1[cH:12][s:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12.[OH:1][CH:2]1[CH2:3][NH:4][CH2:20]1>>[OH:1][CH:2]1[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]2[cH:12][s:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[CH2:20]1 | ClCCCOCCc1csc2ccccc12.OC1CNC1 | OC1CN(CCCOCCc2csc3ccccc23)C1 | null | null | CS(=O)C.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(CCOCCCN3CCC3)csc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:4]-[C:5]-[C:6]-1 | 48.1 | [{"value": 48.1, "product": "S1C=C(C2=C1C=CC=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 3-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 1.10 g of 3-azetidinol trifluoroacetate and 1.63 g of potassium carbonate were added to the solution, after which the resulting mixture was stirred at 70° C. for 2 hours. After the reaction mixture was cooled, water... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1 | HCl | CS(=O)C.O.C(C)(=O)OCC | 70 | 2 | ClCCCOCCc1csc2ccccc12.OC1CNC1>CS(=O)C.O.C(C)(=O)OCC>OC1CN(CCCOCCc2csc3ccccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8598c28fdc514017867c427eb14f28f6 | CC(=O)NC1CNC1.ClCCCOCCc1ccc2sccc2c1>>CC(=O)NC1CN(CCCOCCc2ccc3sccc3c2)C1 | ClCCCOCCC=1C=CC2=C(C=CS2)C1.N1CC(C1)NC(C)=O.O.C(C)(=O)OCC>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)NC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][NH:7][CH2:23]1.Cl[CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][c:14]1[cH:15][cH:16][c:17]2[s:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]3[s:18][cH:19][cH:20][c:21]3[cH:22]2... | CC(=O)NC1CNC1.ClCCCOCCc1ccc2sccc2c1 | CC(=O)NC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:4]-[C:5]-[C:6]-1 | 37.4 | [{"value": 37.4, "product": "S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 12 | HOUR | In 8 mL of N,N-dimethylformamide was dissolved 0.80 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 1.20 g of N-(3-azetidinyl)acetamide was added to the solution, after which the resulting mixture was stirred at 90° C. for 12 hours. After the reaction mixture was cooled, water and ethyl acetate were added there... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1 | HCl | CN(C=O)C | 90 | 12 | CC(=O)NC1CNC1.ClCCCOCCc1ccc2sccc2c1>CN(C=O)C>CC(=O)NC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c19260c8f004085a305aaa6379d532c | OC1CCN(CCOCCc2ccc3ccsc3c2)C1>>OC1CCN(CCOCCc2ccc3ccsc3c2)C1 | S1C=CC2=C1C=C(C=C2)CCOCCN2CC(CC2)O.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.S1C=CC2=C1C=C(C=C2)CCOCCN2CC(CC2)O | [OH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]3[cH:21][cH:22][s:23][c:24]3[cH:25]2)[CH2:26]1>>[OH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]3[cH:21][cH:22][s:23][c:24]3[cH:25]2)[CH2:26]1 | OC1CCN(CCOCCc2ccc3ccsc3c2)C1 | OC1CCN(CCOCCc2ccc3ccsc3c2)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2ccc(CCOCCN3CCCC3)cc2s1 | null | 66.8 | [{"value": 66.8, "product": "C(C(=O)O)(=O)O.S1C=CC2=C1C=C(C=C2)CCOCCN2CC(CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In 2.0 mL of ethyl acetate was dissolved 0.48 g of 1-{2-[2-(1-benzothiophen-6-yl)ethoxy]ethyl}-3-pyrrolidinol, and to the solution was added a solution of 0.15 g of oxalic acid in 2.8 mL of ethyl acetate. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 hour. The crystals precipi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | null | 1 | OC1CCN(CCOCCc2ccc3ccsc3c2)C1>C(C)(=O)OCC>OC1CCN(CCOCCc2ccc3ccsc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4377db9a738d41f1833ff69182bc5eb0 | OC1CCN(CCOCCc2cccc3sccc23)C1>>OC1CCN(CCOCCc2cccc3sccc23)C1 | S1C=CC2=C1C=CC=C2CCOCCN2CC(CC2)O.C(C)(=O)OCC.Cl>>Cl.S1C=CC2=C1C=CC=C2CCOCCN2CC(CC2)O | [OH:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[s:17][cH:18][cH:19][c:20]23)[CH2:21]1>>[OH:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[s:17][cH:18][cH:19][c:20]23)[CH2:21]1 | OC1CCN(CCOCCc2cccc3sccc23)C1 | OC1CCN(CCOCCc2cccc3sccc23)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc(CCOCCN2CCCC2)c2ccsc2c1 | null | null | [] | null | null | 1 | HOUR | In 5.0 mL of ethyl acetate was dissolved 0.63 g of 1-{2-[2-(1-benzothiophen-4-yl)ethoxy]ethyl}-3-pyrrolidinol, and to the solution was added 0.80 mL of a 3.25 mol/L dried hydrogen chloride-ethyl acetate solution. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 hour, after which ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | null | 1 | OC1CCN(CCOCCc2cccc3sccc23)C1>C(C)(=O)OCC>OC1CCN(CCOCCc2cccc3sccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d365d14f8cc54d7b9e28fcf831f9508d | O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1>>O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1 | S1C=C(C2=C1C=CC=C2)CCOCCN2C[C@@H](CC2)O.C(C)(=O)OCC.Cl>>Cl.S1C=C(C2=C1C=CC=C2)CCOCCN2C[C@@H](CC2)O | [OH:2][C@@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][s:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[CH2:21]1>>[OH:2][C@@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][s:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[CH2:21]1 | O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1 | O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(CCOCCN3CCCC3)csc2c1 | null | null | [] | null | null | 1 | HOUR | In 5.0 mL of ethyl acetate was dissolved 0.99 g of (3R)-1-{2-[2-(1-benzothiophen-3-yl)ethoxy]ethyl}-3-pyrrolidinol, and to the solution was added 1.10 mL of a 3.25 mol/L dried hydrogen chloride-ethyl acetate solution, after which the resulting mixture was stirred at room temperature for 1 hour. Then, the solvent was di... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | null | 1 | O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1>C(C)(=O)OCC>O[C@@H]1CCN(CCOCCc2csc3ccccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d4bc93aa5fa4c8bb1255f36b8f6217a | O=C(O)C(=O)O>>O=C(O)C(=O)O.O=C(O)C(=O)O | S1C=CC2=C1C=CC(=C2)CCOCCN2CC(CC2)N.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCN2CC(CC2)N | [O:21]=[C:22]([OH:23])[C:24](=[O:25])[OH:29]>>[O:21]=[C:22]([OH:23])[C:24](=[O:25])[OH:26].[O:27]=[C:28]([OH:29])[C:30](=[O:31])[OH:32] | O=C(O)C(=O)O | O=C(O)C(=O)O.O=C(O)C(=O)O | null | null | C(C)(=O)OCC | Functional Group Addition | OtherReaction | 36e5bb43e493559689955448a76da4d3590058140e444b07c812b01722459df4 | 172f642b99e787a8440acc81dbe0e78f5046ee01971579b6b561a60e52836756 | null | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:6].[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;D1;H1:10] | 89.6 | [{"value": 89.6, "product": "C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCN2CC(CC2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In 3.0 mL of ethyl acetate was dissolved 0.71 g of 1-{2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl}-3-pyrrolidinamine, and to the solution was added a solution of 0.44 g of oxalic acid in 4.0 mL of ethyl acetate. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 hour. The crystals prec... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Carboxylic acid.Carboxylic acid | null | null | null | Other | C(C)(=O)OCC | null | 1 | O=C(O)C(=O)O>C(C)(=O)OCC>O=C(O)C(=O)O.O=C(O)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c31ca254e6764d80bef08c91e727430e | ClCCCOCCc1ccc2sccc2c1.OC1CCNC1>>OC1CCN(CCCOCCc2ccc3sccc3c2)C1 | ClCCCOCCC=1C=CC2=C(C=CS2)C1.N1CC(CC1)O.C([O-])([O-])=O.[K+].[K+].O>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)O | Cl[CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]2[s:16][cH:17][cH:18][c:19]2[cH:20]1.[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:21]1>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[s:16][cH:17][cH:18][c:19]3[cH:20]2)[CH2:21]1 | ClCCCOCCc1ccc2sccc2c1.OC1CCNC1 | OC1CCN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2cc(CCOCCCN3CCCC3)ccc2s1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | 54.2 | [{"value": 54.2, "product": "S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 2.5 | HOUR | In 12 mL of N,N-dimethylformamide was dissolved 1.20 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the solution, after which the resulting mixture was stirred at 85° C. for 2.5 hours. After the reaction mixture was cooled, water and ethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2sccc2c1 | HCl | C(C)(=O)OCC.CN(C=O)C | 85 | 2.5 | ClCCCOCCc1ccc2sccc2c1.OC1CCNC1>C(C)(=O)OCC.CN(C=O)C>OC1CCN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ed3b1ea7a614475b0419ef504b3d359 | O=C([O-])NC1CCN(CCCOCCc2ccc3sccc3c2)C1>>NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | [OH-].[Na+].S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)NC([O-])=O.Cl.O>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)N | O=C([O-])[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[s:16][cH:17][cH:18][c:19]3[cH:20]2)[CH2:21]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[s:16][cH:17][cH:18][c:19]3[cH:20]2)[CH2:21]1 | O=C([O-])NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 017509a577522918fcd61b79a78a9b03bf1c8337f1c76e29f10765017faab5c3 | ac6f378f3e5e6c9b4b710d4e542f71f04a708f2a748ed8cf03d2a10006d6bc94 | c1cc2cc(CCOCCCN3CCCC3)ccc2s1 | O=C(-[O-])-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | null | null | In 7.0 mL of ethyl acetate was dissolved 1.12 g of tert-butyl=1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinylcarbamate, and 1.86 mL of 6 mol/L hydrochloric acid was added to the solution, after which the resulting mixture was heated under reflux for 1 hour. After the reaction mixture was cooled, water and e... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid | Primary amine | null | null | C1CC[NH]C1.c1ccc2sccc2c1 | Other | C(C)(=O)OCC | null | null | O=C([O-])NC1CCN(CCCOCCc2ccc3sccc3c2)C1>C(C)(=O)OCC>NC1CCN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4d75afba23847729c07533600501544 | CC(=O)Cl.NC1CCN(CCCOCCc2ccc3sccc3c2)C1>>CC(=O)NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)N.C(C)N(CC)CC.C(C)(=O)Cl.O>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]3[s:19][cH:20][cH:21][c:22]3[cH:23]2)[CH2:24]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]3[s:19][cH:20][cH:... | CC(=O)Cl.NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | CC(=O)NC1CCN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2cc(CCOCCCN3CCCC3)ccc2s1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[#7:4]-[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:8] | null | [] | -60 | CELSIUS | 1 | HOUR | In 5 mL of methylene chloride was dissolved 0.50 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine, and the solution was cooled to −60° C., after which 0.27 mL of triethylamine and 0.14 mL of acetyl chloride were added to the solution and the resulting mixture was stirred at room temperature for 1 hou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccc2sccc2c1 | HCl | C(C)(=O)OCC.C(Cl)Cl | -60 | 1 | CC(=O)Cl.NC1CCN(CCCOCCc2ccc3sccc3c2)C1>C(C)(=O)OCC.C(Cl)Cl>CC(=O)NC1CCN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a7265b00b8b42af8a454e0899c70e7e | Cl>>Cl.Cl | S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)N(C)C.C(C)(=O)OCC.Cl>>Cl.Cl.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(CC2)N(C)C | [ClH:24]>>[ClH:24].[ClH:25] | Cl | Cl.Cl | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 1 | HOUR | In 4.0 mL of ethyl acetate was dissolved 0.39 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-N,N-dimethyl-3-pyrrolidinamine, and to the solution was added 0.80 mL of a 3.25 mol/L dried hydrogen chloride-ethyl acetate solution. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 h... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | C(C)(=O)OCC | null | 1 | Cl>C(C)(=O)OCC>Cl.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbe896ef33d741a789d2585a245fe8e0 | OC1CN(CCCOCCc2ccc3sccc3c2)C1>>OC1CN(CCCOCCc2ccc3sccc3c2)C1 | S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O | [OH:9][CH:10]1[CH2:11][N:12]([CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]3[s:23][cH:24][cH:25][c:26]3[cH:27]2)[CH2:28]1>>[OH:9][CH:10]1[CH2:11][N:12]([CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]3[s:23][cH:24][cH:25][c:26]3[cH:27]2)[CH2:28]1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | null | 88.4 | [{"value": 88.4, "product": "C(\\C=C/C(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | In 56 mL of acetone was dissolved 8.00 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol, followed by adding thereto 3.19 g of maleic acid, and the resulting mixture was heated at 60° C. to effect dissolution. The reaction mixture was slowly cooled and then stirred at 5° C. for 30 minutes. The crystals pre... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccc2sccc2c1 | null | CC(=O)C | 5 | 0.5 | OC1CN(CCCOCCc2ccc3sccc3c2)C1>CC(=O)C>OC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-999758af2e41431487f6125cd148622b | O=[N+]([O-])O.OC1CN(CCCOCCc2ccc3sccc3c2)C1>>O=[N+]([O-])OC1CN(CCCOCCc2ccc3sccc3c2)C1 | S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O.C(C)(C)O.[N+](=O)(O)[O-]>>[N+](=O)([O-])OC1CN(C1)CCCOCCC=1C=CC2=C(C=CS2)C1 | O[N+:2](=[O:1])[O-:3].[OH:4][CH:5]1[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]3[s:18][cH:19][cH:20][c:21]3[cH:22]2)[CH2:23]1>>[O:1]=[N+:2]([O-:3])[O:4][CH:5]1[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]3[s:18][cH:19][cH:20][c:21]3[cH:22]2)... | O=[N+]([O-])O.OC1CN(CCCOCCc2ccc3sccc3c2)C1 | O=[N+]([O-])OC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC | Functional Group Addition | OtherReaction | 84236784676dc28db118aac7841a317ec45be5a4f9e45f8a29f304d5abfda72c | 809d131d00004833bf3f717e8d00ed32f4f82f9cd53d495fd6c3019fb3ac4a59 | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]1-[C:6]-[#7:7]-[C:8]-1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]1-[C:6]-[#7:7]-[C:8]-1 | null | [] | null | null | 1 | HOUR | In 20 mL of ethyl acetate was dissolved 10.0 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol, and 20 mL of isopropanol was added thereto, after which 2.60 mL of concentrated nitric acid (61%) was added dropwise thereto at room temperature. To the reaction mixture was added dropwise 60 mL of ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Secondary alcohol | Nitrate | null | null | C1C[NH]C1.c1ccc2sccc2c1 | HO- | C(C)(=O)OCC | null | 1 | O=[N+]([O-])O.OC1CN(CCCOCCc2ccc3sccc3c2)C1>C(C)(=O)OCC>O=[N+]([O-])OC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9712d4af6010476b93d689a4fc03c3f7 | OC1CN(CCCOCCc2ccc3sccc3c2)C1>>OC1CN(CCCOCCc2ccc3sccc3c2)C1 | S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O.C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)O>>C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O | [OH:11][CH:12]1[CH2:13][N:14]([CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][c:21]2[cH:22][cH:23][c:24]3[s:25][cH:26][cH:27][c:28]3[cH:29]2)[CH2:30]1>>[OH:11][CH:12]1[CH2:13][N:14]([CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][c:21]2[cH:22][cH:23][c:24]3[s:25][cH:26][cH:27][c:28]3[cH:29]2)[CH2:30]1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | null | 91.8 | [{"value": 91.8, "product": "C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 20 | MINUTE | In 40 mL of ethyl acetate was dissolved 10.0 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol, and 5.15 g of L-tartaric acid and 40 mL of ethanol were added thereto, after which the resulting mixture was heated at 65° C. to effect dissolution. After the resulting solution was stirred at 50° C. for 20 minu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccc2sccc2c1 | null | C(C)(=O)OCC | 65 | 0.333333 | OC1CN(CCCOCCc2ccc3sccc3c2)C1>C(C)(=O)OCC>OC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a36078b27fbd4edfadf1e49381c9fdfa | OC1CN(CCCOCCc2ccc3sccc3c2)C1>>OC1CN(CCCOCCc2ccc3sccc3c2)C1 | C(C)(=O)OCC.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O.O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)(=O)OCC>>C(CC(O)(C(=O)O)CC(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O | [OH:14][CH:15]1[CH2:16][N:17]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][c:24]2[cH:25][cH:26][c:27]3[s:28][cH:29][cH:30][c:31]3[cH:32]2)[CH2:33]1>>[OH:14][CH:15]1[CH2:16][N:17]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][c:24]2[cH:25][cH:26][c:27]3[s:28][cH:29][cH:30][c:31]3[cH:32]2)[CH2:33]1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc2cc(CCOCCCN3CCC3)ccc2s1 | null | 89.8 | [{"value": 89.8, "product": "C(CC(O)(C(=O)O)CC(=O)O)(=O)O.S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1 | HOUR | In 14.4 mL of ethanol was dissolved 10.0 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol, followed by adding thereto 7.21 g of citric acid monohydrate, and the resulting mixture was heated at 50° C. to effect dissolution. To the resulting solution were added 35 mL of ethyl acetate and 5.6 mL of ethanol a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccc2sccc2c1 | null | C(C)O | 25 | 1 | OC1CN(CCCOCCc2ccc3sccc3c2)C1>C(C)O>OC1CN(CCCOCCc2ccc3sccc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-595bfc092f2a49439306456243cac199 | O=C([O-])c1ccccc1>>O=C(O)c1ccccc1 | C(C1=CC=CC=C1)(=O)[O-].C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.C(C1=CC=CC=C1)(=O)O | [O:9]=[C:10]([O-:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:9]=[C:10]([OH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | O=C([O-])c1ccccc1 | O=C(O)c1ccccc1 | null | null | C(C)(=O)OCC | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | c1ccccc1 | [O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | In 3 mL of ethyl acetate was dissolved 0.25 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinyl=benzoate, and 0.07 g of maleic acid was added thereto, after which the resulting mixture was heated to effect dissolution. The reaction mixture was cooled and the crystals precipitated were collected by filtration... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1 | null | C(C)(=O)OCC | null | null | O=C([O-])c1ccccc1>C(C)(=O)OCC>O=C(O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-969acd0d0f2e422ba1015f8da344886c | O=C([O-])[O-]>>O=C(O)O | C([O-])([O-])=O.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.C(O)(O)=O | [O:7]=[C:8]([O-:9])[O-:10]>>[O:7]=[C:8]([OH:9])[OH:10] | O=C([O-])[O-] | O=C(O)O | null | null | C(C)(=O)OCC | Reduction | OtherReaction | be157931565f540889277a3faa1ed27df718fe76a81ac3f6973c07125d76f0ac | f247282e74ebd60e9d676bc22aeaf494bf5c7fa950ed844ada9c6b18709f4cfa | null | [O-;H0;D1:1]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4]>>[O;D1;H0:4]=[C:2](-[OH;D1;+0:1])-[OH;D1;+0:3] | null | [] | null | null | null | null | In 7 mL of ethyl acetate was dissolved 0.31 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinyl=methyl=carbonate, and to the solution was added a solution of 0.10 g of oxalic acid in 1 mL of ethyl acetate, after which the resulting mixture was stirred at room temperature. The crystals precipitated were colle... | 10.6084/m9.figshare.5104873.v1 | null | null | Carbonic Acid | null | null | null | null | C(C)(=O)OCC | null | null | O=C([O-])[O-]>C(C)(=O)OCC>O=C(O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-418ee189789f42de93dac3320c3963b2 | ClCCCN1CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1.OCCc1ccc2sccc2c1>>c1ccc(C(OC2CN(CCCOCCc3ccc4sccc4c3)C2)(c2ccccc2)c2ccccc2)cc1 | [OH-].[Na+].O.S1C=CC2=C1C=CC(=C2)CCO.C(C(=O)O)(=O)O.ClCCCN1CC(C1)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)OC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Cl[CH2:12][CH2:11][CH2:10][N:9]1[CH2:8][CH:7]([O:6][C:5]([c:4]2[cH:3][cH:2][cH:1][cH:39][cH:38]2)([c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:25]1.[OH:13][CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]2[s:20][cH:21][cH:22][c:23]2[cH:24]1>>[cH:1]1[cH:2][cH:3][c:4]([C:5]([O:6]... | ClCCCN1CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1.OCCc1ccc2sccc2c1 | c1ccc(C(OC2CN(CCCOCCc3ccc4sccc4c3)C2)(c2ccccc2)c2ccccc2)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(C(OC2CN(CCCOCCc3ccc4sccc4c3)C2)(c2ccccc2)c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 36.7 | [{"value": 36.7, "product": "S1C=CC2=C1C=CC(=C2)CCOCCCN2CC(C2)OC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a mixture of 0.4 mL of toluene and 7 mL of a 50% (W/V) aqueous sodium hydroxide solution was suspended 0.54 g of 2-(1-benzothiophen-5-yl)-1-ethanol, followed by adding thereto 1.45 g of 1-(3-chloropropyl)-3-(trityloxy)azetidine oxalate and 0.03 g of tetra-n-butylammonium bromide, and the resulting mixture was reflux... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.C1C[NH]C1.c1ccc2sccc2c1.c1ccccc1.c1ccccc1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | null | null | ClCCCN1CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1.OCCc1ccc2sccc2c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>c1ccc(C(OC2CN(CCCOCCc3ccc4sccc4c3)C2)(c2ccccc2)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1be6064558b4bf8b5568e3fb5a9afe1 | O=S(Cl)Cl.OCCCOCCc1cccc2sccc12>>ClCCCOCCc1cccc2sccc12 | S(=O)(Cl)Cl.CN(C=O)C.S1C=CC2=C1C=CC=C2CCOCCCO>>ClCCCOCCC1=CC=CC2=C1C=CS2 | O=S(Cl)[Cl:1].O[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[s:13][cH:14][cH:15][c:16]12>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[s:13][cH:14][cH:15][c:16]12 | O=S(Cl)Cl.OCCCOCCc1cccc2sccc12 | ClCCCOCCc1cccc2sccc12 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc2sccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | In 7.0 mL of methylene chloride was dissolved 1.40 g of 3-[2-(1-benzothiophen-4-yl)ethoxy]-1-propanol, followed by adding thereto 1.10 mL of thionyl chloride and 0.05 mL of N,N-dimethylformamide, and the resulting mixture was heated under reflux for 5 hours. Then, the solvent was distilled off under reduced pressure. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2sccc2c1 | HCl | C(Cl)Cl | null | null | O=S(Cl)Cl.OCCCOCCc1cccc2sccc12>C(Cl)Cl>ClCCCOCCc1cccc2sccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-346526e67551456a954df0d7a3a26aaa | BrBr.COc1cc(O)c(C(C)=O)cc1CCO>>COc1cc(O)c(C(=O)CBr)cc1CCO | OC1=C(C=C(C(=C1)OC)CCO)C(C)=O.BrBr>>BrCC(=O)C1=C(C=C(C(=C1)CCO)OC)O | Br[Br:11].[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([C:8](=[O:9])[CH3:10])[cH:12][c:13]1[CH2:14][CH2:15][OH:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12][c:13]1[CH2:14][CH2:15][OH:16] | BrBr.COc1cc(O)c(C(C)=O)cc1CCO | COc1cc(O)c(C(=O)CBr)cc1CCO | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 1 | HOUR | In 100 mL of methylene chloride was dissolved 10.0 g of 1-[2-hydroxy-5-(2-hydroxyethyl)-4-methoxyphenyl]-1-ethanone, and 2.94 mL of bromine was added dropwise to the solution, after which the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and the organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)Cl | null | 1 | BrBr.COc1cc(O)c(C(C)=O)cc1CCO>C(Cl)Cl>COc1cc(O)c(C(=O)CBr)cc1CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8991ecdc659942da8003d54feb40c8a9 | COc1cc(O)c(C(=O)CBr)cc1CCO>>COc1cc2occc2cc1CCO | BrCC(=O)C1=C(C=C(C(=C1)CCO)OC)O.C(C)(=O)[O-].[Na+].O.C(C)(=O)OCC>>COC1=CC2=C(C=CO2)C=C1CCO | O=[C:8]([CH2:7]Br)[c:9]1[c:5]([OH:6])[cH:4][c:3]([O:2][CH3:1])[c:11]([CH2:12][CH2:13][OH:14])[cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[o:6][cH:7][cH:8][c:9]2[cH:10][c:11]1[CH2:12][CH2:13][OH:14] | COc1cc(O)c(C(=O)CBr)cc1CCO | COc1cc2occc2cc1CCO | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 2da9ec5ab1bb705a33fb0061ef84e613754932d8ffd29c79fa3937eba563d240 | 34be63b8347def13f9b2ddbfcf4b202eb6ddd796689bad590c9b9a590dcf2e49 | c1ccc2occc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7]>>[c:4]:[c:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[o;H0;D2;+0:6]:[c:5]:1:[c:7] | 13.6 | [{"value": 13.6, "product": "COC1=CC2=C(C=CO2)C=C1CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In 70 mL of methanol was dissolved 16.4 g of the aforesaid 2-bromo-1-[2-hydroxy-5-(2-hydroxyethyl)-4-methoxyphenyl]-1-ethanone, and 17.3 g of sodium acetate was added to the solution, after which the resulting mixture was heated under reflux for 5 minutes. After the reaction mixture was cooled, water and ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | null | c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1 | HBr | CO | null | 1 | COc1cc(O)c(C(=O)CBr)cc1CCO>CO>COc1cc2occc2cc1CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc55f392ceb0476c8a806ab8be985509 | CC(C)(C)[O-].COc1cc2occc2cc1CCO.O>>COc1cc2occc2cc1CCOCC(=O)O | COC1=CC2=C(C=CO2)C=C1CCO.CC(C)([O-])C.[K+].O.Cl>>COC1=CC2=C(C=CO2)C=C1CCOCC(=O)O | C[C:16](C)([CH3:15])[O-:17].[CH3:1][O:2][c:3]1[cH:4][c:5]2[o:6][cH:7][cH:8][c:9]2[cH:10][c:11]1[CH2:12][CH2:13][OH:14].[OH2:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[o:6][cH:7][cH:8][c:9]2[cH:10][c:11]1[CH2:12][CH2:13][O:14][CH2:15][C:16](=[O:17])[OH:18] | CC(C)(C)[O-].COc1cc2occc2cc1CCO.O | COc1cc2occc2cc1CCOCC(=O)O | null | null | C(C)(=O)OCC.CN(C=O)C.C(C)(C)(C)O | Acylation | OtherReaction | c4679d53061ae476f752344ab868635aed021ddab8392c06607f96431d580971 | 19a4da83f461c84e2e5fabedc9560bdbecd9f02af3fb120f1f68c45baa4223dc | c1ccc2occc2c1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[O-;H0;D1:3].[C:4]-[C:5]-[OH;D1;+0:6].[OH2;D0;+0:7]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[OH;D1;+0:7] | null | [] | null | null | 30 | MINUTE | In a mixture of 7.0 mL of tert-butanol and 1.75 mL of N,N-dimethylformamide was dissolved 1.75 g of 2-(6-methoxy-1-benzofuran-5-yl)-1-ethanol, and 2.2 g of 1-chloroacetylpiperidine and 1.54 g of potassium tert-butoxide were added to the solution under ice-cooling, after which the resulting mixture was stirred at the sa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid.Ether | null | null | c1ccc2occc2c1 | Other | C(C)(=O)OCC.CN(C=O)C.C(C)(C)(C)O | null | 0.5 | CC(C)(C)[O-].COc1cc2occc2cc1CCO.O>C(C)(=O)OCC.CN(C=O)C.C(C)(C)(C)O>COc1cc2occc2cc1CCOCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-955645a8fc6a4fd1b0144ff9ec621f18 | BrC(Br)(Br)Br.OCCCOCCc1ccc2sccc2c1>>BrCCCOCCc1ccc2sccc2c1 | O.S1C=CC2=C1C=CC(=C2)CCOCCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br>>BrCCCOCCC=1C=CC2=C(C=CS2)C1 | BrC(Br)(Br)[Br:1].O[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[s:12][cH:13][cH:14][c:15]2[cH:16]1>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[s:12][cH:13][cH:14][c:15]2[cH:16]1 | BrC(Br)(Br)Br.OCCCOCCc1ccc2sccc2c1 | BrCCCOCCc1ccc2sccc2c1 | null | null | C(Cl)Cl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccc2sccc2c1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4] | 76.2 | [{"value": 76.2, "product": "BrCCCOCCC=1C=CC2=C(C=CS2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In 40 mL of methylene chloride was dissolved 2.00 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-propanol, and 5.55 g of triphenylphosphine was added to the solution, after which a solution of 8.42 g of carbon tetrabromide in 10 mL of methylene chloride was added dropwise thereto under ice-cooling and the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccc2sccc2c1 | HBr | C(Cl)Cl | null | 0.333333 | BrC(Br)(Br)Br.OCCCOCCc1ccc2sccc2c1>C(Cl)Cl>BrCCCOCCc1ccc2sccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a0bf0cfcfb549828ce701f9b04db88c | COc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl>>COc1cc2nncc(Cl)c2cc1OC.Cl | OC1=CN=NC2=CC(=C(C=C12)OC)OC.S(=O)(Cl)Cl>>Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OC | O[c:9]1[cH:8][n:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12][c:11]21.O=S([Cl:10])[Cl:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][n:7][cH:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15].[ClH:16] | COc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl | COc1cc2nncc(Cl)c2cc1OC.Cl | null | CN(C)C=O | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 03b874008d2d9f5aba975279a4bc336c747d49b5ebd324344c173d0995029d0d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2nnccc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[ClH;D0;+0:10] | null | [] | null | null | null | null | The starting material, 4-chloro-6,7-dimethoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-6,7-dimethoxycinnoline (1 g, 4.8 mmol) in thionyl chloride (20 ml) containing DMF (2 drops) at reflux for 3 hours. After cooling and evaporating the excess thionyl chloride, the solid was triturated with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | Other | CN(C)C=O | null | null | COc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl>CN(C)C=O>COc1cc2nncc(Cl)c2cc1OC.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0ab3c0fa52b4471a489048eafec37c1 | COc1cc(N)c(C(C)=O)cc1OC>>COc1cc2nncc(O)c2cc1OC | N(=O)[O-].[Na+].CC(=O)C1=CC(=C(C=C1N)OC)OC>>OC1=CN=NC2=CC(=C(C=C12)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:11]([C:9]([CH3:8])=[O:10])[cH:12][c:13]1[O:14][CH3:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][n:7][cH:8][c:9]([OH:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc(N)c(C(C)=O)cc1OC | COc1cc2nncc(O)c2cc1OC | null | null | C(C)(=O)O.S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | fb1f3fd767c7acf94e7fb16e7a5cc6bffbefcf96eb86616226124a2e8be227b7 | 9c8d3053f5ebe6f2f3a8561257bee960d9bcebbe98ad5c87d3c6a3d9577ea0fe | c1ccc2nnccc2c1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:8]>>[OH;D1;+0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[#7;a:9]:[n;H0;D2;+0:7]:[c:6](:[c:8]):[c:4]:1:[c:5] | 87.3 | [{"value": 87.0, "product": "OC1=CN=NC2=CC(=C(C=C12)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "OC1=CN=NC2=CC(=C(C=C12)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | The starting material, 4-hydroxy-6,7-dimethoxycinnoline was obtained by adding a solution of sodium nitrite (1.9 g, 27 mmol) to a solution of 2-amino-4,5-dimethoxyacetophenone (5 g, 0.025 mol) in acetic acid (90 ml) and sulphuric acid (15 ml) at a rate to maintain the temperature below 20° C. The mixture was heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | Other | C(C)(=O)O.S(O)(O)(=O)=O | 80 | null | COc1cc(N)c(C(C)=O)cc1OC>C(C)(=O)O.S(O)(O)(=O)=O>COc1cc2nncc(O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab4f8a23c5f44853b3e7c6c03e59182c | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1ccc(N)cc1O>>COCCOc1cc2nncc(Nc3ccc(C)c(O)c3)c2cc1OC | ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.OC=1C=C(N)C=CC1C.C(C)(C)O>>OC=1C=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=CC1C | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23][c:22]21.[NH2:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[c:19]([OH:20])[cH:21]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([CH3:18])[c:19]([OH:20])[c... | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1ccc(N)cc1O | COCCOc1cc2nncc(Nc3ccc(C)c(O)c3)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.4 g, 1.5 mmol) and 3-hydroxy-4-methylaniline (0.2 g, 1.6 mmol) in DMF (5 ml) was heated at 150° C. for 20 minutes. After cooling, isopropanol (15 ml) was added and the resulting solid filtered off, washed with isopropanol and dried under vacuum to give 4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1ccc(N)cc1O>CN(C)C=O>COCCOc1cc2nncc(Nc3ccc(C)c(O)c3)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2038e2c80790471a92c60a139f03a652 | COCCOc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl>>COCCOc1cc2nncc(Cl)c2cc1OC | OC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.S(=O)(Cl)Cl.CN(C)C=O>>ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC | O[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:16]([O:17][CH3:18])[cH:15][c:14]21.O=S(Cl)[Cl:13]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([Cl:13])[c:14]2[cH:15][c:16]1[O:17][CH3:18] | COCCOc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl | COCCOc1cc2nncc(Cl)c2cc1OC | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 03b874008d2d9f5aba975279a4bc336c747d49b5ebd324344c173d0995029d0d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2nnccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 74 | [{"value": 74.0, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The starting material 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline was obtained by heating a solution of 4-hydroxy-6-methoxy-7-(2-methoxyethoxy)cinnoline (7.8 g, 0.031 mol) in thionyl chloride (130 ml) containing DMF (0.8 ml) at 80° C. for 2 hours. After dilution with toluene, the mixture was evaporated to dryness. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | HCl | null | null | null | COCCOc1cc2nncc(O)c2cc1OC.O=S(Cl)Cl>>COCCOc1cc2nncc(Cl)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7456a49a4744a4b88f2eea3063a6601 | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Cl)cc1F>>COCCOc1cc2nncc(Nc3ccc(Cl)cc3F)c2cc1OC | ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.ClC1=CC(=C(N)C=C1)F>>ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C1)F | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23][c:22]21.[NH2:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]1[F:21]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[F:21])[... | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Cl)cc1F | COCCOc1cc2nncc(Nc3ccc(Cl)cc3F)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.4 g, 1.5 mmol), (prepared as described for the starting material in Example 2), and 4-chloro-2-fluoroaniline (282 μl, 2.5 mmol) in DMF (5 ml) was treated as described in Example 2, to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methoxyethoxy)cinnolin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Cl)cc1F>CN(C)C=O>COCCOc1cc2nncc(Nc3ccc(Cl)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e8621af0b5e4a71bd5b08d7280c5cb2 | COc1ccc(C)c(OC)c1>>Cc1ccc(O)cc1O | B(Br)(Br)Br.COC1=C(C=CC(=C1)OC)C.C(C)(=O)OCC.[OH-].[Na+]>>OC1=C(C=CC(=C1)O)C | C[O:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([O:9]C)[cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[OH:9] | COc1ccc(C)c(OC)c1 | Cc1ccc(O)cc1O | null | null | CCCCC | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[O;H0;D2;+0:6]-C):[c:7]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[OH;D1;+0:6]):[c:7] | 94.1 | [{"value": 94.0, "product": "OC1=C(C=CC(=C1)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.1, "product": "OC1=C(C=CC(=C1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The starting material 2,4-dihydroxytoluene was prepared by adding boron tribromide (3.1 ml, 3.2 mmol) to a solution of 2,4-dimethoxytoluene (1 g, 6.5 mmol) in pentane (10 ml) at −70° C. The reaction mixture was allowed to warm to ambient temperature and the mixture stirred for a further 2 hours. Ice water and ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | CCCCC | null | 2 | COc1ccc(C)c(OC)c1>CCCCC>Cc1ccc(O)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4999a6c79aa54fdc9a81de8483259748 | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Br)cc1F>>COCCOc1cc2nncc(Nc3ccc(Br)cc3F)c2cc1OC | ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.BrC1=CC(=C(N)C=C1)F>>BrC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C1)F | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23][c:22]21.[NH2:13][c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]1[F:21]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]3[F:21])[... | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Br)cc1F | COCCOc1cc2nncc(Nc3ccc(Br)cc3F)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.2 g, 0.74 mmol), (prepared as described for the starting material in Example 2), and 4-bromo-2-fluoroaniline (155 mg, 0.82 mmol) in DMF (2.5 ml) was heated at 150° C. for 45 minutes. After cooling to ambient temperature the mixture was treated as describe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CN(C)C=O | 150 | null | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1ccc(Br)cc1F>CN(C)C=O>COCCOc1cc2nncc(Nc3ccc(Br)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62d71bbbedcf4e048364ce7e5a1dabe2 | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Nc1cc(O)c(Cl)cc1F>>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)Cl)OC.ClC1=CC(=C(N)C=C1O)F>>C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)NC1=C(C=C(C(=C1)O)Cl)F)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]3[F:16])[cH:1... | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Nc1cc(O)c(Cl)cc1F | COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc3c(Nc4ccccc4)cnnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride (3.4 g, 10 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline, (prepared as described in EP 061741 A2), (1.84 g, 11 mmol) in DMF (42 ml) was heated at 130° C. for 20 minutes. The resulting solid was filtered off, washed with isopropanol, ether and dried unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Nc1cc(O)c(Cl)cc1F>CN(C)C=O>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e19b54f5d19342d087be63f249d49d38 | COc1cc2c(O)cnnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Cl | C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)O)OC.S(=O)(Cl)Cl.CN(C)C=O>>Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)Cl)OC | O[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][n:9][cH:8]1.O=S([Cl:7])[Cl:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[ClH:22] | COc1cc2c(O)cnnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 03b874008d2d9f5aba975279a4bc336c747d49b5ebd324344c173d0995029d0d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(COc2ccc3ccnnc3c2)cc1 | O-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[ClH;D0;+0:9] | null | [] | null | null | null | null | The starting material, 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride, was obtained by heating a solution of 7-benzyloxy-4-hydroxy-6-methoxycinnoline (11 g, 39 mmol) in thionyl chloride (180 ml) containing DMF (1 ml) at reflux for 1 hour. After cooling, excess thionyl chloride was removed by evaporation and azeo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | Other | null | null | null | COc1cc2c(O)cnnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)cnnc2cc1OCc1ccccc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5361ab59f70448ae8738fc7abac188e4 | BrCc1ccccc1.COc1cc(C(C)=O)ccc1O>>COc1cc(C(C)=O)ccc1OCc1ccccc1 | CC(=O)C1=CC(=C(C=C1)O)OC.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>CC(=O)C1=CC(=C(C=C1)OCC2=CC=CC=C2)OC | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.COc1cc(C(C)=O)ccc1O | COc1cc(C(C)=O)ccc1OCc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 99 | [{"value": 99.0, "product": "CC(=O)C1=CC(=C(C=C1)OCC2=CC=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "CC(=O)C1=CC(=C(C=C1)OCC2=CC=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The starting material, 4-benzyloxy-3-methoxyacetophenone, was obtained by heating a solution of 4-hydroxy-3-methoxyacetophenone (20 g, 0.12 mol), benzyl bromide (15.7 ml, 0.13 mol) and potassium carbonate (49.8 g, 0.36 mol), in DMF (400 ml) at 40° C. overnight. After cooling, the mixture was diluted with water, acidifi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O.CN(C)C=O | null | null | BrCc1ccccc1.COc1cc(C(C)=O)ccc1O>O.CN(C)C=O>COc1cc(C(C)=O)ccc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86f02a2df9b34f72ae5e90ef9abd5f91 | CC(=O)OC(C)=O.COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1>>COc1cc2c(Nc3cc(OC(C)=O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 | C(C)(=O)OC(C)=O.C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)NC1=C(C=C(C(=C1)O)Cl)F)OC>>C(C)(=O)OC=1C(=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC2=CC=CC=C2)C1)F)Cl | CC(=O)O[C:12]([CH3:13])=[O:14].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:15]([Cl:16])[cH:17][c:18]3[F:19])[cH:20][n:21][n:22][c:23]2[cH:24][c:25]1[O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([O:11][C:12]([CH3:13])=[... | CC(=O)OC(C)=O.COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 | COc1cc2c(Nc3cc(OC(C)=O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccc(COc2ccc3c(Nc4ccccc4)cnnc3c2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 94 | [{"value": 94.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Acetic anhydride (920 μl, 9.7 mmol) and 4-dimethylaminopyridine (80 mg, 0.65 mmol) were added to a suspension of 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline (3 g, 6.5 mmol), (prepared as described in Example 6), in pyridine (50 ml). After heating at 110° C. for 25 minutes, the solid was filter... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccc2nnccc2c1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | 110 | null | CC(=O)OC(C)=O.COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>COc1cc2c(Nc3cc(OC(C)=O)c(Cl)cc3F)cnnc2cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f87dd80313104b09ac6647d75d7b9c3f | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F>>COCCOc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC | ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.ClC1=CC(=C(N)C=C1O)F>>ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C1O)F | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]21.[NH2:13][c:14]1[cH:15][c:16]([OH:17])[c:18]([Cl:19])[cH:20][c:21]1[F:22]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([NH:13][c:14]3[cH:15][c:16]([OH:17])[c:18]([Cl:19])[cH:20... | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F | COCCOc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 49 | [{"value": 49.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.2 g, 0.74 mmol), (prepared as described for the starting material in Example 2), and 4-chloro-2-fluoro-5-hydroxyaniline (132 mg, 0.82 mmol), (prepared as described in EP 061741 A2), in DMF (2.5 ml) was heated at 140° C. for 45 minutes. The work up procedu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CN(C)C=O | 140 | null | COCCOc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F>CN(C)C=O>COCCOc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d9c8fe8bd4f4677b9f2be711a09a26f | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Nc1cc(O)c(Cl)cc1F>>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccncc1 | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC1=CC=NC=C1.ClC1=CC(=C(N)C=C1O)F.C(C)(C)O>>ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC2=CC=NC=C2)C=C1O)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][n:28][cH:29][cH:30]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]3[F:16])[cH:17... | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Nc1cc(O)c(Cl)cc1F | COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccncc1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCc4ccncc4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (0.17 g, 0.45 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (102 mg, 0.63 mmol), (prepared as described in EP 061741 A2), in 2-pentanol (3.5 ml) was heated at reflux overnight. After cooling, isopropanol was added. The solid formed was filter... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.c1ccncc1 | HCl | CC(CCC)O | null | null | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Nc1cc(O)c(Cl)cc1F>CC(CCC)O>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1925b59d42954b6c9cf79949b3a51998 | COc1cc2c(Cl)cnnc2cc1O.OCc1ccncc1>>COc1cc2c(Cl)cnnc2cc1OCc1ccncc1 | C(CCC)P(CCCC)CCCC.ClC1=CN=NC2=CC(=C(C=C12)OC)O.OCC1=CC=NC=C1.Cl.C(C)(C)O.N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1>>Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC1=CC=NC=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[OH:14].O[CH2:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | COc1cc2c(Cl)cnnc2cc1O.OCc1ccncc1 | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc(COc2ccc3ccnnc3c2)ccn1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1):[c:13] | 122 | [{"value": 55.0, "product": "Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 122.0, "product": "Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The starting material, 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride, was obtained by adding 4-chloro-7-hydroxy-6-methoxycinnoline (200 mg, 0.95 mmol), followed by 4-hydroxymethylpyridine (108 mg, 1 mmol) and 1,1′-(azodicarbonyl)dipiperidine (647 mg, 2.5 mmol), in portions, to a solution of tri(n-butyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2nnccc2c1.c1ccncc1 | HO- | C(Cl)Cl | null | 1 | COc1cc2c(Cl)cnnc2cc1O.OCc1ccncc1>C(Cl)Cl>COc1cc2c(Cl)cnnc2cc1OCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15a0570011444c2ebe97c407c3807efe | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1>>COc1cc2c(Cl)cnnc2cc1O | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=CN=NC2=C1)Cl)OC>>ClC1=CN=NC2=CC(=C(C=C12)OC)O | c1ccc(C[O:14][c:13]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]3[cH:12]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[OH:14] | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1 | COc1cc2c(Cl)cnnc2cc1O | null | null | C(=O)(C(F)(F)F)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2nnccc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 94 | [{"value": 94.0, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The starting material, 4-chloro-7-hydroxy-6-methoxycinnoline was obtained by heating a solution of 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride (3.06 g, 9 mmol), (prepared as described for the starting material in Example 6), in TFA (30 ml) at reflux for 5 hours. After evaporation of the solvent, the residue w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2nnccc2c1 | Other | C(=O)(C(F)(F)F)O | null | null | COc1cc2c(Cl)cnnc2cc1OCc1ccccc1>C(=O)(C(F)(F)F)O>COc1cc2c(Cl)cnnc2cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d218b8eacb94ccf8ec1aaec2228ab0f | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>>COCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | C(C)(C)O.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC.FC1=C(N)C=C(C(=C1)C)O>>FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C(C(=C1)C)O | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]21.[NH2:13][c:14]1[cH:15][c:16]([OH:17])[c:18]([CH3:19])[cH:20][c:21]1[F:22]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([NH:13][c:14]3[cH:15][c:16]([OH:17])[c:18]([CH3:19])[cH:... | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O | COCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 64 | [{"value": 64.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.2 g, 0.74 mmol), (prepared as described for the starting material in Example 2), and 2-fluoro-5-hydroxy-4-methylaniline (126 mg 0.89 mmol) in 2-pentanol (2.5 ml) was heated at reflux for 7.5 hours. After cooling, isopropanol was added and the solid was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CC(CCC)O | null | null | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>CC(CCC)O>COCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fadd27d35ed4579aa61b756ed318a83 | COC(=O)Cl.Cc1cc(F)ccc1O>>COC(=O)Oc1ccc(F)cc1C | ClC(=O)OC.FC1=CC(=C(C=C1)O)C>>C(OC1=C(C=C(C=C1)F)C)(OC)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[OH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[CH3:13]>>[CH3:1][O:2][C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[CH3:13] | COC(=O)Cl.Cc1cc(F)ccc1O | COC(=O)Oc1ccc(F)cc1C | null | null | [OH-].[Na+] | Acylation | Schotten-Baumann to ester | 18e63da6830cc445f43af5e9dc21618a6276c35c0e735b25c948aaaf35c35656 | 9d4bf8407389b23766af8e91d21ef1aae6a051b3a051fef2f77a7ae83951845d | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 78.4 | [{"value": 78.0, "product": "C(OC1=C(C=C(C=C1)F)C)(OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "C(OC1=C(C=C(C=C1)F)C)(OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methyl chloroformate (6.8 ml, 88 mmol) was added over 30 minutes to a solution of 4-fluoro-2-methylphenol (10 g, 79 mmol) in 6% aqueous sodium hydroxide solution at 0° C. The mixture was stirred for 2 hours, then extracted with ethyl acetate (100 ml). The ethyl acetate extract was washed with water (100 ml) and dried (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | [OH-].[Na+] | null | 2 | COC(=O)Cl.Cc1cc(F)ccc1O>[OH-].[Na+]>COC(=O)Oc1ccc(F)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98bc7af75928421daa9e6bde92612e3d | COC(=O)Oc1ccc(F)cc1C.O=[N+]([O-])O>>Cc1cc(F)c([N+](=O)[O-])cc1O | [N+](=O)(O)[O-].C(OC1=C(C=C(C=C1)F)C)(OC)=O>>FC1=CC(=C(C=C1[N+](=O)[O-])O)C | COC(=O)[O:12][c:11]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[cH:6][cH:10]1.O[N+:7](=[O:8])[O-:9]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[OH:12] | COC(=O)Oc1ccc(F)cc1C.O=[N+]([O-])O | Cc1cc(F)c([N+](=O)[O-])cc1O | null | null | S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | 3e2a39245aedbc84c9b61745a2d482a502d03a2db04f9415ada8c63d3bdbf546 | 435bda86910f5716a9c2678f2c34372cf7226f9e64c7f303de8399dcd94bdbe9 | c1ccccc1 | C-O-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[c:5](-[F;D1;H0:6]):[c:7]:[c:8]:1.O-[N+;H0;D3:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[F;D1;H0:6]-[c:5]1:[c:7]:[c:8]:[c:2](-[OH;D1;+0:1]):[c:3]:[c;H0;D3;+0:4]:1-[N+;H0;D3:9](-[O;-;D1;H0:10])=[O;D1;H0:11] | 22 | [{"value": 22.0, "product": "FC1=CC(=C(C=C1[N+](=O)[O-])O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of concentrated nitric acid (6 ml) and concentrated sulphuric acid (6 ml) was added slowly to a solution of 4-fluoro-2-methylphenyl methyl carbonate (11.34 g, 62 mmol) in concentrated sulphuric acid (6 ml) such that the temperature of the reaction mixture was kept below 50° C. The mixture was stirred for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrate | Nitro group.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 2 | COC(=O)Oc1ccc(F)cc1C.O=[N+]([O-])O>S(O)(O)(=O)=O>Cc1cc(F)c([N+](=O)[O-])cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-994883380a214f47b45d3a084572d5ee | Cc1cc(F)c([N+](=O)[O-])cc1O>>Cc1cc(F)c(N)cc1O | [OH-].[Na+].FC1=CC(=C(C=C1[N+](=O)[O-])O)C>>FC1=C(N)C=C(C(=C1)C)O | O=[N+:7]([O-])[c:6]1[c:4]([F:5])[cH:3][c:2]([CH3:1])[c:9]([OH:10])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([NH2:7])[cH:8][c:9]1[OH:10] | Cc1cc(F)c([N+](=O)[O-])cc1O | Cc1cc(F)c(N)cc1O | null | [Fe].S(=O)(=O)([O-])[O-].[Fe+2] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 47 | [{"value": 47.0, "product": "FC1=C(N)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.6, "product": "FC1=C(N)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-fluoro-2-methyl-5-nitrophenol (2.1 g, 13 mmol), iron powder (1 g, 18 mmol) and iron(II)sulphate (1.5 g, 10 mmol) in water (40 ml) was heated at reflux for 4 hours. The reaction mixture was allowed to cool, neutralised with 2M aqueous sodium hydroxide solution and extracted with ethyl acetate (100 ml). Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].S(=O)(=O)([O-])[O-].[Fe+2].O | null | null | Cc1cc(F)c([N+](=O)[O-])cc1O>[Fe].S(=O)(=O)([O-])[O-].[Fe+2].O>Cc1cc(F)c(N)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-245f2870f5024f29a93ebbc4e31b8a82 | COc1cc2c(Cl)cnnc2cc1O.ClCCCN1CCOCC1>>COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1 | Cl.C([O-])([O-])=O.[K+].[K+].[I-].[K+].ClC1=CN=NC2=CC(=C(C=C12)OC)O.C([O-])([O-])=O.[K+].[K+].ClCCCN1CCOCC1.ClCCCN1CCOCC1>>ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[OH:14].Cl[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1 | COc1cc2c(Cl)cnnc2cc1O.ClCCCN1CCOCC1 | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1 | null | null | O.CO.CN(C)C=O.C(C)(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc2ccc(OCCCN3CCOCC3)cc2nn1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | The starting material 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride was obtained by adding 1-chloro-3-morpholinopropane (190 mg, 0.95 mmol), (prepared as described in U.S. Pat. No. 4,004,007), to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (0.2 g, 0.95 mmol), (prepared as described for the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2nnccc2c1.C1COCC[NH]1 | HCl | O.CO.CN(C)C=O.C(C)(C)O | 80 | 4 | COc1cc2c(Cl)cnnc2cc1O.ClCCCN1CCOCC1>O.CO.CN(C)C=O.C(C)(C)O>COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83bb9ee9edd94868a9d634d247df59ab | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1cc(O)c(Cl)cc1F>>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.ClC1=CC(=C(N)C=C1O)F>>ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCCC2)C=C1O)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]... | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1cc(O)c(Cl)cc1F | COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCCCN4CCCC4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride (0.1 g, 0.25 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (57 mg, 0.35 mmol), (prepared as described in EP 061741 A2), in 2-pentanol (5 ml) was heated at 120° C. for 2.5 hours. The solid was filtered off, washed with isopropanol and then e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.C1CC[NH]C1 | HCl | CC(CCC)O | null | null | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1cc(O)c(Cl)cc1F>CC(CCC)O>COc1cc2c(Nc3cc(O)c(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d27b32ced974eb7a6b88307c6cfb13f | COc1ccc2c(Cl)cnnc2c1.Cc1ccc(N)cc1O>>COc1ccc2c(Nc3ccc(C)c(O)c3)cnnc2c1 | Cl.ClC1=CN=NC2=CC(=CC=C12)OC.OC=1C=C(N)C=CC1C>>OC=1C=C(NC2=CN=NC3=CC(=CC=C23)OC)C=CC1C | Cl[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([CH3:13])[c:14]([OH:15])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([CH3:13])[c:14]([OH:15])[cH:16]3)[cH:17][n:18][n:19][c:20]2[cH:21]1 | COc1ccc2c(Cl)cnnc2c1.Cc1ccc(N)cc1O | COc1ccc2c(Nc3ccc(C)c(O)c3)cnnc2c1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-7-methoxycinnoline hydrochloride (196 mg, 0.85 mmol) and 3-hydroxy-4-methylaniline (123 mg, 1 mmol) in 2-pentanol (5 ml) was heated at reflux for 2 hours. After cooling, the solid was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(3-hydroxy-4methylanilino)-7-meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1 | HCl | CC(CCC)O | null | null | COc1ccc2c(Cl)cnnc2c1.Cc1ccc(N)cc1O>CC(CCC)O>COc1ccc2c(Nc3ccc(C)c(O)c3)cnnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d4c3752ba7f4c5eae803cc519e25ef9 | COc1ccc2c(O)cnnc2c1.O=S(Cl)Cl>>COc1ccc2c(Cl)cnnc2c1.Cl | OC1=CN=NC2=CC(=CC=C12)OC.S(=O)(Cl)Cl.CN(C)C=O>>Cl.ClC1=CN=NC2=CC(=CC=C12)OC | O[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[n:11][n:10][cH:9]1.O=S([Cl:8])[Cl:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([Cl:8])[cH:9][n:10][n:11][c:12]2[cH:13]1.[ClH:14] | COc1ccc2c(O)cnnc2c1.O=S(Cl)Cl | COc1ccc2c(Cl)cnnc2c1.Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 03b874008d2d9f5aba975279a4bc336c747d49b5ebd324344c173d0995029d0d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2nnccc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[ClH;D0;+0:9] | 97 | [{"value": 97.0, "product": "Cl.ClC1=CN=NC2=CC(=CC=C12)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The starting material 4-chloro-7-methoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-7-methoxycinnoline (352 mg, 2 mmol), (prepared as described in J. Chem. Soc. 1955, 2100), in thionyl chloride (3.5 ml) containing DMF (20 μl) at reflux, for 1 hour. After removing excess thionyl chloride by e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | Other | null | null | null | COc1ccc2c(O)cnnc2c1.O=S(Cl)Cl>>COc1ccc2c(Cl)cnnc2c1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81ac5a108f83462b91d6cd5c4ab875c1 | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Cc1cc(F)c(N)cc1O>>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCCCN1CCOCC1 | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.Cl.FC1=C(N)C=C(C(=C1)C)O>>FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C(C(=C1)C)O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:1... | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Cc1cc(F)c(N)cc1O | COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCCCN1CCOCC1 | null | C(C)(C)O | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCCCN4CCOCC4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 84 | [{"value": 84.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (132 mg, 0.33 mmol), (prepared as described for the starting material in Example 12), and 2-fluoro-5-hydroxy-4-methylaniline (56 mg, 0.39 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (2.5 ml) contain... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.C1COCC[NH]1 | HCl | C(C)(C)O.CC(CCC)O | null | null | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Cc1cc(F)c(N)cc1O>C(C)(C)O.CC(CCC)O>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f542f7bd4d94ed8a301abc03c7231f0 | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Cc1cc(F)c(N)cc1O>>COc1nnc2cc(OCCCN3CCCC3)ccc2c1Nc1cc(O)c(C)cc1F | CC(CCC)O.Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.FC1=C(N)C=C(C(=C1)C)O>>FC1=C(NC2=C(N=NC3=CC(=CC=C23)OCCCN2CCCC2)OC)C=C(C(=C1)C)O | Cl[c:21]1[cH:3][n:4][n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[c:18]([O:2][CH3:1])[cH:19][c:20]21.[NH2:22][c:23]1[cH:24][c:25]([OH:26])[c:27]([CH3:28])[cH:29][c:30]1[F:31]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:1... | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Cc1cc(F)c(N)cc1O | COc1nnc2cc(OCCCN3CCCC3)ccc2c1Nc1cc(O)c(C)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 519039d3db63f1c4ca7c624611cb4d13c78f1c2287567dc04f2fcb95f329b71f | dd6312cf5878aa4be982f2f3b710674b0b7ce828888957540ba6b1c490003fd2 | c1ccc(Nc2cnnc3cc(OCCCN4CCCC4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[#7;a:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7](-[#8:8]):[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-[C;D1;H3:11]):[c:12]:[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[#8:8]-[c:7]1:[c:6]:[c:5]2:[#7;a:4]:[#7;a:3]:[c;H0;D3;+0:2](-[O;H0;D2;+0:10]-[C;D1;H3:11]):[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c... | 27 | [{"value": 27.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride (158 mg, 0.4 mmol), (prepared as described for the starting material in Example 13), and 2-fluoro-5-hydroxy-4-methylaniline (67 mg, 0.48 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (5 ml) was heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine | Ether.Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.C1CC[NH]C1.c1ccccc1 | HCl | null | null | null | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Cc1cc(F)c(N)cc1O>>COc1nnc2cc(OCCCN3CCCC3)ccc2c1Nc1cc(O)c(C)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e7581b52af94d42a3848dfce08231a1 | COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1.Cc1cc(F)c(N)cc1O>>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1csc(C)n1 | ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N=C(SC1)C.FC1=C(N)C=C(C(=C1)C)O.Cl>>Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N=C(SC2)C)C=C(C(=C1)C)O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[cH:26][s:27][c:28]([CH3:29])[n:30]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]3[F:16])[cH... | COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1.Cc1cc(F)c(N)cc1O | COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1csc(C)n1 | null | null | CC(CCC)O.C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCc4cscn4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 89.2 | [{"value": 82.0, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N=C(SC2)C)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N=C(SC2)C)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline (150 mg, 0.46 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (78 mg, 0.56 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml) and a 5M solution of hydrogen chloride in isopropanol (105 μl) was heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.c1cscn1 | HCl | CC(CCC)O.C(C)(C)O | null | null | COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1.Cc1cc(F)c(N)cc1O>CC(CCC)O.C(C)(C)O>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1csc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc1a01f5223a4d3995b814ec8f9224a4 | COc1cc2c(Cl)cnnc2cc1O.Cc1nc(CCl)cs1>>COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1 | Cl.C([O-])([O-])=O.[K+].[K+].ClCC=1N=C(SC1)C.ClC1=CN=NC2=CC(=C(C=C12)OC)O>>ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N=C(SC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[OH:14].Cl[CH2:15][c:16]1[cH:17][s:18][c:19]([CH3:20])[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][s:18][c:19]([CH3:20])[n:21]1 | COc1cc2c(Cl)cnnc2cc1O.Cc1nc(CCl)cs1 | COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc2ccc(OCc3cscn3)cc2nn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1):[c:12] | 48 | [{"value": 48.0, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N=C(SC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N=C(SC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4.5 | HOUR | The starting material 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline was obtained by adding potassium carbonate (786 mg, 5.7 mmol) followed by 4-chloromethyl-2-methylthiazole (308 mg, 2 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (0.4 g, 1.9 mmol), (prepared as described for the starti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2nnccc2c1.c1cscn1 | HCl | O.CN(C)C=O | 60 | 4.5 | COc1cc2c(Cl)cnnc2cc1O.Cc1nc(CCl)cs1>O.CN(C)C=O>COc1cc2c(Cl)cnnc2cc1OCc1csc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ef1353ef9b0448aa2e55a73c9130f30 | COc1cc2c(Cl)cnnc2cc1OCc1nccn1C.Cc1cc(F)c(N)cc1O>>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1nccn1C | Cl.C(C)(C)O.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N(C=CN1)C.FC1=C(N)C=C(C(=C1)C)O>>Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N(C=CN2)C)C=C(C(=C1)C)O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[n:26][cH:27][cH:28][n:29]3[CH3:30])[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]3[F:16])[cH:... | COc1cc2c(Cl)cnnc2cc1OCc1nccn1C.Cc1cc(F)c(N)cc1O | COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1nccn1C | null | null | CC(CCC)O.CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCc4ncc[nH]4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.5 | [{"value": 73.0, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N(C=CN2)C)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC=2N(C=CN2)C)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-[( 1-methylimidazol-2-yl)methoxy]cinnoline (109 mg, 0.35 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml), DMF (0.5 ml) and a 5M solution of hydrogen chloride in isopropanol (74 μl, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.c1ncc[nH]1 | HCl | CC(CCC)O.CN(C)C=O | 0 | null | COc1cc2c(Cl)cnnc2cc1OCc1nccn1C.Cc1cc(F)c(N)cc1O>CC(CCC)O.CN(C)C=O>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1nccn1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2793211692d4541affe62f1da13a23a | COc1cc2c(Cl)cnnc2cc1O.Cn1ccnc1CCl>>COc1cc2c(Cl)cnnc2cc1OCc1nccn1C | C([O-])([O-])=O.[K+].[K+].ClCC=1N(C=CN1)C.ClC1=CN=NC2=CC(=C(C=C12)OC)O>>ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N(C=CN1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[OH:14].Cl[CH2:15][c:16]1[n:17][cH:18][cH:19][n:20]1[CH3:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[n:17][cH:18][cH:19][n:20]1[CH3:21] | COc1cc2c(Cl)cnnc2cc1O.Cn1ccnc1CCl | COc1cc2c(Cl)cnnc2cc1OCc1nccn1C | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc2ccc(OCc3ncc[nH]3)cc2nn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7].[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7]):[c:13] | 29 | [{"value": 29.0, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N(C=CN1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "ClC1=CN=NC2=CC(=C(C=C12)OC)OCC=1N(C=CN1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 8 | HOUR | The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2nnccc2c1.c1ncc[nH]1 | HCl | O.CN(C)C=O | 40 | 8 | COc1cc2c(Cl)cnnc2cc1O.Cn1ccnc1CCl>O.CN(C)C=O>COc1cc2c(Cl)cnnc2cc1OCc1nccn1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ede3ca8d119b49a8ac2e73f1d9c835b8 | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Cc1cc(F)c(N)cc1O>>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1ccncc1 | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCC1=CC=NC=C1.FC1=C(N)C=C(C(=C1)C)O>>Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC2=CC=NC=C2)C=C(C(=C1)C)O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][n:28][cH:29][cH:30]3)[cH:21][c:20]2[n:19][n:18][cH:17]1.[NH2:7][c:8]1[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]1[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]3[F:16])[cH:... | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Cc1cc(F)c(N)cc1O | COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1ccncc1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCc4ccncc4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 29.3 | [{"value": 29.0, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC2=CC=NC=C2)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.3, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCC2=CC=NC=C2)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (268 mg, 0.71 mmol), (prepared as described for the starting material in Example 10), and 2-fluoro-5-hydroxy-4-methylaniline, (109 mg, 0.77 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (6 ml) was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.c1ccncc1 | HCl | CC(CCC)O | null | null | COc1cc2c(Cl)cnnc2cc1OCc1ccncc1.Cc1cc(F)c(N)cc1O>CC(CCC)O>COc1cc2c(Nc3cc(O)c(C)cc3F)cnnc2cc1OCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3806cfe94ac247309d3610fb7b304642 | COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC>>COCCOc1cc2nncc(Oc3cc(O)c(C)cc3F)c2cc1OC | C(C1=CC=CC=C1)OC=1C(=CC(=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C1)F)C>>FC1=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C(C(=C1)C)O | c1ccc(C[O:17][c:16]2[cH:15][c:14]([O:13][c:12]3[cH:11][n:10][n:9][c:8]4[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]43)[c:21]([F:22])[cH:20][c:18]2[CH3:19])cc1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([O:13][c:14]3[cH:15][c:16]([OH:17])[c:18]([CH3:19])... | COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC | COCCOc1cc2nncc(Oc3cc(O)c(C)cc3F)c2cc1OC | null | [Pd] | CO.CN(C)C=O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Oc2cnnc3ccccc23)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 46.5 | [{"value": 44.0, "product": "FC1=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.5, "product": "FC1=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 9 | HOUR | A solution of 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline (242 mg 0.5 mmol) in a mixture of methanol (9 ml) and DMF (10.5 ml) containing 10% palladium-on-charcoal catalyst (100 mg) was stirred under hydrogen at 5 atmospheres pressure for 9 hours. The catalyst was removed by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2nnccc2c1.c1ccccc1 | Other | [Pd].CO.CN(C)C=O | null | 9 | COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC>[Pd].CO.CN(C)C=O>COCCOc1cc2nncc(Oc3cc(O)c(C)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-125e886930dd4d1cb5902be4df9435c0 | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(O)cc1OCc1ccccc1>>COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC | C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)O)F)C.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOC>>C(C1=CC=CC=C1)OC=1C(=CC(=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C1)F)C | Cl[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][c:30]21.[OH:13][c:14]1[cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]([CH3:26])[cH:27][c:28]1[F:29]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([O:13][... | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(O)cc1OCc1ccccc1 | COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 70690c5363a5ec8ca78f5f5d08ac497aab9ecc68d6712c68effecd652b19420f | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2cccc(Oc3cnnc4ccccc34)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 53.2 | [{"value": 53.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C1)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(OC2=CN=NC3=CC(=C(C=C23)OC)OCCOC)C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The starting material, 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline was obtained by heating a solution of 5-benzyloxy-2-fluoro-4-methylphenol (314 mg, 1.3 mmol) and 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (280 mg, 1 mmol), (prepared as described for the starting material in Ex... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | COCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(O)cc1OCc1ccccc1>N1=CC=CC=C1>COCCOc1cc2nncc(Oc3cc(OCc4ccccc4)c(C)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-051c546095a445e08c053b9eb100de40 | Cc1cc(F)c(N)cc1OCc1ccccc1>>Cc1cc(F)c(O)cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(=CC(=C(N)C1)F)C.N(=O)[O-].[Na+]>>C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)O)F)C | N[c:6]1[c:4]([F:5])[cH:3][c:2]([CH3:1])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([OH:7])[cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1cc(F)c(N)cc1OCc1ccccc1 | Cc1cc(F)c(O)cc1OCc1ccccc1 | null | [Cu]=O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-] | O.C(C)(=O)O.S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 5476e3e4f8e8862ba087972a35863ca0b6ebf27577a68b3ac2018e9a7004c864 | ed7617b9cd113fcbf3232da782e35483fef55189a64648ab4bdbc41767cd9a80 | c1ccc(COc2ccccc2)cc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;D1;H1:7]):[c:2]:[c:3] | 27 | [{"value": 27.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)O)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | The starting material 5-benzyloxy-2-fluoro-4-methylphenol, was obtained by adding a solution of sodium nitrite (1.68 g, 24mmol) in water (3.5 ml), dropwise, to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (82 ml) and 70% sulphuric acid (3.15 ml) cooled at 10° C. The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | [Cu]=O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].O.C(C)(=O)O.S(O)(O)(=O)=O | null | 0.333333 | Cc1cc(F)c(N)cc1OCc1ccccc1>[Cu]=O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].O.C(C)(=O)O.S(O)(O)(=O)=O>Cc1cc(F)c(O)cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8db631387344b1d934a549994ef9606 | Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1>>Cc1cc(F)c(N)cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)[N+](=O)[O-])F)C>>C(C1=CC=CC=C1)OC=1C(=CC(=C(N)C1)F)C | O=[N+:7]([O-])[c:6]1[c:4]([F:5])[cH:3][c:2]([CH3:1])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([NH2:7])[cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1 | Cc1cc(F)c(N)cc1OCc1ccccc1 | null | [Fe] | O.C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(COc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 87.7 | [{"value": 87.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(N)C1)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(N)C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 10 | MINUTE | The starting material, 5-benzyloxy-2-fluoro-4-methylaniline, was obtained by adding iron powder (2.88 g, 51 mmol), in portions, to a solution of 5-benzyloxy-2-fluoro-4-methylnitrobenzene (4.8 g, 18 mmol) in acetic acid (33 ml) and water (5.7 ml), at ambient temperature. The mixture was heated and after stirring at 100°... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Fe].O.C(C)(=O)O | 100 | 0.166667 | Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1>[Fe].O.C(C)(=O)O>Cc1cc(F)c(N)cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aeca40a5c11b49e09fe5ba429ff41801 | BrCc1ccccc1.Cc1cc(F)c([N+](=O)[O-])cc1O>>Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1 | C(C1=CC=CC=C1)Br.FC1=C(C=C(C(=C1)C)O)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)[N+](=O)[O-])F)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[OH:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.Cc1cc(F)c([N+](=O)[O-])cc1O | Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 80.4 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)[N+](=O)[O-])F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)[N+](=O)[O-])F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | The starting material 5-benzyloxy-2-fluoro-4-methylnitrobenzene was obtained by adding benzyl bromide (3 ml, 25 mmol) to a solution of 2-fluoro-5-hydroxy-4-methylnitrobenzene (3.92 mg, 23 mmol) in DMF (70 ml) containing potassium carbonate (9.5 g, 68 mmol). After stirring for 3 hours at 60° C. the mixture was diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O.CN(C)C=O | 60 | 3 | BrCc1ccccc1.Cc1cc(F)c([N+](=O)[O-])cc1O>O.CN(C)C=O>Cc1cc(F)c([N+](=O)[O-])cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb93562e983447698dff568eaa5a224c | COC(=O)Oc1cc([N+](=O)[O-])c(F)cc1C>>Cc1cc(F)c([N+](=O)[O-])cc1O | [OH-].[Na+].FC1=C(C=C(C(=C1)C)OC(=O)OC)[N+](=O)[O-]>>FC1=C(C=C(C(=C1)C)O)[N+](=O)[O-] | COC(=O)[O:12][c:11]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[OH:12] | COC(=O)Oc1cc([N+](=O)[O-])c(F)cc1C | Cc1cc(F)c([N+](=O)[O-])cc1O | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccccc1 | C-O-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "FC1=C(C=C(C(=C1)C)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "FC1=C(C=C(C(=C1)C)O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The starting material 2-fluoro-5-hydroxy-4-methylnitrobenzene, was obtained by adding 2M aqueous sodium hydroxide solution (13.1 ml), dropwise, to a solution of 2-fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene (6 g, 26 mmol), (prepared as described in European Patent Publication No. 307777), in methanol (70 ml) coole... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | c1ccccc1 | HO- | CO | null | 0.5 | COC(=O)Oc1cc([N+](=O)[O-])c(F)cc1C>CO>Cc1cc(F)c([N+](=O)[O-])cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2a6c961afe74bd9b766dbe37ed3ddaf | COc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>>COc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OC.FC1=C(N)C=C(C(=C1)C)O>>FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OC)C=C(C(=C1)C)O | Cl[c:9]1[cH:8][n:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21][c:20]21.[NH2:10][c:11]1[cH:12][c:13]([OH:14])[c:15]([CH3:16])[cH:17][c:18]1[F:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][n:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([OH:14])[c:15]([CH3:16])[cH:17][c:18]3[F:19])[c:20]2[cH:21][c:22]1[O:23]... | COc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O | COc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 82 | [{"value": 82.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 4-chloro-6,7-dimethoxycinnoline hydrochloride (261 mg, 1 mmol), (prepared as described for the starting material in Example 1), and 2-fluoro-5-hydroxy-4-methylaniline (170 mg, 1.2 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (5 ml) was heated at 120° C. for 3 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | CC(CCC)O | 120 | null | COc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>CC(CCC)O>COc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d29e30eaff2e49f7b83d2079dc785726 | COc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F>>COc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OC.ClC1=CC(=C(N)C=C1O)F>>ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OC)C=C1O)F | Cl[c:9]1[cH:8][n:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21][c:20]21.[NH2:10][c:11]1[cH:12][c:13]([OH:14])[c:15]([Cl:16])[cH:17][c:18]1[F:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][n:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([OH:14])[c:15]([Cl:16])[cH:17][c:18]3[F:19])[c:20]2[cH:21][c:22]1[O:23][C... | COc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F | COc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 82 | [{"value": 82.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6,7-dimethoxycinnoline hydrochloride (261 mg, 1 mmol), (prepared as described for the starting material in Example 1), and 4-chloro-2-fluoro-5-hydroxyaniline (193 mg, 1.2 mmol), (prepared as described in EP 061741), was treated in a manner similar to that described in Example 21 in order to produ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2nncc(Cl)c2cc1OC.Nc1cc(O)c(Cl)cc1F>>COc1cc2nncc(Nc3cc(O)c(Cl)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b74e9513a51b49eb94d36645a0f6e775 | COCCOCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>>COCCOCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | ClC1=CN=NC2=CC(=C(C=C12)OC)OCCOCCOC.FC1=C(N)C=C(C(=C1)C)O.Cl>>FC1=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCOCCOC)C=C(C(=C1)C)O | Cl[c:15]1[cH:14][n:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][c:26]21.[NH2:16][c:17]1[cH:18][c:19]([OH:20])[c:21]([CH3:22])[cH:23][c:24]1[F:25]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][n:13][cH:14][c:15]([NH:16][c:17... | COCCOCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O | COCCOCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC | null | C(C)(C)O | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:6]:[c:5]1:[#7;a:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | 88 | [{"value": 88.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline (130 mg, 0.41 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml) containing 5M hydrogen chloride in isopropanol (2 drops) was heated at reflux for 45... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccc2nnccc2c1.c1ccccc1 | HCl | C(C)(C)O.CC(CCC)O | null | null | COCCOCCOc1cc2nncc(Cl)c2cc1OC.Cc1cc(F)c(N)cc1O>C(C)(C)O.CC(CCC)O>COCCOCCOc1cc2nncc(Nc3cc(O)c(C)cc3F)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd18bbde8c2547a8bc703e52823b5e37 | Cc1cc(F)c(N)cc1O.Clc1ccc2nncc(Cl)c2c1>>Cc1cc(F)c(Nc2cnnc3ccc(Cl)cc23)cc1O.Cl | ClC1=CN=NC2=CC=C(C=C12)Cl.FC1=C(N)C=C(C(=C1)C)O>>Cl.ClC=1C=C2C(=CN=NC2=CC1)NC1=C(C=C(C(=C1)O)C)F | [CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([NH2:7])[cH:19][c:20]1[OH:21].[c:8]1([Cl:22])[cH:9][n:10][n:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]12>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([NH:7][c:8]2[cH:9][n:10][n:11][c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]23)[cH:19][c:20]1[OH:21].[ClH:22] | Cc1cc(F)c(N)cc1O.Clc1ccc2nncc(Cl)c2c1 | Cc1cc(F)c(Nc2cnnc3ccc(Cl)cc23)cc1O.Cl | null | Cl | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:7]:[c:6]1:[#7;a:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:1:[c:9] | 95.8 | [{"value": 95.0, "product": "Cl.ClC=1C=C2C(=CN=NC2=CC1)NC1=C(C=C(C(=C1)O)C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "Cl.ClC=1C=C2C(=CN=NC2=CC1)NC1=C(C=C(C(=C1)O)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,6-dichlorocinnoline (200 mg, 1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (169 mg, 1.2 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (4 ml) containing 7M isopropanolic hydrogen chloride (2 drops) was heated at reflux for 45 minutes. After cooling the solid was f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1 | null | Cl.CC(CCC)O | null | null | Cc1cc(F)c(N)cc1O.Clc1ccc2nncc(Cl)c2c1>Cl.CC(CCC)O>Cc1cc(F)c(Nc2cnnc3ccc(Cl)cc23)cc1O.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b7086452ac64a56a87f5db7ea740a99 | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Nc1ccc(Cl)cc1F>>COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCOCC1 | Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=CC(=C(N)C=C1)F.C(C)(C)O>>Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[cH:20][c:19]2[n:18][n:17][cH:16]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[c... | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Nc1ccc(Cl)cc1F | COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCOCC1 | null | null | CC(CCC)O.Cl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCCCN4CCOCC4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 106.3 | [{"value": 98.0, "product": "Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.3, "product": "Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (150 mg, 0.36 mmol), (prepared as described for the starting material in Example 12), 4-chloro-2-fluoroaniline (77 mg, 0.53 mmol) in 2-pentanol (4 ml) and 5M isopropanolic hydrogen chloride (1 ml) was heated at 120° C. for 1 hour. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.C1COCC[NH]1 | HCl | CC(CCC)O.Cl | 120 | null | COc1cc2c(Cl)cnnc2cc1OCCCN1CCOCC1.Nc1ccc(Cl)cc1F>CC(CCC)O.Cl>COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbcfff9f2a264929a15bd17703e21756 | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1ccc(Cl)cc1F>>COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 | Cl.Cl.ClC1=CN=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.ClC1=CC(=C(N)C=C1)F>>Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCCC2)C=C1)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:20][c:19]2[n:18][n:17][cH:16]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[cH:16][... | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1ccc(Cl)cc1F | COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3cc(OCCCN4CCCC4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 73.6 | [{"value": 66.0, "product": "Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCCC2)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "Cl.ClC1=CC(=C(NC2=CN=NC3=CC(=C(C=C23)OC)OCCCN2CCCC2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride (130 mg, 0.32 mmol), (prepared as described for the starting material in Example 13), and 4-chloro-2-fluoroaniline (70 mg, 0.48 mmol), in 2-pentanol (4 ml) and 5M isopropanolic hydrogen chloride (1 ml) was heated at 120° C. for 2.5 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1.C1CC[NH]C1 | HCl | CC(CCC)O | null | null | COc1cc2c(Cl)cnnc2cc1OCCCN1CCCC1.Nc1ccc(Cl)cc1F>CC(CCC)O>COc1cc2c(Nc3ccc(Cl)cc3F)cnnc2cc1OCCCN1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbd7290e07da4dfdac2dff3ae8a033b9 | COCCOc1ccc2c(Cl)cnnc2c1.Cc1cc(F)c(N)cc1O>>COCCOc1ccc2c(Nc3cc(O)c(C)cc3F)cnnc2c1 | ClC1=CN=NC2=CC(=CC=C12)OCCOC.FC1=C(N)C=C(C(=C1)C)O.Cl>>Cl.FC1=C(NC2=CN=NC3=CC(=CC=C23)OCCOC)C=C(C(=C1)C)O | Cl[c:10]1[c:9]2[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:25][c:24]2[n:23][n:22][cH:21]1.[NH2:11][c:12]1[cH:13][c:14]([OH:15])[c:16]([CH3:17])[cH:18][c:19]1[F:20]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][c:14]([OH:15])[c:16]([CH3:17])[cH:18][c:19]3[F:20])[cH:21][n:... | COCCOc1ccc2c(Cl)cnnc2c1.Cc1cc(F)c(N)cc1O | COCCOc1ccc2c(Nc3cc(O)c(C)cc3F)cnnc2c1 | null | null | CC(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 84 | [{"value": 84.0, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=CC=C23)OCCOC)C=C(C(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "Cl.FC1=C(NC2=CN=NC3=CC(=CC=C23)OCCOC)C=C(C(=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-7-(2-methoxyethoxy)cinnoline (156 mg, 0.65 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (111 mg, 0.78 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (8 ml) and 5M isopropanolic hydrogen chloride (1 ml) was heated at 120° C. for 2.5 hours. The solid was filte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1ccccc1.c1ccc2nnccc2c1 | HCl | CC(CCC)O | null | null | COCCOc1ccc2c(Cl)cnnc2c1.Cc1cc(F)c(N)cc1O>CC(CCC)O>COCCOc1ccc2c(Nc3cc(O)c(C)cc3F)cnnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40bee509c4af45dea8ed128cbd63add2 | COc1ccc2c(Cl)cnnc2c1>>Oc1ccc2c(Cl)cnnc2c1 | [Cl-].[Cl-].[Cl-].[Al+3].ClC1=CN=NC2=CC(=CC=C12)OC>>ClC1=CN=NC2=CC(=CC=C12)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][n:9][n:10][c:11]2[cH:12]1 | COc1ccc2c(Cl)cnnc2c1 | Oc1ccc2c(Cl)cnnc2c1 | null | null | C1=CC=CC=C1 | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2nnccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 53.6 | [{"value": 53.0, "product": "ClC1=CN=NC2=CC(=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.6, "product": "ClC1=CN=NC2=CC(=CC=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Aluminium trichloride (2.6 g, 19 mmol) was added in portions to a suspension of 4-chloro-7-methoxycinnoline (0.9 g, 3.8 mmol), (J. Chem. Soc. 1955, 2100), in benzene (15 ml) and the mixture was heated at reflux for 1 hour. The solvent was removed by evaporation and the residue was partitioned between ice/water and ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2nnccc2c1 | Other | C1=CC=CC=C1 | null | null | COc1ccc2c(Cl)cnnc2c1>C1=CC=CC=C1>Oc1ccc2c(Cl)cnnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cabf1b5deefc47dab71d1501ee332e9c | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccccc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2)NC(C)(C)C)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:24].[NH2:4][c:23]1[n:18][cH:19][cH:20][cH:21][cH:22]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[cH:19][cH:20... | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2cn3ccccc3[nH+]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[Cl;H0;D1;+0:15])=[O;D1;H0:16].[NH2;D1;+0:17]-[c:18](:[c:19]):[n;H0;D2;+0:20]:[c:21]:[c:22]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:8]-[c;H... | null | [] | null | null | null | null | Example 1 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccccc1.C1=CC2=[NH+]C=CN2C=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0ba9380ec10483696e9cccc1e07c5c7 | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccncc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CN=C1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=NC=C2)NC(C)(C)C)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:24].[NH2:4][c:23]1[n:18][cH:19][cH:20][n:21][cH:22]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[cH:19][cH:20]... | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccncc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 2dc6caedca6974bff0fc06e1cf3081b16bc107cf26d0c20b0c2051dfc216e0e4 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2cn3ccncc3[nH+]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[Cl;H0;D1;+0:15])=[O;D1;H0:16].[NH2;D1;+0:17]-[c:18]1:[c:19]:[#7;a:20]:[c:21]:[c:22]:[n;H0;D2;+0:23]:1>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2... | null | [] | null | null | null | null | Example 2 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrazine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cnccn1 | C1=CN2C=C[NH+]=C2C=N1 | c1ccccc1.C1=CN2C=C[NH+]=C2C=N1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccncc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ebe5abfa2ca49b9841445d97976bc23 | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2cccnc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=N1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=CC=C2)NC(C)(C)C)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:24].[NH2:4][c:23]1[n:18][cH:19][cH:20][cH:21][n:22]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[cH:19][cH:20]... | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2cccnc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2cn3cccnc3[nH+]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[Cl;H0;D1;+0:15])=[O;D1;H0:16].[NH2;D1;+0:17]-[c:18]1:[#7;a:19]:[c:20]:[c:21]:[c:22]:[n;H0;D2;+0:23]:1>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2... | null | [] | null | null | null | null | Example 3 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccccc1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2cccnc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3530e699346948b5a62efd1270abe4aa | CC(=O)Cl.Nc1nccs1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccsc21.[Cl-] | C(C)(=O)Cl.NC=1SC=CN1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1SC=C2)NC(C)(C)C)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:23].[NH2:4][c:22]1[n:18][cH:19][cH:20][s:21]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[cH:19][cH:20][s:21][... | CC(=O)Cl.Nc1nccs1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccsc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | cad224a622aa3b848cba21f80ef7955c393bc57e9344944a7d6b7055cf6d93f3 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2cn3ccsc3[nH+]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[Cl;H0;D1;+0:15])=[O;D1;H0:16].[NH2;D1;+0:17]-[c:18]1:[#16;a:19]:[c:20]:[c:21]:[n;H0;D2;+0:22]:1>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:8]... | null | [] | null | null | null | null | Example 4 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-thiazole (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cscn1 | C1=CN2C=CSC2=[NH+]1 | c1ccccc1.C1=CN2C=CSC2=[NH+]1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1nccs1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC(C)(C)C)n2ccsc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-779ad3fbf89541cb9a272f3ad6e35d8a | CC(=O)Cl.Nc1ccc2ccccc2n1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2c3ccccc3ccc21.[Cl-] | C(C)(=O)Cl.NC1=NC2=CC=CC=C2C=C1.C1(CCCCC1)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC1=CC=CC=C21)NC2CCCCC2)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:30].[NH2:4][c:29]1[n:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[cH:27][cH:28]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][CH:14]2[CH2... | CC(=O)Cl.Nc1ccc2ccccc2n1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2c3ccccc3ccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | c43cbd154c907b3e542f07742fb1edae7caa2bed127423db05b4897415e9db56 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ccc4ccccc4n3c2NC2CCCCC2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20](:[c:21]):[c:22]>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:... | null | [] | null | null | null | null | Example 5 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-quinoline (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | C1=CN2C(=[NH+]1)C=Cc1ccccc12 | c1ccccc1.C1CCCCC1.C1=CN2C(=[NH+]1)C=Cc1ccccc12 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccc2ccccc2n1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2c3ccccc3ccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c75393935092495082753744d346cd4a | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2cccnc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=N1.C1(CCCCC1)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=CC=C2)NC2CCCCC2)C2=CC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:26].[NH2:4][c:25]1[n:20][cH:21][cH:22][cH:23][n:24]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][... | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2cccnc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ncccn3c2NC2CCCCC2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[c:20]:[c:21]:[n;H0;D2;+0:22]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[... | null | [] | null | null | null | null | Example 6 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccccc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccc1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccc2)c(NC2CCCCC2)n2cccnc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-efb2df06a3ae44799f8795ccf59d72ac | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccc(OCc3ccccc3)c21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1OCC1=CC=CC=C1.C1(CCCCC1)[N+]#[C-].C(C)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C(=CC=C2)OCC2=CC=CC=C2)NC2CCCCC2)C | [CH3:1][C:2](=[O:3])[Cl:29].O=[CH:5][CH3:6].[NH2:4][c:28]1[n:15][cH:16][cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[C-:7]#[N+:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH3:6])[c:7]([NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[n:15... | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccc(OCc3ccccc3)c21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(COc2cccn3c(NC4CCCCC4)c[nH+]c23)cc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C-;H0;D1:3]#[N+;H0;D2:4]-[C:5](-[C:6])-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[Cl;H0;D1;+0:10])=[O;D1;H0:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[n;H0;D2;+0:15]:[c:16]:[c:17]>>[C:6]-[C:5](-[NH;D2;+0:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n+;H0;D3:12](-[C;H0;D3;+0:9](-[C;D1;H3:8])=[O;D1;H0:11... | null | [] | null | null | null | null | Example 7 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-3-benzyloxypyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1.c1ccccc1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccc(OCc3ccccc3)c21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a15bd302b0f40aeacc3b2b1e11e8715 | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(=O)[n+]1c(C)c(NC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1OCC1=CC=CC=C1.C(C)(C)(C)[N+]#[C-].C(C)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C(=CC=C2)OCC2=CC=CC=C2)NC(C)(C)C)C | [CH3:1][C:2](=[O:3])[Cl:27].O=[CH:5][CH3:6].[NH2:4][c:26]1[n:13][cH:14][cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[C-:7]#[N+:8][C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13]2[cH:14][cH:15][cH:16][c:17](... | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)C | CC(=O)[n+]1c(C)c(NC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(COc2cccn3cc[nH+]c23)cc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C-;H0;D1:3]#[N+;H0;D2:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[C;H0;D3;+0:10](-[Cl;H0;D1;+0:11])=[O;D1;H0:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[n;H0;D2;+0:16]:[c:17]:[c:18]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3... | null | [] | null | null | null | null | Example 8 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-3-benzyloxypyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | C1=CC2=[NH+]C=CN2C=C1.c1ccccc1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C)c(NC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35de8171a48847fc924677310cf7789a | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)CC(C)(C)C>>CC(=O)[n+]1c(C)c(NC(C)(C)CC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1OCC1=CC=CC=C1.CC(CC(C)(C)C)(C)[N+]#[C-].C(C)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C(=CC=C2)OCC2=CC=CC=C2)NC(CC(C)(C)C)(C)C)C | [CH3:1][C:2](=[O:3])[Cl:31].O=[CH:5][CH3:6].[NH2:4][c:30]1[n:17][cH:18][cH:19][cH:20][c:21]1[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[C-:7]#[N+:8][C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9]([CH3:10])([CH3:11])[CH2:12][C... | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)CC(C)(C)C | CC(=O)[n+]1c(C)c(NC(C)(C)CC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(COc2cccn3cc[nH+]c23)cc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C-;H0;D1:3]#[N+;H0;D2:4]-[C:5](-[C:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[C;H0;D3;+0:10](-[Cl;H0;D1;+0:11])=[O;D1;H0:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[n;H0;D2;+0:16]:[c:17]:[c:18]>>[C:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n+;H0;... | null | [] | null | null | null | null | Example 9 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-3-benzyloxypyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) 1,1,3,3-tetramethylbutylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchlor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | C1=CC2=[NH+]C=CN2C=C1.c1ccccc1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.CC=O.Nc1ncccc1OCc1ccccc1.[C-]#[N+]C(C)(C)CC(C)(C)C>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C)c(NC(C)(C)CC(C)(C)C)n2cccc(OCc3ccccc3)c21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb1d1f9e1bc94670a80cb99ed22a0e19 | Nc1ccccn1.O=C(Cl)C1CCCCC1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CC(C)(C)N(C(=O)C1CCCCC1)c1c(-c2ccccc2)[n+](C(=O)C2CCCCC2)c2ccccn12.[Cl-] | C1(CCCCC1)C(=O)Cl.NC1=NC=CC=C1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(C)(C)N(C1=C([N+](=C2N1C=CC=C2)C(=O)C2CCCCC2)C2=CC=CC=C2)C(=O)C2CCCCC2 | [NH2:22][c:31]1[cH:32][cH:33][cH:34][cH:35][n:36]1.[CH2:10]1[CH2:11][CH2:12][CH2:13][CH:25]([C:23](=[O:24])[Cl:37])[CH2:26]1.[CH:6](=[O:7])[c:16]1[cH:17][cH:18][cH:28][cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([N+:5]#[C-:14])[CH3:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]([C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH... | Nc1ccccn1.O=C(Cl)C1CCCCC1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CC(C)(C)N(C(=O)C1CCCCC1)c1c(-c2ccccc2)[n+](C(=O)C2CCCCC2)c2ccccn12.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | ba79f3a7ebb97e38a58722a69a38060f37d04f817917a634ad2cbcf853642f2f | 5962e0833a57e08ba3cb8d81775c86f72b46631c2e2e33cd1bbfa553aa5111cc | O=C(Nc1c(-c2ccccc2)[n+](C(=O)C2CCCCC2)c2ccccn12)C1CCCCC1 | [C-;H0;D1:1]#[N+;H0;D2:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH3;D1;+0:6].[Cl;H0;D1;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-1.[NH2;D1;+0:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20]:[c:21].[O;D1;H0:22]=[CH;D2;+0:23]-[c;H0;D3;+0:24]1:[c:25]:[cH;... | null | [] | null | null | null | null | Example 10 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Tertiary amide | c1ccncc1.C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | C1CCCCC1.c1ccccc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | null | Cl(=O)(=O)(=O)O | null | null | Nc1ccccn1.O=C(Cl)C1CCCCC1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CC(C)(C)N(C(=O)C1CCCCC1)c1c(-c2ccccc2)[n+](C(=O)C2CCCCC2)c2ccccn12.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fed35cec3dc043e3b9de4b02712093a2 | CCCCCCCC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>>CCCCCCC(=O)N(c1c(-c2ccccc2)[n+](C(=O)CCCCCC)c2ccccn12)C(C)(C)C.[Cl-] | C(CCCCCC)C(=O)Cl.NC1=NC=CC=C1.C(C)(C)(C)[N+]#[C-].C(C1=CC=CC=C1)=O>>[Cl-].C(C)(C)(C)N(C1=C([N+](=C2N1C=CC=C2)C(CCCCCC)=O)C2=CC=CC=C2)C(CCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:24][CH2:23][CH2:22][CH2:21][C:19](=[O:20])[Cl:37].[NH2:18][c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1.[O:8]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH3:4][C:33]([CH3:5])([N+:9]#[C-:10])[CH3:36]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]([c:10]1[c:11](-[c:12]2[cH:1... | CCCCCCCC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C | CCCCCCC(=O)N(c1c(-c2ccccc2)[n+](C(=O)CCCCCC)c2ccccn12)C(C)(C)C.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | a28ffe1c0fcccf1e1f91d136c7a3bc7973d1dd7d50e3c7cccac39074ecfaecbc | 5962e0833a57e08ba3cb8d81775c86f72b46631c2e2e33cd1bbfa553aa5111cc | c1ccc(-c2cn3ccccc3[nH+]2)cc1 | [C-;H0;D1:1]#[N+;H0;D2:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[CH3;D1;+0:5])-[CH3;D1;+0:6].[C;D1;H3:7]-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[C:12]-[C:13]-[C;H0;D3;+0:14](-[Cl;H0;D1;+0:15])=[O;D1;H0:16].[NH2;D1;+0:17]-[c:18](:[c:19]):[n;H0;D2;+0:20]:[c:21]:[c:22].[O;H0;D1;+0:23]=[CH;D2;+0:24]-[c;H0;D3;+0:25](:[c:26]:[c:2... | null | [] | null | null | null | null | Example 11 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) tert.-butylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) benzaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Tertiary amide | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccccc1.C1=CC2=[NH+]C=CN2C=C1 | null | Cl(=O)(=O)(=O)O | null | null | CCCCCCCC(=O)Cl.Nc1ccccn1.O=Cc1ccccc1.[C-]#[N+]C(C)(C)C>Cl(=O)(=O)(=O)O>CCCCCCC(=O)N(c1c(-c2ccccc2)[n+](C(=O)CCCCCC)c2ccccn12)C(C)(C)C.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3274ece290144c2abdb1366b6665f24 | CC(=O)Cl.Nc1ccccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1.C1(CCCCC1)[N+]#[C-].C(C1=CC=CO1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2)NC2CCCCC2)C=2OC=CC2 | [CH3:1][C:2](=[O:3])[Cl:25].[NH2:4][c:24]1[n:19][cH:20][cH:21][cH:22][cH:23]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][o:10]1.[C-:11]#[N+:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][o:10]2)[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[n:19]... | CC(=O)Cl.Nc1ccccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1coc(-c2[nH+]c3ccccn3c2NC2CCCCC2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1.[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20]:[c:21]>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[#8;a:3]:[c:4]... | null | [] | null | null | null | null | Example 12 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) furfural solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in proce... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccoc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7941388a77b2446a975114c8d3571489 | CC(=O)Cl.Nc1ncccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2cccnc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=N1.C1(CCCCC1)[N+]#[C-].C(C1=CC=CO1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=CC=C2)NC2CCCCC2)C=2OC=CC2 | [CH3:1][C:2](=[O:3])[Cl:25].[NH2:4][c:24]1[n:19][cH:20][cH:21][cH:22][n:23]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][o:10]1.[C-:11]#[N+:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][o:10]2)[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[n:19]2... | CC(=O)Cl.Nc1ncccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2cccnc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1coc(-c2[nH+]c3ncccn3c2NC2CCCCC2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1.[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[c:20]:[c:21]:[n;H0;D2;+0:22]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[#8... | null | [] | null | null | null | null | Example 13 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) furfural solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in pro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccoc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ncccn1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2cccnc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c88361f1cc54467bfce9e050513d95e | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)Cl)N.C1(CCCCC1)[N+]#[C-].C(C1=CC=CO1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2N)Cl)NC2CCCCC2)C=2OC=CC2 | [CH3:1][C:2](=[O:3])[Cl:27].[NH2:4][c:26]1[n:19][c:20]([NH2:21])[cH:22][c:23]([Cl:24])[n:25]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][o:10]1.[C-:11]#[N+:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][o:10]2)[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]... | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1coc(-c2[nH+]c3ncccn3c2NC2CCCCC2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1.[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[N;D1;H2:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21](-[NH2;D1;+0:22]):[n;H0;D2;+0:23]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H... | null | [] | null | null | null | null | Example 14 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloropyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) furfural solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccoc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b48604124234defbb7814cf012db827 | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccccc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:26].[NH2:4][c:25]1[n:20][cH:21][cH:22][cH:23][cH:24]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C... | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ccccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20]:[c:21]>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[#7;a:3]:[c:4])... | null | [] | null | null | null | null | Example 15 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccncc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eaa1edd7c46b4a0391401b349c4af6d3 | CC(=O)Cl.Nc1ccc([N+](=O)[O-])cn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cc([N+](=O)[O-])ccc21.[Cl-] | C(C)(=O)Cl.NC1=NC=C(C=C1)[N+](=O)[O-].C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC(=C2)[N+](=O)[O-])NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:29].[NH2:4][c:28]1[n:20][cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][C... | CC(=O)Cl.Nc1ccc([N+](=O)[O-])cn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cc([N+](=O)[O-])ccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ccccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20]:[c:21]>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[#7;a:3]:[c:4])... | null | [] | null | null | null | null | Example 16 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-5-nitropyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric aci... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccncc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccc([N+](=O)[O-])cn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cc([N+](=O)[O-])ccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a9a5a55964142e78ccc611ae497d3f7 | CC(=O)Cl.Cc1cccc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cccc21.[Cl-] | NC1=NC(=CC=C1)C.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O.Cl(=O)(=O)(=O)O.C(C)(=O)Cl>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2C)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:27].[NH2:4][c:26]1[n:20][c:21]([CH3:22])[cH:23][cH:24][cH:25]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][... | CC(=O)Cl.Cc1cccc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cccc21.[Cl-] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ccccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[C;D1;H3:16]-[c:17](:[c:18]):[n;H0;D2;+0:19]:[c:20](-[NH2;D1;+0:21]):[c:22]>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:... | null | [] | null | null | null | null | Example 17 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-6-methylpyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 ill perchloric a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccncc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | null | null | null | CC(=O)Cl.Cc1cccc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7f6f74d3a9f43fa8b7eb8ec0624032a | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccncc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CN=C1.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=NC=C2)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:26].[NH2:4][c:25]1[n:20][cH:21][cH:22][n:23][cH:24]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH... | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccncc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 2dc6caedca6974bff0fc06e1cf3081b16bc107cf26d0c20b0c2051dfc216e0e4 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3cnccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[c:18]:[#7;a:19]:[c:20]:[c:21]:[n;H0;D2;+0:22]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[#7;... | null | [] | null | null | null | null | Example 18 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrazine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cnccn1 | C1=CN2C=C[NH+]=C2C=N1 | c1ccncc1.C1CCCCC1.C1=CN2C=C[NH+]=C2C=N1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cnccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccncc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1cc3531c804049d985d00a34b502b64b | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cccnc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=N1.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=CC=C2)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:26].[NH2:4][c:25]1[n:20][cH:21][cH:22][cH:23][n:24]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH... | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cccnc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ncccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[c:20]:[c:21]:[n;H0;D2;+0:22]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[#7;... | null | [] | null | null | null | null | Example 19 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccncc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ncccn1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2cccnc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a84129bb511c44ffb0e8e3eade59bb5b | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)Cl)N.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2N)Cl)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:28].[NH2:4][c:27]1[n:20][c:21]([NH2:22])[cH:23][c:24]([Cl:25])[n:26]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][C... | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ncccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[N;D1;H2:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21](-[NH2;D1;+0:22]):[n;H0;D2;+0:23]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0... | null | [] | null | null | null | null | Example 20 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μL perchl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccncc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-368f336e81b8446b9e73adc393321be5 | CC(=O)Cl.Cc1cc(C)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cc(C)nc21.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)C)C.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2C)C)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:28].[NH2:4][c:27]1[n:20][c:21]([CH3:22])[cH:23][c:24]([CH3:25])[n:26]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][... | CC(=O)Cl.Cc1cc(C)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cc(C)nc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3ncccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[C;D1;H3:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21](-[NH2;D1;+0:22]):[n;H0;D2;+0:23]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0... | null | [] | null | null | null | null | Example 21 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-4,6-dimethylpyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchlo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccncc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Cc1cc(C)nc(N)n1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2c(C)cc(C)nc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae6a67ef2da04b86bbc2bf27489624ee | CC(=O)Cl.Nc1nccs1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccsc21.[Cl-] | C(C)(=O)Cl.NC=1SC=CN1.C1(CCCCC1)[N+]#[C-].N1=C(C=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1SC=C2)NC2CCCCC2)C2=NC=CC=C2 | [CH3:1][C:2](=[O:3])[Cl:25].[NH2:4][c:24]1[n:20][cH:21][cH:22][s:23]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)... | CC(=O)Cl.Nc1nccs1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccsc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | cad224a622aa3b848cba21f80ef7955c393bc57e9344944a7d6b7055cf6d93f3 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccc(-c2[nH+]c3sccn3c2NC2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[n;H0;D2;+0:21]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[#7;a:3]:[... | null | [] | null | null | null | null | Example 22 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-aminothiazole (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) pyridine-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cscn1 | C1=CN2C=CSC2=[NH+]1 | c1ccncc1.C1CCCCC1.C1=CN2C=CSC2=[NH+]1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1nccs1.O=Cc1ccccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2ccccn2)c(NC2CCCCC2)n2ccsc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6b7304d14924773a356ec02ce0f21c6 | CC(=O)Cl.Nc1ccccn1.O=CC1CCCCC1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(C2CCCCC2)c(NC2CCCCC2)n2ccccc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=C1.C1(CCCCC1)[N+]#[C-].C1(CCCCC1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2)NC2CCCCC2)C2CCCCC2 | [CH3:1][C:2](=[O:3])[Cl:26].[NH2:4][c:25]1[n:20][cH:21][cH:22][cH:23][cH:24]1.O=[CH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.[C-:12]#[N+:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[c:12]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:... | CC(=O)Cl.Nc1ccccn1.O=CC1CCCCC1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(C2CCCCC2)c(NC2CCCCC2)n2ccccc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1ccn2c(NC3CCCCC3)c(C3CCCCC3)[nH+]c2c1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C-;H0;D1:5]#[N+;H0;D2:6]-[C:7](-[C:8])-[C:9].[C;D1;H3:10]-[C;H0;D3;+0:11](-[Cl;H0;D1;+0:12])=[O;D1;H0:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[n;H0;D2;+0:17]:[c:18]:[c:19]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[c;H0;D3;+0:5](-[NH;D2;+0:6]-[C:7](-[C:8])-[C:9]):[n;H0;D3;+0:17](:[c:18]:[c:19]):[c:15... | null | [] | null | null | null | null | Example 23 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyridine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) cyclohexane carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | C1CCCCC1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1ccccn1.O=CC1CCCCC1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C2CCCCC2)c(NC2CCCCC2)n2ccccc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0df49b2497040b5aed415ee76af723d | CC(=O)Cl.CC=O.Nc1ncccn1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccnc21.[Cl-] | C(C)(=O)Cl.NC1=NC=CC=N1.C1(CCCCC1)[N+]#[C-].C(C)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=CC=C2)NC2CCCCC2)C | [CH3:1][C:2](=[O:3])[Cl:21].O=[CH:5][CH3:6].[NH2:4][c:20]1[n:15][cH:16][cH:17][cH:18][n:19]1.[C-:7]#[N+:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH3:6])[c:7]([NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[n:15]2[cH:16][cH:17][cH:18][n:19][c:20]12.[Cl-:21] | CC(=O)Cl.CC=O.Nc1ncccn1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccnc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1cnc2[nH+]cc(NC3CCCCC3)n2c1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C-;H0;D1:3]#[N+;H0;D2:4]-[C:5](-[C:6])-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[Cl;H0;D1;+0:10])=[O;D1;H0:11].[NH2;D1;+0:12]-[c:13]1:[#7;a:14]:[c:15]:[c:16]:[c:17]:[n;H0;D2;+0:18]:1>>[C:6]-[C:5](-[NH;D2;+0:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n+;H0;D3:12](-[C;H0;D3;+0:9](-[C;D1;H3:8])=... | null | [] | null | null | null | null | Example 24 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.CC=O.Nc1ncccn1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccnc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d226efdb4de84acf86dab433a563b9d9 | CC(=O)Cl.CC=O.Nc1cc(Cl)nc(N)n1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)Cl)N.C1(CCCCC1)[N+]#[C-].C(C)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2N)Cl)NC2CCCCC2)C | [CH3:1][C:2](=[O:3])[Cl:23].O=[CH:5][CH3:6].[NH2:4][c:22]1[n:15][c:16]([NH2:17])[cH:18][c:19]([Cl:20])[n:21]1.[C-:7]#[N+:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5]([CH3:6])[c:7]([NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[n:15]2[c:16]([NH2:17])[cH:18][c:19]([Cl:20])... | CC(=O)Cl.CC=O.Nc1cc(Cl)nc(N)n1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(C)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1cnc2[nH+]cc(NC3CCCCC3)n2c1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C-;H0;D1:3]#[N+;H0;D2:4]-[C:5](-[C:6])-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[Cl;H0;D1;+0:10])=[O;D1;H0:11].[N;D1;H2:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17](-[NH2;D1;+0:18]):[n;H0;D2;+0:19]:1>>[C:6]-[C:5](-[NH;D2;+0:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n+;H0;D3:18](-[C;H0;D3;+0:9]... | null | [] | null | null | null | null | Example 25 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μL perchloric acid (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.CC=O.Nc1cc(Cl)nc(N)n1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(C)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bfc1863edf9411185dcb4289134a90b | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1cccs1.[C-]#[N+]C1CCCCC1>>CC(=O)[n+]1c(-c2cccs2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)Cl)N.C1(CCCCC1)[N+]#[C-].S1C(=CC=C1)C=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2N)Cl)NC2CCCCC2)C=2SC=CC2 | [CH3:1][C:2](=[O:3])[Cl:27].[NH2:4][c:26]1[n:19][c:20]([NH2:21])[cH:22][c:23]([Cl:24])[n:25]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][s:10]1.[C-:11]#[N+:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]... | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1cccs1.[C-]#[N+]C1CCCCC1 | CC(=O)[n+]1c(-c2cccs2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1csc(-c2[nH+]c3ncccn3c2NC2CCCCC2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1.[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[N;D1;H2:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21](-[NH2;D1;+0:22]):[n;H0;D2;+0:23]:1>>[C:10]-[C:9](-[NH;D2;+0:8]-[c;H0;D3;+0:7]1:[c;H0;D3;+0:1](-[c;... | null | [] | null | null | null | null | Example 26 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) thiophene-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perch... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccsc1.C1CCCCC1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1cccs1.[C-]#[N+]C1CCCCC1>Cl(=O)(=O)(=O)O>CC(=O)[n+]1c(-c2cccs2)c(NC2CCCCC2)n2c(N)cc(Cl)nc21.[Cl-] |
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