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-c3a75813d0b24864aa4f7cd526efd6aa | ord-5147f22926644af284b6b32cf7616792 | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCl)N1CCc2ccccc21>>O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 | Cl.ClC1=C(C=CC=C1Cl)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].ClCCC(=O)N1CCC2=CC=CC=C12>>ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCC(=O)N1CCC2=CC=CC=C12 | [NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[Cl:16])[CH2:17][CH2:18]1.Cl[CH2:4][CH2:3][C:2](=[O:1])[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21>>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[Cl:16])[CH2:17][CH2... | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCl)N1CCc2ccccc21 | O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 | null | null | CC(CC)=O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCN1CCN(c2ccccc2)CC1)N1CCc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C:6]-[#7:5](-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1)-[c:7] | null | [] | 50 | CELSIUS | null | null | A mixture of 1-(2,3-dichlorophenyl)piperazine, hydrochloride (8.0 g) and potassium carbonate (15 g) in a mixture of butanone (50 mL) and dimethyl formamide (5 mL) was heated to 50° C. followed by the addition of 3-chloro-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one (6.0 g). The resulting mixture was boiled under reflux fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CC(CC)=O.CN(C=O)C | 50 | null | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCl)N1CCc2ccccc21>CC(CC)=O.CN(C=O)C>O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43478e91f8c64eae94c35aa44c372d3c | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCCBr)N1CCc2ccccc21>>O=C(CCCCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 | Cl.ClC1=C(C=CC=C1Cl)N1CCNCC1.C(C)(C)N(CC)C(C)C.BrCCCCC(=O)N1CCC2=CC=CC=C12>>ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCCC(=O)N1CCC2=CC=CC=C12 | [NH:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]2[Cl:18])[CH2:19][CH2:20]1.Br[CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:21]1[CH2:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([Cl... | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCCBr)N1CCc2ccccc21 | O=C(CCCCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCCN1CCN(c2ccccc2)CC1)N1CCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | 45 | CELSIUS | null | null | A mixture of 1-(2,3-dichlorophenyl)piperazine hydrochloride (8.0 g) and diisopropylethylamine (15 mL) in butanone (50 mL) was heated to 45° C. followed by the addition of 5-bromo-1-(2,3-dihydro-1H-indol-1-yl)pentan-1-one (5.4 g). The resulting mixture was boiled under reflux for 40 h and filtered hot. The remaining org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | CC(CC)=O | 45 | null | Clc1cccc(N2CCNCC2)c1Cl.O=C(CCCCBr)N1CCc2ccccc21>CC(CC)=O>O=C(CCCCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bb40dc82a3a4afea345f53344ad0ac4 | Clc1ccccc1N1CCNCC1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2ccccc2Cl)CC1)N1CCc2ccccc21 | Cl.ClC1=C(C=CC=C1)N1CCNCC1.ClCCCC(=O)N1CCC2=CC=CC=C12>>ClC1=C(C=CC=C1)N1CCN(CC1)CCCC(=O)N1CCC2=CC=CC=C12 | [NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2:18]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2... | Clc1ccccc1N1CCNCC1.O=C(CCCCl)N1CCc2ccccc21 | O=C(CCCN1CCN(c2ccccc2Cl)CC1)N1CCc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccccc2)CC1)N1CCc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | from 1-(2-chlorophenyl)piperazine, hydrochloride and 4-chloro-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one. Mp 119–121° C. 1H NMR (DMSO-d6): 1.75–1.85 (m, 2H); 2.35–2.50 (m, 4H); 2.55 (s, 4H); 3.95 (s, 4H); 3.15 (t, 2H); 4.10 (t, 2H); 6.95 (t, 1H); 7.05 (t, 1H); 7.10 (d, 1H); 7.15 (t, 1H); 7.20 (d, 1H); 7.25 (t, 1H); 7.40 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | Clc1ccccc1N1CCNCC1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2ccccc2Cl)CC1)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-22d2c8fcfcd84c428fb38bd7d6223c47 | Clc1cccc(N2CCNCC2)c1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2cccc(Cl)c2)CC1)N1CCc2ccccc21 | Cl.Cl.ClC=1C=C(C=CC1)N1CCNCC1.ClCCCC(=O)N1CCC2=CC=CC=C12>>ClC=1C=C(C=CC1)N1CCN(CC1)CCCC(=O)N1CCC2=CC=CC=C12 | [NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]2)[CH2:17][CH2:18]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]2)[CH2:17]... | Clc1cccc(N2CCNCC2)c1.O=C(CCCCl)N1CCc2ccccc21 | O=C(CCCN1CCN(c2cccc(Cl)c2)CC1)N1CCc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccccc2)CC1)N1CCc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | from 1-(3-chlorophenyl)piperazine, dihydrochloride and 4-chloro-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one. Mp 102–107° C. 1H NMR (DMSO-d6): 1.75–1.85 (m, 2H); 2.35 (t, 2H); 2.45–2.55 (m, 6H); 3.10–3.20 (m, 6H); 4.10 (t, 2H); 6.75 (d, 1H); 6.85 (d, 1H); 6.90 (s, 1H); 6.95 (t, 1H); 7.10 (t, 1H); 7.15–7.25 (m, 2H); 8.10 (d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | Clc1cccc(N2CCNCC2)c1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2cccc(Cl)c2)CC1)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d38d6c6f0c5a41f987fe4567dbc73965 | O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21.O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21>>Cl.Clc1cccc(N2CCN(CCCN3CCc4ccccc43)CC2)c1Cl | ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCC(=O)N1CCC2=CC=CC=C12.ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCC(=O)N1CCC2=CC=CC=C12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3]>>Cl.ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCN1CCC2=CC=CC=C12 | O=C(CCN1CCN(c2cccc(Cl)c2[Cl:1])CC1)N1CCc2ccccc21.O=[C:14]([CH2:13][CH2:12][N:11]1[CH2:10][CH2:9][N:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([Cl:2])[c:26]2[Cl:27])[CH2:25][CH2:24]1)[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[ClH:1].[Cl:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12]... | O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21.O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21 | Cl.Clc1cccc(N2CCN(CCCN3CCc4ccccc43)CC2)c1Cl | null | null | O1CCCC1 | Miscellaneous | OtherReaction | d26035f3bac55deefa8a21c9f376455003c56b07b74c94ffc8ec018719015d9a | 52131a42c0c53e6809c722d2ccee9ef8cfbddf0557566469c2697d2902198f9c | c1ccc(N2CCN(CCCN3CCc4ccccc43)CC2)cc1 | Cl-c1:c:c:c:c(-N2-C-C-N(-C-C-C(=O)-N3-C-C-c4:c:c:c:c:c:4-3)-C-C-2):c:1-[Cl;H0;D1;+0:1].O=[C;H0;D3;+0:2](-[C:3]-[C:4])-[#7:5](-[C:6])-[c:7]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[#7:5](-[C:6])-[c:7].[ClH;D0;+0:1] | null | [] | 5 | CELSIUS | 30 | MINUTE | Lithium aluminium hydride (1.8 g) was suspended in tetrahydrofuran (30 mL) at 0° C., and the suspension was added a solution of aluminium trichloride (1.8 g) in tetrahydrofuran (30 mL) at 0–5° C. over 15 min. To this mixture, a solution of 1a, 3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide.Tertiary amide.Tertiary amine.Tertiary amine | null | C1CNCCN1.c1ccccc1.c1ccc2c(c1)CCN2 | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2c(c1)CC[NH]2 | HCl | O1CCCC1 | 5 | 0.5 | O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21.O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2ccccc21>O1CCCC1>Cl.Clc1cccc(N2CCN(CCCN3CCc4ccccc43)CC2)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5336bacc510e450986497bcfc85c5b3a | BrCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl>>Cl.Clc1cccc(N2CCN(CCCc3c[nH]c4ccccc34)CC2)c1Cl | BrCCCC1=CNC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].ClC1=C(C=CC=C1Cl)N1CCNCC1>>Cl.ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCC1=CNC2=CC=CC=C12 | Br[CH2:12][CH2:13][CH2:14][c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12.[Cl:1][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:24][CH2:25]2)[c:26]1[Cl:27]>>[ClH:1].[Cl:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][c:15]3[cH:16][nH:17][c:18]4[cH:19]... | BrCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl | Cl.Clc1cccc(N2CCN(CCCc3c[nH]c4ccccc34)CC2)c1Cl | null | null | C(C)#N | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 34ecf698ba4c3d229136de4eafceea7425b5555faba807457b006ad2633abdb9 | 55cb0223d3535b9197d8f7ec112fe586b516e0475448133020904f1839920be7 | c1ccc(N2CCN(CCCc3c[nH]c4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5](:[c:6]-[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1):[c;H0;D3;+0:13](-[Cl;H0;D1;+0:14]):[c:15]:[c:16]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7](-[c:6]:[c:5](-[Cl;D1;H0:4]):[c;H0;D3;+0:13](-[Cl;D1;H0:17]):[c:15]:[c:16])-[C:8]-[C:9]-1.[ClH;D0;+0:... | null | [] | null | null | null | null | A mixture of 3-(3-bromopropyl)-1H-indole (1.19 g), potassium carbonate (1.4 g) and 1-(2,3-dichlorophenyl)piperazine (1.27 g) in anhydrous acetonitrile (10 mL) was boiled under reflux for 5 h and cooled to room temperature. The mixture was added silicagel (7 g), and the solvent was evaporated in vacuo. The compound was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Secondary amine | Aromatic halide.Tertiary amine | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | null | C(C)#N | null | null | BrCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl>C(C)#N>Cl.Clc1cccc(N2CCN(CCCc3c[nH]c4ccccc34)CC2)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9094f1f8b12457f9aa9cb2169657c75 | BrCCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl>>Cl.Clc1cccc(N2CCN(CCCCc3c[nH]c4ccccc34)CC2)c1Cl | ClC1=C(C=CC=C1Cl)N1CCNCC1.BrCCCCC1=CNC2=CC=CC=C12>>Cl.ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCCC1=CNC2=CC=CC=C12 | Br[CH2:12][CH2:13][CH2:14][CH2:15][c:16]1[cH:17][nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12.[Cl:1][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:25][CH2:26]2)[c:27]1[Cl:28]>>[ClH:1].[Cl:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][c:16]3[cH:17][nH:1... | BrCCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl | Cl.Clc1cccc(N2CCN(CCCCc3c[nH]c4ccccc34)CC2)c1Cl | null | null | null | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 34ecf698ba4c3d229136de4eafceea7425b5555faba807457b006ad2633abdb9 | 55cb0223d3535b9197d8f7ec112fe586b516e0475448133020904f1839920be7 | c1ccc(N2CCN(CCCCc3c[nH]c4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5](:[c:6]-[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1):[c;H0;D3;+0:13](-[Cl;H0;D1;+0:14]):[c:15]:[c:16]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7](-[c:6]:[c:5](-[Cl;D1;H0:4]):[c;H0;D3;+0:13](-[Cl;D1;H0:17]):[c:15]:[c:16])-[C:8]-[C:9]-1.[ClH;D0;+0:... | null | [] | null | null | null | null | from 1-(2,3-dichlorophenyl)piperazine and 3-(4-bromobutyl)-1H-indole. Mp 121–122° C. 1H NMR (DMSO-d6): 1.45–1.55 (m, 2H); 1.65–1.75 (m, 2H); 2.35 (t, 2H); 2.50 (b s, 4H); 2.70 (t, 2H); 2.95 (b s, 4H); 6.95 (t, 1H); 7.05 (t, 1H); 7.10–7.15 (m, 2H); 7.25–7.30 (m, 2H); 7.35 (d, 1H); 7.50 (d, 1H); 10.75 (b s, 1H). Ms m/z: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Secondary amine | Aromatic halide.Tertiary amine | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | null | null | null | null | BrCCCCc1c[nH]c2ccccc12.Clc1cccc(N2CCNCC2)c1Cl>>Cl.Clc1cccc(N2CCN(CCCCc3c[nH]c4ccccc34)CC2)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-399ea26007484f3396cee9cf2d6969d1 | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2[nH]cc(CCCCl)c2c1>>Fc1ccc2[nH]cc(CCCN3CCN(c4cccc(Cl)c4Cl)CC3)c2c1 | ClC1=C(C=CC=C1Cl)N1CCNCC1.ClCCCC1=CNC2=CC=C(C=C12)F>>ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCC1=CNC2=CC=C(C=C12)F | [NH:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][cH:19][c:20]([Cl:21])[c:22]2[Cl:23])[CH2:24][CH2:25]1.Cl[CH2:11][CH2:10][CH2:9][c:8]1[cH:7][nH:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:27][c:26]21>>[F:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][N:15]([c:16]4[cH:17][cH:18][c... | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2[nH]cc(CCCCl)c2c1 | Fc1ccc2[nH]cc(CCCN3CCN(c4cccc(Cl)c4Cl)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCCc3c[nH]c4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | from 1-(2,3-dichlorophenyl)piperazine and 3-(3-chloropropyl)-5-fluoro-1H-indole. Mp 147–148° C. 1H NMR (DMSO-d6): 1.75–1.85 (m, 2H); 2.30–2.45 (t, 2H); 2.45–2.60 (m, 2H); 2.70 (t, 2H); 3.00 (b s, 4H); 3.35 (b s, 2H); 6.85–6.95 (m, 1H); 7.05–7.15 (m, 1H); 7.20 (s, 1H); 7.20–7.35 (m, 4H); 10.85 (b s, 1H). Ms m/z: 406 (MH... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | null | null | null | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2[nH]cc(CCCCl)c2c1>>Fc1ccc2[nH]cc(CCCN3CCN(c4cccc(Cl)c4Cl)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5dd867193b449d4bcf48c923e1b0011 | Clc1cccc(N2CCNCC2)c1Cl.O=C1CCc2ccccc2N1CCCCBr>>O=C1CCc2ccccc2N1CCCCN1CCN(c2cccc(Cl)c2Cl)CC1 | Cl.ClC1=C(C=CC=C1Cl)N1CCNCC1.N.BrCCCCN1C(CCC2=CC=CC=C12)=O.C([O-])([O-])=O.[K+].[K+]>>ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCCCN1C(CCC2=CC=CC=C12)=O | [NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][cH:23][c:24]([Cl:25])[c:26]2[Cl:27])[CH2:28][CH2:29]1.Br[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:... | Clc1cccc(N2CCNCC2)c1Cl.O=C1CCc2ccccc2N1CCCCBr | O=C1CCc2ccccc2N1CCCCN1CCN(c2cccc(Cl)c2Cl)CC1 | null | null | CC(CC)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CCc2ccccc2N1CCCCN1CCN(c2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | The free base of 1-(2,3-dichlorophenyl)piperazine, hydrochloride (6.0 g) was liberated by the use ethyl acetate and aqueous ammonia. The remaining oil was dissolved in butanone (500 mL) followed by the addition of potassium carbonate (9.7 g), and the mixture was heated to reflux temperature. To this mixture was added a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2c(c1)CCC[NH]2.C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(CC)=O.C(C)(=O)OCC | null | null | Clc1cccc(N2CCNCC2)c1Cl.O=C1CCc2ccccc2N1CCCCBr>CC(CC)=O.C(C)(=O)OCC>O=C1CCc2ccccc2N1CCCCN1CCN(c2cccc(Cl)c2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-326998311bbe455d9881ea3eb9391ede | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2c(c1)CCN2.O=C(Cl)CCBr>>O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2cc(F)ccc21 | ClC1=C(C=CC=C1Cl)N1CCNCC1.C(C)(C)N(CC)C(C)C.[Al+3].[Cl-].[Cl-].[Cl-].BrCCC(=O)Cl.ClCCl.C(C)(C)N(CC)C(C)C.FC=1C=C2CCNC2=CC1.[OH-].[Na+]>>ClC1=C(C=CC=C1Cl)N1CCN(CC1)CCC(=O)N1CCC2=CC(=CC=C12)F | [NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[Cl:16])[CH2:17][CH2:18]1.[NH:19]1[CH2:20][CH2:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]21.Cl[C:2](=[O:1])[CH2:3][CH2:4]Br>>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[Cl:16])[... | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2c(c1)CCN2.O=C(Cl)CCBr | O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2cc(F)ccc21 | null | null | C(C)#N | Acylation | OtherReaction | e6ee41d9f586f8b18421fe58ac66cc363ad58542c3491ff27206bb457448ba5a | ef8b84f1e1da90e48fb3c0bc44e43a80cb90e07afa1034aea7a1477489231c3f | O=C(CCN1CCN(c2ccccc2)CC1)N1CCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1.[c:11]:[c:12]1:[c:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1)-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[c:13]:[c:12]-1:[c:11] | null | [] | null | null | 8 | HOUR | 3-Bromopropanoyl chloride (1 g in 10 ml dry dichloromethane) was added with stirring at 0° C. to a suspension of 1 g Wang resin (Rapp polymere, loading 0.95 mmol/g) in 10 ml dry dichloromethane containing 5 equivalents of diisopropylethyl amine. The mixture was stirred overnight at room temperature, filtered and washed... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Secondary amine.Secondary amine | Tertiary amide.Tertiary amine | C1CNCC[NH]1.c1ccc2c(c1)CCN2 | C1C[NH]CC[NH]1.c1ccc2c(c1)CC[NH]2 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl.Br- | C(C)#N | null | 8 | Clc1cccc(N2CCNCC2)c1Cl.Fc1ccc2c(c1)CCN2.O=C(Cl)CCBr>C(C)#N>O=C(CCN1CCN(c2cccc(Cl)c2Cl)CC1)N1CCc2cc(F)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-312d7d2a6a2543d7a04ff7f6190d2754 | Clc1ncnc(Cl)n1.Nc1nc2ccccc2[nH]1>>Nc1nc2ccccc2n1-c1ncnc(Cl)n1 | ClC1=NC=NC(=N1)Cl.CCN(C(C)C)C(C)C.O.O.NC=1NC2=C(N1)C=CC=C2>>ClC1=NC(=NC=N1)N1C(=NC2=C1C=CC=C2)N | Cl[c:11]1[n:12][cH:13][n:14][c:15]([Cl:16])[n:17]1.[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[nH:10]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1-[c:11]1[n:12][cH:13][n:14][c:15]([Cl:16])[n:17]1 | Clc1ncnc(Cl)n1.Nc1nc2ccccc2[nH]1 | Nc1nc2ccccc2n1-c1ncnc(Cl)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | de8ca90b6a87d8cb2c34d2d3043201922cff5cf5653513773b5948279865a7ce | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ncn2-c1ncncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[#7;a:7]:1.[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[nH;D2;+0:15]:1>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:15]2:[c:9](-[N;D1;H2:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:2:[c:14]):[#7;a:7]:1 | 83 | [{"value": 83.0, "product": "ClC1=NC(=NC=N1)N1C(=NC2=C1C=CC=C2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.7, "product": "ClC1=NC(=NC=N1)N1C(=NC2=C1C=CC=C2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.9 | HOUR | To 1.0 g (6.67 mmol) of 2,4-dichloro-1,3,5-triazine in 3 mL of DMF at 0° C. is added 1.16 mL (6.67 mmol) of DIEA. The resulting yellow solution is stirred at 0° C. for 10 min when-888 mg (6.67 mmol) of 2-aminobenzimidazole is added portionwise over 5 min, followed by an additional 1 mL of DMF. The resulting mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncncn1.c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1.c1ncncn1 | c1nc2ccccc2[nH]1.c1ncncn1 | HCl | CN(C)C=O | 0 | 1.9 | Clc1ncnc(Cl)n1.Nc1nc2ccccc2[nH]1>CN(C)C=O>Nc1nc2ccccc2n1-c1ncnc(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3775196ad1a841a887da7e8896b6bcf3 | CC(=O)OC(C)=O.CCC(N)C(=O)O>>CCC(NC(C)=O)C(=O)O | NC(C(=O)O)CC.C(C)(=O)OC(C)=O>>C(C)(=O)NC(C(=O)O)CC | CC(=O)O[C:5]([CH3:6])=[O:7].[CH3:1][CH2:2][CH:3]([NH2:4])[C:8](=[O:9])[OH:10]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5]([CH3:6])=[O:7])[C:8](=[O:9])[OH:10] | CC(=O)OC(C)=O.CCC(N)C(=O)O | CCC(NC(C)=O)C(=O)O | null | null | C(C)(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | 100 | CELSIUS | 2 | HOUR | 163 g (1.58 mol) 2-aminobutanoic acid are dissolved in acetic acid, and 242 g (2.37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100° C. until completion of reaction, then the solution is evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | null | HO- | C(C)(=O)O | 100 | 2 | CC(=O)OC(C)=O.CCC(N)C(=O)O>C(C)(=O)O>CCC(NC(C)=O)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e9da760204a424b95349e789bfbea5b | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl>>CCOC(=O)C(=O)C(CC)NC(C)=O | ClC(C(=O)OCC)=O.C(C)(=O)NC(C(=O)O)CC.N1=CC=CC=C1>>C(C)(=O)NC(C(C(=O)OCC)=O)CC | O=C(O)[CH:8]([CH2:9][CH3:10])[NH:11][C:12]([CH3:13])=[O:14].Cl[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12]([CH3:13])=[O:14] | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl | CCOC(=O)C(=O)C(CC)NC(C)=O | null | null | O1CCCC1 | C-C Coupling | Ketonization by decarboxylation of acid halides | aaebaa0d813a71dc889ae147df75d12dcb32900152f1a5154d5b3ca46552ea1b | 3f61ba26fe9791436c27b93d0c669474775a60e3446708a267a9de08824bde1e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].O-C(=O)-[CH;D3;+0:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C:12]-[C;D1;H3:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C:12]-[C;D1;H3:13] | null | [] | null | null | null | null | 9.2 g (63.4 mmol) 2-(acetylamino)butanoic acid are suspended in 120 ml tetrahydrofuran and heated to reflux together with 15.0 g (190 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 17.3 g (127 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at reflux un... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ester | Ketone | null | null | null | HCl | O1CCCC1 | null | null | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl>O1CCCC1>CCOC(=O)C(=O)C(CC)NC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-923e5209c9ad44c6922b3b07fafeed4a | CCC(N)C(=O)O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)C(=O)O | NC(C(=O)O)CC.Cl[Si](C)(C)C.C1(CCCC1)C(=O)Cl.C(C)N(CC)CC>>C1(CCCC1)C(=O)NC(C(=O)O)CC | [CH3:1][CH2:2][CH:3]([NH2:4])[C:12](=[O:13])[OH:14].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[C:12](=[O:13])[OH:14] | CCC(N)C(=O)O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)C(=O)O | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7](-[C:6])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:5] | null | [] | 0 | CELSIUS | 1 | HOUR | 35 g (339 mmol) 2-aminobutanoic acid and 75.6 g (747 mmol) triethylamine are suspended in 300 ml of dichloromethane and stirred at 0° C. 81 g (747 mmol) chlorotrimethylsilane are added dropwise, then the mixture is stirred for 1 hour at room temperature and for 1 hour at 40° C. After cooling down to −10° C., 45 g (339 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1 | HCl | ClCCl.O | 0 | 1 | CCC(N)C(=O)O.O=C(Cl)C1CCCC1>ClCCl.O>CCC(NC(=O)C1CCCC1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a59515024644f7f9268fc7d7abe72fa | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl>>CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 | ClC(C(=O)OCC)=O.C1(CCCC1)C(=O)NC(C(=O)O)CC.N1=CC=CC=C1>>C1(CCCC1)C(=O)NC(C(C(=O)OCC)=O)CC | O[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.O=C(Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 | null | null | O1CCCC1 | C-C Coupling | Ketonization by decarboxylation of acid halides | aaebaa0d813a71dc889ae147df75d12dcb32900152f1a5154d5b3ca46552ea1b | 3f61ba26fe9791436c27b93d0c669474775a60e3446708a267a9de08824bde1e | C1CCCC1 | Cl-C(=O)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | 1.6 g (8 mmol) 2-[(cyclopentylcarbonyl)amino]butanoic acid are suspended in 30 ml tetrahydrofuran and heated to reflux together with 1.91 g (24 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 2.19 g (16 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ester | Ketone | null | null | C1CCCC1 | HCl | O1CCCC1 | null | null | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl>O1CCCC1>CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e2a99234f7f4c078ff0b3dc5a472c6e | CCOC(=O)C(=O)C(CC)NC(C)=O.CCOC(=O)c1ccc(C(=N)N)cc1.NN>>CCOC(=O)c1ccc(-c2nnc(C(CC)NC(C)=O)c(=O)[nH]2)cc1 | C(C)(=O)NC(C(C(=O)OCC)=O)CC.Cl.NC(C1=CC=C(C(=O)OCC)C=C1)=N.O.NN>>C(C)(=O)NC(CC)C=1C(NC(=NN1)C1=CC=C(C(=O)OCC)C=C1)=O | CCO[C:21]([C:13](=O)[CH:14]([CH2:15][CH3:16])[NH:17][C:18]([CH3:19])=[O:20])=[O:22].N[C:10]([c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:25][cH:24]1)=[NH:23].[NH2:11][NH2:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][n:12][c:13]([CH:14]([CH2:15][CH3:16])[NH:17][C:18]([CH3:1... | CCOC(=O)C(=O)C(CC)NC(C)=O.CCOC(=O)c1ccc(C(=N)N)cc1.NN | CCOC(=O)c1ccc(-c2nnc(C(CC)NC(C)=O)c(=O)[nH]2)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e7bab37df0829099558b3ea1b1d6c14ca29d111a0fe7c4e70294ed15a1035365 | b9a6c12d0e1239b0cb412542e52dae4bfecd4fc5a7cf6f6405348266ba7aff2e | O=c1cnnc(-c2ccccc2)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C:4](-[C:5])-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].N-[C;H0;D3;+0:10](=[NH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[C:5]-[C:4](-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[c;H0;D3;+0:3]1:[n;H0;D2;+0:18]:[n;H0;D2;+0:17]:[... | null | [] | null | null | 1 | HOUR | 1.98 g (8.66 mmol) ethyl 4-[amino(imino)methyl]benzoate hydrochloride are suspended in 50 ml of ethanol and 1.47 g (10.2 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 2.59 g (13 mmol, 1.5 equiv.) of the compound of Example 2A, dissolved in 10 ml of ethanol, are added. The... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Primary amine | null | null | c1cnncn1 | c1ccccc1.c1cnncn1 | HO- | C(C)O | null | 1 | CCOC(=O)C(=O)C(CC)NC(C)=O.CCOC(=O)c1ccc(C(=N)N)cc1.NN>C(C)O>CCOC(=O)c1ccc(-c2nnc(C(CC)NC(C)=O)c(=O)[nH]2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d63c930ad8b54bf6bec77254a03a4189 | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccc(C(N)=O)cc1.NN>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C(N)=O)cc2)[nH]c1=O | C1(CCCC1)C(=O)NC(C(C(=O)OCC)=O)CC.Cl.NC(C1=CC=C(C(=O)N)C=C1)=N.O.NN>>C1(CCCC1)C(=O)NC(CC)C=1C(NC(=NN1)C1=CC=C(C(=O)N)C=C1)=O | CCO[C:26]([C:12](=O)[CH:3]([CH2:2][CH3:1])[NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:27].N=[C:15]([c:16]1[cH:17][cH:18][c:19]([C:20]([NH2:21])=[O:22])[cH:23][cH:24]1)[NH2:25].[NH2:13][NH2:14]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-[c... | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccc(C(N)=O)cc1.NN | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C(N)=O)cc2)[nH]c1=O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e7bab37df0829099558b3ea1b1d6c14ca29d111a0fe7c4e70294ed15a1035365 | b9a6c12d0e1239b0cb412542e52dae4bfecd4fc5a7cf6f6405348266ba7aff2e | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C:4](-[C:5])-[#7:6]-[C:7]=[O;D1;H0:8].N=[C;H0;D3;+0:9](-[NH2;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[C:5]-[C:4](-[#7:6]-[C:7]=[O;D1;H0:8])-[c;H0;D3;+0:3]1:[n;H0;D2;+0:16]:[n;H0;D2;+0:17]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1... | null | [] | 60 | CELSIUS | 1 | HOUR | 2.84 g (14.2 mmol, 1 equiv.) 4-[amino(imino)methyl]benzamide hydrochloride are suspended in 10 ml of ethanol and 1.37 g (26.8 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at 60° C. for 1 hour, 6.28 g (24.6 mmol, 1.1 equiv.) ethyl 3-[(cyclopentylcarbonyl)-amino]-2-oxopentanoate (Example 4A), dissolved i... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Primary amine | null | null | c1cnncn1 | C1CCCC1.c1cnncn1.c1ccccc1 | HO- | C(C)O | 60 | 1 | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccc(C(N)=O)cc1.NN>C(C)O>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C(N)=O)cc2)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1660cc2acdb4b9a91f01468284b9579 | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-])=O.C1(CCCC1)C(=O)Cl>>[N+](=O)([O-])C=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2)[nH:25][c:26]1=[O:27].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17... | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 16A, 3.0 g (10.9 mmol) 6-(1-aminopropyl)-3-(3-nitrophenyl)-1,2,4-triazin-5(4H)-one (Example 15A), 2.2 g (16.3 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.c1ccccc1 | HCl | null | null | null | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfcdddc5545c4ae5a70abee645f7a605 | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-])=O.C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)Cl>>C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)NC(CC)C=1C(NC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-])=O | Cl[C:5](=[O:6])[C@@H:7]1[CH2:8][CH2:9][C@H:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:17]1[n:18][n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29]2)[nH:30][c:31]1=[O:32]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C@H:7]1[CH2:8][CH2:9][C@@H:10]([... | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 16A, 3.2 g (11.6 mmol) 6-(1-aminopropyl)-3-(3-nitrophenyl)-1,2,4-triazin-5(4H)-one (Example 15A), 2.4 g (11.6 mmol) cis-4-tert.-butylcyclohexanecarbonyl chloride (Example 42A) and proportionate amounts of the other reagents are used. The crude product is used in the next step wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnncn1.c1ccccc1 | HCl | null | null | null | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb90fbfc22ad4b189a6629d9ec2fd186 | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | [N+](=O)([O-])C=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.O=P(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C2=CC(=CC=C2)[N+](=O)[O-])=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:26]1[n:11][n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22]2)[nH:23][c:24]1=[O:25])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([N+... | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | null | null | ClC(C)Cl | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | 0 | CELSIUS | null | null | 3.5 g (9.4 mmol) N-{1-[3-(3-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-cyclopentanecarboxamide (Example 19A) are suspended in 60 ml dichloroethane, and 1.45 g (9.4 mmol) phosphoroxychloride are added. The mixture is stirred at reflux for 3 hour. After cooling down to 0° C., 10 ml saturated NaHCO3 (aq) is... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | HO- | ClC(C)Cl | 0 | null | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>ClC(C)Cl>CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc632e6c43e7444987fca0e1a90e6503 | CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCc1nc(C2CCC(C(C)(C)C)CC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)NC(CC)C=1C(NC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-])=O.P(=O)(Cl)(Cl)Cl>>C(C)(C)(C)C1CCC(CC1)C1=NC(=C2C(NC(=NN21)C2=CC(=CC=C2)[N+](=O)[O-])=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:31]1[n:16][n:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27]2)[nH:28][c:29]1=[O:30])[C@H:6]1[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH:9]([C:10]([CH3:11])([CH3:1... | CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | CCc1nc(C2CCC(C(C)(C)C)CC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C@@H;D3;+0:13](-[C:14]-[C:15])-[C:16]-[C:17]>>[C:15]-[C:14]-[CH;D3;+0:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]... | null | [] | null | null | null | null | In analogy to the procedure for Example 21A, 5.1 g (11.6 mmol) crude cis-4-tert-butyl-N-{1-[3-(3-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclo-hexanecarboxamide (Example 20A), 2.7 g (17.4 mmol) phosphoric trichloride are stirred at reflux for 3 hours and proportionate amounts of the solvents are used.
... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.c1ccccc1 | HO- | null | null | null | CCC(NC(=O)[C@H]1CC[C@@H](C(C)(C)C)CC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCc1nc(C2CCC(C(C)(C)C)CC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-22e1a08ab57f4e1e9d83778a11c66ea6 | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN>>CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O | C(C)(=O)NC(C(C(=O)OCC)=O)CC.Cl.BrC=1C=C(C=CC1)C(N)=N.O.NN>>BrC=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(C)=O | CCO[C:20]([C:8](=O)[CH:3]([CH2:2][CH3:1])[NH:4][C:5]([CH3:6])=[O:7])=[O:21].N=[C:11]([c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1)[NH2:19].[NH2:9][NH2:10]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5]([CH3:6])=[O:7])[c:8]1[n:9][n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]2)[nH:19][c:20]1=[O:21] | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN | CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e7bab37df0829099558b3ea1b1d6c14ca29d111a0fe7c4e70294ed15a1035365 | b9a6c12d0e1239b0cb412542e52dae4bfecd4fc5a7cf6f6405348266ba7aff2e | O=c1cnnc(-c2ccccc2)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C:4](-[C:5])-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].N=[C;H0;D3;+0:10](-[NH2;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[C:5]-[C:4](-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[c;H0;D3;+0:3]1:[n;H0;D2;+0:18]:[n;H0;D2;+0:17]:... | null | [] | null | null | 1 | HOUR | 2.02 g (8.6 mmol, 1 equiv.) 3-bromobenzenecarboximidamide hydrochloride (Example 31A) are suspended in 50 ml of ethanol, and 1.47 g (10.2 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 2.59 g (13 mmol, 1.5 equiv.) of the compound of Example 2A, dissolved in 10 l of ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Primary amine | null | null | c1cnncn1 | c1cnncn1.c1ccccc1 | HO- | C(C)O | null | 1 | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN>C(C)O>CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93fdfe881a7d4298bc877d00cd996986 | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O>>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 | NC(CC)C=1C(NC(=NN1)C1=CC=C(C=C1)Br)=O.C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)Cl>>BrC1=CC=C(C=C1)C1=NN2C(C(N1)=O)=C(N=C2[C@@H]2CC[C@@H](CC2)C(C)(C)C)CC | O=[C:5](Cl)[C@@H:6]1[CH2:7][CH2:8][C@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:29]1[n:16][n:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:1... | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d528f61cb17ffa5934389707620e92dc49083bef6ae6ec9976a5efa729d467e2 | f4550a08821e4f2624eeee345c16eafd026df7c9988e01c5dbe20cc7df2780e1 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | Cl-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[C:4].[C;D1;H3:5]-[C:6]-[CH;D3;+0:7](-[NH2;D1;+0:8])-[c:9]1:[n;H0;D2;+0:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:7](-[C:6]-[C;D1;H3:5]):[c:9]2:[c:14](=[O;D1;H0:15]):[#7;a:13]:[c:12]:[#7;a:11]:[n;H0;D3;+0:10]:2:1)-[C... | null | [] | null | null | null | null | In analogy to the procedure for Example 23A, 7.6 g (24.6 mmol) 6-(1-aminopropyl)-3-(4-bromophenyl)-1,2,4-triazin-5(4H)-one (Example 29A), 4.98 g (24.55 mmol) cis-4-tert-butylcyclohexylcarbonyl chloride (Example 42A) and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.c1ccccc1 | HCl | null | null | null | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1.CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O>>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c56de4fcd326441085356916ca06878c | N#Cc1cccc(Br)c1.[Cl-].[NH4+]>>Cl.N=C(N)c1cccc(Br)c1 | BrC=1C=C(C#N)C=CC1.[Cl-].[NH4+].C[Al](C)C.CO>>Cl.BrC=1C=C(C=CC1)C(N)=N | [N:2]#[C:3][c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1 | N#Cc1cccc(Br)c1.[Cl-].[NH4+] | Cl.N=C(N)c1cccc(Br)c1 | null | null | CCCCCC.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccccc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[ClH;D0;+0:1].[NH2;D1;+0:7]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | 1.18 g (22 mmol, 2 equiv.) ammonium chloride are suspended in 40 ml of dry toluene under an argon atmosphere, and the mixture is cooled to 0° C. 11 ml (22 mmol, 2 equiv.) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | CCCCCC.C1(=CC=CC=C1)C | 0 | null | N#Cc1cccc(Br)c1.[Cl-].[NH4+]>CCCCCC.C1(=CC=CC=C1)C>Cl.N=C(N)c1cccc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da9f0d343f6d4457a3b2671de9eb68a5 | CC(C)(C)[C@@H]1CC[C@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl>>CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1 | C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)O.C(C(=O)Cl)(=O)Cl>>C(C)(C)(C)[C@H]1CC[C@H](CC1)C(=O)Cl | O[C:9]([C@@H:8]1[CH2:7][CH2:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH2:12]1)=[O:10].O=C(Cl)C(=O)[Cl:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@@H:8]([C:9](=[O:10])[Cl:11])[CH2:12][CH2:13]1 | CC(C)(C)[C@@H]1CC[C@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl | CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | C1CCCCC1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:6] | null | [] | null | null | 1 | HOUR | 2.0 g (10.85 mmol) cis-4-tert-Butylcyclohexanecarboxylic acid are dissolved in 50 ml dichloromethane, 1.65 g (13.02 mmol) ethanedioyl dichloride are added and the solution is stirred at room temperature for one hour. The mixture is then stirred at reflux for two hours and, after cooling down to room temperature, evapor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | C1CCCCC1 | HCl | ClCCl | null | 1 | CC(C)(C)[C@@H]1CC[C@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl>ClCCl>CC(C)(C)[C@@H]1CC[C@H](C(=O)Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-57330aed75694e0fb1c2e0f3489fd77b | CC(C)(C)[C@@H]1CC[C@@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl>>CC(C)(C)[C@@H]1CC[C@@H](C(=O)Cl)CC1 | C(C(=O)Cl)(=O)Cl.C(C)(C)(C)[C@@H]1CC[C@H](CC1)C(=O)O>>C(C)(C)(C)[C@@H]1CC[C@H](CC1)C(=O)Cl | O[C:9]([C@H:8]1[CH2:7][CH2:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH2:12]1)=[O:10].O=C(Cl)C(=O)[Cl:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@H:8]([C:9](=[O:10])[Cl:11])[CH2:12][CH2:13]1 | CC(C)(C)[C@@H]1CC[C@@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl | CC(C)(C)[C@@H]1CC[C@@H](C(=O)Cl)CC1 | null | CN(C)C=O | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | C1CCCCC1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:6] | null | [] | null | null | 1 | HOUR | 11.0 g (59.7 mmol) trans-4-tert-Butylcyclohexanecarboxylic acid are dissolved in 400 ml dichloromethane plus a few drops of DMF, 9.09 g (71.6 mmol) ethanedioyl dichloride are added and the solution is stirred at room temperature for one hour. The mixture is then stirred at reflux for two hours and, after cooling down t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | C1CCCCC1 | HCl | CN(C)C=O.ClCCl | null | 1 | CC(C)(C)[C@@H]1CC[C@@H](C(=O)O)CC1.O=C(Cl)C(=O)Cl>CN(C)C=O.ClCCl>CC(C)(C)[C@@H]1CC[C@@H](C(=O)Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ca737ecba18b4b259414def625785f5c | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc([N+](=O)[O-])cc3)[nH]c(=O)c12>>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(N)cc3)[nH]c(=O)c12 | C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C2=CC=C(C=C2)[N+](=O)[O-])=O)CC.[H][H]>>NC1=CC=C(C=C1)C1=NN2C(C(N1)=O)=C(N=C2[C@@H]2CC[C@@H](CC2)C(C)(C)C)CC | O=[N+:23]([O-])[c:22]1[cH:21][cH:20][c:19](-[c:18]2[n:17][n:16]3[c:5]([C@H:6]4[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]4)[n:4][c:3]([CH2:2][CH3:1])[c:29]3[c:27](=[O:28])[nH:26]2)[cH:25][cH:24]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3... | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc([N+](=O)[O-])cc3)[nH]c(=O)c12 | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(N)cc3)[nH]c(=O)c12 | null | [Pd] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 580 mg (1.37 mmol) cis-7-(4-tert-butylcyclohexyl)-5-ethyl-2-(4-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 36A) are dissolved in 50 ml tetrahydrofuran and catalytic amounts of palladium (10% on charcoal) are added. The mixture is stirred for 18 hour at room temperature in a 3 bar hydrogen atmosphere. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CCCCC1.c1ncc2cncn2n1.c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc([N+](=O)[O-])cc3)[nH]c(=O)c12>[Pd].O1CCCC1>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3ccc(N)cc3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-706b6d16575d4ae18beff0d43bed92fb | C=CC(=O)OCC.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(Br)c3)[nH]c(=O)c12>>CCOC(=O)/C=C/c1cccc(-c2nn3c([C@H]4CC[C@@H](C(C)(C)C)CC4)nc(CC)c3c(=O)[nH]2)c1 | BrC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2[C@@H]2CC[C@@H](CC2)C(C)(C)C)CC.C(C=C)(=O)OCC.C(C)N(CC)CC>>C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C=CC2)/C=C/C(=O)OCC)=O)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].Br[c:8]1[cH:9][cH:10][cH:11][c:12](-[c:13]2[n:14][n:15]3[c:16]([c:17]([CH2:18][CH3:19])[n:20][c:21]3[C@H:22]3[CH2:23][CH2:24][C@@H:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[c:32](=[O:33])[nH:34]2)[cH:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8... | C=CC(=O)OCC.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(Br)c3)[nH]c(=O)c12 | CCOC(=O)/C=C/c1cccc(-c2nn3c([C@H]4CC[C@@H](C(C)(C)C)CC4)nc(CC)c3c(=O)[nH]2)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH2;D1;+0:11]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])/[C:10]=[CH;D2;+0:11]/[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 740 mg (1.62 mmol) cis-2-(3-bromophenyl)-7-(4-tert-butylcyclohexyl)-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 27A), 1.6 g (16.2 mmol) ethyl acrylate, 327 mg (3.24 mmol) triethylamine and 227 mg (0.32 mmol) dichlorobis(triphenylphosphine)palladium(II) are stirred at 120° C. in 20 ml DMF in an argon atmosphe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ncc2cncn2n1.C1CCCCC1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | null | null | C=CC(=O)OCC.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(Br)c3)[nH]c(=O)c12>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CCOC(=O)/C=C/c1cccc(-c2nn3c([C@H]4CC[C@@H](C(C)(C)C)CC4)nc(CC)c3c(=O)[nH]2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-51044c91d0ff457886ab82df0c68c972 | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12>>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(N)=O)c3)[nH]c(=O)c12 | ClCCl.C([O-])([O-])=O.[K+].[K+].C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C#N)C=CC2)=O)CC>>C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C(=O)N)C=CC2)=O)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]2)[n:16]2[n:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:27]3)[nH:28][c:29](=[O:30])[c:31]12>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:1... | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12 | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(N)=O)c3)[nH]c(=O)c12 | null | null | O.C(C)O | Functional Group Addition | Nitrile to amide | 538c271df55faf6c40eed3b4a4f85f3f4e5c19a479326ea2f666ed82bd9b2b69 | 276fda5d5f5a53d66ac109e4f504751b1c2e3eef2b30a60eb746c3377c075030 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 18 | HOUR | 100 mg (0.25 mmol) cis-3-[7-(4-tert-butylcyclohexyl)-5-ethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl]benzonitrile (Example 40A) are dissolved in 5 ml ethanol and 10 ml water. 342 mg (2.48 mmol) potassium carbonate and 281 mg (2.48 mmol) hydrogene peroxide are added. The reaction mixture is stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | C1CCCCC1.c1ncc2cncn2n1.c1ccccc1 | Other | O.C(C)O | null | 18 | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12>O.C(C)O>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(N)=O)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8989254712ee4cc1a25f2470b71bdd04 | CCOC(C)=O.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12.[OH-]>>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(=O)O)c3)[nH]c(=O)c12 | C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C#N)C=CC2)=O)CC.[OH-].[Na+].C(C)OC(C)=O>>C(C)(C)(C)[C@H]1CC[C@H](CC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C(=O)O)C=CC2)=O)CC | CCOC(C)=[O:25].N#[C:24][c:23]1[cH:22][cH:21][cH:20][c:19](-[c:18]2[n:17][n:16]3[c:5]([C@H:6]4[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]4)[n:4][c:3]([CH2:2][CH3:1])[c:31]3[c:29](=[O:30])[nH:28]2)[cH:27]1.[OH-:26]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([C:10]([CH3:1... | CCOC(C)=O.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12.[OH-] | CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(=O)O)c3)[nH]c(=O)c12 | null | null | Cl | Acylation | OtherReaction | 974e60925fd89af1c3b044d933553cce925faa6db18d80fa0703702af6700b36 | 35145860eafb9e213e05cd391336310346475d6c08ca0007d2df89a15df4c11f | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCC3)ncc12 | C-C-O-C(-C)=[O;H0;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | 95 | CELSIUS | 3 | HOUR | 108 mg (0.27 mmol) cis-3-[7-(4-tert-butylcyclohexyl)-5-ethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl]benzonitrile (Example 40A) are dissolved in concentrated hydrochloric acid, and the reaction mixture is stirred at 95° C. for three hours. Sodium hydroxide (10% aqueous solution) (until a pH of 6–7 is achieve... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Carboxylic acid | null | null | C1CCCCC1.c1ncc2cncn2n1.c1ccccc1 | HO- | Cl | 95 | 3 | CCOC(C)=O.CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C#N)c3)[nH]c(=O)c12.[OH-]>Cl>CCc1nc([C@H]2CC[C@@H](C(C)(C)C)CC2)n2nc(-c3cccc(C(=O)O)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4efe20b2dcc24235867d1b924dfb1180 | CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12>>CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12 | C1(CCCC1)C1=NC(=C2C(NC(=NN21)C2=CC(=CC=C2)[N+](=O)[O-])=O)CC.[H][H].[H][H]>>NC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | O=[N+:19]([O-])[c:18]1[cH:17][cH:16][cH:15][c:14](-[c:13]2[n:12][n:11]3[c:5]([CH:6]4[CH2:7][CH2:8][CH2:9][CH2:10]4)[n:4][c:3]([CH2:2][CH3:1])[c:24]3[c:22](=[O:23])[nH:21]2)[cH:20]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([NH2:19])[cH:... | CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 1.8 g (5.1 mmol) 7-cyclopentyl-5-ethyl-2-(3-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 21A) are dissolved in 100 ml methanol, and 200 mg palladium (10% on charcoal) are added. The mixture is exposed to an hydrogen atmosphere until no more hydrogen is absorbed. Then the palladium/charcoal is removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | Other | [Pd].CO | null | null | CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12>[Pd].CO>CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c08076cfb544b0ab431d668be6fd6ed | CC(C)(C)C(=O)Cl.CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12>>CCc1nc(C2CCCC2)n2nc(-c3cccc(NC(=O)C(C)(C)C)c3)[nH]c(=O)c12 | NC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC.C(C)N(CC)CC.CC(C(=O)Cl)(C)C>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C=CC2)NC(C(C)(C)C)=O)=O)CC | Cl[C:20](=[O:21])[C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([NH2:19])[cH:26]3)[nH:27][c:28](=[O:29])[c:30]12>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:... | CC(C)(C)C(=O)Cl.CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12 | CCc1nc(C2CCCC2)n2nc(-c3cccc(NC(=O)C(C)(C)C)c3)[nH]c(=O)c12 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | 50 mg (0.16 mmol) 2-(3-aminophenyl)-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]-triazin-4(3H)-one (Example 29) and 78 mg (0.77 mmol) triethylamine are dissolved in 4 ml dichloromethane. 37 mg (0.31 mmol) 2,2-dimethylpropanoyl chloride are added dropwise. The mixture is stirred for 2 hours at room temperature and then wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | HCl | ClCCl | null | 2 | CC(C)(C)C(=O)Cl.CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12>ClCCl>CCc1nc(C2CCCC2)n2nc(-c3cccc(NC(=O)C(C)(C)C)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2177943fabb401aba978188f1d2b8c8 | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=C(Cl)c1ccccc1>>CCc1nc(C2CCCC2)n2nc(-c3cccc(N(C(=O)c4ccccc4)C(=O)c4ccccc4)c3)[nH]c(=O)c12 | NC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)N(C(C1=CC=CC=C1)=O)C1=CC(=CC=C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([NH2:19])[cH:36]3)[nH:37][c:38](=[O:39])[c:40]12.Cl[C:20](=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c... | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=C(Cl)c1ccccc1 | CCc1nc(C2CCCC2)n2nc(-c3cccc(N(C(=O)c4ccccc4)C(=O)c4ccccc4)c3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f3ae2e26e5c36d950e8992dbf8a0d4cd9801e072d869a545bd74b2e75d5c8d9d | 62c5d788e8fa1e7e363d67f0f0f1fa483cc214ddb72adc066e5c9da856c4fbfe | O=C(c1ccccc1)N(C(=O)c1ccccc1)c1cccc(-c2nn3c(C4CCCC4)ncc3c(=O)[nH]2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:6](-[C:10](=[O;D1;H0:11])-[c:12])-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | In analogy to the procedure for Example 31, 50 mg (0.15 mmol) 2-(3-aminophenyl)-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 29), 43 mg (0.31 mmol) benzoyl chloride and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Substituted dicarboximide | null | c1ccccc1 | C1CCCC1.c1ncc2cncn2n1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=C(Cl)c1ccccc1>>CCc1nc(C2CCCC2)n2nc(-c3cccc(N(C(=O)c4ccccc4)C(=O)c4ccccc4)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ada23c7cb8648bc9f3e1d83868ffd3c | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=Cc1ccccc1>>CCc1nc(C2CCCC2)n2nc(-c3cccc(NCc4ccccc4)c3)[nH]c(=O)c12 | NC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC.C(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)NC=1C=C(C=CC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([NH2:19])[cH:27]3)[nH:28][c:29](=[O:30])[c:31]12.O=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c... | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=Cc1ccccc1 | CCc1nc(C2CCCC2)n2nc(-c3cccc(NCc4ccccc4)c3)[nH]c(=O)c12 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=c1[nH]c(-c2cccc(NCc3ccccc3)c2)nn2c(C3CCCC3)ncc12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | In analogy to the procedure for Example 8, 100 mg (0.31 mmol) 2-(3-aminophenyl)-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 29), 52 mg (0.49 mmol) benzaldehyde and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCCC1.c1ncc2cncn2n1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCc1nc(C2CCCC2)n2nc(-c3cccc(N)c3)[nH]c(=O)c12.O=Cc1ccccc1>>CCc1nc(C2CCCC2)n2nc(-c3cccc(NCc4ccccc4)c3)[nH]c(=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3b36a21bf3042018d6e832c2ae48db7 | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]>>COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N | COC(=O)C1=C(C=C(C=C1)C1=C(C=CC=C1)C(F)(F)F)[N+](=O)[O-].[H][H]>>COC(=O)C1=C(C=C(C=C1)C1=C(C=CC=C1)C(F)(F)F)N | O=[N+:21]([O-])[c:20]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][c:20]1[NH2:21] | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-] | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 18 | HOUR | In a Parr apparatus, hydrogenate an ethanolic solution of 3-nitro-2′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (5.54 g, 0.0169 mol) under 55 psi of hydrogen using tetrakis(triphenylphosphine)palladium(0) (300 mg). After 18 hours, filter the mixture through celite and concentrate under reduced pressure to ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | 18 | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55ccd850a1ba47d9acc11261c2133a02 | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N.N=CN>>O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12 | COC(=O)C1=C(C=C(C=C1)C1=C(C=CC=C1)C(F)(F)F)N.C(C)(=O)O.C(=N)N>>FC(C1=C(C=CC=C1)C1=CC=C2C(NC=NC2=C1)=O)(F)F | CO[C:2](=[O:1])[c:21]1[c:6]([NH2:5])[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1.N[CH:4]=[NH:3]>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]12 | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N.N=CN | O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12 | null | null | COCCO.[OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | 530017bcdfdaa01ed48948cb6a4af5f6e6064762ac85d2ad3985f28bd32a3b8a | 36efa24579e0043fdba8918e78f1d75cb4504837c08d344d01203f5fa64bfaef | O=c1[nH]cnc2cc(-c3ccccc3)ccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].N-[CH;D2;+0:8]=[NH;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | null | null | null | null | Heat a solution of 3-amino-2′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (5.0 g, 0.0169 mol) and formamidine acetate (2.8 g, 0.0203 mol) in 2-methoxyethanol at reflux for 8 hours. Cool the mixture and concentrate under reduced pressure to give a dark oil. Dissolve the residue in 10% NaOH and wash the aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1.c1ccccc1 | HO- | COCCO.[OH-].[Na+] | null | null | COC(=O)c1ccc(-c2ccccc2C(F)(F)F)cc1N.N=CN>COCCO.[OH-].[Na+]>O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85096be6402a44cfbf3fe7673cde7d26 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12>>FC(F)(F)c1ccccc1-c1ccc2c(Cl)ncnc2c1 | FC(C1=C(C=CC=C1)C1=CC=C2C(NC=NC2=C1)=O)(F)F.O=P(Cl)(Cl)Cl>>ClC1=NC=NC2=CC(=CC=C12)C1=C(C=CC=C1)C(F)(F)F | O=P(Cl)(Cl)[Cl:16].O=[c:15]1[c:14]2[cH:13][cH:12][c:11](-[c:10]3[c:5]([C:2]([F:1])([F:3])[F:4])[cH:6][cH:7][cH:8][cH:9]3)[cH:21][c:20]2[n:19][cH:18][nH:17]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]2[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]2[cH:21]1 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12 | FC(F)(F)c1ccccc1-c1ccc2c(Cl)ncnc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ccc3cncnc3c2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | Reflux a solution of 7-(2-Trifluoromethyl-phenyl)-3H-quinazolin-4-one (1.12 g, 0.0039 mol) in POCl3 for 16 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between saturated aqueous NaHCO3 and EtOAc. Wash the EtOAc layer once with additional NaHCO3, dry it (Na2SO4), and concentrate ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccccc3C(F)(F)F)ccc12>>FC(F)(F)c1ccccc1-c1ccc2c(Cl)ncnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b14ae749108a4bd3898ed601b3fb77a8 | OB(O)c1ccccc1C(F)(F)F.Oc1ccnc2cc(Cl)ccc12>>Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12 | C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].ClC1=CC=C2C(=CC=NC2=C1)O.FC(C1=C(C=CC=C1)B(O)O)(F)F>>FC(C1=C(C=CC=C1)C1=CC=C2C(=CC=NC2=C1)O)(F)F | OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18].Cl[c:8]1[cH:7][c:6]2[n:5][cH:4][cH:3][c:2]([OH:1])[c:21]2[cH:20][cH:19]1>>[OH:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]12 | OB(O)c1ccccc1C(F)(F)F.Oc1ccnc2cc(Cl)ccc12 | Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C1(=CC=CC=C1)C.CCOC(=O)C | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[C:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[F;D1;H0:16]):[c:17]>>[F;D1;H0:14]-[C:13](-[F;D1;H0:15])(-[F;D1;H0:16])-[c:12](:[c:17]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1... | 6.9 | [{"value": 6.9, "product": "FC(C1=C(C=CC=C1)C1=CC=C2C(=CC=NC2=C1)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Combine 7-chloroquinolin-4-ol (1000 mg, 5.55 mmol,) 2-(trifluoromethyl)phenylboronic acid (1583 mg, 8.33 mmol) and toluene (50 mL), and bubble nitrogen into the solution for 10 minutes. Add palladium acetate (25 mg, 0.11 mmol), 2-(dicyclohexylphosphino)biphenyl (78 mg, 0.22 mmol), and K3PO4 (2353 mg, 11.1 mmol) and hea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | HCl.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1(=CC=CC=C1)C.CCOC(=O)C | null | null | OB(O)c1ccccc1C(F)(F)F.Oc1ccnc2cc(Cl)ccc12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1(=CC=CC=C1)C.CCOC(=O)C>Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25f5926006814ac5acea8cf5bef902fc | O=P(Cl)(Cl)Cl.Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12>>FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1 | FC(C1=C(C=CC=C1)C1=CC=C2C(=CC=NC2=C1)O)(F)F.O=P(Cl)(Cl)Cl>>ClC1=CC=NC2=CC(=CC=C12)C1=C(C=CC=C1)C(F)(F)F | O=P(Cl)(Cl)[Cl:16].O[c:15]1[c:14]2[cH:13][cH:12][c:11](-[c:10]3[c:5]([C:2]([F:1])([F:3])[F:4])[cH:6][cH:7][cH:8][cH:9]3)[cH:21][c:20]2[n:19][cH:18][cH:17]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]2[c:15]([Cl:16])[cH:17][cH:18][n:19][c:20]2[cH:21]1 | O=P(Cl)(Cl)Cl.Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12 | FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | Heat a mixture of 7-(2-trifluoromethyl-phenyl)-quinolin-4-ol (50 mg, 0.17 mmol) in POCl3 (10 mL) at 90° C. for 16 hours. Evaporate the POCl3, and add ice (100 g) followed by careful addition of saturated NaHCO3. Extract with EtOAc, dry (Na2SO4), and evaporate to provide 4-chloro-7-(2-trifluoromethyl-phenyl)-quinoline a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1ccnc2cc(-c3ccccc3C(F)(F)F)ccc12>>FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d5f6a01c648471eabeceb164af85f3f | CC(C)(C)c1ccc(N)cc1.FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1>>CC(C)(C)c1ccc(Nc2ccnc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 | ClC1=CC=NC2=CC(=CC=C12)C1=C(C=CC=C1)C(F)(F)F.C(C)(C)(C)C1=CC=C(N)C=C1>>C(C)(C)(C)C1=CC=C(C=C1)NC1=CC=NC2=CC(=CC=C12)C1=C(C=CC=C1)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:30][cH:31]1.Cl[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]([F:24])([F:25])[F:26])[cH:27][cH:28][c:29]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][n:13][c:14]3[c... | CC(C)(C)c1ccc(N)cc1.FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1 | CC(C)(C)c1ccc(Nc2ccnc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc3cc(-c4ccccc4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c: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]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | null | [] | null | null | null | null | Heat a mixture of 4-chloro-7-(2-trifluoromethyl-phenyl)-quinoline (42 mg, 0.14 mmol) and 4-(tert-butyl)aniline (41 mg, 0.29 mmol) in 2-propanol (10 mL) at reflux for 3 hours. Evaporate the mixture, add 1M NaOH (10 mL), extract twice with EtOAc (10 mL each), dry (Na2SO4), and evaporate to provide the crude product. Puri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HCl | CC(C)O | null | null | CC(C)(C)c1ccc(N)cc1.FC(F)(F)c1ccccc1-c1ccc2c(Cl)ccnc2c1>CC(C)O>CC(C)(C)c1ccc(Nc2ccnc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a51a6fbac0844e1938e16615a729bdb | O=[N+]([O-])c1cc(Br)cnc1Br>>N#Cc1ncc(Br)cc1[N+](=O)[O-] | BrC1=NC=C(C=C1[N+](=O)[O-])Br.CN(C(C)=O)C>>BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-] | Br[c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12] | O=[N+]([O-])c1cc(Br)cnc1Br | N#Cc1ncc(Br)cc1[N+](=O)[O-] | null | null | O | Miscellaneous | OtherReaction | 8bb970223fb9058022a1c0cc1f9e538de973681a8f3a5dcbab2e4e1d78c06c44 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Heat a solution of 2,5-dibromo-3-nitropyridine (1.77 g, 6.3 mmol; Malinowski (1988) Bull. Soc. Chim. Belg. 97:51; see also U.S. Pat. No. 5,801,183) and cuprous cyanide (0.60 g, 6.69 mmol) in N,N-dimethylacetamide (25 mL) at 100° C. for 72 hours. After cooling, dilute the mixture with water (25 mL) and extract twice wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | O | null | null | O=[N+]([O-])c1cc(Br)cnc1Br>O>N#Cc1ncc(Br)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2083691b1f084ed88c88f49ded1090c7 | N#Cc1ncc(Br)cc1[N+](=O)[O-]>>N#Cc1ncc(Br)cc1N | BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-].[OH-].[Na+]>>NC=1C(=NC=C(C1)Br)C#N | O=[N+:10]([O-])[c:9]1[c:3]([C:2]#[N:1])[n:4][cH:5][c:6]([Br:7])[cH:8]1>>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[NH2:10] | N#Cc1ncc(Br)cc1[N+](=O)[O-] | N#Cc1ncc(Br)cc1N | null | null | Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[#7;a:7]:[c:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[#7;a:7]:[c:8]):[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 8 | HOUR | Mix 5-bromo-3-nitropyridine-2-carbonitrile (1.5 g, 5.3 mmol) and SnCl2-dihydrate (5.00 g, 26.3 mmol) in concentrated HCl and allow to stir at room temperature overnight. Work up by adding ice and carefully adding 10 M NaOH until basic. Extract twice with Et2O (200 mL), dry (Na2SO4) and evaporate. Purify by silica gel c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | Cl | null | 8 | N#Cc1ncc(Br)cc1[N+](=O)[O-]>Cl>N#Cc1ncc(Br)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ee57e5de1aa44ac9b53be26be235c4c | CC(C)(C)c1ccc(N)cc1.Clc1nncc2cc(Br)ccc12>>CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1 | BrC=1C=C2C=NN=C(C2=CC1)Cl.C(C)(C)(C)C1=CC=C(N)C=C1>>BrC=1C=C2C=NN=C(C2=CC1)NC1=CC=C(C=C1)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:21][cH:22]1.Cl[c:10]1[n:11][n:12][cH:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][n:12][cH:13][c:14]3[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]23)[cH:21][cH:22]1 | CC(C)(C)c1ccc(N)cc1.Clc1nncc2cc(Br)ccc12 | CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | df3bfedad2a7f0f256464ab6dcf71ec93640ec0ccd579b3524f93860b3777b00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nncc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:7]:[c:6]1:[c:5]:[c:4]:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | Heat a mixture of 6-bromo-1-chloro-phthalazine (500 mg, 2.05 mmol) and 4-(tert-butyl)aniline (611 mg, 4.10 mmol) in 2-propanol (10 mL) at reflux for 3 hours. Evaporate the mixture, add 1M NaOH (10 mL), extract twice with EtOAc (10 mL each), dry (Na2SO4), and evaporate to provide the crude product. Purify by silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccccc1.c1ccc2cnncc2c1 | HCl | CC(C)O | null | null | CC(C)(C)c1ccc(N)cc1.Clc1nncc2cc(Br)ccc12>CC(C)O>CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f05793046f79432d89909773a45ee04d | CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1.OB(O)c1ccccc1C(F)(F)F>>CC(C)(C)c1ccc(Nc2nncc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC=1C=C2C=NN=C(C2=CC1)NC1=CC=C(C=C1)C(C)(C)C.FC(C1=C(C=CC=C1)B(O)O)(F)F>>C(C)(C)(C)C1=CC=C(C=C1)NC1=NN=CC2=CC(=CC=C12)C1=C(C=CC=C1)C(F)(F)F | Br[c:16]1[cH:15][c:14]2[cH:13][n:12][n:11][c:10]([NH:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]3)[c:29]2[cH:28][cH:27]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][n:12][cH:13][c:14]3[... | CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1.OB(O)c1ccccc1C(F)(F)F | CC(C)(C)c1ccc(Nc2nncc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 765124a941a4c2fe32bcda035a01876b5b57c8176ac5bdf9422b29a396026af6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Nc2nncc3cc(-c4ccccc4)ccc23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]):[c:16]>>[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]):[c:16]):[c:6]:[c:7] | null | [] | null | null | 48 | HOUR | Combine (6-bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine (60 mg, 0.19 mmol), 2-(trifluoromethyl)phenyl-boronic acid (50 mg, 0.26 mmol) in 1,2-dimethoxyethane (10 mL) and bubble nitrogen into the mixture for 10 minutes. Add tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) and 2M Na2CO3 (1 mL) and heat at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cnncc2c1.c1ccccc1 | c1ccc2cnncc2c1.c1ccccc1 | c1ccccc1.c1ccc2cnncc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | 48 | CC(C)(C)c1ccc(Nc2nncc3cc(Br)ccc23)cc1.OB(O)c1ccccc1C(F)(F)F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CC(C)(C)c1ccc(Nc2nncc3cc(-c4ccccc4C(F)(F)F)ccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-379f8681ec584b4c8d13c1cdd41f476a | CC(C)(C)Nc1ccccc1>>Nc1ccccc1 | C(C)(C)N(CC)C(C)C.C(C)(C)(C)NC1=CC=CC=C1.C(C)(C)(C)C1=CC=C(C=C1)NC=1C2=C(N=C(N1)Cl)N=C(C=C2)C2=C(C=CC=C2)C(F)(F)F>>C(C)(C)(C)C1=CC=C(C=C1)NC=1C2=C(N=C(N1)Cl)N=C(C=C2)C2=C(C=CC=C2)C(F)(F)F.NC2=CC=CC=C2 | CC(C)(C)[NH:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[NH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1 | CC(C)(C)Nc1ccccc1 | Nc1ccccc1 | null | null | C(C)#N | Deprotection | Tert-butyl deprotection of amine | 943c3301bc8692208363af5a150ec6960d70d9b046717b9510b73482a3b682a4 | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccccc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | To a mixture of diisopropylethylamine (260 mg, 2.0 mmol) in acetonitrile (5 mL), add t-butylaniline (124 mg, 1.0 mmol) followed by (4-tert-Butyl-phenyl)-[2-chloro-7-(2-trifluoromethyl-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-amine (310 mg, 1.0 mmol). Heat the mixture to 80° C. for six hours. Evaporate the solvent, and part... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | null | null | c1ccccc1 | Other | C(C)#N | 80 | null | CC(C)(C)Nc1ccccc1>C(C)#N>Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e3a059aa84b42eca801680bf25c1ced | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(Br)ccc12>>Clc1ncnc2cc(Br)ccc12 | BrC1=CC=C2C(NC=NC2=C1)=O.O=P(Cl)(Cl)Cl>>BrC1=CC=C2C(=NC=NC2=C1)Cl | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]12 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(Br)ccc12 | Clc1ncnc2cc(Br)ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | Reflux a solution of 7-bromo-3H-quinazolin-4-one (1.24 g, 0.0055 mol) in POCl3 for 3.5 h. Remove the excess POCl3 under reduced pressure and partition the residue between EtOAc and saturated aqueous NaHCO3. Dry the EtOAc layer and remove the solvent under reduced pressure to give 7-bromo-4-chloro-quinazoline as a yello... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(Br)ccc12>>Clc1ncnc2cc(Br)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21e4402921fa4633ac07f6e8ca557001 | Clc1ncnc2cc(Br)ccc12.Nc1ccc(C(F)(F)F)cn1>>FC(F)(F)c1ccc(Nc2ncnc3cc(Br)ccc23)nc1 | BrC1=CC=C2C(=NC=NC2=C1)Cl.NC1=NC=C(C=C1)C(F)(F)F>>BrC1=CC=C2C(=NC=NC2=C1)NC1=NC=C(C=C1)C(F)(F)F | Cl[c:10]1[n:11][cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[n:21][cH:22]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]23)[n:21][cH:22]1 | Clc1ncnc2cc(Br)ccc12.Nc1ccc(C(F)(F)F)cn1 | FC(F)(F)c1ccc(Nc2ncnc3cc(Br)ccc23)nc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3ccccc23)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]):[c:7]:1:[c:8] | null | [] | null | null | null | null | Heat a mixture of 7-bromo-4-chloro-quinazoline (200 mg, 0.821 mmol) and 2-amino-5-trifluoromethyl-pyridine (239 mg, 1.48 mmol) at 230° C. for 2 minutes. Cool and partition the solid residue between EtOAc and 10% NaOH. Dry the EtOAc layer (Na2SO4), remove the solvent under reduced pressure, and purify via flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccncc1.c1ccc2ncncc2c1 | HCl | null | null | null | Clc1ncnc2cc(Br)ccc12.Nc1ccc(C(F)(F)F)cn1>>FC(F)(F)c1ccc(Nc2ncnc3cc(Br)ccc23)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6380d983a4184ff791f58c0af08cb0a2 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cccnc1Br>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1F | C(CCC)[Sn](CCCC)(CCCC)Cl.BrC1=NC=CC=C1F.C(CCC)[Li]>>FC=1C(=NC=CC1)[Sn](CCCC)(CCCC)CCCC | [Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].Br[c:14]1[n:15][cH:16][cH:17][cH:18][c:19]1[F:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[n:15][cH:16][cH:17][cH:18][c:19]1[F:20] | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cccnc1Br | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1F | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 595ac0abb5e92435d058c6ee48fc895ec9c292bdbe417f57a54b9f065eff0354 | d9bf9bd3fc00efb5d713d9ac7f168986c2c94f1f455d32bdc9901567c1014c76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]-[C:8]-[Sn;H0;D4;+0:9](-[Cl])(-[C:10]-[C:11])-[C:12]-[C:13]>>[C:7]-[C:8]-[Sn;H0;D4;+0:9](-[C:10]-[C:11])(-[C:12]-[C:13])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | null | [] | -78 | CELSIUS | 1.5 | HOUR | Cool a solution of 2-bromo-3-fluoro-pyridine (542 mg, 3.08 mmol) in dry THF to −78° C. using a dry ice acetone bath. Add n-butyl-lithium (1.6 M in THF, 2.0 mL) to the reaction mixture dropwise via syringe over a 20 minute period. After stirring for 1.5 hours at −78° C., add tributyltin chloride slowly via syringe and r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | C1CCOC1 | -78 | 1.5 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cccnc1Br>C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4080763d33fc4969b23659b3cd2ed48e | O=[N+]([O-])c1cc(Br)ccc1Br>>N#Cc1ccc(Br)cc1[N+](=O)[O-] | BrC1=C(C=C(C=C1)Br)[N+](=O)[O-].C(#N)[Cu]>>BrC1=CC(=C(C#N)C=C1)[N+](=O)[O-] | Br[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12] | O=[N+]([O-])c1cc(Br)ccc1Br | N#Cc1ccc(Br)cc1[N+](=O)[O-] | null | null | CC(=O)N(C)C.CCOC(=O)C | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | null | [] | null | null | null | null | Stir the mixture of 1,4-dibromo-2-nitro-benzene (3.56 mmol)and CuCN (3.74 mmol) in DMA (4 ml) at 100° C. for 5hours. Cool to room temperature, dilute with EtOAc, filter through celite, wash the organic layer with brine, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography (4:1 hexan... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CC(=O)N(C)C.CCOC(=O)C | null | null | O=[N+]([O-])c1cc(Br)ccc1Br>CC(=O)N(C)C.CCOC(=O)C>N#Cc1ccc(Br)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41e29dcecaa84db69b632fdb529c9fb7 | N#Cc1ccc(Br)cc1[N+](=O)[O-]>>N#Cc1ccc(Br)cc1N | BrC1=CC(=C(C#N)C=C1)[N+](=O)[O-].[OH-].[Na+]>>NC1=C(C#N)C=CC(=C1)Br | O=[N+:10]([O-])[c:9]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([Br:7])[cH:8]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[NH2:10] | N#Cc1ccc(Br)cc1[N+](=O)[O-] | N#Cc1ccc(Br)cc1N | null | null | Cl | 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] | null | [] | null | null | null | null | To a suspension of 4-bromo-2-nitro-benzonitrile (2.60 g, 0.0115 mol) in 12N HCl at 0° C., add SnCl2-2H2O portionwise. As the reaction is stirred vigorously, a white precipitate will form. After 1 h add ice to the reaction vessel followed by 10N NaOH until the solution is basic. Extract the aqueous mixture with ether (2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | Cl | null | null | N#Cc1ccc(Br)cc1[N+](=O)[O-]>Cl>N#Cc1ccc(Br)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-644bf33342364541a0db4fab617e76e7 | N#Cc1ccc(Br)cc1N>>O=c1[nH]cnc2cc(Br)ccc12 | [OH-].[Na+].NC1=C(C#N)C=CC(=C1)Br.C(C)(=O)[O-].[Na+]>>BrC1=CC=C2C(NC=NC2=C1)=O | [C:2](#[N:3])[c:12]1[c:6]([NH2:5])[cH:7][c:8]([Br:9])[cH:10][cH:11]1>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]12 | N#Cc1ccc(Br)cc1N | O=c1[nH]cnc2cc(Br)ccc12 | null | null | C(=O)O | Aromatic Heterocycle Formation | OtherReaction | 5d271e61807d16bbd3b0249b3cad4800dd1a5c4c451f2dd66ecf5447cbc2c902 | 7e3cbeb103ea1acdb1099adcfd389a4cbc40c9251b7e8442079d7b87a6dddf23 | O=c1[nH]cnc2ccccc12 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7]>>[O;D1;H0:8]=[c;H0;D3;+0:2]1:[nH;D2;+0:1]:[c:9]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | null | null | 1 | HOUR | To a solution of 2-amino-4-bromo-benzonitrile (550 mg, 2.79 mmol) in formic acid, add sodium acetate (435 mg, 5.30 mmol) in one portion. Reflux the reaction mixture for 16 h then remove the formic acid under reduced pressure to give a solid. Add 20% aqueous NaOH and stir for 1 hour. Remove the undissolved solids via fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | Other | C(=O)O | null | 1 | N#Cc1ccc(Br)cc1N>C(=O)O>O=c1[nH]cnc2cc(Br)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89f287ff532043e496e44917243ee117 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.O=c1[nH]cnc2cc(Br)ccc12>>O=c1[nH]cnc2cc(-c3ccccn3)ccc12 | BrC1=CC=C2C(NC=NC2=C1)=O.C(CCC)[Sn](C1=NC=CC=C1)(CCCC)CCCC>>N1=C(C=CC=C1)C1=CC=C2C(NC=NC2=C1)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.Br[c:8]1[cH:7][c:6]2[n:5][cH:4][nH:3][c:2](=[O:1])[c:17]2[cH:16][cH:15]1>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[cH:15][cH:16][c:17]12 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.O=c1[nH]cnc2cc(Br)ccc12 | O=c1[nH]cnc2cc(-c3ccccn3)ccc12 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C.O1CCOCC1 | C-C Coupling | Stille reaction_aryl | 1ad2daad2d66c7e83cb253b81bfefe414ab612665cdcf7bedd9a2df9ae159cf2 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=c1[nH]cnc2cc(-c3ccccn3)ccc12 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:14]:[c:15]>>[c:15]:[c:14]:[c;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1):[#7;a:12]:[c:13] | null | [] | 115 | CELSIUS | 16 | HOUR | To a solution of 7-bromo-3H-quinazolin-4-one (100 mg, 0.444 mmol) in toluene/dioxane (3:1), add 2-tributylstannanyl-pyridine (162 mg, 0.444 mmol) followed by tetrakis-(triphenylphosphine)-palladium(0) (26 mg, 0.022 mmol). Bubble dry nitrogen through the solution for 10 minutes then heat the stirring solution to 115° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccc2cncnc2c1 | c1ccc2cncnc2c1.c1ccncc1 | c1ccc2cncnc2c1.c1ccncc1 | HBr.Sn | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.O1CCOCC1 | 115 | 16 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.O=c1[nH]cnc2cc(Br)ccc12>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.O1CCOCC1>O=c1[nH]cnc2cc(-c3ccccn3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e8cb0995cf849da806203796dbca3c7 | FC(F)(F)c1cccnc1-c1ccc(Br)cc1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br | BrC1=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F.[N+](=O)(O)[O-]>>BrC1=C(C=C(C=C1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | [cH:4]1[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20] | FC(F)(F)c1cccnc1-c1ccc(Br)cc1.O=[N+]([O-])O | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccccn2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Br;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 30 | MINUTE | To a solution of 2-(4-bromophenyl)-3-(trifluoromethyl)-pyridine (0.93 mmol) in H2SO4 (4 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture 30 minutes at room temperature. Pour the mixture onto ice-water (20 mL) and collect the precipitate. Dissolve the precipitate in EtOAc and neutralize with saturated NaHCO3, dry... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | OS(=O)(=O)O | null | 0.5 | FC(F)(F)c1cccnc1-c1ccc(Br)cc1.O=[N+]([O-])O>OS(=O)(=O)O>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d65313b8e7bb46489d82036d77557d52 | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br>>N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | BrC1=C(C=C(C=C1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-].C(#N)[Cu]>>[N+](=O)([O-])C1=C(C#N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | Br[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | CC(=O)N(C)C.CCOC(=O)C | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | null | [] | 110 | CELSIUS | 4 | HOUR | To a solution of 2-(4-bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine (0.55 mmol) in DMA (4 mL) add CuCN (0.60 mmol). Stir the mixture 4 hours at 110° C. Cool to room temperature, dilute with 20 ml of EtOAc, and filter through celite pad. Wash the filtrated with brine, dry over Na2SO4, concentrate under vacuum, and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Br- | CC(=O)N(C)C.CCOC(=O)C | 110 | 4 | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)ccc1Br>CC(=O)N(C)C.CCOC(=O)C>N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20d9af898f4c46f19487c1a42313c410 | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N | [OH-].[Na+].[N+](=O)([O-])C1=C(C#N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.Cl[Sn]Cl>>NC1=C(C#N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | O=[N+:19]([O-])[c:18]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[NH2:19] | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N | null | null | Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | To an ice-water cooled solution of 2-nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzonitrile (0.44 mmol) in conc. HCl (6 mL) add SnCl2 (1.457 mmol). Stir the mixture 2 h at room temperature. neutralize with NaOH, extract with EtOAc, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | Cl | null | 2 | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>Cl>N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59c0121a94384cc9816e0179000b2cbe | O=P(Cl)(Cl)Cl.Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12>>FC(F)(F)c1cccnc1-c1ccc2c(Cl)ncnc2c1 | FC(C=1C(=NC=CC1)C1=CC=C2C(=NC=NC2=C1)O)(F)F.O=P(Cl)(Cl)Cl>>ClC1=NC=NC2=CC(=CC=C12)C1=NC=CC=C1C(F)(F)F | O=P(Cl)(Cl)[Cl:16].O[c:15]1[c:14]2[cH:13][cH:12][c:11](-[c:10]3[c:5]([C:2]([F:1])([F:3])[F:4])[cH:6][cH:7][cH:8][n:9]3)[cH:21][c:20]2[n:19][cH:18][n:17]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]2[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]2[cH:21]1 | O=P(Cl)(Cl)Cl.Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12 | FC(F)(F)c1cccnc1-c1ccc2c(Cl)ncnc2c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | b0b0f8b7642d018e3b261231985ddd65d16d4d42cce7aa11791e49c826337b90 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccc3cncnc3c2)nc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | Reflux 7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ol (0.38 mmol) for 18 hours in POCl3 (5 mL). Evaporate the solvent in vacuo, then carefully neutralize with saturated NaHCO3, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum to obtain 4-chloro-7-(3-trifluoromethyl-pyridin-2-yl)-quinazoline.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccncc1.c1ccc2ncncc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12>>FC(F)(F)c1cccnc1-c1ccc2c(Cl)ncnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d720991a8abf4ff597f1a39c481956a4 | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N.[OH-]>>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | NC1=C(C#N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.[OH-].[Na+]>>NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | [N:1]#[C:2][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20].[OH-:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N.[OH-] | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | null | null | OS(=O)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccc(-c2ccccn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Stir a mixture of 2-amino-4(3-trifluoromethyl-pyridin-2-yl)-benzo-nitrile (0.50 mmol) in 70% H2SO4 (10 ml) at 110° C. for 1 hour. Cool to room temperature, neutralize with NaOH, extract with EtOAc, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography (3:2 hexanes/EtOAc) to give 2-am... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1.c1ccncc1 | null | OS(=O)(=O)O | null | null | N#Cc1ccc(-c2ncccc2C(F)(F)F)cc1N.[OH-]>OS(=O)(=O)O>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dad51120f4da48c1b3c59053ef01c1a9 | CC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O | NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.N1=CC=CC=C1.C(C)(=O)Cl>>C(C)(=O)NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][c:20]1[C:21]([NH2:22])=[O:23]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][c:20]1[C:21]([NH2:22])=[O:23] | CC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2ccccn2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](-[N;D1;H2:4])=[O;D1;H0:6] | null | [] | null | null | 10 | MINUTE | To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (0.5 mmol) and pyridine (0.55 mmol) in THF (5 ml) add acetyl chloride (0.55 mmol). Stir the mixture 10 minutes at room temperature. Concentrate under vacuum, extract with EtOAc, wash with brine, dry over Na2SO4, and concentrate under vacuum. Triturat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C1CCOC1 | null | 0.166667 | CC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>C1CCOC1>CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f16507baa8324bfd8e8a7be323aad471 | CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O>>Cc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | C(C)(=O)NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F>>CC1=NC2=CC(=CC=C2C(=N1)O)C1=NC=CC=C1C(F)(F)F | O=[C:2]([CH3:1])[NH:22][c:21]1[c:6]([C:4]([NH2:3])=[O:5])[cH:7][cH:8][c:9](-[c:10]2[n:11][cH:12][cH:13][cH:14][c:15]2[C:16]([F:17])([F:18])[F:19])[cH:20]1>>[CH3:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][c:9](-[c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[C:16]([F:17])([F:18])[F:19])[cH:20][c:21]2[n:22]1 | CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O | Cc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | null | null | [OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | 2f062f807c82221b053d8e69b1222d7c6a9c8bd3dfea25f1341bdd9b6ded7751 | b315f5051658d018f21ccded5f298d0b6fc5d41ed682f748b2c9a0a662ea20dc | c1ccc(-c2ccc3cncnc3c2)nc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[O;H0;D1;+0:9]):[c:10]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:10]):[c;H0;D3;+0:7](-[OH;D1;+0:9]):[n;H0;D2;+0:8]:1 | null | [] | null | null | 30 | MINUTE | Suspend 2-acetylamino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide in 20 ml of 20% NaOH, stir for 30 minutes at room temperature. Filter, acidify to pH=6, extract with EtOAc, and concentrate under vacuum to give 2-methyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ol.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccncc1 | HO- | [OH-].[Na+] | null | 0.5 | CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O>[OH-].[Na+]>Cc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c67d5a5246c43f6b27f534f46c29b96 | CC(C)(C)c1ccc(N)cc1.Cc1nc(Cl)c2ccc(-c3ncccc3C(F)(F)F)cc2n1>>Cc1nc(Nc2ccc(C(C)(C)C)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | ClC1=NC(=NC2=CC(=CC=C12)C1=NC=CC=C1C(F)(F)F)C.C(C)(C)(C)C1=CC=C(N)C=C1>>C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC2=CC(=CC=C12)C1=NC=CC=C1C(F)(F)F)C | [NH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15]1.Cl[c:4]1[n:3][c:2]([CH3:1])[n:32][c:31]2[c:16]1[cH:17][cH:18][c:19](-[c:20]1[n:21][cH:22][cH:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29])[cH:30]2>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])... | CC(C)(C)c1ccc(N)cc1.Cc1nc(Cl)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | Cc1nc(Nc2ccc(C(C)(C)C)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3cc(-c4ccccn4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c: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:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | null | [] | null | null | null | null | Using procedures analogous to those already described, (4-tert-Butyl-phenyl)-[2-methyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine is prepared by condensing 4-chloro-2-methyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazoline with 4-tert-butylaniline. Mass spec. 436.2.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | HCl | null | null | null | CC(C)(C)c1ccc(N)cc1.Cc1nc(Cl)c2ccc(-c3ncccc3C(F)(F)F)cc2n1>>Cc1nc(Nc2ccc(C(C)(C)C)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff5bf02e260d4b349a75ea60e675fe3b | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | ClC1=NC=CC=C1C(F)(F)F.B(C=1C=CC(=CC1)C)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1.Cl[c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl | Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[#7;a:2]:[c:3] | null | [] | 80 | CELSIUS | 8 | HOUR | To a de-gassed mixture of 2-chloro-3-(trifluoromethyl)-pyridine (70.1 mmol), p-tolylboronic acid (70.6 mmol), and 2M Na2CO3 (175.0 mmol), in DME (200 mL) under nitrogen add Pd(PPh3)4 (2.8 mmol). Stir the mixture at 80° C. for overnight, concentrate, extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, pass a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | 80 | 8 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ebbf801a55804f969f2c1ed3987f9bf7 | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C.[N+](=O)(O)[O-]>>CC1=C(C=C(C=C1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.O[N+:18](=[O:19])[O-:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O | Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccccn2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 60 | MINUTE | To a solution of 2-p-tolyl-3-trifluoromethyl-pyridine (8.4 mmol) in H2SO4 (6 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture 60 minutes at room temperature. Pour the mixture onto ice-water (30 mL), extract with EtOAc, neutralize with 1 N NaOH, dry over Na2SO4, and concentrate under vacuum to obtain 2-(4-methyl-... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | OS(=O)(=O)O | null | 1 | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>OS(=O)(=O)O>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5526c94546d94210aab6ec50f967604d | O=C(O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O | [N+](=O)([O-])C1=C(C(=O)O)C=CC(=C1)C1=NC=CC=C1C(F)(F)F>>NC1=C(C(=O)O)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][c:17]1[C:18](=[O:19])[OH:20]>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][c:17]1[C:18](=[O:19])[OH:20] | O=C(O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O | null | [Pd] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | null | null | Hydrogenate the solution of 2-nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzoic acid (3.84 mmol) in 95% EtOH (100 mL) with 10% Pd-C (150 mg) for over night. Filter through a celite pad and concentrate the filtrate to give 2-amino-4(3-trifluoromethyl-pyridin-2-yl)-benzoic acid.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Pd].CCO | null | null | O=C(O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>[Pd].CCO>Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3adbc372bc5406985e2d7235123dadd | NC=O.Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O>>Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12 | NC1=C(C(=O)O)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.C(=O)N>>FC(C=1C(=NC=CC1)C1=CC=C2C(=NC=NC2=C1)O)(F)F | O=[CH:4][NH2:3].O=[C:2]([OH:1])[c:21]1[c:6]([NH2:5])[cH:7][c:8](-[c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[OH:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[n:10][cH:11][cH:12][cH:13][c:14]3[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]12 | NC=O.Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O | Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 807899eca8aaecfbdeb908b04e93e4879b6b55eeb0c8734b3c80bf4c35c09f84 | 4f04e8811a54bdec385d5b77090c28cd7db5e4c638bda2b6e8fa910a109c2f98 | c1ccc(-c2ccc3cncnc3c2)nc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H1:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | null | null | null | null | Stir the mixture of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzoic acid (1.95 mmol) in HCONH2 (10 mL) for 4 hours at 145° C. Cool to room temperature, dilute with 20 ml of water, and collect the precipitate to give 7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ol.
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccncc1 | HO- | O | null | null | NC=O.Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(=O)O>O>Oc1ncnc2cc(-c3ncccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2e2eccf6d8f41b5a9eb8ad2f9b6aa0c | CC(C)(C)c1ccc([N-]c2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>CC(C)(C)c1ccc(Nc2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | Cl.C(C)(C)(C)C1=CC=C(C=C1)[N-]C1=NC=NC2=CC(=CC=C12)C1=NC=CC=C1C(F)(F)F.FC(C=1C(=NC=CC1)C1=CC=C2C(=NC=NC2=C1)O)(F)F>>Cl.C(C)(C)(C)C1=CC=C(C=C1)NC1=NC=NC2=CC(=CC=C12)C1=NC=CC=C1C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N-:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][c:16](-[c:17]4[n:18][cH:19][cH:20][cH:21][c:22]4[C:23]([F:24])([F:25])[F:26])[cH:27][cH:28][c:29]23)[cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][c... | CC(C)(C)c1ccc([N-]c2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | CC(C)(C)c1ccc(Nc2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | null | null | null | Reduction | OtherReaction | 5899c0b633c6821428aeb398f81b78a3426e5426f42dc475166a23c6e1174732 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(Nc2ncnc3cc(-c4ccccn4)ccc23)cc1 | [c:1]:[c:2](-[N-;H0;D2:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1):[c:10]>>[c:1]:[c:2](-[NH;D2;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1):[c:10] | null | [] | null | null | null | null | Using procedures analogous to those described above (see, for example, Schemes 1 and 2), (4-tert-Butyl-phenyl)-[7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amide hydrochloride is prepared from 7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ol in two steps. Mass spec. 422.2.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | null | null | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | null | null | null | null | CC(C)(C)c1ccc([N-]c2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>CC(C)(C)c1ccc(Nc2ncnc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eff5ad7dd6fd44f08cb701595aa21c78 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | ClC1=NC=CC=C1C(F)(F)F.B(C=1C=CC(=CC1)C)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1.Cl[c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl | Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[#7;a:2]:[c:3] | null | [] | 80 | CELSIUS | 8 | HOUR | To a de-gassed mixture of 2-chloro-3-(trifluoromethyl)-pyridine (70.1 mmol), p-tolylboronic acid (70.6 mmol), and 2M Na2CO3 (175.0 mmol), in dimethyl ether (DME; 200 mL) under nitrogen, add Pd(PPh3)4 (2.8 mmol). Stir the mixture at 80° C. overnight, concentrate, and extract with EtOAc. Dry over Na2SO4, concentrate unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COC | 80 | 8 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COC>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61f36f4f067542aeb4b717764343315a | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C.[N+](=O)(O)[O-]>>CC1=C(C=C(C=C1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.O[N+:18](=[O:19])[O-:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O | Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccccn2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 60 | MINUTE | To a solution of 2-p-tolyl-3-trifluoromethyl-pyridine (8.4 mmol) in H2SO4 (6 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture for 60 minutes at room temperature. Pour the mixture onto ice-water (30 mL), extract with EtOAc, neutralize with 1 N NaOH, dry over Na2SO4, and concentrate under vacuum to obtain 2-(4-met... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | OS(=O)(=O)O | null | 1 | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>OS(=O)(=O)O>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25c98ecb65a643498749bfa24400f231 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | [N+](=O)([O-])C1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F>>NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | O=[N+:20]([O-])[c:19]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 16 | HOUR | Hydrogenate 2-nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (1.0 g, 0.0032 mol) with 50 psi of H2 and 100 mg of 10% Pd/C in ethanol. After 16 hours, filter the mixture through celite and concentrate under reduced pressure to give 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide as a solid.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Pd].C(C)O | null | 16 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>[Pd].C(C)O>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b3eac05377a4c0c8c5e134d87874074 | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.ClCC(OC)(OC)OC>>ClCC1=NC2=CC(=CC=C2C(N1)=O)C1=NC=CC=C1C(F)(F)F | CO[C:4](OC)(OC)[CH2:5][Cl:6].[O:1]=[C:2]([NH2:3])[c:23]1[c:8]([NH2:7])[cH:9][c:10](-[c:11]2[n:12][cH:13][cH:14][cH:15][c:16]2[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1>>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][Cl:6])[n:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][cH:13][cH:14][cH:15][c:16]3[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22][c... | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 292ab66b88620748fa9d06e6e4d9b67ede3a8fd233d74022944407012fccec37 | 7ad6d407a4f6c8573e2bc724851922f3f76bd08d2e3d3a3ddf0a52cbc9de261c | O=c1[nH]cnc2cc(-c3ccccn3)ccc12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:4]:1 | null | [] | null | null | null | null | Heat a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (100 mg, 0.356 mmol) in 2-chloro-1,1,1-trimethoxyethane (bp 138° C.) at 130° C. for 4 hours. Concentrate the mixture under reduced pressure to give 2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-quinazolin-4-one as an oil which crystallizes o... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1.c1ccncc1 | HO- | null | null | null | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87c2238b1c034b13987037b2f6511d44 | C1CCNC1.FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | Cl.ClCC1=NC2=CC(=CC=C2C(=N1)NC1=CC=C(C=C1)C(F)(F)F)C1=NC=CC=C1C(F)(F)F.N1CCCC1>>N1(CCCC1)CC1=NC2=CC(=CC=C2C(=N1)NC1=CC=C(C=C1)C(F)(F)F)C1=NC=CC=C1C(F)(F)F | [NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.Cl[CH2:13][c:12]1[n:11][c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:37][cH:36]2)[c:35]2[c:20]([n:19]1)[cH:21][c:22](-[c:23]1[n:24][cH:25][cH:26][cH:27][c:28]1[C:29]([F:30])([F:31])[F:32])[cH:33][cH:34]2>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([NH:9... | C1CCNC1.FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ccccn4)ccc23)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[c:4]:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Heat a solution of [2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine HCl (30 mg, 0.058 mmol) in pyrrolidine (1 mL) at 100° C. for 1 hour. Remove the excess pyrrolidine under reduced pressure and partition the residue between EtOAc and 10% NaOH solution. Dry the EtOAc l... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1ccc2ncncc2c1.c1ccncc1 | HCl | null | null | null | C1CCNC1.FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3838968a21b64ac69cc878ec3d8ac56a | CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1Cl | C(C)OC(C1=CN=C(C=C1O)C1=C(C=CC=C1)C(F)(F)F)=O.O=P(Cl)(Cl)Cl>>C(C)OC(C1=CN=C(C=C1Cl)C1=C(C=CC=C1)C(F)(F)F)=O | O[c:21]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]([F:17])([F:18])[F:19])[cH:20]1.O=P(Cl)(Cl)[Cl:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]([F:17])([F:18])[F:19])[cH:20][c:21]1[Cl:22] | CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1O.O=P(Cl)(Cl)Cl | CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccccn2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[c:8]1:[c:7]:[#7;a:6]:[c:4](-[c:5]):[c:3]:[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | Heat a mixture of 4-Hydroxy-6-(2-trifluoromethyl-phenyl)-nicotinic acid ethyl ester (9.0 g, 0.029 mol) in POCl3 (22 g) at 110° C. for 2 hours. Evaporate the POCl3, and add ice (100 g) followed by careful addition of saturated NaHCO3. Extract with EtOAc, dry (MgSO4), and evaporate to provide 4-chloro-6-(2-trifluoromethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc(-c2ccccc2C(F)(F)F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-903c4ac65eb141e68dc8be222cbf9a17 | CC1CN(Cc2nc(O)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1.O=P(Cl)(Cl)Cl>>CC1CN(Cc2nc(Cl)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1 | CC1CN(CC(O1)C)CC=1N=C(C2=C(N1)C=C(N=C2)C2=C(C=CC=C2)C(F)(F)F)O.N1=C(C=CC=C1C)C.O=P(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)CN1CC(OC(C1)C)C)C=C(N=C2)C2=C(C=CC=C2)C(F)(F)F | O[c:8]1[n:7][c:6]([CH2:5][N:4]2[CH2:3][CH:2]([CH3:1])[O:30][CH:28]([CH3:29])[CH2:27]2)[n:26][c:25]2[c:10]1[cH:11][n:12][c:13](-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[C:20]([F:21])([F:22])[F:23])[cH:24]2.O=P(Cl)(Cl)[Cl:9]>>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[n:7][c:8]([Cl:9])[c:10]3[cH:11][n:12][c:13](-[c:14]4[... | CC1CN(Cc2nc(O)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1.O=P(Cl)(Cl)Cl | CC1CN(Cc2nc(Cl)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | aadd06203830e902e59b15792f3dac5d156894dc4789a75d727b008defc19073 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cc3nc(CN4CCOCC4)ncc3cn2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:1 | null | [] | null | null | null | null | Reflux a mixture of 2-(2,6-dimethyl-morpholin-4-ylmethyl)-7-(2-trifluoromethyl-phenyl)-pyrido[4,3-d]-pyrimidin-4-ol (0.6 g), 2,6-lutidine (0.62 g), and POCl3 (1.1 g) in CHCl3 (15 mL) for 20 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between EtOAc and saturated NaHCO3 solution.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cc2ncncc2cn1 | c1cc2ncncc2cn1 | C1COCC[NH]1.c1cc2ncncc2cn1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | null | CC1CN(Cc2nc(O)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1.O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>CC1CN(Cc2nc(Cl)c3cnc(-c4ccccc4C(F)(F)F)cc3n2)CC(C)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9cff6c91ca054fd6816673ec0f99cc15 | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl>>COc1ccc(-c2ncccc2C(F)(F)F)cn1 | ClC1=NC=CC=C1C(F)(F)F.COC1=NC=C(C=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:18][cH:17]1.Cl[c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][n:18]1 | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl | COc1ccc(-c2ncccc2C(F)(F)F)cn1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 2e12f1697d123c35af029842984dda76c08cdd06401f05924c6b1363bf342af9 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1):[#7;a:2]:[c:3] | 95 | [{"value": 95.0, "product": "COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Heat a mixture of 2-chloro-3-trifluoromethylpyridine (37 g, 0.2 mol), 2-methoxypyridine-5-boronic acid (32 g, 0.21 mol), tetrakis(triphenylphosphine) palladium(0) (9 g, 7 mmol) and 2M potassium carbonate (150 mL) in toluene (500 mL) under a nitrogen atmosphere, at 90° C. for 8 hours. Cool the reaction mixture and separ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | HCl.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | 8 | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>COc1ccc(-c2ncccc2C(F)(F)F)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d6e6a6a37c1d44189bc651ece3388da5 | COc1ccc(-c2ncccc2C(F)(F)F)cn1>>O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F>>FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F | C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][n:17]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][nH:17]1 | COc1ccc(-c2ncccc2C(F)(F)F)cn1 | O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | null | null | Br.CC(=O)O | Miscellaneous | OtherReaction | ffbb4288e7102e6f227d930be4a9510dc9e13ff3142954fd43347db64909ca58 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1ccc(-c2ccccn2)c[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1 | 93.7 | [{"value": 93.0, "product": "FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Heat 6′-methoxy-3-trifluoromethyl-[2,3′]bipyridinyl (41 g, 0.16 mol) in 30% HBr/AcOH (100 mL) to reflux for 1 hour. Cool the mixture and filter, and wash the precipitate with ether (100 mL). Transfer the precipitate into 10M sodium hydroxide (500 mL) and stir for 1 hour, and treat the solution with hydrochloric acid un... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1cccnc1 | c1cccnc1.c1ccncc1 | Other | Br.CC(=O)O | null | 1 | COc1ccc(-c2ncccc2C(F)(F)F)cn1>Br.CC(=O)O>O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9d0b11af3a8457186a777d347054dd5 | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1>>O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F.[N+](=O)(O)[O-]>>[N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F | O[N+:18](=[O:19])[O-:20].[O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 26a878e97e02b420c859859d3c94a295b28ee7e9c7a3a499b0358675c34410cd | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1ccc(-c2ccccn2)c[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 3-trifluoromethyl-1′H-[2,3′]bipyridinyl-6′-one (25 g, 0.1 mol) in concentrated sulfuric acid (100 mL) at 0° C., add dropwise a solution of fuming nitric acid (35 mL) and concentrated sulfuric acid (10 mL). Heat the reaction mixture to 70° C. for 1 hour, cool and pour onto ice (500 mL). Filter the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cccnc1 | c1cnccc1 | c1cnccc1.c1ccncc1 | HO- | S(O)(O)(=O)=O | 70 | null | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1>S(O)(O)(=O)=O>O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-633bc18231fa495e998db535d27a7700 | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | [N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F.S(=O)(Cl)Cl>>ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | O=S(Cl)[Cl:20].O=[c:19]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][nH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][n:18][c:19]1[Cl:20] | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | ad993f9ce2ce60b71a2afb3182d5e182b0d0de1be8200a3f161e73174c9a6ebf | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cccnc2)nc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1-[#7;+:8]>>[#7;+:8]-[c:7]1:[c:6]:[c:5]:[c:4]:[n;H0;D2;+0:3]:[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | 93 | [{"value": 93.0, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5′-nitro-3-trifluoromethyl-1′H[2,3′]bipyridinyl-6′-one (25 g, 0.088 mol), thionyl chloride (300 mL) and DMF (3 mL) to reflux for 4 hours. Remove the volatiles by rotary evaporation and partition the residue between ethyl acetate (350 mL) and saturated sodium bicarbonate solution (250 mL). Extract the... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnccc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HCl | CN(C)C=O | null | null | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>CN(C)C=O>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1a11252fbf44ab2a075573749a25439 | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl>>Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl | ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-]>>ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][n:16][c:17]1[Cl:18]>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][n:16][c:17]1[Cl:18] | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl | null | [Fe] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccnc2)nc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]>>[Cl;D1;H0:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 85 | [{"value": 85.0, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6′-chloro-5′-nitro-3-trifluoromethyl-[2,3′]bipyridinyl (25 g, 0.082 mol) and calcium chloride (11 g, 0.1 mol) in ethanol (300 mL) and water (50 mL), add iron powder (45 g, 0.82 mol). Heat the solution to reflux for 1.5 hours, cool and filter through Celite. Concentrate the mixture under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccncc1 | Other | [Fe].O.C(C)O | null | null | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl>[Fe].O.C(C)O>Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6601c51f2bb4dacac86f554f419c803 | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+]>>NC(=O)c1ncc(-c2ncccc2C(F)(F)F)cc1N | CN(C)C=O.[Cl-].[NH4+].[OH-].[NH4+].ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N>>NC=1C(=NC=C(C1)C1=NC=CC=C1C(F)(F)F)C(=O)N | CN(C)[CH:2]=[O:3].Cl[c:4]1[n:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20].[NH4+:1]>>[NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+] | NC(=O)c1ncc(-c2ncccc2C(F)(F)F)cc1N | null | C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C... | O | Acylation | OtherReaction | e1863fb77b18a4f8a4f6f62e441a7222b67756c377f9188d3bd53f6c3965f65f | e877213e19171755e0934a74438f863139f6bd24cdbe9c4b94ecbf55b1179c4e | c1ccc(-c2cccnc2)nc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[N;D1;H2:7]):[c:8].[NH4+;D0:9]>>[N;D1;H2:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[O;D1;H0:2]):[#7;a:4]:[c:5] | 90 | [{"value": 90.0, "product": "NC=1C(=NC=C(C1)C1=NC=CC=C1C(F)(F)F)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Heat a solution of 6′-chloro-3-trifluoromethyl-[2,3′]bipyridinyl-5′-ylamine (25 g, 0.091 mol), zinc cyanide (6.75 g, 0.058 mol), tris[dibenzylidineacetone]di-palladium (also referred to as “pd2(dba)3”; 2.63 g, 2.86 mmol), 1,1′-bis(diphenylphosphino)ferrocene (also referred to as “DPPF”; 3.16 g, 5.72 mmol) in DMF (250 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HCl | C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C... | 0 | 1 | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+]>C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a766d9f6940a49f19eb8ff062f5be56a | CCOC(=O)CCBr.OCc1ccccc1>>O=C(O)CCOCc1ccccc1 | O.[H-].[Na+].C(C1=CC=CC=C1)O.BrCCC(=O)OCC>>C(C1=CC=CC=C1)OCCC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5]Br.[OH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCOC(=O)CCBr.OCc1ccccc1 | O=C(O)CCOCc1ccccc1 | null | null | [OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 649e704edbb364f9da7d07cbe4234c4a92fb1da39cfc9c27b4b5f45f135ea332 | 618df49e449d2d4d71a5c69761039aa60d2846715c5b4fde87b9028fc160ed45 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C.[OH;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:7]-[c:8] | 34.2 | [{"value": 34.0, "product": "C(C1=CC=CC=C1)OCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "C(C1=CC=CC=C1)OCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In small portions, add sodium hydride (2.22 g, 60% dispersion in mineral oil, 55.4 mmol) to a cold (0° C.) solution of benzyl alcohol (4.0 g, 37 mmol) in toluene (100 mL). Add ethyl 3-bromopropionate (8.0 g, 44 mmol) dropwise to the mixture, allow the resulting solution to warm to room temperature and stir for 1 hour. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HBr | [OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | null | 1 | CCOC(=O)CCBr.OCc1ccccc1>[OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC>O=C(O)CCOCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9cb24f038e524d4db0b88314e757605e | CCOC(=O)CCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>CCOC(=O)CCc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.N1=CC=CC=C1.[Cl-].C(C)OC(CCC(=O)Cl)=O.CC[O-].[Na+]>>C(C)OC(CCC1=NC2=CC(=CC=C2C(=N1)O)C1=NC=CC=C1C(F)(F)F)=O | O=[C:8](Cl)[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[C:22]([F:23])([F:24])[F:25])[cH:26][c:27]1[NH2:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[n:9][c:10]([OH:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3[n:17][cH... | CCOC(=O)CCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | CCOC(=O)CCc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | null | null | CCO.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 421874b4cd55eaa20f24b1cd7ba94b5870b5c4e9b00f756449eff425c4e3a153 | d5ef1961d36ab2d05e773eb9e606a89406d1ee5463b381ad4c7037e46428ccb9 | c1ccc(-c2ccc3cncnc3c2)nc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;H0;D1;+0:13]):[c:14]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c:8](:[c:9]):[c:10](:[c:14]):[c;H0;D3;+0:11](-[OH;D1;+0:13]):[n;H0;D2;+0:12]:1 | null | [] | null | null | 20 | MINUTE | To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (0.5 mmol) and pyridine (0.55 mmol) in THF (5 ml), add 3-chlorocarbonyl-propionic acid ethyl ester chloride (0.55 mmol). Stir the mixture for 20 minutes at room temperature, add 20 ml of 21% NaOEt in EtOH, and stir for 30 minutes at 50° C. Concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccncc1 | HCl | CCO.C1CCOC1 | null | 0.333333 | CCOC(=O)CCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>CCO.C1CCOC1>CCOC(=O)CCc1nc(O)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb4891bb14ab4be5a0f03b575865206f | COC(CCl)(OC)OC.NC(=O)c1ccc(Br)cc1N>>O=c1[nH]c(CCl)nc2cc(Br)ccc12 | NC1=C(C(=O)N)C=CC(=C1)Br.ClCC(OC)(OC)OC>>BrC1=CC=C2C(NC(=NC2=C1)CCl)=O | CO[C:4](OC)(OC)[CH2:5][Cl:6].[O:1]=[C:2]([NH2:3])[c:14]1[c:8]([NH2:7])[cH:9][c:10]([Br:11])[cH:12][cH:13]1>>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][Cl:6])[n:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]12 | COC(CCl)(OC)OC.NC(=O)c1ccc(Br)cc1N | O=c1[nH]c(CCl)nc2cc(Br)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 292ab66b88620748fa9d06e6e4d9b67ede3a8fd233d74022944407012fccec37 | 7ad6d407a4f6c8573e2bc724851922f3f76bd08d2e3d3a3ddf0a52cbc9de261c | O=c1[nH]cnc2ccccc12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:4]:1 | null | [] | null | null | null | null | Reflux a solution of 2-amino-4-bromobenzamide (27 g, 0.13 mol; see Joshi and Chaudhari, (1987) Indian J. Chem., Sect. B, 26B(6):602-4) in 2-chloro-1,1,1-trimethoxyethane (50 mL) for 30 minutes, during which time a large precipitate appears. Evaporate the mixture fully and triturate with ether to collect 28 g of 7-bromo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | HO- | null | null | null | COC(CCl)(OC)OC.NC(=O)c1ccc(Br)cc1N>>O=c1[nH]c(CCl)nc2cc(Br)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d14c368a73f7413183370a1f21e7e743 | O=P(Cl)(Cl)Cl.O=c1[nH]c(CCl)nc2cc(Br)ccc12>>ClCc1nc(Cl)c2ccc(Br)cc2n1 | BrC1=CC=C2C(NC(=NC2=C1)CCl)=O.N1=C(C=CC=C1C)C.P(=O)(Cl)(Cl)Cl>>BrC1=CC=C2C(=NC(=NC2=C1)CCl)Cl | O=P(Cl)(Cl)[Cl:6].O=[c:5]1[nH:4][c:3]([CH2:2][Cl:1])[n:14][c:13]2[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12]2>>[Cl:1][CH2:2][c:3]1[n:4][c:5]([Cl:6])[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]2[n:14]1 | O=P(Cl)(Cl)Cl.O=c1[nH]c(CCl)nc2cc(Br)ccc12 | ClCc1nc(Cl)c2ccc(Br)cc2n1 | null | null | COCCOC | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[C:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[C:5]-[c:4]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:3]:1 | null | [] | null | null | null | null | Heat a mixture of 7-bromo-2-chloromethyl-3H-quinazolin-4-one (5 g, 18.2 mmol), 2,6-lutidine (5 g), and phosphorus oxychloride (5 mL) in 1,2-dimethoxyethane (500 mL) at 80° C. for 16 hours. Cool the mixture to room temperature and fully evaporate the mixture, then dilute with ether and wash with water. Dry the solvent (... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | COCCOC | null | null | O=P(Cl)(Cl)Cl.O=c1[nH]c(CCl)nc2cc(Br)ccc12>COCCOC>ClCc1nc(Cl)c2ccc(Br)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6b5fb3780714f14b948c387c47db230 | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-]>>N#Cc1ncc(Br)cc1[N+](=O)[O-] | NC1=NC=C(C=C1[N+](=O)[O-])Br.C(C)(C)(C)ON=O.C(C)#N>>BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-] | C[C:2]#[N:1].N[c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12] | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-] | N#Cc1ncc(Br)cc1[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 7be32428aabd580dfbed2e434f7904a98f0e54bc30b8b5f4dba0a6d14252e209 | 5270ba81df65d040f7a2858a28254c13e4f1fb0313393de6d45aa339bf5619bd | c1ccncc1 | C-[C;H0;D2;+0:1]#[N;D1;H0:2].N-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[#7;+:7]):[c:8]>>[#7;+:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[C;H0;D2;+0:1]#[N;D1;H0:2]):[#7;a:4]:[c:5] | 41 | [{"value": 41.0, "product": "BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 2-amino-5-bromo-3-nitropyridine (2.18 g, 10 mmol), cuprous cyanide (1.33 g, 15 mmol) and tert-butylnitrite (2.0 mL, 15 mmol) in acetonitrile (50 mL) to 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (100 mL) and saturated aqueous NaHCO3 (100 mL). Extract the aqueous solutio... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-]>>N#Cc1ncc(Br)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00d87abac6bf41acb621916e25883907 | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-]>>Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-].[Br-].CC=1C(=NC=CC1)[Zn+]>>CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-] | [Zn+][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1.Br[c:8]1[cH:9][n:10][c:11]([C:12]#[N:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([C:12]#[N:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-] | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1 | C-C Coupling | OtherReaction | e4ecd4c8f01d2effb96acd4b7efc6dcca828274ea1bedd77506f1b8e3573c914 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccnc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[Zn+]):[#7;a:11]:[c:12]>>[C;D1;H3:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[#7;a:11]:[c:12] | 88 | [{"value": 88.0, "product": "CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5-bromo-3-nitropyridine-2-carbonitrile (228 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg), 3-methyl-2-pyridylzinc bromide (0.5 M in THF, 3 mL, 1.5 mmol) in THF (5 mL) to 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | Br-.Zn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1 | null | null | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-]>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1>Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c77edee4a9fb4053b89ebe1c870aac40 | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1>>Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 | CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-].C(C)O>>NC=1C(=NC=C(C1)C1=NC=CC=C1C)C(=O)N | [O-][N+:16](=[O:14])[c:15]1[c:11]([C:12]#[N:13])[n:10][cH:9][c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]2)[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([C:12]([NH2:13])=[O:14])[c:15]([NH2:16])[cH:17]1 | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 | null | [Fe] | O | Functional Group Interconversion | OtherReaction | ede7d2a6ee11f3b3697b1dfb480a8f492854589e148f2058b38ac2e2cd797a36 | cb5481c22f68622a17796d4a172dd074a4fb2bd7f9c138bcaa93b97fc12e084f | c1ccc(-c2cccnc2)nc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[N+;H0;D3:7](-[O-])=[O;H0;D1;+0:8]):[c:9]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:8])-[c:3](:[#7;a:4]:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:9] | 94 | [{"value": 94.0, "product": "NC=1C(=NC=C(C1)C1=NC=CC=C1C)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5-(3-methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile (1 g, 4.1 mmol), iron (2.3 g, 40 mmol) and calcium chloride (560 mg, 5 mmol) in ethanol (15 mL) and water (4 mL) to reflux for 1 hour. Cool the mixture, filter through Celite and wash with ethyl acetate. Evaporate the filtrate and re-dissolve the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitro group | Primary amide.Primary amine | null | null | c1ccncc1.c1ccncc1 | Other | [Fe].O | null | null | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1>[Fe].O>Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a37a88c4ed6045039b710a3512e968d7 | Cc1cccnc1-c1cnc(C(N)=O)c(N)c1.FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>Cc1cccnc1-c1cnc2c(Nc3ccc(C(F)(F)F)cc3)nc(CN3CCCC3)nc2c1 | N1(CCCC1)CC1=NC2=CC(=CC=C2C(=N1)NC1=CC=C(C=C1)C(F)(F)F)C1=NC=CC=C1C(F)(F)F.NC=1C(=NC=C(C1)C1=NC=CC=C1C)C(=O)N>>CC=1C(=NC=CC1)C1=CC=2N=C(N=C(C2N=C1)NC1=CC=C(C=C1)C(F)(F)F)CN1CCCC1 | NC(=O)c1c(N)c[c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]2)[cH:9][n:10]1.FC(F)(F)c1cccnc1-c1cc[c:11]2[c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]3)[n:24][c:25]([CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][c:33]2[cH:34]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]... | Cc1cccnc1-c1cnc(C(N)=O)c(N)c1.FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | Cc1cccnc1-c1cnc2c(Nc3ccc(C(F)(F)F)cc3)nc(CN3CCCC3)nc2c1 | null | null | null | Miscellaneous | OtherReaction | 3fa4615a74505ac221315fc120db2d1bd3ef7488a92e7ae41a1b3502c3a29c1d | 152ebe6d56cfc57e37cbb47d883f614870fc78ae305247312422e940fef02ee9 | c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ccccn4)cnc23)cc1 | F-C(-F)(-F)-c1:c:c:c:n:c:1-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[#7:7]):[c;H0;D3;+0:8]:2:c:c:1.N-C(=O)-c1:[n;H0;D2;+0:9]:[c:10]:[c;H0;D3;+0:11](-[c:12](:[c:13]):[#7;a:14]:[c:15]):c:c:1-N>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]2:[cH;D2;+0:1]:[c;H0;D3;+0:11](-[c:12](:[c:13]):[#7;a:14]:[c:15]):[c:10]... | null | [] | null | null | null | null | The title compound is prepared from 3-amino-5-(3-methyl(2-pyridyl))pyridine-2-carboxamide in a manner analogous to that used for the preparation of [2-pyrrolidin-1-ylmethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine (Example 2.A, steps 6 to 9).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Primary amide.Primary amine | null | c1ccncc1.c1ccncc1.c1ccc2ncncc2c1 | c1cnc2cncnc2c1 | c1ccncc1.c1ccccc1.c1cnc2cncnc2c1.C1CC[NH]C1 | HF | null | null | null | Cc1cccnc1-c1cnc(C(N)=O)c(N)c1.FC(F)(F)c1ccc(Nc2nc(CN3CCCC3)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>Cc1cccnc1-c1cnc2c(Nc3ccc(C(F)(F)F)cc3)nc(CN3CCCC3)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d6813fe288124993a7c918a7f8a55b39 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | ClC1=NC=CC=C1C(F)(F)F.B(C=1C=CC(=CC1)C)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1.Cl[c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl | Cc1ccc(-c2ncccc2C(F)(F)F)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[#7;a:2]:[c:3] | null | [] | 80 | CELSIUS | 8 | HOUR | To a de-gassed mixture of 2-chloro-3-(trifluoromethyl)-pyridine (70.1 mmol), p-tolylboronic acid (70.6 mmol), and 2M Na2CO3 (175.0 mmol), in dimethyl ether (DME; 200 mL) under nitrogen add Pd(PPh3)4 (2.8 mmol). Stir the mixture at 80° C. overnight, concentrate, and extract with EtOAc. Dry over Na2SO4, concentrate under... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COC | 80 | 8 | Cc1ccc(B(O)O)cc1.FC(F)(F)c1cccnc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COC>Cc1ccc(-c2ncccc2C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a74422cb03ef40a2afe09f0d7d70af8c | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | C1(=CC=C(C=C1)C1=NC=CC=C1C(F)(F)F)C.[N+](=O)(O)[O-]>>CC1=C(C=C(C=C1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.O[N+:18](=[O:19])[O-:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O | Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccccn2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 60 | MINUTE | To a solution of 2-p-tolyl-3-trifluoromethyl-pyridine (8.4 mmol) in H2SO4 (6 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture for 60 minutes at room temperature. Pour the mixture onto ice-water (30 mL), extract with EtOAc, neutralize with 1 N NaOH, dry over Na2SO4, and concentrate under vacuum to obtain 2-(4-met... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | OS(=O)(=O)O | null | 1 | Cc1ccc(-c2ncccc2C(F)(F)F)cc1.O=[N+]([O-])O>OS(=O)(=O)O>Cc1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ae2729437fd4a318279beede51d1186 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | [N+](=O)([O-])C1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F>>NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F | O=[N+:20]([O-])[c:19]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 16 | HOUR | Hydrogenate 2-nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (1.0 g, 0.0032 mol) with 50 psi of H2 and 100 mg of 10% Pd/C in ethanol. After 16 hours, filter the mixture through celite and concentrate under reduced pressure to give 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide as a solid.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Pd].C(C)O | null | 16 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>[Pd].C(C)O>NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85afb19869af47839581787a5e3a7eae | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.ClCC(OC)(OC)OC>>ClCC1=NC2=CC(=CC=C2C(N1)=O)C1=NC=CC=C1C(F)(F)F | CO[C:4](OC)(OC)[CH2:5][Cl:6].[O:1]=[C:2]([NH2:3])[c:23]1[c:8]([NH2:7])[cH:9][c:10](-[c:11]2[n:12][cH:13][cH:14][cH:15][c:16]2[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1>>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][Cl:6])[n:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][cH:13][cH:14][cH:15][c:16]3[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22][c... | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 292ab66b88620748fa9d06e6e4d9b67ede3a8fd233d74022944407012fccec37 | 7ad6d407a4f6c8573e2bc724851922f3f76bd08d2e3d3a3ddf0a52cbc9de261c | O=c1[nH]cnc2cc(-c3ccccn3)ccc12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:4]:1 | null | [] | null | null | null | null | Heat a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (100 mg, 0.356 mmol) in 2-chloro-1,1,1-trimethoxyethane (bp 138° C.) at 130° C. for 4 hours. Concentrate the mixture under reduced pressure to give 2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-quinazolin-4-one as an oil which crystallizes o... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1.c1ccncc1 | HO- | null | null | null | COC(CCl)(OC)OC.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N>>O=c1[nH]c(CCl)nc2cc(-c3ncccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a01df7e0ea84826859deaf88f3393f7 | CC(C)[O][Na].FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>>CC(C)OCc1nc(Nc2ccc(C(F)(F)F)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | Cl.ClCC1=NC2=CC(=CC=C2C(=N1)NC1=CC=C(C=C1)C(F)(F)F)C1=NC=CC=C1C(F)(F)F.O([Na])C(C)C>>C(C)(C)OCC1=NC2=CC(=CC=C2C(=N1)NC1=CC=C(C=C1)C(F)(F)F)C1=NC=CC=C1C(F)(F)F | [Na][O:4][CH:2]([CH3:1])[CH3:3].Cl[CH2:5][c:6]1[n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][c:23](-[c:24]3[n:25][cH:26][cH:27][cH:28][c:29]3[C:30]([F:31])([F:32])[F:33])[cH:34][c:35]2[n:36]1>>[CH3:1][CH:2]([CH3:3])[O:4][CH2:5][c:6]1[n:7][c:8]([NH:9][c:1... | CC(C)[O][Na].FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1 | CC(C)OCc1nc(Nc2ccc(C(F)(F)F)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3dd6ea90858eede84ece2f60931b760bd509d5f421f2feb2b0fe7a2c006d84f0 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | c1ccc(Nc2ncnc3cc(-c4ccccn4)ccc23)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[O;H0;D2;+0:10]-[Na]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | 60 | CELSIUS | 5 | HOUR | To a suspension of [2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine hydrochloride (1.9 g, 0.0037 mol) in dry isopropanol (100 mL), add 20 equivalents of NaO-i-Pr (prepared from Na and isopropanol). Stir the pale yellow mixture at 60° C. for 5 hours, cool and evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | null | null | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | Na | C(C)(C)O | 60 | 5 | CC(C)[O][Na].FC(F)(F)c1ccc(Nc2nc(CCl)nc3cc(-c4ncccc4C(F)(F)F)ccc23)cc1>C(C)(C)O>CC(C)OCc1nc(Nc2ccc(C(F)(F)F)cc2)c2ccc(-c3ncccc3C(F)(F)F)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3d32619db8c454f91c6ff0ecdea30c6 | CCOC(=O)CCBr.OCc1ccccc1>>O=C(O)CCOCc1ccccc1 | O.[H-].[Na+].C(C1=CC=CC=C1)O.BrCCC(=O)OCC>>C(C1=CC=CC=C1)OCCC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5]Br.[OH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCOC(=O)CCBr.OCc1ccccc1 | O=C(O)CCOCc1ccccc1 | null | null | [OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 649e704edbb364f9da7d07cbe4234c4a92fb1da39cfc9c27b4b5f45f135ea332 | 618df49e449d2d4d71a5c69761039aa60d2846715c5b4fde87b9028fc160ed45 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C.[OH;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:7]-[c:8] | 34.2 | [{"value": 34.0, "product": "C(C1=CC=CC=C1)OCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "C(C1=CC=CC=C1)OCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Add sodium hydride (2.22 g, 60% dispersion in mineral oil, 55.4 mmol) in small portions to a cold (0° C.) solution of benzyl alcohol (4.0 g, 37 mmol) in toluene (100 mL). Add ethyl 3-bromopropionate (8.0 g, 44 mmol) dropwise to the mixture, allow the resulting solution to warm to room temperature and stir for 1 hour. Q... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HBr | [OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | null | 1 | CCOC(=O)CCBr.OCc1ccccc1>[OH-].[Na+].C1(=CC=CC=C1)C.CO.C(C)(=O)OCC>O=C(O)CCOCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0d3d7aa5188492bb4f3d74489d05f49 | COCCCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.c1ccncc1>>Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | [OH-].[Na+].NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.N1=CC=CC=C1.COCCCC(=O)Cl.C1CCOC1>>C(C1=CC=CC=C1)OCCCC1=NC2=CC(=CC=C2C(=N1)O)C1=NC=CC=C1C(F)(F)F | O=[C:4](Cl)[CH2:5][CH2:6][CH2:7][O:8][CH3:9].[O:1]=[C:2]([NH2:3])[c:32]1[c:17]([NH2:16])[cH:18][c:19](-[c:20]2[n:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1.n1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[OH:1][c:2]1[n:3][c:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14]... | COCCCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.c1ccncc1 | Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b34f8adda3824855b490c3a1513f656f30d682b61c7e67001560ba564ef0b0c2 | d626de740818142cd15e2d01aa83dff506457ddae8038f340ed9da5ea4e481c5 | c1ccc(COCCCc2ncc3ccc(-c4ccccn4)cc3n2)cc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3]-[C:4]-[#8:5]-[CH3;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;H0;D1;+0:13]):[c:14].[c:15]1:[c:16]:[c:17]:[cH;D2;+0:18]:n:[cH;D2;+0:19]:1>>[OH;D1;+0:13]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:1](-[C:2]-[C:3]-[C:4]-[#8:5]-[CH2;D2;+0:6]-[c:20]2:[... | null | [] | null | null | 20 | MINUTE | To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (3.56 mmol) and pyridine (3.91 mmol) in THF (20 ml), add 4-methoxy-butyryl chloride (3.91 mmol). Stir the mixture 20 minutes at room temperature, add 20 ml of 20% NaOH, stir for 60 minutes at 50° C. Concentrate, add water, filter, acidify to pH=6, co... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amide.Primary amine | Ether.Aromatic alcohol | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | HCl | null | null | 0.333333 | COCCCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.c1ccncc1>>Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76f21bcd99754d0cb5b8bcefa0ae7101 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.O=C(Cl)CCCOCc1ccccc1>>Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | [OH-].[Na+].NC1=C(C(=O)N)C=CC(=C1)C1=NC=CC=C1C(F)(F)F.N1=CC=CC=C1.C(C1=CC=CC=C1)OCCCC(=O)Cl>>C(C1=CC=CC=C1)OCCCC1=NC2=CC(=CC=C2C(=N1)O)C1=NC=CC=C1C(F)(F)F | [O:1]=[C:2]([NH2:3])[c:32]1[c:17]([NH2:16])[cH:18][c:19](-[c:20]2[n:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1.O=[C:4](Cl)[CH2:5][CH2:6][CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[OH:1][c:2]1[n:3][c:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH... | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.O=C(Cl)CCCOCc1ccccc1 | Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 421874b4cd55eaa20f24b1cd7ba94b5870b5c4e9b00f756449eff425c4e3a153 | d5ef1961d36ab2d05e773eb9e606a89406d1ee5463b381ad4c7037e46428ccb9 | c1ccc(COCCCc2ncc3ccc(-c4ccccn4)cc3n2)cc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[O;H0;D1;+0:10]):[c:11]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:11]):[c;H0;D3;+0:8](-[OH;D1;+0:10]):[n;H0;D2;+0:9]:1 | null | [] | null | null | 20 | MINUTE | To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (3.56 mmol) and pyridine (3.91 mmol) in THF (20 ml) add 4-benzyloxy-butyryl chloride (3.91 mmol). Stir the mixture 20 minutes at room temperature, add 20 ml of 20% NaOH, stir for 60 minutes at 50° C. Concentrate, add water, filter, acidify to pH=6, c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | HCl | C1CCOC1 | null | 0.333333 | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N.O=C(Cl)CCCOCc1ccccc1>C1CCOC1>Oc1nc(CCCOCc2ccccc2)nc2cc(-c3ncccc3C(F)(F)F)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-634b8a8802314e3aae7783e948e46790 | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl>>COc1ccc(-c2ncccc2C(F)(F)F)cn1 | ClC1=NC=CC=C1C(F)(F)F.COC1=NC=C(C=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:18][cH:17]1.Cl[c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][n:18]1 | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl | COc1ccc(-c2ncccc2C(F)(F)F)cn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 2e12f1697d123c35af029842984dda76c08cdd06401f05924c6b1363bf342af9 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1):[#7;a:2]:[c:3] | 95 | [{"value": 95.0, "product": "COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a mixture of 2-chloro-3-trifluoromethylpyridine (37 g, 0.2 mol), 2-methoxypyridine-5-boronic acid (32 g, 0.21 mol), tetrakis(triphenylphosphine)palladium(0) (9 g, 7 mmol) and 2M potassium carbonate (150 mL) in toluene (500 mL) under a nitrogen atmosphere at 90° C. for 8 hours. Cool the reaction mixture and separat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | COc1ccc(B(O)O)cn1.FC(F)(F)c1cccnc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>COc1ccc(-c2ncccc2C(F)(F)F)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19017cea450249218e3f99d4c973dc72 | COc1ccc(-c2ncccc2C(F)(F)F)cn1>>O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | COC1=CC=C(C=N1)C1=NC=CC=C1C(F)(F)F>>FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F | C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][n:17]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][nH:17]1 | COc1ccc(-c2ncccc2C(F)(F)F)cn1 | O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | null | null | Br.CC(=O)O | Miscellaneous | OtherReaction | ffbb4288e7102e6f227d930be4a9510dc9e13ff3142954fd43347db64909ca58 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1ccc(-c2ccccn2)c[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1 | 93.7 | [{"value": 93.0, "product": "FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Heat 6′-Methoxy-3-trifluoromethyl-[2,3′]bipyridinyl (41 g, 0.16 mol) in 30% HBr/AcOH (100 mL) to reflux for 1 hour. Cool the mixture, filter and wash the precipitate with ether (100 mL). Transfer the precipitate into 10M sodium hydroxide (500 mL) and stir for 1 hour. Treat the solution with hydrochloric acid until the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1cccnc1 | c1cccnc1.c1ccncc1 | Other | Br.CC(=O)O | null | 1 | COc1ccc(-c2ncccc2C(F)(F)F)cn1>Br.CC(=O)O>O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05492f6a96b7429db4e0da67867767ff | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1>>O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | FC(C=1C(=NC=CC1)C1=CNC(C=C1)=O)(F)F.[N+](=O)(O)[O-]>>[N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F | O[N+:18](=[O:19])[O-:20].[O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1 | O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 26a878e97e02b420c859859d3c94a295b28ee7e9c7a3a499b0358675c34410cd | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1ccc(-c2ccccn2)c[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 3-trifluoromethyl-1′H-[2,3′]bipyridinyl-6′-one (25 g, 0.1 mol) in concentrated sulfuric acid (100 mL) at 0° C., add dropwise a solution of fuming nitric acid (35 mL) and concentrated sulfuric acid (10 mL). Heat the reaction mixture to 70° C. for 1 hour, cool and pour onto ice (500 mL). Filter the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cccnc1 | c1cnccc1 | c1cnccc1.c1ccncc1 | HO- | S(O)(O)(=O)=O | 70 | null | O=[N+]([O-])O.O=c1ccc(-c2ncccc2C(F)(F)F)c[nH]1>S(O)(O)(=O)=O>O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3648be0c925346ff99a238ce1ea29109 | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | [N+](=O)([O-])C1=CC(=CNC1=O)C1=NC=CC=C1C(F)(F)F.S(=O)(Cl)Cl>>ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-] | O=S(Cl)[Cl:20].O=[c:19]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][nH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[cH:17][n:18][c:19]1[Cl:20] | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-] | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | ad993f9ce2ce60b71a2afb3182d5e182b0d0de1be8200a3f161e73174c9a6ebf | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cccnc2)nc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1-[#7;+:8]>>[#7;+:8]-[c:7]1:[c:6]:[c:5]:[c:4]:[n;H0;D2;+0:3]:[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | 93 | [{"value": 93.0, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5′-nitro-3-trifluoromethyl-1′H[2,3′]bipyridinyl-6′-one (25 g, 0.088 mol), thionyl chloride (300 mL) and DMF (3 mL) to reflux for 4 hours. Remove the volatiles by rotary evaporation and partition the residue between ethyl acetate (350 mL) and saturated sodium bicarbonate solution (250 mL). Extract the... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnccc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HCl | CN(C)C=O | null | null | O=S(Cl)Cl.O=c1[nH]cc(-c2ncccc2C(F)(F)F)cc1[N+](=O)[O-]>CN(C)C=O>O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1135e8d12c4344768805a1fcbbf87482 | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl>>Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl | ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-]>>ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][n:16][c:17]1[Cl:18]>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[cH:15][n:16][c:17]1[Cl:18] | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl | Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl | null | [Fe] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccnc2)nc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]>>[Cl;D1;H0:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 85 | [{"value": 85.0, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6′-chloro-5′-nitro-3-trifluoromethyl-[2,3′]bipyridinyl (25 g, 0.082 mol) and calcium chloride (11 g, 0.1 mol) in ethanol (300 mL) and water (50 mL), add iron powder (45 g, 0.82 mol). Heat the solution to reflux for 1.5 hours, cool and filter through Celite. Concentrate the mixture under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccncc1 | Other | [Fe].O.C(C)O | null | null | O=[N+]([O-])c1cc(-c2ncccc2C(F)(F)F)cnc1Cl>[Fe].O.C(C)O>Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-269008a3e97d454a9e8ef3f4ef800056 | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+]>>NC(=O)c1ncc(-c2ncccc2C(F)(F)F)cc1N | ClC1=C(C=C(C=N1)C1=NC=CC=C1C(F)(F)F)N.CN(C)C=O.[Cl-].[NH4+].[OH-].[NH4+]>>NC=1C(=NC=C(C1)C1=NC=CC=C1C(F)(F)F)C(=O)N | CN(C)[CH:2]=[O:3].Cl[c:4]1[n:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20].[NH4+:1]>>[NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+] | NC(=O)c1ncc(-c2ncccc2C(F)(F)F)cc1N | null | [C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O | Acylation | OtherReaction | e1863fb77b18a4f8a4f6f62e441a7222b67756c377f9188d3bd53f6c3965f65f | e877213e19171755e0934a74438f863139f6bd24cdbe9c4b94ecbf55b1179c4e | c1ccc(-c2cccnc2)nc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[N;D1;H2:7]):[c:8].[NH4+;D0:9]>>[N;D1;H2:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[O;D1;H0:2]):[#7;a:4]:[c:5] | 90 | [{"value": 90.0, "product": "NC=1C(=NC=C(C1)C1=NC=CC=C1C(F)(F)F)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Heat a solution of 6′-chloro-3-trifluoromethyl-[2,3′]bipyridinyl-5′-ylamine (25 g, 0.091 mol), zinc cyanide (6.75 g, 0.058 mol), tris[dibenzylidineacetone]di-palladium (pd2(dba)3; 2.63 g, 2.86 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (DPPF; 3.16 g, 5.72 mmol) in DMF (250 mL) and water (2.5 mL), under a nitrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HCl | [C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O | 0 | 1 | CN(C)C=O.Nc1cc(-c2ncccc2C(F)(F)F)cnc1Cl.[NH4+]>[C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O>NC(=O)c1ncc(-c2ncccc2C(F)(F)F)cc1N |
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