dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-063d21c295f14515abcd47ec336c942e | CS(=O)(=O)Cl.OC1CCCc2ccc(Br)nc21>>CS(=O)(=O)OC1CCCc2ccc(Br)nc21 | C(=O)(O)[O-].[Na+].C(C)N(CC)CC.BrC1=NC=2C(CCCC2C=C1)O.CS(=O)(=O)Cl>>CS(=O)(=O)OC1CCCC=2C=CC(=NC12)Br | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH:6]1[CH2:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[n:15][c:16]21>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH:6]1[CH2:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[n:15][c:16]21 | CS(=O)(=O)Cl.OC1CCCc2ccc(Br)nc21 | CS(=O)(=O)OC1CCCc2ccc(Br)nc21 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | c1cnc2c(c1)CCCC2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]:[c:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7;a:5]:[c:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | 88 | [{"value": 88.0, "product": "CS(=O)(=O)OC1CCCC=2C=CC(=NC12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "CS(=O)(=O)OC1CCCC=2C=CC(=NC12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a cold (0° C.) stirred solution of 2-bromo-5,6,7,8-tetrahydroquinolin-8-ol (500 mg, 2.36 mmol) in dry CH2Cl2 (10 mL) was added triethylamine (0.72 mL, 5.2 mmol) followed by methanesulfonyl chloride (0.35 mL, 3.6 mmol). The resulting mixture was stirred at 0° C. for 1 h, then warmed slowly to room temperature and sti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | c1cnc2c(c1)CCCC2 | HCl | C(Cl)Cl | 0 | 1 | CS(=O)(=O)Cl.OC1CCCc2ccc(Br)nc21>C(Cl)Cl>CS(=O)(=O)OC1CCCc2ccc(Br)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f64908372ab9400c9c9007ca6470f69b | COc1ccnc2c1CCCC2O.NC1CCCc2cccnc21>>COc1ccnc2c1CCCC2N | NC1CCCC=2C=CC=NC12.OC1CCCC=2C(=CC=NC12)OC>>NC1CCCC=2C(=CC=NC12)OC | OC1CCC[c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][n:6][c:7]21.c1cnc2c(c1)[CH2:9][CH2:10][CH2:11][CH:12]2[NH2:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]2[c:8]1[CH2:9][CH2:10][CH2:11][CH:12]2[NH2:13] | COc1ccnc2c1CCCC2O.NC1CCCc2cccnc21 | COc1ccnc2c1CCCC2N | null | null | null | C-C Coupling | OtherReaction | b15fd67fc5205a41f52639ab27f0e90a711cfdd3db40021b214613b914c0037f | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | c1cnc2c(c1)CCCC2 | O-C1-C-C-C-[c;H0;D3;+0:1]2:[c:2](-[#8:3]):[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:2-1.[N;D1;H2:8]-[CH;D3;+0:9]1-[C:10]-[C:11]-[CH2;D2;+0:12]-c2:c:c:c:n:c:2-1>>[#8:3]-[c:2]1:[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]2:[c;H0;D3;+0:1]:1-[CH2;D2;+0:12]-[C:11]-[C:10]-[CH;D3;+0:9]-2-[N;D1;H2:8] | 68 | [{"value": 68.0, "product": "NC1CCCC=2C(=CC=NC12)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-amino-4-methoxy-5,6,7,8-tetrahydroquinoline was prepared in 68% yield from 8-hydroxy-4-methoxy-5,6,7,8-tetrahydroquinoline (preparation and characterization described by: Uchida, M.; Morita, S.; Chihiro, M.; Kanbe, T.; Yamasaki, K.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull. 1989, 37, 1517–1523) using the same pro... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1cnc2c(c1)CCCC2.c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | HO- | null | null | null | COc1ccnc2c1CCCC2O.NC1CCCc2cccnc21>>COc1ccnc2c1CCCC2N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a42fb88b0a3b471bb9c9218f3e6c9b60 | COc1ccnc2c1CCCC2NCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1>>COc1ccnc2c1CCCC2NCc1ccc(CNCc2ccccn2)cc1 | N1=C(C=CC=C1)CN(CC1=CC=C(C=C1)CNC1CCCC=2C(=CC=NC12)OC)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-].C1(=CC=CC=C1)S.C(=O)([O-])[O-].[K+].[K+]>>N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CNC1CCCC=2C(=CC=NC12)OC | O=[N+]([O-])c1ccccc1S(=O)(=O)[N:20]([CH2:19][c:18]1[cH:17][cH:16][c:15]([CH2:14][NH:13][CH:12]2[c:7]3[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]3[CH2:9][CH2:10][CH2:11]2)[cH:29][cH:28]1)[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]2[c:8]1[CH2:9][CH2:10][CH2:11][CH:12]2[NH:13... | COc1ccnc2c1CCCC2NCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 | COc1ccnc2c1CCCC2NCc1ccc(CNCc2ccccn2)cc1 | null | null | CC#N | Reduction | Hydrogenolysis of tertiary amines | 2ee1c0e9d4745d3380f36a903a208d80738098f20b6f379514928935fd24c5c9 | 1e653e20ac001d92972e72ca6294e607303822683eea0adc1fa0a988ff7782b7 | c1ccc(CNCc2ccc(CNC3CCCc4cccnc43)cc2)nc1 | O=[N+](-[O-])-c1:c:c:c:c:c:1-S(=O)(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[c:3] | 82 | [{"value": 82.0, "product": "N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CNC1CCCC=2C(=CC=NC12)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CNC1CCCC=2C(=CC=NC12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using general procedure C: N-(2-pyridinylmethyl)-N-(2-nitrobenzenesulfonyl)-N′-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.269 g, 0.50 mmol) was treated with thiophenol (0.35 mL, 3.41 mmol) and K2CO3 (0.757 g, 5.48 mmol) in CH3CN (10 mL). Purification of the crude material by radial chromato... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Secondary amine | c1ccccc1 | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccncc1 | HO- | CC#N | null | null | COc1ccnc2c1CCCC2NCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1>CC#N>COc1ccnc2c1CCCC2NCc1ccc(CNCc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5203239c158e446e9e84abab6abb16bf | Brc1cnc2ccccc2c1.C[O-]>>COc1cnc2ccccc2c1 | BrC=1C=NC2=CC=CC=C2C1.C[O-].[Na+]>>COC=1C=NC2=CC=CC=C2C1 | Br[c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1 | Brc1cnc2ccccc2c1.C[O-] | COc1cnc2ccccc2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | dd6932defb2e2d09070bf47b6101415c37de430a4951062bc340a73ed05c28e0 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[O-;H0;D1:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 6.2 | [{"value": 6.0, "product": "COC=1C=NC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.2, "product": "COC=1C=NC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A solution of 3-bromoquinoline (22.54 g, 108 mmol) in anhydrous DMF (110 mL) was treated with sodium methoxide (11.70 g, 217 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was then concentrated and the residue taken up in ethyl acetate (300 mL) and water (60 mL). The organic phase was separated, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Br- | CN(C)C=O | 80 | 16 | Brc1cnc2ccccc2c1.C[O-]>CN(C)C=O>COc1cnc2ccccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe74ddfe194440d1ab2d85f342beb1c2 | COc1cnc2ccccc2c1.O=C(O)C(F)(F)F>>COc1cnc2c(c1)CCCC2O | COC=1C=NC2=CC=CC=C2C1.C(=O)(C(F)(F)F)O>>COC=1C=NC=2C(CCCC2C1)O | [CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[cH:9][cH:10][cH:11][cH:12]2.OC(C(F)(F)F)=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][CH:12]2[OH:13] | COc1cnc2ccccc2c1.O=C(O)C(F)(F)F | COc1cnc2c(c1)CCCC2O | null | [Pt]=O | null | Heteroatom Alkylation and Arylation | OtherReaction | 6170665dbc06afe761cf2ade6d058dafb8fcf212324218640cebde7afa1346c9 | 968bb4bdb0642159455562fda3c135200bcb9c14e8df842f07d3711d087b4103 | c1cnc2c(c1)CCCC2 | F-C(-F)(-F)-C(-O)=[O;H0;D1;+0:1].[c:2]:[#7;a:3]:[c:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:1:[c:10]>>[OH;D1;+0:1]-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:4]-1:[#7;a:3]:[c:2] | 87 | [{"value": 87.0, "product": "COC=1C=NC=2C(CCCC2C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-methoxyquinoline (1.06 g, 6.7 mmol) in TFA (22 mL) under nitrogen was added platinum oxide (225 mg, 1.3 mmol) and the suspension bubbled with hydrogen gas 16 h at 60° C. The mixture was then cooled to room temperature, neutralized to pH 12 with 10 N NaOH and extracted with CH2Cl2 (3×50 mL). The organ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid | Secondary alcohol | c1ccc2ncccc2c1 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | Other | [Pt]=O | null | null | COc1cnc2ccccc2c1.O=C(O)C(F)(F)F>[Pt]=O>COc1cnc2c(c1)CCCC2O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0dfc334a49974f34ab99a1a915a5b67b | COc1cnc2c(c1)CCCC2N=[N+]=[N-]>>COc1cnc2c(c1)CCCC2N | COC=1C=NC=2C(CCCC2C1)N=[N+]=[N-].[H][H]>>COC=1C=NC=2C(CCCC2C1)N | [N-]=[N+]=[N:13][CH:12]1[c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][CH2:11]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][CH:12]2[NH2:13] | COc1cnc2c(c1)CCCC2N=[N+]=[N-] | COc1cnc2c(c1)CCCC2N | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1cnc2c(c1)CCCC2 | [#7;a:1]:[c:2]-[C:3](-[N;H0;D2;+0:4]=[N+]=[N-])-[C:5]>>[#7;a:1]:[c:2]-[C:3](-[NH2;D1;+0:4])-[C:5] | 98.2 | [{"value": 96.0, "product": "COC=1C=NC=2C(CCCC2C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "COC=1C=NC=2C(CCCC2C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (3-methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-azide (0.33 g, 1.6 mmol) in MeOH (16 mL) was added palladium on activated carbon, (10%, 50 mg) and the reaction mixture stirred under 1 atmosphere of hydrogen for 4 h. The mixture was filtered through celite, the cake washed with methanol and the solvent from... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1cnc2c(c1)CCCC2 | Other | [Pd].CO | null | null | COc1cnc2c(c1)CCCC2N=[N+]=[N-]>[Pd].CO>COc1cnc2c(c1)CCCC2N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a832f23b312745c0993b83e0f8ba811c | CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ccccn1.COc1cnc2c(c1)CCCC2N>>COc1cnc2c(c1)CCCC2NCc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].COC=1C=NC=2C(CCCC2C1)N.C(C)(C)(C)OC(=O)N(CC1=NC=CC=C1)CC1=CC=C(C=O)C=C1>>C(C)(C)(C)OC(N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CNC1CCCC=2C=C(C=NC12)OC)=O | O=[CH:14][c:15]1[cH:16][cH:17][c:18]([CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][n:27]2)[C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35][cH:36]1.[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][CH:12]2[NH2:13]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9... | CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ccccn1.COc1cnc2c(c1)CCCC2N | COc1cnc2c(c1)CCCC2NCc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(CNC3CCCc4cccnc43)cc2)nc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7;a:5]:[c:6]-[C:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9] | 58 | [{"value": 58.0, "product": "C(C)(C)(C)OC(N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CNC1CCCC=2C=C(C=NC12)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Using General Procedure B: To a solution of (3-methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-amine (0.27 g, 1.5 mmol) and 4-[[N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)amino]methyl]benzaldehyde (prepared as described by Bridger et al, U.S. patent application Ser. No. 09/535,314) (0.57 g, 1.7 mmol) in CH2Cl2 (15 mL) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccncc1 | Other | C(Cl)Cl | null | 16 | CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ccccn1.COc1cnc2c(c1)CCCC2N>C(Cl)Cl>COc1cnc2c(c1)CCCC2NCc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fa1502fea41463483475920aac8fca9 | OC1CCCc2cccnc21>>O=C1CCCc2cccnc21 | OC1CCCC=2C=CC=NC12>>N1=CC=CC=2CCCC(C12)=O | [OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21 | OC1CCCc2cccnc21 | O=C1CCCc2cccnc21 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | b220980a208eb9fed81b429942ce2ac6d169e7e8c5f1ebb0cf2306e7beb5e86a | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCc2cccnc21 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 82 | [{"value": 82.0, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline (13.96 g, 93.6 mmol) in dry CH2Cl2 (400 mL) was added activated manganese dioxide (85% purity, 82.22 g, 804 mmol). The resulting heterogeneous mixture was stirred 18 h, at which point the black slurry was filtered through a cake of celite and washed with CH... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | 18 | OC1CCCc2cccnc21>[O-2].[O-2].[Mn+4].C(Cl)Cl>O=C1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac86493adafa4fabbddb1c0ee2a32e96 | Clc1nc2ccccc2o1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3o2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)N(CC)CC.ClC=1OC2=C(N1)C=CC=C2>>O1C(=NC2=C1C=CC=C2)NCC2=CC=C(C=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1 | Cl[c:19]1[n:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[o:27]1.[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:28][cH:29]1)[CH2:30][c:31]1[n:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]2[nH:39]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[... | Clc1nc2ccccc2o1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3o2)cc1)Cc1nc2ccccc2[nH]1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 56122dec6b9213d311e74462a865e17687f4178b6e2e5d6eb3cc0c5bc48da7a7 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3o2)cc1)Cc1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1 | 50.4 | [{"value": 37.0, "product": "O1C(=NC2=C1C=CC=C2)NCC2=CC=C(C=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.4, "product": "O1C(=NC2=C1C=CC=C2)NCC2=CC=C(C=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the General N-Alkylation Procedure: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (128 mg, 0.32 mmol) and triethylamine (100 ul, 0.72 mmol) in THF (5 mL) was added 2-chlorobenzoxazole (50 uL, 0.44 mmol) and the mixture was stirred at reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccc2ocnc2c1.c1ccc2[nH]cnc2c1 | HCl | C1CCOC1 | null | null | Clc1nc2ccccc2o1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3o2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea0c4929da2f428f81be0a64ddc30905 | N#Cc1ccc(C=O)cc1.NC1CCCc2cccnc21>>N#Cc1ccc(CNC2CCCc3cccnc32)cc1 | NC1CCCC=2C=CC=NC12.C(#N)C1=CC=C(C=O)C=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1=CC=CC=2CCCC(C12)NCC1=CC=C(C=C1)C#N | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:20][cH:19]1.[NH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]21>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][n:17][c:18]32)[cH:19][cH:20]1 | N#Cc1ccc(C=O)cc1.NC1CCCc2cccnc21 | N#Cc1ccc(CNC2CCCc3cccnc32)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNC2CCCc3cccnc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7;a:5]:[c:6]-[C:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9] | 72 | [{"value": 72.0, "product": "N1=CC=CC=2CCCC(C12)NCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "N1=CC=CC=2CCCC(C12)NCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 42 | HOUR | To a stirred solution of 8-amino-5,6,7,8-tetrahydroquinoline (24.3 g, 164 mmol) in dichloromethane (600 mL), at room temperature, was added 4-cyanobenzaldehyde (21.5 g, 164 mmol) and sodium triacetoxyborohydride (45 g, 210 mmol). After 42 hours, the reaction was quenched with 1N NaOH (250 mL). The phases were separated... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1cnc2c(c1)CCCC2 | Other | ClCCl | null | 42 | N#Cc1ccc(C=O)cc1.NC1CCCc2cccnc21>ClCCl>N#Cc1ccc(CNC2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8796c8cf3334b43b0cdd5ad9d83bed5 | CCCCc1ccc(C=O)nc1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>CCCCc1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(CCC)C=1C=CC(=NC1)C=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(CCC)C=1C=CC(=NC1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2 | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[cH:41][n:40]1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]([CH2:18][c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[nH:27]2)[CH:28]2[CH2:29][CH2:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][n:36][c:37]32)[cH:38][cH:39]1>>[CH3:1][CH2:2][CH2:3]... | CCCCc1ccc(C=O)nc1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CCCCc1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Using general procedure B: N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.1258 g, 0.316 mmol) and 5-n-butylpyridine-2-carboxaldehyde (0.0603 g, 0.294 mmol) were reacted with NaBH(OAc)3 (0.0942 g, 0.444 mmol) in CH2Cl2 (2.5 mL). Purification of the crude material by radial... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C(Cl)Cl | null | null | CCCCc1ccc(C=O)nc1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C(Cl)Cl>CCCCc1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0ed2b81d0864736adc41f19e2b2dd94 | CC(=O)O.Cc1cccnc1C>>CC(=O)OCc1ncccc1C | OO.N1=C(C(=CC=C1)C)C.OO.C(C)(=O)O>>C(C)(=O)OCC1=NC=CC=C1C | [CH3:1][C:2](=[O:3])[OH:4].[CH3:5][c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[CH3:12]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[CH3:12] | CC(=O)O.Cc1cccnc1C | CC(=O)OCc1ncccc1C | null | null | C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccncc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | 6 | HOUR | To a stirred solution of 2,3-lutidine (4.8363 g, 45.13 mmol) in glacial acetic acid (30 mL) at room temperature was added 30% H2O2 (4.6 mL) and the resultant solution was heated to 70° C. After 6 hours, the reaction mixture was cooled to room temperature, additional H2O2 (4.6 mL) was added, and the solution was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccncc1 | null | C(C)(=O)OC(C)=O | null | 6 | CC(=O)O.Cc1cccnc1C>C(C)(=O)OC(C)=O>CC(=O)OCc1ncccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b276c372b2c47e7b5b6464e07e242b6 | Cc1cccnc1CO>>Cc1cccnc1C=O | OCC1=NC=CC=C1C>>CC=1C(=NC=CC1)C=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH2:8][OH:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]=[O:9] | Cc1cccnc1CO | Cc1cccnc1C=O | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccncc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 64 | [{"value": 64.0, "product": "CC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "CC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 21 | HOUR | To a stirred solution of 2-(hydroxymethyl)-3-methylpyridine (1.08 g, 8.77 mmol) in dry CH2Cl2 (45 mL) at room temperature was added MnO2 (8.09 g, 79.1 mmol). The mixture was stirred for 21 hrs then filtered through celite. The filtrate was concentrated to give 0.68 g (64%) of 3-methylpyridine-2-carboxaldehyde. 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccncc1 | null | O=[Mn]=O.C(Cl)Cl | null | 21 | Cc1cccnc1CO>O=[Mn]=O.C(Cl)Cl>Cc1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41a445326c2b4979809438ee5d7e9725 | CCCOC(=O)c1ncccc1OCCC>>CCCOc1cccnc1C=O | C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+].C(CC)OC(C1=NC=CC=C1OCCC)=O.CC(C)C[AlH]CC(C)C>>C(CC)OC=1C(=NC=CC1)C=O | CCCO[C:11]([c:10]1[c:5]([O:4][CH2:3][CH2:2][CH3:1])[cH:6][cH:7][cH:8][n:9]1)=[O:12]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[CH:11]=[O:12] | CCCOC(=O)c1ncccc1OCCC | CCCOc1cccnc1C=O | null | O=[Mn]=O | C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccncc1 | C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 113.5 | [{"value": 113.5, "product": "C(CC)OC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a stirred solution of 3-n-propoxypicolinic acid n-propyl ester (0.1209 g, 0.541 mmol) in dry CH2Cl2 (5 mL) at −78° C. was added DIBAL-H (1.0 M, 2.5 mL, 2.5 mmol). The mixture was stirred at −78° C. for 1 hr, then at room temperature for 3 hrs. The mixture was poured into saturated aqueous sodium potassium tartrate (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccncc1 | HO- | O=[Mn]=O.C(Cl)Cl | -78 | 1 | CCCOC(=O)c1ncccc1OCCC>O=[Mn]=O.C(Cl)Cl>CCCOc1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-548c5f5faaa54f73a91f52023cd1b6f8 | CC(=O)O.Cc1cc(C)nc(C)c1>>CC(=O)OCc1cc(C)cc(C)n1 | OO.N1=C(C=C(C=C1C)C)C.OO.C(C)(=O)O>>C(C)(=O)OCC1=NC(=CC(=C1)C)C | [CH3:1][C:2](=[O:3])[OH:4].[CH3:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([CH3:12])[n:13]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([CH3:12])[n:13]1 | CC(=O)O.Cc1cc(C)nc(C)c1 | CC(=O)OCc1cc(C)cc(C)n1 | null | null | C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccncc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | 24 | [{"value": 24.0, "product": "C(C)(=O)OCC1=NC(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a stirred solution of 2,4,6-collidine (3.22 g, 26.6 mmol) in glacial acetic acid (21 mL) at room temperature was added 30% H2O2 (3.0 mL) and the resultant solution was heated to 70° C. After 6 hours, the reaction mixture was cooled to room temperature, additional H2O2 (3.0 mL) was added, and the solution was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccncc1 | null | C(C)(=O)OC(C)=O | null | 6 | CC(=O)O.Cc1cc(C)nc(C)c1>C(C)(=O)OC(C)=O>CC(=O)OCc1cc(C)cc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-594b6de69a4045a7b88d2074291bbbed | O=C(O)c1cc2ccccc2cn1>>OCc1cc2ccccc2cn1 | CO.C1=NC(=CC2=CC=CC=C12)C(=O)O.B.C1CCOC1>>OCC=1N=CC2=CC=CC=C2C1 | O=[C:2]([OH:1])[c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11][n:12]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11][n:12]1 | O=C(O)c1cc2ccccc2cn1 | OCc1cc2ccccc2cn1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc2cnccc2c1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 12.3 | [{"value": 12.3, "product": "OCC=1N=CC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0.75 | CELSIUS | 17 | HOUR | To a stirred solution of isoquinoline-3-carboxylic acid (0.3179 g, 1.84 mmol) in dry THF (10 mL) at room temperature was added BH3-THF (1.0 M, 7.5 mL, 7.5 mmol). The mixture was stirred for 17 hrs, dry CH3OH (10 mL) was added, and the reaction was heated to 0.75° C. with stirring for a further 24 hrs. The mixture was c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2cnccc2c1 | Other | C1CCOC1 | 0.75 | 17 | O=C(O)c1cc2ccccc2cn1>C1CCOC1>OCc1cc2ccccc2cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f4859518ebb480b9bc417db7ce45ca2 | CO.O=C(O)c1ncccc1O>>COC(=O)c1ncccc1O | OC=1C(=NC=CC1)C(=O)O.OS(=O)(=O)O.CO>>COC(C1=NC=CC=C1O)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11] | CO.O=C(O)c1ncccc1O | COC(=O)c1ncccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | To a stirred solution of 3-hydroxypicolinic acid (0.7122 g, 5.1 mmol) in CH3OH (32 mL) at room temperature was added concentrated H2SO4 (4 mL). The mixture was heated to reflux for 18 hrs then concentrated. The residue was diluted with saturated aqueous Na2CO3 (45 mL) and extracted with CH2Cl2 (4×30 mL). The combined o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccncc1 | HO- | null | null | null | CO.O=C(O)c1ncccc1O>>COC(=O)c1ncccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5d0730dc5f14fbd876c5c487555fef6 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1O>>Oc1ccccc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C=1C(O)=CC=CC1)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>OC1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2 | [NH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][N:16]([CH2:17][c:18]2[n:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[nH:26]2)[CH:27]2[CH2:28][CH2:29][CH2:30][c:31]3[cH:32][cH:33][cH:34][n:35][c:36]32)[cH:37][cH:38]1.O=[CH:8][c:7]1[c:2]([OH:1])[cH:3][cH:4][cH:5][cH:6]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1O | Oc1ccccc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[c:7]-[C:6]-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 54 | [{"value": 54.0, "product": "OC1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.7, "product": "OC1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (147 mg, 0.37 mmol) and salicylaldehyde (0.04 mL, 0.38 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (100 mg, 0.47 mmol) and the resultant mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C(Cl)Cl | null | null | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1O>C(Cl)Cl>Oc1ccccc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d7df6fce5eb41f7a498dfec62199b0a | [O-][n+]1cccc(F)c1>>N#Cc1ncccc1F | [Si](C)(C)(C)C#N.FC=1C=[N+](C=CC1)[O-].CCN(CC)CC>>FC=1C(=NC=CC1)C#N | [O-][n+:4]1[cH:3][c:8]([F:9])[cH:7][cH:6][cH:5]1>>[N:1]#[C:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[F:9] | [O-][n+]1cccc(F)c1 | N#Cc1ncccc1F | null | null | CC#N.C(Cl)Cl | Miscellaneous | OtherReaction | c0c80df06675fdbdd79462aedc4dec8e941957e4eee3edebb6a9bcbeed226fe8 | 11eb82ea929cff4d1755ea39be3c9f0c09f93aea3fc48e5d62bd3dbda502eb7c | c1ccncc1 | [F;D1;H0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[n+;H0;D3:6](-[O-]):[cH;D2;+0:7]:1>>[F;D1;H0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[n;H0;D2;+0:6]:[c;H0;D3;+0:7]:1-[C:8]#[N;D1;H0:9] | 77.3 | [{"value": 77.0, "product": "FC=1C(=NC=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "FC=1C(=NC=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-fluoropyridine 1-oxide (1.21 g, 10.7 mmol) in CH3CN (10 mL) was added Et3N (4.4 mL, 31.6 mmol) followed by TMSCN (4.3 mL, 32.2 mmol) and the reaction was stirred at reflux for 6.5 hours. The mixture was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer w... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | CC#N.C(Cl)Cl | null | null | [O-][n+]1cccc(F)c1>CC#N.C(Cl)Cl>N#Cc1ncccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccee693cbf364a5ab48c75de7b438da3 | CCOc1cccnc1C(=O)O>>CCOc1cccnc1CO | C(C)OC=1C(=NC=CC1)C(=O)O.B.C1CCOC1>>C(C)OC=1C(=NC=CC1)CO | O=[C:10]([c:9]1[c:4]([O:3][CH2:2][CH3:1])[cH:5][cH:6][cH:7][n:8]1)[OH:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH2:10][OH:11] | CCOc1cccnc1C(=O)O | CCOc1cccnc1CO | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 124.6 | [{"value": 124.6, "product": "C(C)OC=1C(=NC=CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 3-ethoxypicolinic acid (0.202 g, 1.21 mmol) in dry THF (1 mL) was added BH3.THF (1.0 M in THF, 5.0 mL, 5.0 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The mixture was then quenched with methanol (20 mL), stirred at reflux for 4 hours and concentrated under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 2.5 | CCOc1cccnc1C(=O)O>C1CCOC1>CCOc1cccnc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-493790f571d847c0aaa1ed77fe3bc67c | Cc1ncccc1Br>>O=Cc1ncccc1Br | BrC=1C(=NC=CC1)C.[Se](=O)=O>>BrC=1C(=NC=CC1)C=O | [CH3:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Br:9]>>[O:1]=[CH:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Br:9] | Cc1ncccc1Br | O=Cc1ncccc1Br | null | null | O1CCOCC1 | Oxidation | OtherReaction | f82793a7e1ee6561b7709c4a971f65b04fd777875bf3438ec6d6e1a0cf7ef2e4 | 4f1055c03ef3f74f7ecbf5450c9237f5c3ae016780958675e61943dfb81da1e6 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[O;D1;H0:6]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 29 | [{"value": 29.0, "product": "BrC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "BrC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-bromo-2-picoline (prepared as described by Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871–880) (249 mg, 1.45 mmol) in dioxane (2 mL) was added selenium(IV) oxide (212 mg, 1.91 mmol) and the mixture stirred at reflux overnight... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1ccncc1 | Other | O1CCOCC1 | null | null | Cc1ncccc1Br>O1CCOCC1>O=Cc1ncccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-993a754e79ee4cedb82df3462a06dec6 | CB(O)O.N#Cc1cccnc1Cl>>Cc1ncccc1C#N | C(#N)C=1C(=NC=CC1)Cl.CB(O)O.C(=O)([O-])[O-].[K+].[K+]>>C(#N)C=1C(=NC=CC1)C | OB(O)[CH3:1].Cl[c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8]#[N:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8]#[N:9] | CB(O)O.N#Cc1cccnc1Cl | Cc1ncccc1C#N | 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 | O1CCOCC1.C(Cl)Cl | C-C Coupling | Suzuki coupling with boronic acids | e6427a06cf763f629ade010ec8edb6d572dcafeb9186c64e3948e154bc0e8e0d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].O-B(-O)-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7] | 46.1 | [{"value": 46.0, "product": "C(#N)C=1C(=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "C(#N)C=1C(=NC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-cyano-2-chloro-pyridine (422 mg, 3.05 mmol), methylboronic acid (209 mg, 3.49 mmol) and K2CO3 (1.22 g, 8.83 mmol) in degassed dioxane (5 mL) under argon was added Pd(PPh3)4 (222 mg, 0.19 mmol) and the mixture stirred at reflux over the weekend. The reaction was cooled to room temperature, diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | 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.O1CCOCC1.C(Cl)Cl | null | null | CB(O)O.N#Cc1cccnc1Cl>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.O1CCOCC1.C(Cl)Cl>Cc1ncccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c91b9e7b100246bd91748a1ae525db65 | Cc1ncccc1C#N>>N#Cc1cccnc1C=O | C(#N)C=1C(=NC=CC1)C.O.[Se](=O)=O>>C(#N)C=1C(=NC=CC1)C=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH:9]=[O:10] | Cc1ncccc1C#N | N#Cc1cccnc1C=O | null | null | O1CCOCC1 | Oxidation | OtherReaction | f82793a7e1ee6561b7709c4a971f65b04fd777875bf3438ec6d6e1a0cf7ef2e4 | 4f1055c03ef3f74f7ecbf5450c9237f5c3ae016780958675e61943dfb81da1e6 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[O;D1;H0:6]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 10 | [{"value": 10.0, "product": "C(#N)C=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.7, "product": "C(#N)C=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1ccncc1 | Other | O1CCOCC1 | null | null | Cc1ncccc1C#N>O1CCOCC1>N#Cc1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1781f000e508492c963f107d63b76858 | Cc1ncccc1NS(C)(=O)=O>>CS(=O)(=O)Nc1cccnc1C=O | CS(=O)(=O)NC=1C(=NC=CC1)C.O.[Se](=O)=O>>CS(=O)(=O)NC=1C(=NC=CC1)C=O | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[CH3:12]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[CH:12]=[O:13] | Cc1ncccc1NS(C)(=O)=O | CS(=O)(=O)Nc1cccnc1C=O | null | null | O1CCOCC1 | Oxidation | OtherReaction | f82793a7e1ee6561b7709c4a971f65b04fd777875bf3438ec6d6e1a0cf7ef2e4 | 4f1055c03ef3f74f7ecbf5450c9237f5c3ae016780958675e61943dfb81da1e6 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[O;D1;H0:6]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 83.6 | [{"value": 83.0, "product": "CS(=O)(=O)NC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "CS(=O)(=O)NC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-methylsulfonamido-2-methylpyridine (310 mg, 1.66 mmol) in dioxane (8 mL) was added water (0.8 mL) and selenium(IV) oxide (241 mg, 2.17 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (H... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1ccncc1 | Other | O1CCOCC1 | null | null | Cc1ncccc1NS(C)(=O)=O>O1CCOCC1>CS(=O)(=O)Nc1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b54507cbfb14b84b0322c01958b4f77 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1>>c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 | C(C1=CC=CC=C1)=O.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.[BH4-].[Na+]>>C(C1=CC=CC=C1)NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2 | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][N:13]([CH2:14][c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH:24]2[CH2:25][CH2:26][CH2:27][c:28]3[cH:29][cH:30][cH:31][n:32][c:33]32)[cH:34][cH:35]1.O=[CH:5][c:4]1[cH:3][cH:2][cH:1][cH:37][cH:36]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[c... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C:6]-[c:7]):[c:4] | 26 | [{"value": 26.0, "product": "C(C1=CC=CC=C1)NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.9, "product": "C(C1=CC=CC=C1)NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzaldehyde (0.5 mL, 4.92 mmol) was condensed with N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (170 mg, 0.428 mmol) in dry MeOH (3 mL) for 17 h at room temperature and the resultant imine was reduced with sodium borohydride (329 mg, 8.70 mmol) for 1 h (see General Proc... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | CO | null | null | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ccccc1>CO>c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3693043f7ce14a37a932a4eb4f180ad8 | CN(C)C=O.Clc1cccnc1>>O=Cc1ncccc1Cl | CN(C)C=O.CN(C)CCN(C)C.C(CCC)[Li].ClC=1C=NC=CC1>>ClC=1C(=NC=CC1)C=O | CN(C)[CH:2]=[O:1].[cH:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Cl:9]>>[O:1]=[CH:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Cl:9] | CN(C)C=O.Clc1cccnc1 | O=Cc1ncccc1Cl | null | null | CCOCC | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[#7;a:7]:[c:8]>>[Cl;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[#7;a:7]:[c:8] | 27 | [{"value": 27.0, "product": "ClC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.0, "product": "ClC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of TMEDA (660 uL, 2.58 mmol) in ether (20 mL) at −78° C. was added a solution of n-butyl lithium in ether (2.5 M, 1.76 mL, 4.40 mmol). After 30 minutes at −78° C., 3-chloropyridine (419 uL, 4.40 mmol) was added. After another 2 hours at −78° C., DMF (375 uL, 4.84 mmol) was added. After a further 2 hours a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CCOCC | null | 0.5 | CN(C)C=O.Clc1cccnc1>CCOCC>O=Cc1ncccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6b46ff1aa0f44429113e55ed89eb2bc | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ncc(C(F)(F)F)cc1Cl>>FC(F)(F)c1cnc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c(Cl)c1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.ClC=1C(=NC=C(C1)C(F)(F)F)C=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>ClC=1C(=NC=C(C1)C(F)(F)F)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2 | [NH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]([CH2:18][c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[nH:27]2)[CH:28]2[CH2:29][CH2:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][n:36][c:37]32)[cH:38][cH:39]1.O=[CH:9][c:8]1[n:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:42][c:40]1[Cl:41]>>[F:1][C:2]([F:3])([... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ncc(C(F)(F)F)cc1Cl | FC(F)(F)c1cnc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c(Cl)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 26 | [{"value": 26.0, "product": "ClC=1C(=NC=C(C1)C(F)(F)F)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.4, "product": "ClC=1C(=NC=C(C1)C(F)(F)F)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 16 | HOUR | Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (133 mg, 0.34 mmol) and 3-chloro-5-(trifluoromethyl)-pyridine-2-carboxaldehyde (66 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (93 mg, 0.44 mmol) and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C(Cl)Cl | null | 16 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1ncc(C(F)(F)F)cc1Cl>C(Cl)Cl>FC(F)(F)c1cnc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a94a42113b9747d29ec261a62954dea4 | CN(C)C=O.Fc1cccnc1>>O=Cc1ccncc1F | CN(C)C=O.CN(C)CCN(C)C.C(CCC)[Li].FC=1C=NC=CC1>>FC=1C=NC=CC1C=O | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[F:9]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[F:9] | CN(C)C=O.Fc1cccnc1 | O=Cc1ccncc1F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[F;D1;H0:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[F;D1;H0:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 37.3 | [{"value": 37.0, "product": "FC=1C=NC=CC1C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.3, "product": "FC=1C=NC=CC1C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of TMEDA (389 uL, 2.58 mmol) in THF (10 mL) at −78° C. was added a solution of n-butyl lithium in THF (2.5M, 1.03 mL, 2.58 mmol). After 30 minutes at −78° C., 3-fluoropyridine (221 uL, 2.57 mmol) was added. After another 2 hours at −78° C., DMF (219 uL, 2.83 mmol) was added. After a further 2 hours at −78... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C1CCOC1 | null | 0.5 | CN(C)C=O.Fc1cccnc1>C1CCOC1>O=Cc1ccncc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-75f811fe78684dafa9ebd08ab40247d8 | Brc1cccnc1.CN(C)C=O>>O=Cc1ccncc1Br | CN(C)C=O.CN(C)CCN(C)C.[Li+].CC(C)[N-]C(C)C.BrC=1C=NC=CC1>>BrC=1C=NC=CC1C=O | [cH:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[Br:9].CN(C)[CH:2]=[O:1]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[Br:9] | Brc1cccnc1.CN(C)C=O | O=Cc1ccncc1Br | null | null | CCOCC | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Br;D1;H0:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Br;D1;H0:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 51 | [{"value": 51.0, "product": "BrC=1C=NC=CC1C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.8, "product": "BrC=1C=NC=CC1C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | To a solution of TMEDA (1.91 mL, 12.7 mmol) and LDA (12.7 mmol) in ether (50 mL) at −78° C. was added 3-bromo-pyridine (1.22 mL, 12.7 mmol). After 60 minutes at −78° C., DMF (1.08 mL, 13.9 mmol) was added, and the mixture allowed to warm to room temperature. After 1 hour at room temperature the reaction was quenched wi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CCOCC | null | 1 | Brc1cccnc1.CN(C)C=O>CCOCC>O=Cc1ccncc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae7961b104604450beaed78f4ad54709 | CN(C)C=O.Fc1ccccn1>>O=Cc1cccnc1F | [NH4+].[Cl-].FC1=NC=CC=C1.C(C)(C)[N-]C(C)C.[Li+].CN(C)C=O>>FC1=NC=CC=C1C=O | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[F:9]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[F:9] | CN(C)C=O.Fc1ccccn1 | O=Cc1cccnc1F | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[F;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[F;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 15 | [{"value": 15.0, "product": "FC1=NC=CC=C1C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.7, "product": "FC1=NC=CC=C1C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 4 | HOUR | A solution of 2-fluoropyridine (306 mg, 3.15 mmol) in THF (1 mL) was added to a solution of lithium diisopropylamide in THF (0.20 M, 17 mL, 3.4 mmol) at −78° C. The solution was stirred at −78° C. for 4 h, then DMF (0.73 mL, 9.4 mmol) was added dropwise and stirring was continued at −78° C. for 2.5 h. Saturated NH4Cl(a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C1CCOC1.CCOC(=O)C | -78 | 4 | CN(C)C=O.Fc1ccccn1>C1CCOC1.CCOC(=O)C>O=Cc1cccnc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ca8621f578e448293bc81423498fb78 | CSC1(C(=O)O)C=CC=CN1>>CSc1ncccc1CO | CSC1(NC=CC=C1)C(=O)O.B.C1CCOC1>>CSC1=NC=CC=C1CO | O=[C:9]([C:3]1([S:2][CH3:1])[NH:4][CH:5]=[CH:6][CH:7]=[CH:8]1)[OH:10]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][OH:10] | CSC1(C(=O)O)C=CC=CN1 | CSc1ncccc1CO | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | be1351ce06d13bc4947729fb7a14df7c0d3a7aea8a8bd2d652b67b5af807b4b8 | 583b5355f2b8ff734e4fcb4767efe54ebebfd9e660d2628902aaef957e1929df | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C;H0;D4;+0:3]1(-[#16:4]-[C;D1;H3:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[NH;D2;+0:10]-1>>[C;D1;H3:5]-[#16:4]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[cH;D2;+0:8]:[cH;D2;+0:7]:[c;H0;D3;+0:6]:1-[CH2;D2;+0:1]-[O;D1;H1:2] | 30.3 | [{"value": 30.0, "product": "CSC1=NC=CC=C1CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.3, "product": "CSC1=NC=CC=C1CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To 2-(methylthio)picolinic acid (1.00 g, 5.91 mmol) was added BH3.THF (1.0 M/THF, 15 mL, 15 mmol) and the mixture heated at 80° C. for 24 h. Methanol (30 mL) was carefully added at room temperature and the solution was concentrated in vacuo. Purification of the crude material on silica gel (20% EtOAc/hexanes) gave the ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid.Monosulfide.Conjugated diene | Primary alcohol.Monosulfide | C1=CCNC=C1 | c1ccncc1 | c1ccncc1 | Other | CO | 80 | null | CSC1(C(=O)O)C=CC=CN1>CO>CSc1ncccc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1245e15db51147829497f5c1ab0ba500 | CO.O=C(O)c1cnccn1>>COC(=O)c1cnccn1 | N1=C(C=NC=C1)C(=O)O.OS(=O)(=O)O.CO>>COC(=O)C1=NC=CN=C1 | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1 | CO.O=C(O)c1cnccn1 | COC(=O)c1cnccn1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1cnccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | 59 | [{"value": 59.0, "product": "COC(=O)C1=NC=CN=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-pyrazinecarboxylic acid (2.00 g, 16.1 mmol) and H2SO4 (catalytic) in MeOH (50 mL) was heated at reflux for 45 minutes, then concentrated in vacuo. The residue was partitioned between EtOAc (40 mL) and saturated NaHCO3(aq) (20 mL). The organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1cnccn1 | HO- | null | null | null | CO.O=C(O)c1cnccn1>>COC(=O)c1cnccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0911da83313443a48e5e67c1ea659593 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1cc[nH]n1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | N1N=C(C=C1)C=O.NCC1=CC=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1.[BH4-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=NNC=C2 | [cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:25][cH:26]1)[CH2:27][c:28]1[n:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[nH:36]1.O=[CH:19][c:20]1[cH:21][cH:22][nH:23][n:24]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9]... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1cc[nH]n1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1 | 60 | [{"value": 60.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=NNC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=NNC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: A solution of pyrazol-3-carboxaldehyde (26.6 mg, 0.28 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (110 mg, 0.28 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (21.2 mg, 0.56 mmol) was added and the resultant ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1cn[nH]c1.c1ccc2[nH]cnc2c1 | Other | CO | null | null | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1cc[nH]n1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ab4549260ae492c980f2cd8534f6614 | Cc1nc(C=O)c[nH]1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>Cc1nc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c[nH]1 | CC=1NC=C(N1)C=O.NCC1=CC=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1.[BH4-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N=C(NC2)C | O=[CH:5][c:4]1[n:3][c:2]([CH3:1])[nH:37][cH:36]1.[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][N:13]([CH2:14][c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH:24]2[CH2:25][CH2:26][CH2:27][c:28]3[cH:29][cH:30][cH:31][n:32][c:33]32)[cH:34][cH:35]1>>[CH3:1][c:2]1[n:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[c... | Cc1nc(C=O)c[nH]1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Cc1nc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2c[nH]cn2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 53 | [{"value": 53.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N=C(NC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N=C(NC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: A solution of 2-methyl-1H-imidazole-4-carbaldehyde (27.7 mg, 0.25 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (18.9 mg, 0.50 mmol) was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1c[nH]cn1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | CO | null | null | Cc1nc(C=O)c[nH]1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>Cc1nc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)c[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a059695fa0041618a8dc164a748bfc6 | Cn1ccnc1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>Cn1ccnc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CN1C(=NC=C1)C=O.NCC1=CC=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1.[BH4-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N(C=CN2)C | O=[CH:7][c:6]1[n:2]([CH3:1])[cH:3][cH:4][n:5]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]([CH2:16][c:17]2[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[nH:25]2)[CH:26]2[CH2:27][CH2:28][CH2:29][c:30]3[cH:31][cH:32][cH:33][n:34][c:35]32)[cH:36][cH:37]1>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1[CH2:7][NH:8][CH... | Cn1ccnc1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Cn1ccnc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2ncc[nH]2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:7]-[#7;a:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[NH;D2;+0:8]-[C:9]-[c:10] | 67.5 | [{"value": 67.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N(C=CN2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC=2N(C=CN2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: A solution of 1-methyl-2-imidazole carboxaldehyde (27.5 mg, 0.25 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (37.5, 0.75 mmol) was added and the re... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ncc[nH]1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | CO | null | null | Cn1ccnc1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>Cn1ccnc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ca2b5d6aeca4a05a709d82bcf7c8951 | O=C(O)c1cccnc1O>>OCc1cccnc1O | OC1=C(C(=O)O)C=CC=N1.B.C1CCOC1.CO>>OCC=1C(=NC=CC1)O | O=[C:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[OH:9]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[OH:9] | O=C(O)c1cccnc1O | OCc1cccnc1O | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5](-[O;D1;H1:6]):[#7;a:7]:[c:8]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5](-[O;D1;H1:6]):[#7;a:7]:[c:8] | 29 | [{"value": 29.0, "product": "OCC=1C(=NC=CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.6, "product": "OCC=1C(=NC=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of 2-Hydroxynicotinic acid (1.01 g, 7.26 mmol) in THF (2 mL) was added BH3.THF (1.0 m in THF, 18 mL, 18 mmol) and the mixture was heated to 80° C. for 18 hours. MeOH (2 mL) was added and the mixture was heated to 80° C. for an additional 2 hours before being cooled to room temperature and concentrated u... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | 80 | null | O=C(O)c1cccnc1O>C1CCOC1>OCc1cccnc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e8c842ed3224a8bbc5a5afdb8fca125 | Cc1ncccc1C(=O)O>>Cc1ncccc1CO | CC1=C(C(=O)O)C=CC=N1.B.C1CCOC1>>CC1=NC=CC=C1CO | O=[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)[OH:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:9] | Cc1ncccc1C(=O)O | Cc1ncccc1CO | null | null | CO | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:4] | 80 | [{"value": 80.0, "product": "CC1=NC=CC=C1CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "CC1=NC=CC=C1CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To 2-Methylnicotinic acid (1.00 g, 7.29 mmol) was added BH3.THF (1.0 m in THF, 18 mL, 18 mmol) and the resultant mixture was heated to 80° C. for 20 hours. MeOH (6 mL) was added and the mixture was heated to 80° C. for an additional 2 hours before being cooled to room temperature and concentrated under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | CO | 80 | null | Cc1ncccc1C(=O)O>CO>Cc1ncccc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30602e1a95384396af94ffad27829b43 | Cc1ncccc1C=O>>Cc1ncccc1CO | CC1=NC=CC=C1C=O.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>CC1=NC=CC=C1CO | [CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:9] | Cc1ncccc1C=O | Cc1ncccc1CO | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccncc1 | [C;D1;H3:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]>>[C;D1;H3:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8] | 151.9 | [{"value": 37.0, "product": "CC1=NC=CC=C1CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 151.9, "product": "CC1=NC=CC=C1CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Using General Procedure B: To a stirred solution of 2-methyl-pyridine-3-carbaldehyde (75 mg, 0.62 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (246 mg, 0.62 mmol) and AcOH (40 uL, 0.62 mmol) in THF (6.2 mL) was added NaBH(OAc)3 (394 mg, 1.86 mmol) and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccncc1 | null | C1CCOC1 | null | 8 | Cc1ncccc1C=O>C1CCOC1>Cc1ncccc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f56ce14538b4073988d127770bef125 | COc1ccccc1C(C)=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>COc1ccccc1C(C)NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | COC1=C(C=CC=C1)C(C)=O.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC(C)C2=C(C=CC=C2)OC | O=[C:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[CH3:10].[NH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][N:18]([CH2:19][c:20]2[n:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[nH:28]2)[CH:29]2[CH2:30][CH2:31][CH2:32][c:33]3[cH:34][cH:35][cH:36][n:37][c:38]32)[cH:39][cH:40]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | COc1ccccc1C(C)=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | COc1ccccc1C(C)NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 31.2 | [{"value": 27.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC(C)C2=C(C=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.2, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC(C)C2=C(C=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Using General Procedure B: To a stirred solution of 1-(2-methoxy-phenyl)-ethanone (69 uL, 0.50 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) and AcOH (0.10 mL, 1.4 mmol) in THF (5 mL) was added NaBH(OAc)3 and the mixture was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C1CCOC1 | null | 48 | COc1ccccc1C(C)=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1>COc1ccccc1C(C)NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a5f860b3be242f1a3d8f0aaa4eee0e7 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1c[nH]c2ccccc12>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2c[nH]c3ccccc23)cc1)Cc1nc2ccccc2[nH]1 | N1C=C(C2=CC=CC=C12)C=O.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.[BH4-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=CNC1=CC=CC=C21 | [cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:29][cH:30]1)[CH2:31][c:32]1[n:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]2[nH:40]1.O=[CH:19][c:20]1[cH:21][nH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12>>[cH:1]1[cH:2][n:3][c:4]2[c:5](... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1c[nH]c2ccccc12 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2c[nH]c3ccccc23)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2c[nH]c3ccccc23)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | Using General Procedure B: 1H-Indole-3-carbaldehyde (73 mg, 0.50 mmol) and N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) were stirred at 40° C. in MeOH (5 mL) for 4 hours. NaBH4 (38 mg, 1.0 mmol) was added and the resultant mixture stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1 | Other | CO | null | null | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.O=Cc1c[nH]c2ccccc12>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2c[nH]c3ccccc23)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a1d7d25ee944766945434c34744294c | O=C(O)c1cc2ccccc2[nH]1>>OCc1cc2ccccc2[nH]1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].N1C(=CC2=CC=CC=C12)C(=O)O.CO>>N1C(=CC2=CC=CC=C12)CO | O=[C:2]([OH:1])[c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[nH:11]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[nH:11]1 | O=C(O)c1cc2ccccc2[nH]1 | OCc1cc2ccccc2[nH]1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc2[nH]ccc2c1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 68 | [{"value": 68.0, "product": "N1C(=CC2=CC=CC=C12)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "N1C(=CC2=CC=CC=C12)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | LiAlH4 (1.0 m in THF, 5.0 mL, 5.0 mmol) was slowly added to a solution of indole-2-carboxylic acid (403 mg, 2.5 mmol) in dry THF (18 mL) at 0° C. The resultant yellow solution was warmed to room temperature and stirred for 18 hours. MeOH (0.5 mL) was added and the solution concentrated under reduced pressure (3×). The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C1CCOC1 | null | 18 | O=C(O)c1cc2ccccc2[nH]1>C1CCOC1>OCc1cc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f60b003fd2d94e8d9b9542ea7a90f1dd | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | C(C)(C)(C)OC(=O)N1[C@@H](C=O)CCC1.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2NCCC2 | CC(C)(C)OC(=O)[N:24]1[C@@H:20]([CH:19]=O)[CH2:21][CH2:22][CH2:23]1.[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:25][cH:26]1)[CH2:27][c:28]1[n:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[nH:36]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1... | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | c6034fb5b09e65785045519387e9a947b72a28ded0337fe3fed71e12ff33c5b3 | b1e84babab4e88dfc6c1d4e2061c6bec5561b93ae8da5c12f0ba228aa308d90e | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C@@H;D3;+0:5]-1-[CH;D2;+0:6]=O.[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[CH2;D2;+0:6]-[CH;D3;+0:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 40 | MINUTE | Using General Procedure B: To a stirred solution of N-(tert-butoxycarbonyl)-D-prolinal (0.121 g, 0.61 mmol) in dry CH2Cl2 (9 mL) was added N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.236 g, 0.59 mmol) at room temperature and the mixture stirred for 40 min. To the res... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Primary amine.Boc | Secondary amine.Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1cnc2c(c1)CCCC2.c1ccccc1.C1CCNC1.c1ccc2[nH]cnc2c1 | HO- | C(Cl)Cl | null | 0.666667 | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C(Cl)Cl>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4917a90c527846658d1f6ac607d77074 | CC(C)(C)OC(=O)N1CCC[C@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | [BH4-].[Na+].N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)(C)OC(=O)N1[C@H](C=O)CCC1>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2NCCC2 | CC(C)(C)OC(=O)[N:24]1[C@H:20]([CH:19]=O)[CH2:21][CH2:22][CH2:23]1.[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:25][cH:26]1)[CH2:27][c:28]1[n:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[nH:36]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)... | CC(C)(C)OC(=O)N1CCC[C@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c6034fb5b09e65785045519387e9a947b72a28ded0337fe3fed71e12ff33c5b3 | b1e84babab4e88dfc6c1d4e2061c6bec5561b93ae8da5c12f0ba228aa308d90e | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C@H;D3;+0:5]-1-[CH;D2;+0:6]=O.[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[CH2;D2;+0:6]-[CH;D3;+0:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 54.2 | [{"value": 45.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2NCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.2, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2NCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.231 g, 0.58 mmol) in dry MeOH (5.5 mL) was added N-(tert-butoxycarbonyl)-L-prolinal (0.116 g, 0.58 mmol) and the mixture was stirred at room temperature for 2.5 h. The reaction mixture was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Primary amine.Boc | Secondary amine.Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1cnc2c(c1)CCCC2.c1ccccc1.C1CCNC1.c1ccc2[nH]cnc2c1 | HO- | CO | null | 2.5 | CC(C)(C)OC(=O)N1CCC[C@H]1C=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCC2CCCN2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ff3ba42618041fc8e5a90fd6e987d41 | C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | C[Si](CCOCN1C(=NC2=C1C=CC=C2)C=O)(C)C.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.[BH4-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=NC1=C(N2)C=CC=C1 | C[Si](C)(C)CCOC[n:28]1[c:20]([CH:19]=O)[n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][NH2:18])[cH:29][cH:30]1)[CH2:31][c:32]1[n:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]2[nH:40]1>>[cH:1]1[cH:2][n... | C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 8427c2bc9a8f66f64f86465cc422d9f2272cb77b1f88abacc20222ccce6be697 | 306b65dbdd395f384c126164bf864d4a5ccf71d492d167903c3221fff12c20d7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[CH;D2;+0:3]=O):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[c:11]-[C:10]-[NH;D2;+0:9]-[CH2;D2;+0:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:1]:1 | 47 | [{"value": 47.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCC2=NC1=C(N2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a stirred solution of 1-(2-trimethylsilylethoxymethyl)-2-formyl-benzimidazole (prepared as described by Bridger et al. U.S. patent application Ser. No. 09/535,314) (0.150 g, 0.54 mmol) in dry MeOH (2.5 mL) was added a dry MeOH (2.5 mL) solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine.Silyl protective group | Secondary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | HO- | CO | null | 1.5 | C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNCc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63bb147b6d0d4522afb48bb9b822d120 | CN(C)C=O.CSc1cccnc1>>CSc1cccnc1C=O | [Li]CCCC.CN(C)C=O.C([O-])(O)=O.[Na+].CSC=1C=NC=CC1.CN(C)CCN(C)C>>CSC=1C(=NC=CC1)C=O | CN(C)[CH:9]=[O:10].[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH:9]=[O:10] | CN(C)C=O.CSc1cccnc1 | CSc1cccnc1C=O | null | null | C(C)OCC | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#16:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[#7;a:7]:[c:8]>>[#16:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[#7;a:7]:[c:8] | 19.4 | [{"value": 19.0, "product": "CSC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.4, "product": "CSC=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | To a cold (−78° C.) stirred solution of TMEDA (0.60 mL, 4.0 mmol) in dry diethyl ether (15 mL) was added a 2.5 M solution of nBuLi in hexanes (1.6 mL, 4.0 mmol). The resulting mixture was stirred 30 min at −78° C., at which point a solution of 3-(methylthio)pyridine (prepared as described by Trecourt, F.; Breton, G.; B... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C(C)OCC | -78 | 2 | CN(C)C=O.CSc1cccnc1>C(C)OCC>CSc1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f57dfddb92f34d988cc9313ce5f4d5bb | CSc1cccnc1C=O>>CS(=O)c1cccnc1C=O | CSC=1C(=NC=CC1)C=O.OOS(=O)[O-].[K+]>>CS(=O)C=1C(=NC=CC1)C=O | [CH3:1][S:2][c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH:10]=[O:11]>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH:10]=[O:11] | CSc1cccnc1C=O | CS(=O)c1cccnc1C=O | null | null | CO.O.C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccncc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C:6]=[O;D1;H0:7]):[#7;a:8]:[c:9]>>[C;D1;H3:1]-[S;H0;D3;+0:2](=[O;D1;H0:10])-[c:3](:[c:4]):[c:5](-[C:6]=[O;D1;H0:7]):[#7;a:8]:[c:9] | 23 | [{"value": 23.0, "product": "CS(=O)C=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.6, "product": "CS(=O)C=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a cold (0° C.), stirred solution of 3-methylsulfanyl-pyridine-2-carbaldehyde (prepared as described for AMD9574) (280 mg, 1.83 mmol) in a mixture of MeOH (20 mL) and water (2 mL) was added solid oxone (2.25 g, 3.66 mmol) and the resulting heterogeneous mixture was stirred for 5 h. At this point, the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccncc1 | null | CO.O.C(Cl)Cl | null | 5 | CSc1cccnc1C=O>CO.O.C(Cl)Cl>CS(=O)c1cccnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9059553ff0014d51a2fe1da9bed22a25 | CC(NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)c1ccccc1.O=Cc1ccccn1>>CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1 | N1=C(C=CC=C1)C=O.N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC(=CC=C2)CNC(C)C2=CC=CC=C2.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC(=CC=C2)CN(CC2=NC=CC=C2)C(C)C2=CC=CC=C2 | [CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[NH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]([CH2:18][c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[nH:27]2)[CH:28]2[CH2:29][CH2:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][n:36][c:37]32)[cH:38]1.O=[CH:39][c:40]1[cH:41][cH:42][cH:43][cH:44][n:4... | CC(NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)c1ccccc1.O=Cc1ccccn1 | CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN(Cc2cccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)c2)Cc2ccccn2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7](-[c:8])-[NH;D2;+0:9]-[C:10]-[c:11]>>[C;D1;H3:6]-[C:7](-[c:8])-[N;H0;D3;+0:9](-[C:10]-[c:11])-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 50 | [{"value": 50.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC(=CC=C2)CN(CC2=NC=CC=C2)C(C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using general procedure B: Reaction of Pyridine-2-carbaldehyde (22 mg, 0.20 mmol, (1H-Benzimidazol-2-ylmethyl)-{3-[(1-phenyl-ethylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (101 mg, 0.20 mmol) and sodium triacetoxyborohydride (58 mg, 0.26 mmol) in CH2Cl2 (2 mL) at room temperature under N2 for 20 h... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2.c1ccncc1 | Other | C(Cl)Cl | null | null | CC(NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)c1ccccc1.O=Cc1ccccn1>C(Cl)Cl>CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cf759bc757143e7bba62c72bc8bb078 | O=Cc1ccc(C=O)cc1>>O=Cc1ccc(CO)cc1 | C1=CC(=CC=C1C=O)C=O.NCC1=NC=CC=C1.[H][H]>>OCC1=CC=C(C=O)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][cH:10]1 | O=Cc1ccc(C=O)cc1 | O=Cc1ccc(CO)cc1 | null | [Pd] | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 78 | [{"value": 78.0, "product": "OCC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "OCC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Terephthaldicarboxaldehyde (30.02 g, 224 mmol), methanol (200 mL), palladium on activated carbon, (10%, 3.02 g) and 2-(aminomethyl)pyridine (2.3 mL, 22 mol, 0.01 mol equiv) were combined in a hydrogenation vessel and the reaction mixture was shaken on a Parr hydrogenator for 2.5 hours at 40 psi of hydrogen. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | [Pd].CO | null | null | O=Cc1ccc(C=O)cc1>[Pd].CO>O=Cc1ccc(CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47eedb33bf164f6fbd23e37cca184a59 | Nc1cc[nH]n1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.NC1=NNC=C1.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC2=NNC=C2 | [NH2:18][c:19]1[cH:20][cH:21][nH:22][n:23]1.O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:26][c:27]2[n:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[nH:35]2)[cH:25][cH:24]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N... | Nc1cc[nH]n1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | null | null | C1CCOC1.C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[#7;a:8]:[c:9]:[c:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6]1:[#7;a:7]:[#7;a:8]:[c:9]:[c:10]:1):[c:4] | 23 | [{"value": 23.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC2=NNC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.4, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC2=NNC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: To a stirred solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (199 mg, 0.50 mmol) and 3-aminopyrazole (60 mg, 0.72 mmol) in THF (5 mL) and acetic acid (0.2 mL) was added NaBH(OAc)3 (166 mg, 0.78 mmol) and the resultant mixture stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1cn[nH]c1.c1ccc2[nH]cnc2c1 | Other | C1CCOC1.C(C)(=O)O | null | null | Nc1cc[nH]n1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1.C(C)(=O)O>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3399affb5e9484d901d531f62b141b6 | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.c1ccc2c(c1)CCNC2>>c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2 | C1NCCC2=CC=CC=C12.N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CC1=CC=CC=C1CC2 | O=[CH:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][N:16]([CH2:17][c:18]2[n:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[nH:26]2)[CH:27]2[CH2:28][CH2:29][CH2:30][c:31]3[cH:32][cH:33][cH:34][n:35][c:36]32)[cH:37][cH:38]1.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][NH:9][CH2:39]2>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:... | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | reductive amination | 69051b00f3392c174e95a93950f1d0a74b8591fff7595d217f56c39a2f3ebd43 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[c:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[c:9] | 78.4 | [{"value": 78.4, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CC1=CC=CC=C1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Using General Procedure B: To a stirred solution of 1,2,3,4-tetrahydroisoquinoline (49 mg, 0.37 mmol), 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (140 mg, 0.34 mmol), and AcOH 0.020 mL, 0.35 mmol) in THF (3.5 mL) was added NaBH(OAc)3 (94 mg, 0.44 mmol) and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2.c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C1CCOC1 | null | 2 | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.c1ccc2c(c1)CCNC2>C1CCOC1>c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31bd20a9662e4534960e36dc214e3c85 | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>O=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)[C@@H]1CCCN1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)(C)OC(=O)N1[C@H](C(=O)O)CCC1.C(C)(C)N(C(C)C)CC.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(CNC(=O)[C@H]1NCCC1)C=C2 | CC(C)(C)OC(=O)[N:37]1[C@H:33]([C:2](O)=[O:1])[CH2:34][CH2:35][CH2:36]1.[NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]2)[CH:21]2[CH2:22][CH2:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][n:29][c:30]32)[cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[c... | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | O=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)[C@@H]1CCCN1 | null | null | C([O-])(O)=O.[Na+].C(Cl)Cl | Acylation | OtherReaction | 8899da95932e3324f1403e459ddb4b49454b709b00c364f61cbcfd02ca1e98f0 | 9f74be20683ae20656a7135e9a9eaad2dfa782f75ac656d32f38d1324fe876ad | O=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)[C@@H]1CCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:8]-[C:9]-[c:10])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 116.9 | [{"value": 85.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(CNC(=O)[C@H]1NCCC1)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 116.9, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(CNC(=O)[C@H]1NCCC1)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (148 mg, 0.37 mmol) in dry CH2Cl2 (5 mL) was added N-(tert-butoxycarbonyl)-L-proline (88 mg, 0.41 mmol), N,N-diisopropylethylamine (0.13 mL, 0.75 mmol), 1-hydroxybenzotriazole hydrate (68 mg, 0.50 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2.C1CCNC1 | HO- | C([O-])(O)=O.[Na+].C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C([O-])(O)=O.[Na+].C(Cl)Cl>O=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)[C@@H]1CCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1bf96c7fefb149cc8ee915c4ce2cbeca | Nc1nc2ccccc2[nH]1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.NC=1NC2=C(N1)C=CC=C2.[BH3-]C#N.[Na+]>>N1C(=NC2=C1C=CC=C2)NCC2=CC=C(CN(C1CCCC=3C=CC=NC13)CC1=NC3=C(N1)C=CC=C3)C=C2 | [NH2:18][c:19]1[n:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[nH:27]1.O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:30][c:31]2[n:32][c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]3[nH:39]2)[cH:29][cH:28]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH... | Nc1nc2ccccc2[nH]1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1):[c:4] | null | [] | null | null | 20 | HOUR | Using General Procedure A: To a stirred solution of 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (140 mg, 0.34 mmol) and 2-aminobenzimidazole (45 mg, 0.0.34 mmol) in MeOH (4 mL) was added NaBH3CN (64 mg, 1.1 mmol) and the mixture was stirred at room temperature for 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | Other | CO | null | 20 | Nc1nc2ccccc2[nH]1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76360ddc2db14f1a907a8fb6ad638412 | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2ncc[nH]2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.[BH3-]C#N.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC=2NC=CN2 | O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:26][c:27]2[n:20][c:29]3[cH:30][cH:21][cH:32][cH:33][c:34]3[nH:23]2)[cH:25][cH:24]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([CH... | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2ncc[nH]2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d36e5c5d8d3ddf1af6bce2b3a6ca1095456c0de2b151e9f5785776ce75d5cc22 | 52276dc0d71015bbaf3f6ea7f27b8e68bd688a6d9cbdd0add04958750f53a97a | c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2ncc[nH]2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:[c;H0;D3;+0:14]:2:[nH;D2;+0:15]:1>>[#7:5]-[C:6]-[c;H0;D3;+0:7]1:[#7;a:16]:[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[c:17]:[cH;D2;+0:12]:[c:13]:[c;H0;D3;+0:14]:2:[#7;a:18]:1.[c:3]:[c:2](-[... | 19.4 | [{"value": 10.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC=2NC=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.4, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC=2NC=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | Using General Procedure A: To a stirred solution of 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (200 mg, 0.49 mmol) and the amine (41 mg, 0.49 mmol) from above in MeOH (5 mL) was added NaBH3CN (94.3 mg, 1.5 mmol) and the mixture was stirred at room temperature for 5 d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary amine | c1ccc2[nH]cnc2c1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1 | c1cnc2c(c1)CCCC2.c1ccccc1.c1c[nH]cn1.c1ccc2[nH]cnc2c1 | null | CO | null | 120 | O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2ncc[nH]2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a2f7a20ec2f494cadf3ca0313a915ff | Nc1ccccn1.O=Cc1ccc(CO)cc1>>OCc1ccc(CNc2ccccn2)cc1 | OCC1=CC=C(C=O)C=C1.NC1=NC=CC=C1.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1=C(C=CC=C1)NCC1=CC=C(C=C1)CO | [NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.O=[CH:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:16][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[cH:15][cH:16]1 | Nc1ccccn1.O=Cc1ccc(CO)cc1 | OCc1ccc(CNc2ccccn2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2ccccn2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:8]:[c:9] | 74 | [{"value": 74.0, "product": "N1=C(C=CC=C1)NCC1=CC=C(C=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "N1=C(C=CC=C1)NCC1=CC=C(C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using general procedure B: Reaction of 4-hydroxymethyl-benzaldehyde (1.01 g, 7.42 mmol), 2-aminopyridine (697 mg, 7.42 mmol), acetic acid (0.5 mL) and sodium triacetoxyborohydride (3.2 g, 14.8 mmol) in THF (20 mL) at room temperature under N2 for 40 min., then one hour at 50° C., followed by purification of crude mater... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1 | Other | C1CCOC1 | null | null | Nc1ccccn1.O=Cc1ccc(CO)cc1>C1CCOC1>OCc1ccc(CNc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f466dc70f6664a43a2e59685051e375f | OCc1ccc(CNc2ccccn2)cc1>>O=Cc1ccc(CNc2ccccn2)cc1 | CCN(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.N1=C(C=CC=C1)NCC1=CC=C(C=C1)CO>>N1=C(C=CC=C1)NCC1=CC=C(C=O)C=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[cH:15][cH:16]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[cH:15][cH:16]1 | OCc1ccc(CNc2ccccn2)cc1 | O=Cc1ccc(CNc2ccccn2)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(CNc2ccccn2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 31 | [{"value": 31.0, "product": "N1=C(C=CC=C1)NCC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.8, "product": "N1=C(C=CC=C1)NCC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | To a solution of oxalyl chloride (0.9 ml, 10.32 mmol) in CH2Cl2 (15 ml) at −78° C. was added a solution of DMSO (1.5 ml, 21.11 mmol) in CH2Cl2 (10 ml) and the mixture allowed to stir for 20 min. at −78° C., after which [4-(Pyridin-2-ylaminomethyl)-phenyl]-methanol (1.1 g, 5.13 mmol) in CH2Cl2 (10 ml) was added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccncc1 | null | C(Cl)Cl | -78 | 0.333333 | OCc1ccc(CNc2ccccn2)cc1>C(Cl)Cl>O=Cc1ccc(CNc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15d5d18150f24e24bfc1e48c827f0b3d | CCOC(=O)Cc1cccnc1COC(C)=O>>CCOC(=O)Cc1cccnc1CO | C(C)OC(CC=1C(=NC=CC1)COC(C)=O)=O.[OH-].[K+]>>C(C)OC(CC=1C(=NC=CC1)CO)=O | CC(=O)[O:14][CH2:13][c:12]1[c:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:8][cH:9][cH:10][n:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[CH2:13][OH:14] | CCOC(=O)Cc1cccnc1COC(C)=O | CCOC(=O)Cc1cccnc1CO | null | null | CCO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#7;a:4]>>[#7;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | 52.8 | [{"value": 52.0, "product": "C(C)OC(CC=1C(=NC=CC1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "C(C)OC(CC=1C(=NC=CC1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of ethyl-2-[2-(acetoxymethyl)-pyridin-3-yl]-acetate (prepared from 2-methylnicotinic acid as described by Y. Sato et al., Chem. Pharm. Bull.; EN. 1960, 8, 427) (2.37 g, 10 mmol) in EtOH (50 mL) was added KOH (3 g, 53 mmol) and the mixture stirred at reflux overnight. The mixture was cooled, concen... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | CCO | null | null | CCOC(=O)Cc1cccnc1COC(C)=O>CCO>CCOC(=O)Cc1cccnc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a94411701474d1b8e1c6e2c85202c12 | O=C(Cc1cccnc1CO)NCc1ccccc1>>OCc1ncccc1CCNCc1ccccc1 | C(C1=CC=CC=C1)NC(CC=1C(=NC=CC1)CO)=O.B>>C(C1=CC=CC=C1)NCCC=1C(=NC=CC1)CO | O=[C:10]([CH2:9][c:8]1[c:3]([CH2:2][OH:1])[n:4][cH:5][cH:6][cH:7]1)[NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[OH:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=C(Cc1cccnc1CO)NCc1ccccc1 | OCc1ncccc1CCNCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CNCCc2cccnc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[C:3] | 41 | [{"value": 41.0, "product": "C(C1=CC=CC=C1)NCCC=1C(=NC=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "C(C1=CC=CC=C1)NCCC=1C(=NC=CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of N-benzyl-2-[2-(hydroxymethyl)-pyridin-3-yl]-acetamide (357 mg, 1.5 mmol) in THF (2 mL) was added borane in THF (5 mL of a 1.0 M solution, 5 mmol) and the mixture heated at 50° C. for 3 h. The reaction was cooled, quenched with MeOH (5 mL) and heated at 50° C. for 1 h. The resultant mixture was cooled, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccncc1.c1ccccc1 | Other | C1CCOC1 | 50 | null | O=C(Cc1cccnc1CO)NCc1ccccc1>C1CCOC1>OCc1ncccc1CCNCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b02c5e32cf643398422b61880a7076a | CC(C)(C)OC(=O)NC1CCCCC1=O.Nc1ccccc1>>CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1 | C(C)(C)(C)OC(=O)NC1C(CCCC1)=O.NC1=CC=CC=C1.C(C)(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C1(=CC=CC=C1)N[C@H]1[C@H](CCCC1)NC(=O)OC(C)(C)C | O=[C:14]1[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[NH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CC(C)(C)OC(=O)NC1CCCCC1=O.Nc1ccccc1 | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1 | null | null | C1CCOC1.C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b3c233679044776f397868647ebe4ff6248540afeba9e0b29baba9f61657514b | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2CCCCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]-1-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[#7:7]-[C@H;D3;+0:6]1-[C:5]-[C:4]-[C:3]-[C:2]-[C@H;D3;+0:1]-1... | 9 | [{"value": 9.0, "product": "C1(=CC=CC=C1)N[C@H]1[C@H](CCCC1)NC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-[N-(t-butyloxycarbonyl)]amino-cyclohexanone (0.785 g, 3.69 mmol, aniline (0.68 mL, 7.46 mmol) and glacial acetic acid (0.22 mL) in THF (10 mL) was added NaBH(OAc)3 (1.173 g, 5.53 mmol) and the mixture was stirred at 60□ C. overnight. The reaction was cooled to room temperature, diluted with CH2Cl2 (6... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | Other | C1CCOC1.C(Cl)Cl | null | null | CC(C)(C)OC(=O)NC1CCCCC1=O.Nc1ccccc1>C1CCOC1.C(Cl)Cl>CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c09c4ea714e44078cb8dba8f34d5adb | CN(C)C=O.C[Si](C)(C)CCOCCl.c1ccc2[nH]cnc2c1>>C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21 | C[Si](CCOCCl)(C)C.N1=CNC2=C1C=CC=C2.C(C)(C)N(C(C)C)CC.CN(C)C=O>>C[Si](CCOCN1C(=NC2=C1C=CC=C2)C=O)(C)C | CN(C)[CH:11]=[O:12].Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[c:10]([CH:11]=[O:12])[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CN(C)C=O.C[Si](C)(C)CCOCCl.c1ccc2[nH]cnc2c1 | C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21 | null | null | null | C-C Coupling | OtherReaction | 7b29bb3a08174d2c5fe19932083d4ba85197db68ae217af78dd8b0428f91c991 | fe5536152bdf27dd8e7687307c6c86126d7629f7410b72b5fffa91bac6e2897c | c1ccc2[nH]cnc2c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].Cl-[CH2;D2;+0:3]-[#8:4]-[C:5].[c:6]:[c:7]1:[#7;a:8]:[cH;D2;+0:9]:[nH;D2;+0:10]:[c:11]:1:[c:12]>>[C:5]-[#8:4]-[CH2;D2;+0:3]-[n;H0;D3;+0:10]1:[c:11](:[c:12]):[c:7](:[c:6]):[#7;a:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 76 | [{"value": 76.0, "product": "C[Si](CCOCN1C(=NC2=C1C=CC=C2)C=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a stirred solution of benzimidazole (2.00 g, 16.9 mmol) in anhydrous DMF (25 mL) was added N,N-diisopropylethylamine (7.3 mL, 42.2 mmol) followed by 2-(trimethylsilyl)ethoxymethyl chloride (3.3 mL, 18.6 mmol) and the resultant solution was heated to 80□ C. for 4 hours. Purification of the crude brown oil through a p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Tertiary amide | Aldehyde.Ether | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1 | HCl | null | null | 4 | CN(C)C=O.C[Si](C)(C)CCOCCl.c1ccc2[nH]cnc2c1>>C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77c7461546cf4e08b92e4d0aa416cd1b | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1>>N[C@H]1CCCC[C@H]1Nc1ccccc1 | C1(=CC=CC=C1)N[C@H]1[C@H](CCCC1)NC(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C1(=CC=CC=C1)N[C@H]1[C@H](CCCC1)N | CC(C)(C)OC(=O)[NH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[NH2:1][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1 | N[C@H]1CCCC[C@H]1Nc1ccccc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(NC2CCCCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | 8 | HOUR | The cis-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine isomer from above (0.095 g, 0.33 mmol) was dissolved in CH2Cl2 (2 mL) and treated with trifluoroacetic acid (2 mL) and the mixture stirred overnight. The reaction was worked up to afford the title compound (0.069 g) as a pale yellow solid. 1H NMR (CDCl3) ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1ccccc1>C(Cl)Cl>N[C@H]1CCCC[C@H]1Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42e2736d1d544ffaa239652e6a28183b | CC(C)(C)OC(=O)N(Cc1ccc(CO)cc1)Cc1ncccc1O>>CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ncccc1O | C(C)(C)(C)OC(N(CC1=NC=CC=C1O)CC1=CC=C(C=C1)CO)=O>>C(C)(C)(C)OC(N(CC1=NC=CC=C1O)CC1=CC=C(C=C1)C=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][OH:15])[cH:16][cH:17]1)[CH2:18][c:19]1[n:20][cH:21][cH:22][cH:23][c:24]1[OH:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([CH:14]=[O:15])[cH:16][cH:17]1)[CH2:18][c:19]1[n:20]... | CC(C)(C)OC(=O)N(Cc1ccc(CO)cc1)Cc1ncccc1O | CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ncccc1O | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(CNCc2ccccn2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "C(C)(C)(C)OC(N(CC1=NC=CC=C1O)CC1=CC=C(C=C1)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "C(C)(C)(C)OC(N(CC1=NC=CC=C1O)CC1=CC=C(C=C1)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (4-hydroxymethyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester (0.99 g, 2.9 mmol) in CH2Cl2 (14 mL) was stirred at room temperature with a suspension of 85% MnO2 (3.0 g, 29 mmol) for 15 hours. The catalyst was removed by filtration, and the filtrate was concentrated to give orange ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccncc1 | null | O=[Mn]=O.C(Cl)Cl | null | null | CC(C)(C)OC(=O)N(Cc1ccc(CO)cc1)Cc1ncccc1O>O=[Mn]=O.C(Cl)Cl>CC(C)(C)OC(=O)N(Cc1ccc(C=O)cc1)Cc1ncccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36f2de1457284bf3b0fda06e472eab7b | C=CC(=O)Cl.CC1(O)C2CC3CC(C2)CC1C3>>C=CC(=O)OC12CC3CC(CC(C3)C1C)C2 | C(C)OCC.CC1(C2CC3CC(CC1C3)C2)O.C(C=C)(=O)Cl>>C(C=C)(=O)OC12C(C3CC(CC(C1)C3)C2)C | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][C:14]1([CH3:15])[CH:6]2[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]1[CH2:13]3)[CH2:16]2>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH:14]1[CH3:15])[CH2:16]2 | C=CC(=O)Cl.CC1(O)C2CC3CC(C2)CC1C3 | C=CC(=O)OC12CC3CC(CC(C3)C1C)C2 | null | null | null | Acylation | OtherReaction | 4fc67eb98152004e9d7b53867de7e874886350ee0147fce7b7275a71fe6d405a | cda6b3bfc0599ee5e7303a58cf8c674c7577cf9fbc7c186a45060ebd8ab26e4f | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C;D1;H3:5]-[C;H0;D4;+0:6]1(-[OH;D1;+0:7])-[C:8]2-[C:9]-[C:10]-[C:11]-[CH;D3;+0:12]-1-[C:13]-[C:14]-[C:15]-2>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;H0;D4;+0:12]12-[C:11]-[C:10]-[C:9]-[C:8](-[C:15]-[C:14]-[C:13]-1)-[CH;D3;+0:6]-2-[C;D1;H3:5] | 55 | [{"value": 55.0, "product": "C(C=C)(=O)OC12C(C3CC(CC(C1)C3)C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 200 mL of diethyl ether was put into a round-neck flask, 41.5 g of 2-methyl-2-adamantanol and 27.6 g of tetraethyl amine were added thereto and then 22.6 g of acryloyl chloride was dropped. The reactant was reacted at room temperature for about 12 hours and then filtered using diethyl ether. Subsequently, the solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary alcohol | Ester | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HCl | null | null | null | C=CC(=O)Cl.CC1(O)C2CC3CC(C2)CC1C3>>C=CC(=O)OC12CC3CC(CC(C3)C1C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a37453ac498b403e8ea58f83bd8e7af0 | O=C1CCC(=O)N1Br.c1ccc2c(c1)Cc1ccccc1-2>>Brc1cccc2c1Cc1ccccc1-2 | C1=CC=CC=2C3=CC=CC=C3CC12.BrN1C(CCC1=O)=O>>BrC1=CC=CC=2C3=CC=CC=C3CC12 | O=C1CCC(=O)N1[Br:1].[cH:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1-2>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1-2 | O=C1CCC(=O)N1Br.c1ccc2c(c1)Cc1ccccc1-2 | Brc1cccc2c1Cc1ccccc1-2 | null | null | C1(OCC(C)O1)=O | Functional Group Interconversion | Bromination | 7ed7d39e1ca7472101c1e40318423ea6ba3ed6c366f5bbf9627e33b67a7598be | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)Cc1ccccc1-2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](:[c:4])-[C:2] | 68 | [{"value": 60.0, "product": "BrC1=CC=CC=2C3=CC=CC=C3CC12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "BrC1=CC=CC=2C3=CC=CC=C3CC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 10 | HOUR | 1.2 litters of propylene carbonate and 160 g (0.96 mol) of fluorene were put into a 2 litter 3-neck round-bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and the resulting mixture was heated to 80° C. so as to make completely dissolved. 179.9 g (1.01 mol) of N-bromo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HO- | C1(OCC(C)O1)=O | 80 | 10 | O=C1CCC(=O)N1Br.c1ccc2c(c1)Cc1ccccc1-2>C1(OCC(C)O1)=O>Brc1cccc2c1Cc1ccccc1-2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7c613e5037143f2acbfe849c8d77347 | BrCc1ccc(Br)cc1.O=Cc1ccc(Br)cc1>>Brc1ccc(C=Cc2ccc(Br)cc2)cc1 | BrC1=CC=C(C=O)C=C1.BrC1=CC=C(CBr)C=C1.C(C)OP(OCC)OCC.[H-].[Na+]>>BrC1=CC=C(C=C1)C=CC1=CC=C(C=C1)Br | Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.O=[CH:6][c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:16][cH:15]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | BrCc1ccc(Br)cc1.O=Cc1ccc(Br)cc1 | Brc1ccc(C=Cc2ccc(Br)cc2)cc1 | null | null | CN(C)C=O | C-C Coupling | Wittig | fb64cfe49b9d38dd70c244824abc3c1ad6b2e83874a0083fb9c9a3476b827743 | a3dca447376ff0c6fe3968bb1ab0785c8926c417c53ba2b61f8ebdb52a7e5a2a | C(=Cc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 65 | [{"value": 63.0, "product": "BrC1=CC=C(C=C1)C=CC1=CC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "BrC1=CC=C(C=C1)C=CC1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 4 | HOUR | 47 g (0.188 mol) of 4-bromobenzylbromide and 37.5 g (0.224 mol) of check triethylphosphite were put into a 500 ml 3-neck round-bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and the resulting mixture was stirred at 150° C. for 4 hours. The temperature was dropped t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | null | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 150 | 4 | BrCc1ccc(Br)cc1.O=Cc1ccc(Br)cc1>CN(C)C=O>Brc1ccc(C=Cc2ccc(Br)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69e50f4a0a4148ad88f1efb062fdfe32 | C#Cc1ccccc1.COc1cc(Br)c(OC)cc1Br>>COc1cc(C#Cc2ccccc2)c(OC)cc1C#Cc1ccccc1 | BrC1=C(C=C(C(=C1)OC)Br)OC.C1(=CC=CC=C1)C#C>>C1(=CC=CC=C1)C#CC1=C(C=C(C(=C1)OC)C#CC1=CC=CC=C1)OC | [cH:6]1[c:21]([C:20]#[CH:19])[cH:22][cH:23][cH:24][cH:25]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18](Br)[cH:17][c:14]1[O:15][CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[C:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]([O:15][CH3:16])[cH:17][c:18]1[C:19]#[C:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | C#Cc1ccccc1.COc1cc(Br)c(OC)cc1Br | COc1cc(C#Cc2ccccc2)c(OC)cc1C#Cc1ccccc1 | null | [Cu](I)I | N1CCCCC1 | C-C Coupling | OtherReaction | f65d2bb59e33071f2905a7116d450fb0d6c19b178f0f41aab08b9d9d17c29caf | 419348b12564e1a67a246262c8ba3c943df70363a18ee6cae4f51075a91eb06c | C(#Cc1ccc(C#Cc2ccccc2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#8:4]):[c;H0;D3;+0:5](-Br):[c:6]:[c:7]:1-[#8:8].[CH;D1;+0:9]#[C:10]-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[#8:4]-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:10]-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:[c:17]:2):[c:7](-[#8:8]):[c:6]:[c;H0;D3;... | 75.7 | [{"value": 72.0, "product": "C1(=CC=CC=C1)C#CC1=C(C=C(C(=C1)OC)C#CC1=CC=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "C1(=CC=CC=C1)C#CC1=C(C=C(C(=C1)OC)C#CC1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | 50 g (160 mmol) of 1,4-dibromo-2,5-dimethoxy benzene, 3.6 g (0.005 mol) of bistriphenylphosphine palladium dichloride and 0.97 g (0.005 mol) of copper iodide were put into a 1 litter 3-neck flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and dissolved in 500 ml of piperidi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Alkyne | Alkyne.Alkyne | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Br- | [Cu](I)I.N1CCCCC1 | 80 | 12 | C#Cc1ccccc1.COc1cc(Br)c(OC)cc1Br>[Cu](I)I.N1CCCCC1>COc1cc(C#Cc2ccccc2)c(OC)cc1C#Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-055226509f2c42309f67211cf933f618 | C#C[Si](C)(C)C.COc1cc(Br)c(OC)cc1Br>>COc1cc(C#C[Si](C)(C)C)c(OC)cc1C#C[Si](C)(C)C | BrC1=C(C=C(C(=C1)OC)Br)OC.C[Si](C)(C)C#C>>C[Si](C)(C)C#CC1=C(C=C(C(=C1)OC)C#C[Si](C)(C)C)OC | [CH:6]#[C:7][Si:8]([CH3:9])([CH3:17])[CH3:22].Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:16](Br)[cH:15][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[C:7][Si:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:16]1[C:17]#[C:18][Si:19]([CH3:20])([CH3:21])[CH3:22] | C#C[Si](C)(C)C.COc1cc(Br)c(OC)cc1Br | COc1cc(C#C[Si](C)(C)C)c(OC)cc1C#C[Si](C)(C)C | null | [Cu](I)I | C(C)(C)NC(C)C | Functional Group Interconversion | OtherReaction | 0655aa521a4718b02d73de7daacf914e9418657090764671b6e0ebf54423b730 | 0ead11fc826c455f7f37b96610d201a4f5d5c6577f213160728196335b89ecb6 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#8:4]):[c;H0;D3;+0:5](-Br):[c:6]:[c:7]:1-[#8:8].[C;D1;H3:9]-[Si;H0;D4;+0:10](-[CH3;D1;+0:11])(-[CH3;D1;+0:12])-[C:13]#[CH;D1;+0:14]>>[#8:4]-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:11]#[C:15]-[#14:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[CH3;D1;+0:12]):[c:7](-[#8:8]):[c:6]:[c;H0;D3;+0:5]:1-[C... | 73.8 | [{"value": 73.0, "product": "C[Si](C)(C)C#CC1=C(C=C(C(=C1)OC)C#C[Si](C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C[Si](C)(C)C#CC1=C(C=C(C(=C1)OC)C#C[Si](C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | 100 g (0.338 mol) of 1,4-dibromo-2,5-dimethoxybenzene, 7.12 g (0.01 mol) of bistriphenylphospine palladium dichloride and 1.93 g (0.01 mol) of copper iodide were put into a 1 litter 3-neck round-bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and dissolved in 600 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Alkyne.Silyl protective group | Alkyne.Alkyne.Silyl protective group.Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [Cu](I)I.C(C)(C)NC(C)C | 80 | 12 | C#C[Si](C)(C)C.COc1cc(Br)c(OC)cc1Br>[Cu](I)I.C(C)(C)NC(C)C>COc1cc(C#C[Si](C)(C)C)c(OC)cc1C#C[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40c021b30b0b44aeab08b6c10bded196 | BrCc1ccccc1.NCCS>>NCCSCc1ccccc1 | Cl.NCCS.N.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)SCCN | Br[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH2:2][CH2:3][SH:4]>>[NH2:1][CH2:2][CH2:3][S:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | BrCc1ccccc1.NCCS | NCCSCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)SCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a suspension of 0.1 mole cysteamine hydrochloride in 20 mL methanol were added 13.6 mL of 25% ammonia solution, followed by dropwise addition of 0.12 mole benzyl bromide at room temperature. The mixture was stirred for 0.5 h, and the formed precipitate of S-dibenzylcysteamine was collected by filtration. The product... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HBr | CO | null | 0.5 | BrCc1ccccc1.NCCS>CO>NCCSCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-469d866e91794e08b6b711bc622a4f31 | COS(=O)(=O)c1ccc(C)cc1>>Cc1ccc(S(=O)(=O)O)cc1 | CI.CBr.CCl.C1(=CC=C(C=C1)S(=O)(=O)OC)C.CN(C(=O)N(C)C)C.CCl>>C1(=CC=C(C=C1)S(=O)(=O)O)C | C[O:9][S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:11][cH:10]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[OH:9])[cH:10][cH:11]1 | COS(=O)(=O)c1ccc(C)cc1 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | C1CCOC1.CC(=O)C.CN(C)C=O.C(C)(C)O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccccc1 | C-[O;H0;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]1:[c:6]:[c:7]:[c:8](-[C;D1;H3:9]):[c:10]:[c:11]:1>>[C;D1;H3:9]-[c:8]1:[c:7]:[c:6]:[c:5](-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[OH;D1;+0:1]):[c:11]:[c:10]:1 | null | [] | null | null | null | null | The methylation of the pyridine nitrogen atom in the compound of the formula XXIII, with formation of the pyridinium salt of the formula XXIV, can be carried out smoothly with numerous methylating agents, for example methyl iodide, methyl bromide, methyl chloride or methyl toluene-4-sulfonate, in a number of solvents, ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | Other | C1CCOC1.CC(=O)C.CN(C)C=O.C(C)(C)O | null | null | COS(=O)(=O)c1ccc(C)cc1>C1CCOC1.CC(=O)C.CN(C)C=O.C(C)(C)O>Cc1ccc(S(=O)(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c3f31a14b3b47a1ba8904aea201e513 | CC(=O)NCC(=O)O.N#Cc1ccc(C=O)cc1>>CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1 | C(C)(=O)OC(C)=O.C(=O)C1=CC=C(C#N)C=C1.C(C)(=O)NCC(=O)O.C(C)(=O)[O-].[Na+]>>CC=1OC(C(N1)=CC1=CC=C(C#N)C=C1)=O | O=[C:2]([CH3:1])[NH:3][CH2:4][C:14](=[O:15])[OH:16].O=[CH:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][C:2]1=[N:3][C:4](=[CH:5][c:6]2[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]2)[C:14](=[O:15])[O:16]1 | CC(=O)NCC(=O)O.N#Cc1ccc(C=O)cc1 | CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1 | null | null | CC(=O)C | Acylation | OtherReaction | 8b99b0c16f550085319f7f5209d25186c966977811563fe06f7ed99655933f3b | f7fa6645f0c32b2b0bf2c3370dc784786dbf5d56094a5b7a639f37830b489fba | O=C1OC=NC1=Cc1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:3]-[C;H0;D3;+0:4](=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1 | null | [] | 50 | CELSIUS | null | null | Acetone (80.0 l) was introduced into a mixture of 4-formylbenzonitrile (15.0 kg, 114.5 mol), N-acetylglycine (19.2 kg, 162.4 mol) and anhydrous sodium acetate (9.4 kg, 114.5 mol) followed by introduction, with stirring, of acetic anhydride (35.0 l, 370.5 mol). The reaction mixture was stirred under reflux for 1 h. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Secondary amide | Ester | null | C1=NCCO1 | C1=NCCO1.c1ccccc1 | HO- | CC(=O)C | 50 | null | CC(=O)NCC(=O)O.N#Cc1ccc(C=O)cc1>CC(=O)C>CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f18edadf937d4e29883868e8d06ea4d1 | CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1.N[C@H](C(=O)O)C1CCCCC1>>CC(=O)NC(=Cc1ccc(C#N)cc1)C(=O)N[C@H](C(=O)O)C1CCCCC1 | C1CCC(CC1)[C@@H](C(=O)O)N.[OH-].[Na+].CC=1OC(C(N1)=CC1=CC=C(C#N)C=C1)=O>>C(C)(=O)NC(C(=O)N[C@H](C(=O)O)C1CCCCC1)=CC1=CC=C(C=C1)C#N | [CH3:1][C:2]1=[N:4][C:5](=[CH:6][c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]2)[C:15](=[O:16])[O:3]1.[NH2:17][C@H:18]([C:19](=[O:20])[OH:21])[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1)[C:15](=[O:16])[NH:17][C@H... | CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1.N[C@H](C(=O)O)C1CCCCC1 | CC(=O)NC(=Cc1ccc(C#N)cc1)C(=O)N[C@H](C(=O)O)C1CCCCC1 | null | null | CC(=O)C | Acylation | OtherReaction | 5bb6e5bb1ea134c439055184f0f7eefdcc91e408a022f7600a7671a86cfcd9a2 | 0c6b0f335ae0a6c53d221da635f42ed94f4d1caadc9baff32cd5d73844920cd4 | O=C(C=Cc1ccccc1)NCC1CCCCC1 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:3]-[C:4](=[C:5]-[c:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:4](=[C:5]-[c:6])-[NH;D2;+0:3]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;H0;D1;+0:9])-[C:13](=... | null | [] | 35 | CELSIUS | 15 | MINUTE | (S)-Cyclohexylglycine (3.14 kg, 20 mol) in acetone (70 l) was heated with stirring at 35° C. With stirring, 1 N aqueous sodium hydroxide solution (20 l) was then added over a period of 10 min. The mixture was heated to 40° C., and at an internal temperature of 40° C., solid 4-(2-methyl-5-oxooxazol-4-ylidenemethyl)benzo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Enamine.Secondary amide.Secondary amide | C1=NCCO1 | null | c1ccccc1.C1CCCCC1 | null | CC(=O)C | 35 | 0.25 | CC1=NC(=Cc2ccc(C#N)cc2)C(=O)O1.N[C@H](C(=O)O)C1CCCCC1>CC(=O)C>CC(=O)NC(=Cc1ccc(C#N)cc1)C(=O)N[C@H](C(=O)O)C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f1fb938305c4ba3a172d5108b3d713d | CC(=O)NCC(=O)O.O=Cc1cccnc1>>CC1=N/C(=C\c2cccnc2)C(=O)O1 | C(C)(=O)OC(C)=O.N1=CC(=CC=C1)C=O.C(C)(=O)NCC(=O)O.C(C)(=O)[O-].[Na+]>>CC=1OC(/C(/N1)=C/C=1C=NC=CC1)=O | O=[C:2]([CH3:1])[NH:3][CH2:4][C:12](=[O:13])[OH:14].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1>>[CH3:1][C:2]1=[N:3]/[C:4](=[CH:5]\[c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[C:12](=[O:13])[O:14]1 | CC(=O)NCC(=O)O.O=Cc1cccnc1 | CC1=N/C(=C\c2cccnc2)C(=O)O1 | null | null | C(C)(C)(C)OC.CC(=O)C | Acylation | OtherReaction | 8b99b0c16f550085319f7f5209d25186c966977811563fe06f7ed99655933f3b | f7fa6645f0c32b2b0bf2c3370dc784786dbf5d56094a5b7a639f37830b489fba | O=C1OC=N/C1=C\c1cccnc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[C;D1;H3:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:3]/[C;H0;D3;+0:4](=[CH;D2;+0:8]\[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13])-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1 | null | [] | 50 | CELSIUS | 30 | MINUTE | Under nitrogen, acetone (40.0 l), followed by pyridine-3-carbaldehyde (20.0 kg, 186.9 mol), was added to N-acetylglycine (32.7 kg, 280.0 mol) and sodium acetate (15.3 kg, 186.9 mol). With stirring, acetic anhydride (40.0 l, 429.0 mol) was added. Within 30 min, the reaction mixture was heated to reflux temperature and t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Secondary amide | Ester | null | C1=NCCO1 | C1=NCCO1.c1ccncc1 | HO- | C(C)(C)(C)OC.CC(=O)C | 50 | 0.5 | CC(=O)NCC(=O)O.O=Cc1cccnc1>C(C)(C)(C)OC.CC(=O)C>CC1=N/C(=C\c2cccnc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48f84ae397d440298551c751c46bf209 | CC1=N/C(=C\c2cccnc2)C(=O)O1.CO>>COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O | C(C)(C)(C)OC.C(C)N(CC)CC.CC=1OC(/C(/N1)=C/C=1C=NC=CC1)=O.CO.F[B-](F)(F)F.[H+]>>F[B-](F)(F)F.C(C)(=O)NC(=CC=1C=[NH+]C=CC1)C(=O)OC | [C:3]1(=[O:4])/[C:5](=[CH:6]/[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[N:13]=[C:14]([CH3:15])[O:16]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][cH:10][nH+:11][cH:12]1)[NH:13][C:14]([CH3:15])=[O:16] | CC1=N/C(=C\c2cccnc2)C(=O)O1.CO | COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O | null | null | null | Protection | OtherReaction | e9565642f7c3ef94f47db126b5e59849289585192ec261de3968bd2e50e41858 | e4180cedd71129bc9e29a121250a8d205504a5f85e0df47f3fea0591d2ef0c80 | c1cc[nH+]cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:3]/[C:4](=[C:5]\[c:6]2:[c:7]:[n;H0;D2;+0:8]:[c:9]:[c:10]:[c:11]:2)-[C;H0;D3;+0:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-1.[C;D1;H3:15]-[OH;D1;+0:16]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:14])-[NH;D2;+0:3]-[C:4](=[C:5]-[c:6]1:[c:7]:[nH+;D2:8]:[c:9]:[c:10]:[c:11]:1)-[C;H0;D3;+0:12](=[... | null | [] | 60 | CELSIUS | 30 | MINUTE | Under nitrogen, a suspension of 2-methyl-4-[pyridin-3-yl-(Z)-methylene]-4H-oxazol-5-one (12.0 kg, 63.83 mol) in methanol (120.0 l) was heated at 60° C. Triethylamine (0.5 l) was pumped in, and the apparatus was rinsed with methanol (0.5 l) (the pH of a sample taken, measured using a glass electrode, was pH 8.15). Withi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Enamine.Ester.Secondary amide | C1=NCCO1.c1ccncc1 | c1cc[n+]cc1 | c1cc[n+]cc1 | null | null | 60 | 0.5 | CC1=N/C(=C\c2cccnc2)C(=O)O1.CO>>COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65376431cfba44e2ae28147dc8a8cf44 | COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O>>COC(=O)[C@H](Cc1ccc[nH+]c1)NC(C)=O | [H][H].O=O.[H][H].F[B-](F)(F)F.[H+].F[B-](F)(F)F.C(C)(=O)NC(=CC=1C=[NH+]C=CC1)C(=O)OC>>F[B-](F)(F)F.C(C)(=O)N[C@@H](CC=1C=[NH+]C=CC1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][cH:10][nH+:11][cH:12]1)[NH:13][C:14]([CH3:15])=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][nH+:11][cH:12]1)[NH:13][C:14]([CH3:15])=[O:16] | COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O | COC(=O)[C@H](Cc1ccc[nH+]c1)NC(C)=O | null | null | CO | Reduction | Hydrogenation (double to single) | c5482e96d32f880dae9cdf88ceb576b12289d0a709a9745c321f8f5233d183f3 | b586296faf9080b398947dcba4825d3daf71a75997a309df19187f20bff3e49d | c1cc[nH+]cc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a;+:10]:[c:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C@@H;D3;+0:5](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a;+:10]:[c:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15] | 99.1 | [{"value": 99.1, "product": "F[B-](F)(F)F.C(C)(=O)N[C@@H](CC=1C=[NH+]C=CC1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 1 | HOUR | In an autoclave, 3-(2-acetylamino-2-methoxycarbonylvinyl)pyridinium tetrafluoroborate (10.3 kg, 33.44 mol) was dissolved in methanol (120.0 l). Tetrafluoroboric acid solution (50% in water, 1.018 kg, 5.8 mol) was added, and the autoclave was closed and carefully inertized using nitrogen. The catalyst solution was prepa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Ester | null | null | c1cc[n+]cc1 | null | CO | 40 | 1 | COC(=O)C(=Cc1ccc[nH+]c1)NC(C)=O>CO>COC(=O)[C@H](Cc1ccc[nH+]c1)NC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-738558fcf0d44307b44295052f5a156d | N.O=C(N[C@@H](Cc1cccnc1)C(=O)O)OCc1ccccc1>>NC(=O)[C@H](Cc1cccnc1)NC(=O)OCc1ccccc1 | N.C(C)N(C(C)C)C(C)C.C(C1=CC=CC=C1)OC(=O)N[C@H](C(=O)O)CC=1C=NC=CC1.ClC(=O)OCC(C)C>>C(N)(=O)[C@H](CC=1C=NC=CC1)NC(OCC1=CC=CC=C1)=O | [NH3:1].O[C:2](=[O:3])[C@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1)[NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[NH2:1][C:2](=[O:3])[C@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1)[NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | N.O=C(N[C@@H](Cc1cccnc1)C(=O)O)OCc1ccccc1 | NC(=O)[C@H](Cc1cccnc1)NC(=O)OCc1ccccc1 | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(NCCc1cccnc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[NH3;D0;+0:8]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2] | null | [] | -9 | CELSIUS | 30 | MINUTE | A suspension of (S)-2-benzyloxycarbonylamino-3-(pyridin-3-yl)propionic acid (2.60 kg, 8.65 mol) in tetrahydrofuran (60 l) was cooled to −9° C. At this temperature, N-ethyldiisopropylamine (1.33 kg, 10.29 mol) was added over a period of 5 min. At −9° C., isobutyl chloroformate (1.36 kg, 9.96 mol) was then added within 2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccncc1.c1ccccc1 | HO- | O1CCCC1 | -9 | 0.5 | N.O=C(N[C@@H](Cc1cccnc1)C(=O)O)OCc1ccccc1>O1CCCC1>NC(=O)[C@H](Cc1cccnc1)NC(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad2378e8729f43cdb3501b2c8a8ba400 | O=C1C[C@H]2CC=CN12>>O.O.O.O=C1C[C@H]2CC=CN12 | Cl.C1C=CN2[C@H]1CC2=O>>O.O.O.Cl.C1C=CN2[C@H]1CC2=O | [O:2]=[C:6]1[CH2:7][C@H:8]2[CH2:9][CH:10]=[CH:11][N:12]12>>[OH2:2].[OH2:3].[OH2:4].[O:5]=[C:6]1[CH2:7][C@H:8]2[CH2:9][CH:10]=[CH:11][N:12]12 | O=C1C[C@H]2CC=CN12 | O.O.O.O=C1C[C@H]2CC=CN12 | null | null | O | Functional Group Addition | OtherReaction | 269547553358ab1085a2897bed2e806c0e46590cddba6555c99e5ab4c4caf54c | e244846285aac15886afcad78d2897377c96201dfaadfac4e1431cb64a989992 | O=C1C[C@H]2CC=CN12 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]2-[C:5]-[C:6]=[C:7]-[#7:8]-2-1>>[O;D1;H0:9]=[C;H0;D3;+0:2]1-[C:3]-[C:4]2-[C:5]-[C:6]=[C:7]-[#7:8]-2-1.[OH2;D0;+0:1] | null | [] | null | null | 1 | HOUR | Water for injection was added to 2000 g titer equivalent amount of novel non-aseptic carbapenem hydrochloride derivative to give 20 kg dispersion. This dispersion was stirred and dissolved under ice-cooling to prepare a charge solution. Thereafter, the solution was aseptically filtered through a 0.2 μm membrane filter ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Tertiary amide | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1 | Other | O | null | 1 | O=C1C[C@H]2CC=CN12>O>O.O.O.O=C1C[C@H]2CC=CN12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06f820af9a9344ca8b49ec7285ba49d2 | O=C1CCCCCN1.ON=C1CCCCC1>>NCCCCCC(=O)O.O=C1CCCCCN1 | Cl.C1(CCCCCN1)=O.C1(CCCCC1)=NO>>C1(CCCCCN1)=O.NCCCCCC(=O)O | [O:8]=[C:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17]1.[N:1](=[C:7]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[OH:9]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[OH:9].[O:10]=[C:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17]1 | O=C1CCCCCN1.ON=C1CCCCC1 | NCCCCCC(=O)O.O=C1CCCCCN1 | null | null | null | Acylation | OtherReaction | 5cc5fc6b79957fc12ce70b967c1b7341df0fa1bd49f52b2eea428951d90bd568 | 5e14af10e49f499e9cad8d012e6de356d53a545126df18c78bcd594acd2c93e8 | O=C1CCCCCN1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[#7:5]-[C:6].[OH;D1;+0:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:15])-[#7:5]-[C:6].[NH2;D1;+0:8]-[CH2;D2;+0:14]-[C:13]-[C:12]-[C:11]-[C:10]-[C;H0;D3;+0:9](=[O;H0;D1;+0:4])-[OH;D1;+0:7] | 96.2 | [{"value": 96.2, "product": "C1(CCCCCN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.5, "product": "NCCCCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the present invention, the oxime that is the substrate can be put into a prescribed high-temperature high-pressure state within a short time, and hence hydrolysis of the oxime can be suppressed, and moreover by making an acid be present in the reaction zone, the lactam can be produced efficiently. Note, ho... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Oxime | Carboxylic acid.Secondary amide.Primary amine | C1CCCNCC1.C1CCCCC1 | C1CCCNCC1 | C1CCCNCC1 | Other | null | null | null | O=C1CCCCCN1.ON=C1CCCCC1>>NCCCCCC(=O)O.O=C1CCCCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e06d4b89f2bc4de2b374369e3673ac29 | COC(=O)OC.Cc1ccncc1N>>COC(=O)Nc1cnccc1C | C(OC)(OC)=O.CC1=C(C=NC=C1)N.CC(C)([O-])C.[K+].C1CCOC1>>COC(NC=1C=NC=CC1C)=O | CO[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][n:8][cH:9][cH:10][c:11]1[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][n:8][cH:9][cH:10][c:11]1[CH3:12] | COC(=O)OC.Cc1ccncc1N | COC(=O)Nc1cnccc1C | null | null | null | Protection | OtherReaction | 914b3a8dcc49acff27aaafd1a7d372703aa14800c9fb526151b0e59a9afcc436 | b8e932aa519e327d0a7f4a36bcfd36a3e8a362a202df3d91c09aeec58c3625ae | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | 89 | [{"value": 89.0, "product": "COC(NC=1C=NC=CC1C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The synthesis was carried out by charging 2 grams (1 equiv., 18.5 mmol) 4-Methyl-pyridin-3-ylamine to a solution of 6.55 grams potassium t-butoxide (3 equiv., 55.5 mmol) in 10 ml THF (6.66 euiv., 123 mmol) at 0° C. Upon anion formation, 2.34 ml dimethyl carbonate (1.5 equiv., 27.7 mmol) were charged to the reaction at ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary amine | Carbamic ester | null | null | c1ccncc1 | HO- | null | null | 0.5 | COC(=O)OC.Cc1ccncc1N>>COC(=O)Nc1cnccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47fcb014ac7747d2a24ac30fac6cca7d | COC(=O)Nc1cnccc1C>>COC(=O)N[C@@H]1CNCC[C@@H]1C | COC(NC=1C=NC=CC1C)=O.[H][H]>>COC(N[C@@H]1CNCC[C@@H]1C)=O | [CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][n:8][cH:9][cH:10][c:11]1[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]1[CH2:7][NH:8][CH2:9][CH2:10][C@@H:11]1[CH3:12] | COC(=O)Nc1cnccc1C | COC(=O)N[C@@H]1CNCC[C@@H]1C | null | [Rh] | C(C)O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C;D1;H3:1]-[C@H;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-[C@H;D3;+0:7]-1-[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | null | null | The hydrogenation was carried out by charging 5 grams (1 equiv., 30.1 mmol) (4-methyl-pyridin-3-yl)-carbamic acid methyl ester, 50 ml ethanol (10 volumes), and 2.5 grams rhodium on alumina (0.5 wt. equivs.) to a bomb hydrogenator. The hydrogenation was performed under 100 psi hydrogen at 100° C. for 24 hours to give on... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Rh].C(C)O | null | null | COC(=O)Nc1cnccc1C>[Rh].C(C)O>COC(=O)N[C@@H]1CNCC[C@@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa9d08d4a8be45e7b7b7d7d151edf62c | COC(=O)N[C@@H]1CNCC[C@@H]1C.O=Cc1ccccc1>>COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C | COC(N[C@@H]1CNCC[C@@H]1C)=O.C(C1=CC=CC=C1)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>COC(N[C@@H]1CN(CC[C@@H]1C)CC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]1[CH2:7][NH:8][CH2:16][CH2:17][C@@H:18]1[CH3:19].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][C@@H:18]1[CH3:19] | COC(=O)N[C@@H]1CNCC[C@@H]1C.O=Cc1ccccc1 | COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCCCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | 70 | [{"value": 70.0, "product": "COC(N[C@@H]1CN(CC[C@@H]1C)CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 30 | MINUTE | The reductive amination of cis-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester was carried out by charging 3.9 grams (1 equiv., 22.6 mmol) to 2.07 ml benzaldehyde (0.9 equiv., 20.4 mmol), 9.6 grams sodium triacetoxyborohydride (2 equivs., 45.3 mmol) and 39 ml methylene chloride (10 volumes). The reaction was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | C(Cl)Cl | 20 | 0.5 | COC(=O)N[C@@H]1CNCC[C@@H]1C.O=Cc1ccccc1>C(Cl)Cl>COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d62a9641240d4a0b86f430ec8ac9107d | COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C>>CNC1CN(Cc2ccccc2)CCC1C | COC(N[C@@H]1CN(CC[C@@H]1C)CC1=CC=CC=C1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)N1CC(C(CC1)C)NC | CO[C:1](=O)[NH:2][C@@H:3]1[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][C@@H:15]1[CH3:16]>>[CH3:1][NH:2][CH:3]1[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][CH:15]1[CH3:16] | COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C | CNC1CN(Cc2ccccc2)CCC1C | null | null | C1CCOC1 | Reduction | OtherReaction | 0162385dd3f2239a186ebaf1047930f21ea49a4113c06354aed30cdbf1cd719c | f6bec327410058c9cba187636b48ed5ef90429f24bf839d7fb4e0588ab9ff83e | c1ccc(CN2CCCCC2)cc1 | C-O-[C;H0;D3;+0:1](=O)-[#7:2]-[C:3]>>[C:3]-[#7:2]-[CH3;D1;+0:1] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)N1CC(C(CC1)C)NC", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | The reduction of cis-(1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester was performed by charging 2 grams substrate (1 equiv., 7.62 mmol) to a solution of 20 ml THF (10 volumes) and 15.2 ml 1 M LAH in THF (2 equiv., 15.2 mmol). The addition was performed at a rate so that the temperature reached 30°-40° C. a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | null | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | 20 | null | COC(=O)N[C@@H]1CN(Cc2ccccc2)CC[C@@H]1C>C1CCOC1>CNC1CN(Cc2ccccc2)CCC1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6580e1657d6048b4bad2318e49008042 | Cl>>Cl | C(C1=CC=CC=C1)N1C[C@H]([C@H](CC1)C)NC.Cl>>Cl.C(C1=CC=CC=C1)N1C[C@H]([C@H](CC1)C)NC | [ClH:17]>>[ClH:17] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 37.5 | [{"value": 37.5, "product": "Cl.C(C1=CC=CC=C1)N1C[C@H]([C@H](CC1)C)NC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | The final salt formation was performed by charging 1.5 grams cis-(1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine (1 equiv., 5.15 mmol) and 4.5 ml ethanol (3 volumes) to a reactor at 0° C. To the 0° C. pot, was charged 0.93 ml 36% HCl (0.625 volumes) so that the temperature stayed below 10° C. Next 3 mis ethanol (2 volu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | 0 | 0.083333 | Cl>C(C)O>Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-53c4bad16d5f4bd785263b5a0042463c | CC1CCNCC1.COC(=O)Cl>>COC(=O)N1CCC(C)CC1 | CC1CCNCC1.C(C)N(CC)CC.COC(=O)Cl.O>>COC(=O)N1CCC(CC1)C | [NH:5]1[CH2:6][CH2:7][CH:8]([CH3:9])[CH2:10][CH2:11]1.Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([CH3:9])[CH2:10][CH2:11]1 | CC1CCNCC1.COC(=O)Cl | COC(=O)N1CCC(C)CC1 | null | null | C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | c6eb958652ca8104567d61601fc03a9cfee33fb7bb328952993831b03fec41c4 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4])-[C:8]-[C:9] | null | [] | null | null | 8 | HOUR | To a three neck round bottom flask was added 360 g of 4-methylpiperdine, 470 mL of triethylamine, and 390 mL of methylene chloride and the mixture was cooled in an ice bath. To this mixture was added methylchloroformate (260 mL) in methylene chloride (215 mL) slowly to maintain a reaction temperature of 20 C or below. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | C(Cl)Cl | null | 8 | CC1CCNCC1.COC(=O)Cl>C(Cl)Cl>COC(=O)N1CCC(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2e4fd09f9334ec984f9a0a948cbd985 | COC(=O)N1CCC(C)C(OC(C)=O)C1OC(C)=O>>COC(=O)N1C=C(OC(C)=O)C(C)CC1 | COC(=O)N1C(C(C(CC1)C)OC(C)=O)OC(C)=O.C(C)(=O)OC1C(N(CCC1C)C(=O)O)O>>COC(=O)N1CCC(C(=C1)OC(C)=O)C | CC(=O)O[CH:6]1[N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH2:14][CH:12]([CH3:13])[CH:7]1[O:8][C:9]([CH3:10])=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH:6]=[C:7]([O:8][C:9]([CH3:10])=[O:11])[CH:12]([CH3:13])[CH2:14][CH2:15]1 | COC(=O)N1CCC(C)C(OC(C)=O)C1OC(C)=O | COC(=O)N1C=C(OC(C)=O)C(C)CC1 | null | null | C(C)(=O)OC(C)=O | Functional Group Interconversion | OtherReaction | 7373d646425987ba3c6ddb21ad6ba54624bbb7d355ce0961244335131ae819c9 | 87fef8a565f6256401bc8b09db4355084cbc1ffaaae5b8ea6626f74ee0a71158 | C1=CNCCC1 | C-C(=O)-O-[CH;D3;+0:1]1-[#7:2](-[C:3](-[#8:4])=[O;D1;H0:5])-[C:6]-[C:7]-[C:8](-[C;D1;H3:9])-[CH;D3;+0:10]-1-[#8:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]>>[#8:4]-[C:3](=[O;D1;H0:5])-[#7:2]1-[C:6]-[C:7]-[C:8](-[C;D1;H3:9])-[C;H0;D3;+0:10](-[#8:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14])=[CH;D2;+0:1]-1 | null | [] | 141 | CELSIUS | 8 | HOUR | 101.9 g (0.649 mol) of the mixture of 2,3-diacetoxy-4-methyl-piperidine-1-carboxylic acid methyl ester and 3-acetoxy-2-hydroxy-4-methyl-piperidine-1-carboxylic acid, was concentrated under reduced pressure until a solid formed. The solid was then added to a 2 L round bottom flask equipped with a nitrogen outlet, conden... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Enamine | C1CC[NH]CC1 | C1=C[NH]CCC1 | C1=C[NH]CCC1 | HO- | C(C)(=O)OC(C)=O | 141 | 8 | COC(=O)N1CCC(C)C(OC(C)=O)C1OC(C)=O>C(C)(=O)OC(C)=O>COC(=O)N1C=C(OC(C)=O)C(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd36c0ffd6af4bbb82b6d263461c6525 | COC(=O)N1C=C(OC(C)=O)C(C)CC1>>COC(=O)N1CCC(C)C(=O)C1 | COC(=O)N1CCC(C(=C1)OC(C)=O)C.O.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>COC(=O)N1CC(C(CC1)C)=O | CC(=O)[O:11][C:10]1=[CH:12][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH:8]1[CH3:9]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([CH3:9])[C:10](=[O:11])[CH2:12]1 | COC(=O)N1C=C(OC(C)=O)C(C)CC1 | COC(=O)N1CCC(C)C(=O)C1 | null | null | CO | Miscellaneous | OtherReaction | 13ce9899dd9c3c7bd902127257eb443f183637152c2f891836604c4a24827280 | 0ddc2989d72e4e22b0a8e621beb9c3b1c66fa26e8a7f2ef09e7a4780c07d581a | O=C1CCCNC1 | C-C(=O)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[#7:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]-[C:10]-1-[C;D1;H3:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[#7:4]1-[C:8]-[C:9]-[C:10](-[C;D1;H3:11])-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH2;D2;+0:3]-1 | 32 | [{"value": 32.0, "product": "COC(=O)N1CC(C(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 1000 ml round bottom flask, 50 g of crude 5-acetoxy-4-methyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester was dissolved in 200 ml of methanol. To 300 ml water was added 30 g of sodium carbonate and 30 g sodium bicarbonate (pH=10). The aqueous buffer was added to the methanol solution. Methanol was added ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester | Ketone | C1=C[NH]CCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HO- | CO | null | null | COC(=O)N1C=C(OC(C)=O)C(C)CC1>CO>COC(=O)N1CCC(C)C(=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1afeb603539e4cb68b366cc59118d27f | CC(=O)CCl.Clc1ccc2[nH]nnc2c1>>CC(=O)Cn1nnc2cc(Cl)ccc21.CC(=O)Cn1nnc2ccc(Cl)cc21 | ClC1=CC2=C(NN=N2)C=C1.ClCC(C)=O.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>ClC1=CC2=C(N(N=N2)CC(C)=O)C=C1.ClC=1C=CC2=C(N(N=N2)CC(C)=O)C1 | [Cl:11][CH2:18][C:16]([CH3:15])=[O:17].[c:1]12[nH:5][n:6][n:7][c:28]1[cH:27][c:25]([Cl:26])[cH:24][cH:23]2>>[CH3:1][C:2](=[O:3])[CH2:4][n:5]1[n:6][n:7][c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]12.[CH3:15][C:16](=[O:17])[CH2:18][n:19]1[n:20][n:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]12 | CC(=O)CCl.Clc1ccc2[nH]nnc2c1 | CC(=O)Cn1nnc2cc(Cl)ccc21.CC(=O)Cn1nnc2ccc(Cl)cc21 | null | null | CC(=O)C | Aromatic Heterocycle Formation | N-alkylation of secondary amines with alkyl halides | d3af98ddff187ea3c39b0debdf039e6740a65620463fb0152b3cf6719fb9a8e2 | 44760ea31d186827031f5c8d476ebf9bc07e8259605971a4ac08cb99df3bb4d1 | c1ccc2[nH]nnc2c1.c1ccc2[nH]nnc2c1 | [#7;a:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3]2:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:2:[nH;D2;+0:9]:1.[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[Cl;H0;D1;+0:14]>>[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[#7;a:15]1:[#7;a:16]:[#7;a:17]:[c:18]2:[cH;D2;+0:7]:[c:6]:[c:5]:[c:4]:[c;H0;D3;+0:3]:1:2.[CH3;D1;+... | null | [] | null | null | null | null | A mixture of 5 g of 5-chlorobenzotriazole, 1.4 g of chloroacetone, 5.1 g of potassium carbonate and 0.5 g of potassium iodide is stirred into 50 ml of acetone at room temperature for 48 h. The mixture is subsequently filtered, the filtrate concentrated by evaporation in a vacuum, and the residue purified by flash chrom... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Aromatic halide.Ketone.Ketone | c1ccc2[nH]nnc2c1 | c1ccc2[nH]nnc2c1.c1ccc2nn[nH]c2c1 | c1ccc2[nH]nnc2c1.c1ccc2nn[nH]c2c1 | Other | CC(=O)C | null | null | CC(=O)CCl.Clc1ccc2[nH]nnc2c1>CC(=O)C>CC(=O)Cn1nnc2cc(Cl)ccc21.CC(=O)Cn1nnc2ccc(Cl)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ed350118fc746a58b79ffe1365ea045 | CC(=O)Cn1nnc2cc(Cl)ccc21.[C-]#N.[NH4+]>>CC(N)(C#N)Cn1nnc2cc(Cl)ccc21 | ClC1=CC2=C(N(N=N2)CC(C)=O)C=C1.C(C)O.[C-]#N.[Na+].[Cl-].[NH4+]>>NC(C#N)(CN1N=NC2=C1C=CC(=C2)Cl)C | O=[C:2]([CH3:1])[CH2:6][n:7]1[n:8][n:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]12.[C-:4]#[N:5].[NH4+:3]>>[CH3:1][C:2]([NH2:3])([C:4]#[N:5])[CH2:6][n:7]1[n:8][n:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]12 | CC(=O)Cn1nnc2cc(Cl)ccc21.[C-]#N.[NH4+] | CC(N)(C#N)Cn1nnc2cc(Cl)ccc21 | null | null | N | Functional Group Interconversion | OtherReaction | bf6fa2c5d28d887cff72f321ae6c28dd716e15f777677717232b44f5fabc2c13 | ff0d0afb9b8e2a9484b4ef42a76d567293aefe55b04928483f9f6aa47c49d0fc | c1ccc2[nH]nnc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#7;a:4].[C-;H0;D1:5]#[N;D1;H0:6].[NH4+;D0:7]>>[#7;a:4]-[C:3]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[NH2;D1;+0:7])-[C;H0;D2;+0:5]#[N;D1;H0:6] | null | [] | null | null | null | null | 240 mg of 1-(5-chlorobenzotriazol-1-yl)-propan-2-one are dissolved in 4 ml of a 2-molar solution of ammonia in ethanol, then 64 mg of sodium cyanide and 91 mg of ammonium chloride are added and the mixture is stirred over night at room temperature. The reaction mixture is subsequently concentrated by evaporation in a v... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Nitrile.Primary amine | null | null | c1ccc2[nH]nnc2c1 | HO- | N | null | null | CC(=O)Cn1nnc2cc(Cl)ccc21.[C-]#N.[NH4+]>N>CC(N)(C#N)Cn1nnc2cc(Cl)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83ed61dbe4a343a899a0eeb5417de98f | C1CCOC1.C1CCOC1.C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12.O=C(c1ccccc1)c1ccccn1>>CC(C)(C)OC(=O)CC(O)(c1ccccc1)c1ccccn1 | Cl.C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C=3C=CN=C4C3C=CC=C4)O.N1=CC=CC=C1.C(C1=CC=CC=C1)(=O)C1=NC=CC=C1.O1CCCC1.O1CCCC1>>OC(CC(=O)OC(C)(C)C)(C1=NC=CC=C1)C1=CC=CC=C1 | C1C[O:5][CH2:2][CH2:1]1.C1OC[CH2:4][CH2:3]1.c1ccc2c([C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4[CH:6]=[CH2:8])[OH:7])ccnc2c1.[C:9](=[O:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9]([OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:... | C1CCOC1.C1CCOC1.C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12.O=C(c1ccccc1)c1ccccn1 | CC(C)(C)OC(=O)CC(O)(c1ccccc1)c1ccccn1 | null | null | null | Acylation | OtherReaction | 3f874dcb3c140b352fa4a8b496f119374a7ad5f987f3c00e658a5ad3479baa5a | 44d9ada2becba6f8b398729c4002f8b492cd4e2b8f900f3430cdcfb857cb06fa | c1ccc(Cc2ccccn2)cc1 | C1-C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-1.C1-O-C-[CH2;D2;+0:4]-[CH2;D2;+0:5]-1.[CH2;D1;+0:6]=[CH;D2;+0:7]-[C@H]1-C-N2-C-C-[C@H]-1-C-[C@@H]-2-[C@@H](-[OH;D1;+0:8])-c1:c:c:n:c2:c:c:c:c:c:1:2.[O;H0;D1;+0:9]=[C;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:14](:[c:15]):[#7;a:16]:[c:17]>>[CH3;D1;+0:3]-[C;H0;D4;+0:2](-[CH... | 98 | [{"value": 98.0, "product": "OC(CC(=O)OC(C)(C)C)(C1=NC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 10 | MINUTE | Under argon atmosphere, cinchonine (440 mg, 1.0 mmol) was suspended in tetrahydrofuran (absolute, 2.0 mL), and to this suspension was added a Reformatsky reagent (0.5 M; 8.0 mL, 4.0 mmol) dropwise under ice-cooling. After stirring for 10 minutes, pyridine (0.30 mL, 2 mmol) was added thereto dropwise. After stirring for... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Secondary alcohol.Tertiary amine.Vinyl | Ester.Tertiary alcohol.Boc | C1CCOC1.C1CCOC1.c1ccc2ncccc2c1.C1CN2CCC1CC2 | null | c1ccccc1.c1ccncc1 | HO- | null | -40 | 0.166667 | C1CCOC1.C1CCOC1.C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12.O=C(c1ccccc1)c1ccccn1>>CC(C)(C)OC(=O)CC(O)(c1ccccc1)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1cd8102a8b040e4af724b1fac0c3aa2 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC(=O)CC(=O)CC(=O)OC(C)(C)C>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C | FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(NC1=CC=CC=C1)=O)C(C)C)CCC(CC(CC(=O)OC(C)(C)C)=O)=O.C1(=CC=CC=C1)C.C(C)N(CC)CC>>FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(NC1=CC=CC=C1)=O)C(C)C)CC[C@H](C[C@H](CC(=O)OC(C)(C)C)O)O | [CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22](-[c:23]2[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]2)[n:30]1[CH2:31][CH2:32][C:33](=[O:34])[CH2:35][C:36](=[O:37])[CH2:38][C:39](=[O:40])[O:41][C:42]([CH3:43])([CH3:4... | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC(=O)CC(=O)CC(=O)OC(C)(C)C | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C | null | null | C(=O)O | Reduction | OtherReaction | 84985cc30f4421175197b9486fb9d72ff4bf85bf8e0a2bdc7ae0cb7c95dd16aa | 0784ca7b37672e11f807ae766332824b43b3717e2904323a6084529a2f9ad255 | O=C(Nc1ccccc1)c1c[nH]c(-c2ccccc2)c1-c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C... | null | [] | null | null | 24 | HOUR | An argon inerted reactor was charged with 7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dioxo-heptanoic acid, t-butyl ester (V-A, 100.0 mmol, prepared as indicated in U.S. Pat. No. 6,476,235) and toluene (245 ml). To the reaction mixture was added triethyl amine (55 ml), followed by slow... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Secondary alcohol.Secondary alcohol | null | null | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(=O)O | null | 24 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC(=O)CC(=O)CC(=O)OC(C)(C)C>C(=O)O>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28f25661c0c749d289fe2eb55676d218 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O | FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(NC1=CC=CC=C1)=O)C(C)C)CC[C@H](C[C@H](CC(=O)OC(C)(C)C)O)O.[OH-].[K+].CO.O.CC(C)O.Cl>>FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(NC1=CC=CC=C1)=O)C(C)C)CC[C@H](C[C@H](CC(=O)O)O)O | CC(C)(C)[O:41][C:39]([CH2:38][C@@H:36]([CH2:35][C@@H:33]([CH2:32][CH2:31][n:30]1[c:4]([CH:2]([CH3:1])[CH3:3])[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1-[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[OH:34])[OH:37])=[O:40]>>[CH3:1]... | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O | null | null | C1(=CC=CC=C1)C | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1ccccc1)c1c[nH]c(-c2ccccc2)c1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | The crude (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid, t-butyl ester (VI-A) was converted to the acid using an excess of KOH/MeOH/Water, followed by lactonization in toluene with catalytic HCl. Chiral HPLC analysis (ChiralCel OF; 1 ml/min; 60° C.; 254 n... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)OC(C)(C)C>C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-056f03b2844a43409ccd9457a545328f | BrC12CC3CC(C1)CC(Br)(C3)C2.Brc1cccc(Br)c1.[Br-]>>Brc1cc(Br)cc(C23CC4CC(C2)CC(c2cc(Br)cc(Br)c2)(C4)C3)c1 | Br.BrC12CC3(CC(CC(C1)C3)C2)Br.[Br-].[Al+3].[Br-].[Br-].BrC1=CC(=CC=C1)Br>>BrC=1C=C(C=C(C1)Br)C12CC3(CC(CC(C1)C3)C2)C2=CC(=CC(=C2)Br)Br | Br[C:8]12[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][C:21]([Br:22])([CH2:14]3)[CH2:25]1)[CH2:24]2.[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][cH:26]1.[Br-:19]>>[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([C:8]23[CH2:9][CH:10]4[CH2:11][CH:12]([CH2:13]2)[CH2:14][C:15]([c:16]2[cH:17][c:18]([Br:19])[cH:20][c:21]([Br:22])[cH:23]... | BrC12CC3CC(C1)CC(Br)(C3)C2.Brc1cccc(Br)c1.[Br-] | Brc1cc(Br)cc(C23CC4CC(C2)CC(c2cc(Br)cc(Br)c2)(C4)C3)c1 | null | null | null | C-C Coupling | OtherReaction | c1abb395e13a41ec74b325615f9bdd0a54b49bd7015ceb5f8eff060ad6edebcd | ca178956dc34ba74492b6d4c95450a243739f7d2f811235777c449e8f15edebd | c1ccc(C23CC4CC(C2)CC(c2ccccc2)(C4)C3)cc1 | Br-[C;H0;D4;+0:1]12-[C:2]-[C:3]3-[C:4]-[C:5](-[CH2;D2;+0:6]-1)-[CH2;D2;+0:7]-[C;H0;D4;+0:8](-[Br;D1;H0:9])(-[CH2;D2;+0:10]-3)-[CH2;D2;+0:11]-2.[Br-;H0;D0:12].[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[c:17]>>[Br;D1;H0:9]-[c;H0;D3;+0:8]1:[c:18]:[c:19](-[Br;H0;D1;+0:12]):[c:20]:[c:21](-[C:22]23-[CH2;D2;+0:10]-[C:3]4-[C:4]-[C:5]... | 194.3 | [{"value": 194.3, "product": "BrC=1C=C(C=C(C1)Br)C12CC3(CC(CC(C1)C3)C2)C2=CC(=CC(=C2)Br)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | After the air inside a 1 litter flask equipped with a thermometer and stirrer was replaced by nitrogen, 43 g of 1,3-dibromoadamantane and 10 g of anhydrous aluminum bromide were placed therein, and then the inside of the flask was cooled to 0° C. Thereto was added 190 g of 1,3-dibromobenzene that was cooled to 5° C. in... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Aromatic halide.Aromatic halide | c1ccccc1.C1C2CC3CC1CC(C2)C3 | c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | Br- | null | 0 | null | BrC12CC3CC(C1)CC(Br)(C3)C2.Brc1cccc(Br)c1.[Br-]>>Brc1cc(Br)cc(C23CC4CC(C2)CC(c2cc(Br)cc(Br)c2)(C4)C3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-befbfb3aff7c451d95620ddeb9864f61 | COC(=O)OC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>COS(=O)(=O)C(F)(F)F | FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.C(OC)(OC)=O>>FC(S(=O)(=O)OC)(F)F | COC(=O)[O:2][CH3:1].O=S(=O)(O[S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[F:9])C(F)(F)F>>[CH3:1][O:2][S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[F:9] | COC(=O)OC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | COS(=O)(=O)C(F)(F)F | null | null | null | Functional Group Interconversion | OtherReaction | c7eee99aa6a4db0f85c8ee01539c1766c880e8a5eb752d7c52b6985b7cc2ac95 | affa3e4a6c3559ef7dde83913ee2edfd339006aec4aff4f15fc4e67a7405c24a | null | C-O-C(=O)-[O;H0;D2;+0:1]-[C;D1;H3:2].F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 197.7 | [{"value": 99.1, "product": "FC(S(=O)(=O)OC)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 197.7, "product": "FC(S(=O)(=O)OC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 731 g (2.59 mol) of trifluoromethanesulfonic anhydride and 232 g (2.58 mol) of dimethyl carbonate are added to the residue, and the process described above is repeated. 837 g of methyl trifluoromethanesulfonate having a purity of greater than 99% are isolated (yield: 99.1%).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Carbonic Ester | Triflate | null | null | null | HF | null | null | null | COC(=O)OC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>COS(=O)(=O)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b47c9918eef431b95489edd655f8465 | COC(=O)OC.O=S(=O)(O)C(F)(F)C(F)(F)F>>COS(=O)(=O)C(F)(F)C(F)(F)F | FC(C(S(=O)(=O)OS(=O)(=O)C(C(F)(F)F)(F)F)(F)F)(F)F.FC(C(S(=O)(=O)O)(F)F)(F)F.C(OC)(OC)=O>>FC(C(S(=O)(=O)OC)(F)F)(F)F | COC(=O)[O:2][CH3:1].O[S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12]>>[CH3:1][O:2][S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12] | COC(=O)OC.O=S(=O)(O)C(F)(F)C(F)(F)F | COS(=O)(=O)C(F)(F)C(F)(F)F | null | null | null | Miscellaneous | O-methylation | b9f7b6257e9ebac1beb06d6909810b2c851f88e65460f2981ec997749e123746 | 761c52bfb8b165230e3488dbb93cb8a32b3c1fa80d867e8900ac6f729f1352b0 | null | C-O-C(=O)-[O;H0;D2;+0:1]-[C;D1;H3:2].O-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | 84.1 | [{"value": 84.1, "product": "FC(C(S(=O)(=O)OC)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.74 g (15.0 mmol) of pentafluoroethanesulfonic anhydride and 0.31 g (1.55 mmol) of pentafluoroethanesulfonic acid are initially introduced in a 10 ml round-necked flask. 1.35 g (15.0 mmol) of dimethyl carbonate are added at room temperature with constant stirring and reflux cooling. The solution is stirred for one hou... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Sulfonic acid | Sulfonate | null | null | null | HO- | null | null | null | COC(=O)OC.O=S(=O)(O)C(F)(F)C(F)(F)F>>COS(=O)(=O)C(F)(F)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a033b9a8a09491ca1a0fe7d07fca5cf | C=O.O=c1cc[nH]c(=O)[nH]1>>O=c1[nH]cc(CO)c(=O)[nH]1 | [OH-].[K+].Cl.NO.N1C(=O)NC(=O)C=C1.C=O>>OCC=1C(NC(NC1)=O)=O | [CH2:6]=[O:7].[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:8](=[O:9])[nH:10]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([CH2:6][OH:7])[c:8](=[O:9])[nH:10]1 | C=O.O=c1cc[nH]c(=O)[nH]1 | O=c1[nH]cc(CO)c(=O)[nH]1 | null | null | O | C-C Coupling | OtherReaction | 67448c64d4a30a61f5e502af4acf85fb4cc3d0f5db899aa52bfc35f9dce8fff1 | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | O=c1cc[nH]c(=O)[nH]1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[cH;D2;+0:9]:1>>[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 14.5 | [{"value": 14.5, "product": "OCC=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 51 | CELSIUS | 68 | HOUR | A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with uracil (185.0 g, 1650 mmol) (Aldrich), paraformaldehyde (61.50 g, 2050 mmol as formaldehyde) (Aldrich), and a solution of potassium hydroxide (86.9%, 59.95 g, 928.5 mmol) (Aldrich) in water ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | c1ccncn1 | c1cncnc1 | c1cncnc1 | null | O | 51 | 68 | C=O.O=c1cc[nH]c(=O)[nH]1>O>O=c1[nH]cc(CO)c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b16208f64b242d0b74b42e9292d9bec | ClCc1cnc(Cl)nc1Cl.[I-]>>Clc1ncc(CI)c(Cl)n1 | [I-].[Na+].ClC1=NC=C(C(=N1)Cl)CCl>>ClC1=NC=C(C(=N1)Cl)CI | Cl[CH2:6][c:5]1[cH:4][n:3][c:2]([Cl:1])[n:10][c:8]1[Cl:9].[I-:7]>>[Cl:1][c:2]1[n:3][cH:4][c:5]([CH2:6][I:7])[c:8]([Cl:9])[n:10]1 | ClCc1cnc(Cl)nc1Cl.[I-] | Clc1ncc(CI)c(Cl)n1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1cncnc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[I-;H0;D0:9]>>[Cl;D1;H0:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[I;H0;D1;+0:9] | null | [] | null | null | 20 | MINUTE | A 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler was charged with sodium iodide (38.5 g, 256.9 mmol) (Aldrich) and acetone (300 mL). After a clear solution was obtained, 2,4-dichloro-5-(chloromethyl)pyrimidine (50.0 g, 253.2 mmol) (from Example 1b supra) was added in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1cncnc1 | Other | CC(=O)C | null | 0.333333 | ClCc1cnc(Cl)nc1Cl.[I-]>CC(=O)C>Clc1ncc(CI)c(Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92a54a1510ba4d6ba7f20261138b43f7 | COc1ccc(NCc2cnc(Cl)nc2Cl)cc1>>O=C=Nc1ccccc1 | ClC1=NC=C(C(=N1)Cl)CNC1=CC=C(C=C1)OC.COC(C)(C)C>>C1(=CC=CC=C1)N=C=O | CO[c:7]1[cH:6][cH:5][c:4]([NH:3][CH2:2]c2cnc(Cl)nc2Cl)[cH:9][cH:8]1>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | COc1ccc(NCc2cnc(Cl)nc2Cl)cc1 | O=C=Nc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | a90fbba18f3c1bc73cd4f1a3c8bb6b6890ff1a91b9ea8ea56fb79329804f2821 | 25afe039fe38569e68b46e719293ced9fba9e582a85bb5b47b0291c091cc09b0 | c1ccccc1 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[CH2;D2;+0:6]-c2:c:n:c(-Cl):n:c:2-Cl):[c:7]:[c:8]:1>>[O;D1;H0:9]=[C;H0;D2;+0:6]=[N;H0;D2;+0:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:8]:[c:7]:1 | null | [] | 55 | CELSIUS | null | null | A 500-mL, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with [(2,4-dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine (59.6 g, 209.7 mmol) (from Example 1d supra) and tert-butyl methyl ether (300 mL) (Aldrich). After heating to 55° C. to give a c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Secondary amine | Isocyanate | c1ccccc1.c1cncnc1 | c1ccccc1 | c1ccccc1 | HCl | null | 55 | null | COc1ccc(NCc2cnc(Cl)nc2Cl)cc1>>O=C=Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e925202aa5c48a68b53aa693faeea25 | O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21>>O=C(F)CNC(=O)OCC1c2ccccc2-c2ccccc21 | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)NCC(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)NCC(=O)F | O[C:2](=[O:1])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[O:1]=[C:2]([F:3])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21 | O=C(F)CNC(=O)OCC1c2ccccc2-c2ccccc21 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6]>>[F;D1;H0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | 8 | HOUR | FMOC-Glycine (5.02 g, 16.82 mmol) (Bachem) was dissolved in dichloromethane (85 mL). Pyridine (1.36 mL, 16.82 mmol) (Aldrich) and cyanuric fluoride (2.27 g, 16.82 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 mL) was added and the resulting slurry... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 8 | O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21>ClCCl>O=C(F)CNC(=O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-342b75f85cff4a119a34830ad8bac12a | CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCSC)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCSC)C(=O)F | O[C:24]([C@H:5]([CH2:4][CH2:3][S:2][CH3:1])[NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21)=[O:25]>>[CH3:1][S:2][CH2:3][CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][cH... | CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 8 | HOUR | FMOC-L-Methionine (5.00 g, 13.46 mmol) (Bachem) was dissolved in dichloromethane (70 mL). Pyridine (1.09 mL, 13.46 mmol) (Aldrich) and cyanuric fluoride (1.82 g, 13.46 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 mL) was added and the resulting s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 8 | CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>ClCCl>CSCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb09cec98f6f4f36902d1ca683505650 | O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(N[C@@H](Cc1ccccc1)C(=O)F)OCC1c2ccccc2-c2ccccc21 | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CC=CC=C1)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CC=CC=C1)C(=O)F | O[C:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:15][CH2:16][CH:17]1[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[O:13]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C:12](=[O:13])[F:14])[O:15][CH2:16][CH:17]1[... | O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21 | O=C(N[C@@H](Cc1ccccc1)C(=O)F)OCC1c2ccccc2-c2ccccc21 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(NCCc1ccccc1)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 3.5 | HOUR | FMOC-L-Phenylalanine (17 g, 44 mmol) (Bachem) was dissolved in dichloromethane (100 mL). Pyridine (3.55 mL, 44 mmol) (Aldrich) and cyanuric fluoride (6 g, 44 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 3.5 hours. Ice cold water (300 mL) was added and the resulting slurry ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 3.5 | O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>ClCCl>O=C(N[C@@H](Cc1ccccc1)C(=O)F)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c73895b2c0a498e9c55ac238f8665f2 | CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC(C)C)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC(C)C)C(=O)F | O[C:24]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21)=[O:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:... | CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 8 | HOUR | FMOC-L-Leucine (5 g, 14.14 mmol) (Bachem) was dissolved in acetonitrile (70 mL). Pyridine (1.14 mL, 14.14 mmol) (Aldrich) and cyanuric fluoride (1.91 g, 14.14 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (300 mL) was added and the resulting slurry was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | null | C(C)#N | null | 8 | CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>C(C)#N>CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0b0ead597824592b4231310bdcdb388 | CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1>>CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)F)cc1 | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CC=C(C=C1)OC(C)(C)C)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CC=C(C=C1)OC(C)(C)C)C(=O)F | O[C:30]([C@H:11]([CH2:10][c:9]1[cH:8][cH:7][c:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[cH:34][cH:33]1)[NH:12][C:13](=[O:14])[O:15][CH2:16][CH:17]1[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21)=[O:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][C@H:11]([NH... | CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1 | CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)F)cc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(NCCc1ccccc1)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 5 | HOUR | N-FMOC-O-t-Butyl-L-tyrosine (5 g, 10.88 mmol) (Bachem) was dissolved in dichloromethane (50 mL). Pyridine (0.88 mL, 10.88 mmol) (Aldrich) and cyanuric fluoride (1.47 g, 10.88 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 5 hours. Ice cold water (100 mL) was added and the re... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 5 | CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1>ClCCl>CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)F)cc1 |
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