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-03ba810b7f464a06b5d8787af2e8b64e | ord-c102a456f8734650b93e4a7c443cdb74 | CCc1ccc(-c2ccc(C=O)nc2-c2ccncc2)cc1.NCCCP(=O)(O)O>>CCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccncc2)cc1 | [BH3-]C#N.[Na+].C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C=O)C1=CC=NC=C1.C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C=O)C1=CC=NC=C1.NCCCP(O)(O)=O>>C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)CNCCCP(O)(O)=O)C1=CC=NC=C1 | O=[CH:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:29][cH:28]2)[c:21](-[c:22]2[cH:23][cH:24][n:25][cH:26][cH:27]2)[n:20]1.[NH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:17])([OH:18])[OH:19]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][P:... | CCc1ccc(-c2ccc(C=O)nc2-c2ccncc2)cc1.NCCCP(=O)(O)O | CCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccncc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccncc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Following General Procedure M, 3-(4-ethyl-phenyl)-[2,4′]-bipyridinyl-6-carbaldehyde (Compound 58, 50 mg, 0.17 mmol), (3-amino-propyl)-phosphonic acid (24 mg, 0.17 mmol), Bu4NOH (0.17 ml, 0.17 mmol, 1 M in MeOH) and NaCNBH3 (11 mg, 0.17 mmol) in MeOH (3 ml) were reacted to produce the title compound as a white solid.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | Other | CO | null | null | CCc1ccc(-c2ccc(C=O)nc2-c2ccncc2)cc1.NCCCP(=O)(O)O>CO>CCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccncc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fb5a8aadbc52484ba89b37b93942889d | CCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCCP(=O)(O)O>>CCc1ccc(-c2ccc(CNCCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | [BH3-]C#N.[Na+].C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O.C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O.NCCCCP(O)(O)=O>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)CNCCCCP(O)(O)=O | O=[CH:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:30][cH:29]2)[c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:21]1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([OH:19])[OH:20]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH2:11][NH:12][CH2:13][CH2:14][C... | CCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCCP(=O)(O)O | CCc1ccc(-c2ccc(CNCCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Following General Procedure M, 5-(4-ethyl-phenyl)-6-phenyl-pyridine-2-carbaldehyde (Compound 56, 58 mg, 0.18 mmol), 4-aminobutylphosphonic acid (21 mg, 0.18 mmol), Bu4NOH (0.18 ml, 0.18 mmol, 1 M in MeOH) and NaCNBH3 (9 mg, 0.18 mmol) in MeOH (2 ml) were reacted to produce the title compound as a white solid.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | CO | null | null | CCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCCP(=O)(O)O>CO>CCc1ccc(-c2ccc(CNCCCCP(=O)(O)O)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7379c5469345430caa35630f18548b1c | CCCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O>>CCCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | [BH3-]C#N.[Na+].C1(=CC=CC=C1)C1=C(C=CC(=N1)C=O)C1=CC=C(C=C1)CCC.C1(=CC=CC=C1)C1=C(C=CC(=N1)C=O)C1=CC=C(C=C1)CCC.NCCCP(O)(O)=O>>C1(=CC=CC=C1)C1=C(C=CC(=N1)CNCCCP(O)(O)=O)C1=CC=C(C=C1)CCC | O=[CH:12][c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][c:4]([CH2:3][CH2:2][CH3:1])[cH:30][cH:29]2)[c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:21]1.[NH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([OH:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH2:12][NH:13][CH2:14][C... | CCCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O | CCCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Following General Procedure M, 6-phenyl-5-(4-propylphenyl)pyridine-2-carbaldehyde (Compound 59, 74 mg, 0.25 mmol), (3-amino-propyl)phosphonic acid (34 mg, 0.25 mmol), Bu4NOH (0.25 ml, 0.25 mmol, 1M in MeOH) and NaCNBH3 (15 mg, 0.25 mmol) in MeOH (5 ml) were reacted to produce the title compound as a white solid.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | CO | null | null | CCCc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O>CO>CCCc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7e670b67f02e4d5097bc1e3d32aa9157 | CCOP(=O)(CCCOCc1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1)OCC>>CCc1ccc(-c2ccc(COCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | C(C)OP(OCC)(=O)CCCOCC1=NC(=C(C=C1)C1=CC=C(C=C1)CC)C1=CC=CC=C1.[Si](C)(C)(C)I>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)COCCCP(O)(O)=O | CC[O:18][P:16]([CH2:15][CH2:14][CH2:13][O:12][CH2:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:29][cH:28]2)[c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[n:20]1)(=[O:17])[O:19]CC>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH2:11][O:12][CH2:13][CH2:14][CH2:15][P:16... | CCOP(=O)(CCCOCc1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1)OCC | CCc1ccc(-c2ccc(COCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | null | null | C(Cl)(Cl)Cl | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | null | [] | null | null | 1 | HOUR | To a solution of crude {3-[5-(4-ethyl-phenyl)-6-phenyl-pyridin-2-ylmethoxy]-propyl}-phosphonic acid diethyl ester (18 mg, 0.039 mmol) in CHCl3 (2 ml) at room temperature was added TMSI (77 mg, 0.39 mmol) dropwise. After the mixture was stirred for 1 hour, the solvent was removed in vacuo to recover a yellow oily residu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | C(Cl)(Cl)Cl | null | 1 | CCOP(=O)(CCCOCc1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1)OCC>C(Cl)(Cl)Cl>CCc1ccc(-c2ccc(COCCCP(=O)(O)O)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a2896fc6ab234e46af24b98823239a8b | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>>CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.CNCCNC.C[Al](C)C>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=O | CCO[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 600d91131af1bb1ee8c20c567e56234839eb0602aa06d3adc0666216769f9a6a | ebe855e3c62a5d82c9c1d005e3b3e8a9e3b63aca37bc8a601a136cf86007489d | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[C;D1;H3:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | 112 | CELSIUS | null | null | General Procedure O. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 246 mg, 0.81 mmol) in toluene (5 ml) was added N,N′-dimethylethylenediamine (DMEDA, 78.7 mg, 0.89 mmol) and trimethylaluminum (1.2 ml, 2.44 mmol, 2 M in toluene) dropwise under argon at room temperature. After the mixture was r... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 112 | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>C1(=CC=CC=C1)C>CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-17477629f93f4d5e92fb9a72fe881df8 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>>CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C(C)[Al](CC)CC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.CNCCNC>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=O | CCO[C:3](=[O:4])[c:5]1[cH:6][cH:7][c: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)[n:22]1.C[CH2][Al]([CH2]C)[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:... | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C | CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].C-[CH2]-[Al](-[CH2;D2;+0:7]-[C;D1;H3:8])-[CH2]-C>>[C;D1;H3:8]-[CH2;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure O, ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 267 mg, 0.81 mmol) in toluene (5 ml), N,N′-dimethylethylenediamine (DMEDA, 85 mg, 0.97 mmol) and triethylaluminum (2.6 ml, 2.64 mmol, 1 M in hexane) were reacted to give the title compound as a yellow solid.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>C1(=CC=CC=C1)C>CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f6180a6a9d6c4c78af7473d6405c1164 | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | C[Al](C)C.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C.CNCCNC>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(C)=O)C1=CC=C(C=C1)C(F)(F)F | CCO[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][cH:21][c... | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 600d91131af1bb1ee8c20c567e56234839eb0602aa06d3adc0666216769f9a6a | ebe855e3c62a5d82c9c1d005e3b3e8a9e3b63aca37bc8a601a136cf86007489d | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[C;D1;H3:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure O, 6-phenyl-5-(4-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid ethyl ester (Compound 25, 49 mg, 0.13 mmol) in toluene (3 ml), N,N′-dimethylethylenediamine (DMEDA, 13 mg, 0.15 mmol) and trimethylaluminum (0.2 ml, 2.64 mmol, 2 M in toluene) were reacted to produce the title compound as a ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-67de139c15fd488b96d4fe1acdce8dbf | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>>CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | C(C)[Al](CC)CC.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.CNCCNC>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(CC)=O)C1=CC=C(C=C1)C(F)(F)F | CCO[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:26]1.C[CH2][Al]([CH2]C)[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:1... | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C | CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].C-[CH2]-[Al](-[CH2;D2;+0:7]-[C;D1;H3:8])-[CH2]-C>>[C;D1;H3:8]-[CH2;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure O, 6-phenyl-5-(4-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid ethyl ester (Compound 25, 94 mg, 0.25 mmol) in toluene (3 ml), N,N′-dimethylethylenediamine (DMEDA, 25 mg, 0.28 mmol) and triethylaluminum (0.7 ml, 0.76 mmol, 1 M in hexane) were reacted to produce the title compound as a oi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>C1(=CC=CC=C1)C>CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fec3f79e1b134d3c9cf24eaca51232e1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.C[CH2][Al]([CH2]C)[CH2]C>>CCC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | C(C)[Al](CC)CC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.CNCCNC>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(CC)=O | CCO[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[n:26]1.C[CH2][Al]([CH2]C)[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH... | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.C[CH2][Al]([CH2]C)[CH2]C | CCC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].C-[CH2]-[Al](-[CH2;D2;+0:7]-[C;D1;H3:8])-[CH2]-C>>[C;D1;H3:8]-[CH2;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure O, 5-phenyl-6-(4-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid ethyl ester (Compound 29, 292 mg, 0.71 mmol) in toluene (5 ml), N,N′-dimethylethylenediamine (DMEDA, 76 mg, 0.86 mmol) and triethylaluminum (2.4 ml, 0.35 mmol, 1 M in hexane) were reacted to produce the title compound as a o... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.C[CH2][Al]([CH2]C)[CH2]C>C1(=CC=CC=C1)C>CCC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-30773829ed824d39bbfeeac19693c48b | CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO>>CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=O.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=O.NO.Cl.N1=CC=CC=C1>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=NO | O=[C:2]([CH3:1])[c:5]1[cH:6][cH:7][c: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)[n:22]1.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[cH:6][cH:7][c: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)[n:22]1 | CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO | CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | 70 | CELSIUS | null | null | General Procedure P. 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone (Compound 75, 119 mg, 0.44 mmol), NH2OH—HCl (103 mg, 1.48 mmol) and pyridine (272 mg, 0.27 mmol) was dissolved in EtOH (2 ml), and the mixture was heated to 70° C. under nitrogen for 3 hours. The reaction was quenched with water, and the product was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CCO | 70 | null | CC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO>CCO>CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-de35d10a8fda445dbd46ff8369b0ab92 | CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO>>CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | N1=CC=CC=C1.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=O.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=O.NO.Cl>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=NO | O=[C:3]([CH2:2][CH3:1])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1.[NH2:4][OH:5]>>[CH3:1][CH2:2][C:3](=[N:4][OH:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2... | CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO | CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[C;D1;H3:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[O;D1;H1:9])-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | Following General Procedure P, 1-(5,6-diphenyl-pyridin-2-yl)-propan-1-one (Compound 76, 90 mg, 0.31 mmol), NH2OH—HCl (87 mg, 1.25 mmol) and pyridine (272 mg, 0.27 mmol) in EtOH (2 ml) were reacted to give title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CCO | null | null | CCC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.NO>CCO>CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ac7e8f852d0443e7b1a6cf595f6c716d | CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI>>CON=C(C)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | CI.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=NO.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(C)=NO.[H-].[Na+]>>CON=C(C)C1=NC(=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 | [OH:2][N:3]=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1.I[CH3:1]>>[CH3:1][O:2][N:3]=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n... | CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI | CON=C(C)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | O-methylation | 55a958662c85c87fbe67d0f10232bc5e23f08b6ecd3a346a539faba050fc0479 | ef919e2263e6992d2ffe563d7821469ee84548538554e35a1fd6a88d710019da | c1ccc(-c2cccnc2-c2ccccc2)cc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])=[#7:6]-[OH;D1;+0:7]>>[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])=[#7:6]-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | null | [] | null | null | 1 | HOUR | General Procedure Q. To a suspension of NaH (20 mg, 0.80 mmol) in THF (2 ml) at 0° C. was added a solution of 1-(5,6-diphenyl-pyridin-2-yl)-ethanone oxime (Compound 80, 46 mg, 0.16 mmol) in THF (1 ml). After the mixture was stirred at the same temperature for 1 hour, MeI (140 mg, 0.99 mmol) was added and the solution w... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HI | C1CCOC1 | null | 1 | CC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI>C1CCOC1>CON=C(C)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d523504399db40809f5e980e4e1ea47f | CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI>>CCC(=NOC)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | CI.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=NO.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(CC)=NO.[H-].[Na+]>>CON=C(CC)C1=NC(=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][C:3](=[N:4][OH:5])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1.I[CH3:6]>>[CH3:1][CH2:2][C:3](=[N:4][O:5][CH3:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][c... | CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI | CCC(=NOC)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | O-methylation | 55a958662c85c87fbe67d0f10232bc5e23f08b6ecd3a346a539faba050fc0479 | ef919e2263e6992d2ffe563d7821469ee84548538554e35a1fd6a88d710019da | c1ccc(-c2cccnc2-c2ccccc2)cc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4](-[C:5])=[#7:6]-[OH;D1;+0:7]>>[#7;a:2]:[c:3]-[C:4](-[C:5])=[#7:6]-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure Q, 1-(5,6-diphenyl-pyridin-2-yl)-propan-1-one oxime (Compound 81, 30 mg, 0.1 mmol), NaH (4.8 mg, 0.20 mmol) and MeI (140 mg, 0.99 mmol) in THF were reacted to obtain the title compound as an oil.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HI | C1CCOC1 | null | null | CCC(=NO)c1ccc(-c2ccccc2)c(-c2ccccc2)n1.CI>C1CCOC1>CCC(=NOC)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-abe31fa958a347139df4202b303ff838 | CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON>>CON=C(C)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | N1=CC=CC=C1.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(C)=O)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(C)=O)C1=CC=C(C=C1)C(F)(F)F.NOC.Cl>>CON=C(C)C1=NC(=C(C=C1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1 | O=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[n:27]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:... | CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON | CON=C(C)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[#8:8]-[NH2;D1;+0:9]>>[C;D1;H3:7]-[#8:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure P, 1-[6-phenyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-ethanone (Compound 77, 15 mg, 0.04 mmol), NH2OMe—HCl (15 mg, 0.18 mmol) and pyridine (14 mg, 0.18 mmol) in EtOH (2 ml) were reacted to give title compound as a white solid. (12 mg, 75%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CCO | null | null | CC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON>CCO>CON=C(C)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-28bcb12bc8624d6c93962d8249bed849 | CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON>>CCC(=NOC)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | N1=CC=CC=C1.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(CC)=O)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(CC)=O)C1=CC=C(C=C1)C(F)(F)F.NOC.Cl>>CON=C(CC)C1=NC(=C(C=C1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1 | O=[C:3]([CH2:2][CH3:1])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]2)[c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[n:28]1.[NH2:4][O:5][CH3:6]>>[CH3:1][CH2:2][C:3](=[N:4][O:5][CH3:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F... | CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON | CCC(=NOC)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C;D1;H3:8]-[#8:9]-[NH2;D1;+0:10]>>[C;D1;H3:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:10]-[#8:9]-[C;D1;H3:8])-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | Following General Procedure P, 1-[6-phenyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-propan-1-one (Compound 78), (24 mg, 0.07 mmol), NH2OMe—HCl (23 mg, 0.25 mmol) and pyridine (21 mg, 0.28 mmol) in EtOH (2 ml) were reacted to give title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Worku... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CCO | null | null | CCC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CON>CCO>CCC(=NOC)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b001ef4de7204123bc89d9ca3f7063f6 | CCOC(=O)CC(C)=O.CS(=O)(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1>>CCOC(=O)Cc1nnc(-c2ccccc2)c(-c2ccccc2)n1 | CS(=O)(=O)C=1N=NC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1.C(CC(=O)C)(=O)OCC.[H-].[Na+].CS(=O)(=O)C=1N=NC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=CC=C1)CC(=O)OCC | C[C:7](=O)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CS(=O)(=O)c1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20... | CCOC(=O)CC(C)=O.CS(=O)(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1 | CCOC(=O)Cc1nnc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 026446767b3ad98dac8127d659c99abccf6914e71f6dd739175361cefe9cedfa | 6ca2e43767575720fec611cebbde4fe6c2ff08dacc229db2124c80e05bc2bb69 | c1ccc(-c2ncnnc2-c2ccccc2)cc1 | C-S(=O)(=O)-c1:[n;H0;D2;+0:1]:[c:2](-[c:3]):[c:4](-[c:5]):[#7;a:6]:[n;H0;D2;+0:7]:1.C-[C;H0;D3;+0:8](=O)-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C:9]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:1]:[c:2](-[c:3]):[c:4](-[c:5]):[#7;a:6]:[n;H0;D2;+0:7]:1 | null | [] | 60 | CELSIUS | 15 | MINUTE | To a suspension of NaH (41 mg, 1.61 mmol) in THF (2 ml) at 0° C. was added ethyl acetoacetate (105 mg. 0.80 mmol) dropwise. After the mixture was stirred for 15 min, a solution of 3-(methylsulfonyl)-5,6-diphenyl-1,2,4-triazine (Compound 87) (250 mg, 0.80 mmol) in THF (3 ml) was cannulated into the solution, and the res... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfone | null | c1cnncn1 | c1cnncn1 | c1cnncn1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | 60 | 0.25 | CCOC(=O)CC(C)=O.CS(=O)(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1>C1CCOC1>CCOC(=O)Cc1nnc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-43af859442634bd7bb2952e0d4381809 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>>O=C(O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | Cl.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.[Li+].[OH-]>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | O=C(O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 40 mg, 0.13 mmol) and LiOH (1N, 1 ml) in EtOH (2 ml) was stirred at room temperature overnight. The mixture was acidified with 10% HCl, then extracted with EtOAc. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | CCO | null | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>CCO>O=C(O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-46ee8680c7cf4c3cbfe56f6085e9b6e3 | CI.OCc1ccc(-c2ccccc2)c(-c2ccccc2)n1>>COCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)CO.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)CO.CI.C(=O)([O-])[O-].[K+].[K+]>>COCC1=CC=C(C(=N1)C1=CC=CC=C1)C1=CC=CC=C1 | I[CH3:1].[OH:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1 | CI.OCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | COCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | [OH-].[K+] | CC(=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31b37b19ff6de58cf584e89bae19f862b01d058b473835fea10bbd4c0a53fd14 | f3e76c16e7df5a83f618c93f8745117d548e410efce45e89753f2c180a9b20f8 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4]-[OH;D1;+0:5]>>[#7;a:2]:[c:3]-[C:4]-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | null | null | A solution of 5,6-diphenylpyridin-2-yl)methanol (Compound 90, 15 mg, 0.06 mmol), MeI (0.1 ml), K2CO3 (50 mg) and KOH (5N, 5 drops) in acetone was heated at 56° C. over night. The mixture was diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with water, and brine, and drie... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HI | [OH-].[K+].CC(=O)C.O | null | null | CI.OCc1ccc(-c2ccccc2)c(-c2ccccc2)n1>[OH-].[K+].CC(=O)C.O>COCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a4b8b340cd66468184e61d265b7d3439 | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1>>CC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | CNCCNC.C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(=O)OC.C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(=O)OC.C[Al](C)C>>C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(C)=O | CO[C:2](=[O:3])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1.CO[C:1](=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]... | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | CC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 9fdfa388309313f8e4120c3f928f8754279dc1088f67d069c68e51a073cc36e3 | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccc(-c2nccnc2-c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=O)-c1:c:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c:c:c:2):n:1.C-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | null | null | Following General Procedure O, methyl 5,6-diphenyl-pyrazine-2-carboxylate (Compound 93, 83 mg, 0.29 mmol), Me3Al (0.4 ml, 2M in toluene), DMEDA (28 mg, 0.32 mmol) in toluene was reacted to afford the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | c1cnccn1.c1ccccc1.c1ccccc1 | null | c1cnccn1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1>C1(=CC=CC=C1)C>CC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c266ff78267141f78cd7efceb38cee8f | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>>CCC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | CNCCNC.C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(=O)OC.C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(=O)OC.[Al](CC)(CC)CC>>C1(=CC=CC=C1)C=1N=CC(=NC1C1=CC=CC=C1)C(CC)=O | CO[C:3](=[O:4])[c:5]1[cH:6][n:7][c: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)[n:22]1.O=C(O[CH3:1])c1cnc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2:2]C>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:1... | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C | CCC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 9fdfa388309313f8e4120c3f928f8754279dc1088f67d069c68e51a073cc36e3 | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccc(-c2nccnc2-c2ccccc2)cc1 | C-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-[CH2;D2;+0:9]-[Al](-[CH2]-C)-[CH2]-C.O=C(-O-[CH3;D1;+0:10])-c1:c:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c:c:c:2):n:1>>[CH3;D1;+0:10]-[CH2;D2;+0:9]-[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 | null | [] | null | null | null | null | Following General Procedure O, methyl 5,6-diphenyl-pyrazine-2-carboxylate (Compound 93) (92 mg, 0.32 mmol), Et3Al (0.9 ml, 1M in hexane), DMEDA (38 mg, 0.35 mmol) in toluene was reacted to afford the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | c1cnccn1.c1ccccc1.c1ccccc1 | null | c1cnccn1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.COC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.C[CH2][Al]([CH2]C)[CH2]C>C1(=CC=CC=C1)C>CCC(=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8e50eceeef0549698f541ac6041518dd | CCOC=O.O=C(Cc1ccccc1)c1ccccc1>>O=C/C(=C(\O)c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(=O)CC1=CC=CC=C1.CC[O-].[Na+].C(=O)OCC>>O\C(=C(/C=O)\C1=CC=CC=C1)\C1=CC=CC=C1 | CCO[CH:2]=[O:1].[CH2:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[CH:2]/[C:3](=[C:4](\[OH:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCOC=O.O=C(Cc1ccccc1)c1ccccc1 | O=C/C(=C(\O)c1ccccc1)c1ccccc1 | null | null | CCO | Acylation | OtherReaction | 0ef67d86b040e78d13b70db2b85ac1c00a4d4b6c654852a8e45afda7c96e0d1a | a345e9bf8e1f1f6d52ec18102328e7026bec90f2739fbd94a4946f078111d416 | C(=Cc1ccccc1)c1ccccc1 | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].[O;H0;D1;+0:3]=[C;H0;D3;+0:4](-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[CH;D2;+0:1]/[C;H0;D3;+0:5](=[C;H0;D3;+0:4](\[OH;D1;+0:3])-[c:9](:[c:10]):[c:11])-[c:6](:[c:7]):[c:8] | null | [] | 2.5 | CELSIUS | 3 | HOUR | To a cooled solution of NaOEt (763 mg, 11.21 mmol) in EtOH (100 ml) was added ethyl formate (0.91 ml, 11.21 mmol) dropwise. The resulting mixture is allowed to stand for 3 hours at 0 to 5° C., and then deoxybenzoin (2 g, 10.19 mmol) was added. The mixture was stirred for 2 hours at 0 to 5° C. and then placed in the ref... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aldehyde.Enol | null | null | c1ccccc1.c1ccccc1 | HO- | CCO | 2.5 | 3 | CCOC=O.O=C(Cc1ccccc1)c1ccccc1>CCO>O=C/C(=C(\O)c1ccccc1)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-14f27c1bba5a4c2dbfbfd7cb6108016d | CNC(N)=O.O=C/C(=C(\O)c1ccccc1)c1ccccc1>>Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O | O\C(=C(/C=O)\C1=CC=CC=C1)\C1=CC=CC=C1.CC=1C=CC(=CC1)S(=O)(=O)O.CNC(=O)N.C(C)OCC>>CN1C(N=CC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | [CH3:1][NH:2][C:19]([NH2:18])=[O:20].O=[CH:17]/[C:10](=[C:3](\O)[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][n:18][c:19]1=[O:20] | CNC(N)=O.O=C/C(=C(\O)c1ccccc1)c1ccccc1 | Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O | null | null | C(Cl)Cl.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 6b4bff70fd8e55a5d3cf9cb5511092a4f2e593ddb37e580c46dc5298bd7aacc0 | 865fdf6833dbea4f5bfdc2b65ba54b54264eb5bc3a40bdb22b7886cb29acfe90 | O=c1ncc(-c2ccccc2)c(-c2ccccc2)[nH]1 | O/[C;H0;D3;+0:1](=[C;H0;D3;+0:2](\[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13].[C;D1;H3:14]-[NH;D2;+0:15]-[C;H0;D3;+0:16](-[NH2;D1;+0:17])=[O;D1;H0:18]>>[C;D1;H3:14]-[n;H0;D3;+0:15]1:[c;H0;D3;+0:16](=[O;D1;H0:18]):[n;H0;D2;+0:17]:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;... | null | [] | null | null | null | null | A solution of (Z)-3-hydroxy-2,3-diphenyl-propenal (105, 423 mg, 1.89 mmol), pTSA (30 mg, 7.56 mmol) and methyl urea (118 mg, 0.62 mmol) in toluene was heated at 110° C. overnight. The reaction was quenched with water, and the products were extracted with ethyl acetate. The organic layer was separated and washed with br... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Urea.Enol | null | null | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1(=CC=CC=C1)C | null | null | CNC(N)=O.O=C/C(=C(\O)c1ccccc1)c1ccccc1>C(Cl)Cl.C1(=CC=CC=C1)C>Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c92f9d8542fc4ac49029ecc678997a58 | Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O.O=P(Cl)(Cl)Cl>>Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1 | CN1C(N=CC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O.P(=O)(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl>>ClC1=NC=C(C(=N1)C1=CC=CC=C1)C1=CC=CC=C1 | C[n:19]1[c:2](=O)[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1-[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O=P(Cl)(Cl)[Cl:1]>>[Cl:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19]1 | Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O.O=P(Cl)(Cl)Cl | Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | null | Functional Group Interconversion | OtherReaction | b0bb6940bdaa4f483f95617a9ee5e6563c160ea710db3fde10ee056459a3fce1 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cncnc2-c2ccccc2)cc1 | C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:1=O.Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:8]>>[Cl;H0;D1;+0:8]-[c;H0;D3;+0:7]1:[#7;a:6]:[c:5]:[c:4]:[c:2](-[c:3]):[n;H0;D2;+0:1]:1 | null | [] | null | null | null | null | A solution of 1-methyl-5,6-diphenyl-1H-pyrimidin-2-one (106, 314 mg, 1.20 mmol), phosphorus oxychloride (0.6 ml, 6.4 mmol) and phosphorus pentachloride (55 mg, 0.26 mmol) was heated at 120° C. for 3 hours. The excess amount of phosphorus oxychloride was removed under reduced pressure and cold water was added to the res... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Cn1c(-c2ccccc2)c(-c2ccccc2)cnc1=O.O=P(Cl)(Cl)Cl>>Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9bea9c85f39b4b5ab7219d457a1b1a99 | CO.Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1>>COC(=O)c1ncc(-c2ccccc2)c(-c2ccccc2)n1 | ClC1=NC=C(C(=N1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[Na+].CO>>C1(=CC=CC=C1)C1=NC(=NC=C1C1=CC=CC=C1)C(=O)OC | [CH3:1][OH:2].Cl[c:5]1[n:6][cH:7][c: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)[n:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c: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)[n:22]1 | CO.Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1 | COC(=O)c1ncc(-c2ccccc2)c(-c2ccccc2)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2] | C1CCOC1 | Acylation | OtherReaction | a2490654381426cb2c79ae9d2777b6a7896105056e33f18573fd9560981588cb | 77e754c2ed5662eb6ce8d94c1d0ccef9863e2f2080e3b99b865c7cb1489d8854 | c1ccc(-c2cncnc2-c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 110 | CELSIUS | null | null | A solution of 2-chloro-4,5-diphenyl-pyrimidine (107, 203 mg, 0.76 mmol) and sodium acetate (188 mg, 2.21 mmol) in MeOH (6 ml) and THF (2 ml) was degassed under argon for 10 min. Pd(OAc)2 (2.1 mg) and DPPF (13 mg) were added and CO (g) was bubbled through the solution. The reaction was heated to 110° C. in a sealed tube... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ester | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].C1CCOC1 | 110 | null | CO.Clc1ncc(-c2ccccc2)c(-c2ccccc2)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].C1CCOC1>COC(=O)c1ncc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-91fe98f3a159420ea2965d62c2c78fad | CC(C)c1ccc(/C=C/CO)cc1>>CC(C)c1ccc(/C=C/C=O)cc1 | C(C)(C)C1=CC=C(C=C1)/C=C/CO.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)N(CC)CC.C(C)(C)C1=CC=C(C=C1)/C=C/CO>>C(C)(C)C1=CC=C(C=C1)/C=C/C=O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](/[CH:8]=[CH:9]/[CH2:10][OH:11])[cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](/[CH:8]=[CH:9]/[CH:10]=[O:11])[cH:12][cH:13]1 | CC(C)c1ccc(/C=C/CO)cc1 | CC(C)c1ccc(/C=C/C=O)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Following General Procedure H, oxalyl chloride (9.5 ml, 19.0 mmol, 2M in CH2Cl2), DMSO (1.8 ml, 25.3 mmol), (E)-3-(4-isopropylphenyl)prop-2-en-1-ol (Compound 109, 2.2 g, 12.6 mmol) and triethylamine (7.1 ml, 50.7 mmol) in CH2Cl2 (100 ml) were reacted to obtain the title compound as an oil.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)c1ccc(/C=C/CO)cc1>C(Cl)Cl>CC(C)c1ccc(/C=C/C=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-592b442687364ab1abccb3c7162513dc | CC(C)c1ccc(/C=C/C=O)cc1.CCOC(=O)CN=[N+]=[N-]>>COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-] | C[O-].[Na+].C(C)(C)C1=CC=C(C=C1)/C=C/C=O.C(C)(C)C1=CC=C(C=C1)/C=C/C=O.N(=[N+]=[N-])CC(=O)OCC>>N(=[N+]=[N-])\C(\C(=O)OC)=C/C=C/C1=CC=C(C=C1)C(C)C | O=[CH:6]/[CH:7]=[CH:8]/[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.C[CH2:1][O:2][C:3](=[O:4])[CH2:5][N:18]=[N+:19]=[N-:20]>>[CH3:1][O:2][C:3](=[O:4])/[C:5](=[CH:6]/[CH:7]=[CH:8]/[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1)[N:18]=[N+:19]=[N-:20] | CC(C)c1ccc(/C=C/C=O)cc1.CCOC(=O)CN=[N+]=[N-] | COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-] | null | null | CO | C-C Coupling | OtherReaction | 96b579ff44c0fff4089c750910104cf990e0a287e373b67fd8e70fc60e740467 | 5d53f2f0eebc91d0a27a3fff71d2085564fbedea85248d599c79f507c8d10a9e | c1ccccc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[#7:6]=[#7;+:7]=[N;-;D1;H0:8].O=[CH;D2;+0:9]/[C:10]=[C:11]/[c:12](:[c:13]):[c:14]>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C;H0;D3;+0:5](-[#7:6]=[#7;+:7]=[N;-;D1;H0:8])=[CH;D2;+0:9]/[C:10]=[C:11]/[c:12](:[c:13]):[c:14] | null | [] | null | null | null | null | Following General Procedure I, a 1.34 M solution of NaOMe in methanol (30 ml), (E)-3-(4-isopropylphenyl)acrylaldehyde (Compound 110, 1.4 g, 8.0 mmol) and ethyl azidoacetate (12 ml, 40.2 mmol) in MeOH (20 ml) were reacted to produce the title compound as a solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Conjugated diene | null | null | c1ccccc1 | HO- | CO | null | null | CC(C)c1ccc(/C=C/C=O)cc1.CCOC(=O)CN=[N+]=[N-]>CO>COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cabc5176c2064bd9a315e20982598b5e | COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=[N+]=[N-])\C(\C(=O)OC)=C/C=C/C1=CC=C(C=C1)C(C)C.N(=[N+]=[N-])\C(\C(=O)OC)=C/C=C/C1=CC=C(C=C1)C(C)C>>COC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)C(C)C | [N-]=[N+]=[N:18]/[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6]\[CH:7]=[CH:8]\[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.[P:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][... | COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | ccc2663030541127fcaca4e5acedd9f2784c38c6800cb643e7bb4815d3139521 | fbd691a01e95e68b66bf8b0666f72e0c6d7102c3827b8153721b6e3b4f7ca6d9 | C(C=Cc1ccccc1)=CN=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C:5](=[C:6]/[C:7]=[C:8]/[c:9])-[N;H0;D2;+0:10]=[N+]=[N-].[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[C:7]=[C:8]-[c:9])-[N;H0;D2;+0:10]=[P;H0;D4;+0:13](-[c:12](:[c:11]):[c:20])(-[c:14]... | null | [] | null | null | null | null | Following General Procedure J, triphenylphosphine (1.4 g, 5.2 mmol), methyl (2Z,4E)-2-azido-5-(4-isopropylphenyl)penta-2,4-dienoate (Compound 111, 1.4 g, 5.2 mmol) in diethyl ether (50 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacte... | 10.6084/m9.figshare.5104873.v1 | null | Azide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)OCC | null | null | COC(=O)/C(=C/C=C/c1ccc(C(C)C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)OCC>COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a03d48d4ac1048bd95386f3dae143d76 | COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1>>COC(=O)c1ccc(-c2ccc(C(C)C)cc2)c(-c2ccccc2)n1 | C(C1=CC=CC=C1)=O.COC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)C(C)C.COC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)C(C)C>>C(C)(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OC | c1ccc(P(c2ccccc2)(c2ccccc2)=[N:25][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=[CH:8][c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]2)cc1.O=[CH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:... | COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1 | COC(=O)c1ccc(-c2ccc(C(C)C)cc2)c(-c2ccccc2)n1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 02f0f968b0b9e802ed3422aadb999224491a6d9de2a1d809a485b6b3f5f050b2 | 68e49bad39abe3d5621e12b41ee11e354e282b66589572f30d80e0f4c6de6ee3 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19])-[N;H0;D2;+0:20]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+... | null | [] | null | null | null | null | Following General Procedure K, Benzaldehyde (0.48 g, 4.6 mmol) and 3-Methoxycarbonyl-1,1,1-triphenyl-6-(4-isopropylphenyl)-2-aza-1λ5-phosphahexa-1,3,5-triene (Compound 112, 2.3 g, 4.6 mmol) in dry acetonitrile (100 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Conjugated diene | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(C)#N | null | null | COC(=O)C(=CC=Cc1ccc(C(C)C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1>C(C)#N>COC(=O)c1ccc(-c2ccc(C(C)C)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6657e0aca0cb44d894f6e71979dee592 | COC(OC)N(C)C.Cc1ccc(CC(=O)c2ccccc2)cc1>>Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1 | C1(=CC=CC=C1)C(CC1=CC=C(C=C1)C)=O.COC(N(C)C)OC>>CN(/C=C(/C(=O)C1=CC=CC=C1)\C1=CC=C(C=C1)C)C | CO[CH:7](OC)[N:8]([CH3:9])[CH3:10].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](/[C:6](=[CH:7]\[N:8]([CH3:9])[CH3:10])[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | COC(OC)N(C)C.Cc1ccc(CC(=O)c2ccccc2)cc1 | Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | [CH]=C(C(=O)c1ccccc1)c1ccccc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])/[CH;D2;+0:1]=[C;H0;D3;+0:8](/[C:6](=[O;D1;H0:5])-[c:7])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | A solution of 1-phenyl-2-p-tolylethanone (2 g, 9.5 mmol) and dimethylformamide dimethylacetal (4.5 g, 38.1 mmol) in DMF (30 ml) was heated at 75° C. for 24 hours. Solvents were removed under high vacuum to obtain the title compound as a yellow oil, which was used directly in the next step without purification.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | COC(OC)N(C)C.Cc1ccc(CC(=O)c2ccccc2)cc1>CN(C)C=O>Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-40e5d926e818402a9e42f4951eaccddd | Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1.N#CCC(N)=O>>Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1 | CN(/C=C(/C(=O)C1=CC=CC=C1)\C1=CC=C(C=C1)C)C.CN(/C=C(/C(=O)C1=CC=CC=C1)\C1=CC=C(C=C1)C)C.C(#N)CC(=O)N.CO.[H-].[Na+]>>OC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C | CN(C)/[CH:7]=[C:6](\[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)[C:14](=O)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH2:8]([C:9]#[N:10])[C:11](=[O:12])[NH2:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([OH:12])[n:13][c:14]2-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1 | Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1.N#CCC(N)=O | Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 9f4795aece256b0763579a92be80f95c9dcec21375df61b8e39ecff673ba2e4f | 1fbddadc9330a1c5cd980810820275587b091a426cc8f9c7758c83e21079d55a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-N(-C)/[CH;D2;+0:1]=[C;H0;D3;+0:2](/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13].[N;D1;H0:14]#[C:15]-[CH2;D2;+0:16]-[C;H0;D3;+0:17](-[NH2;D1;+0:18])=[O;H0;D1;+0:19]>>[N;D1;H0:14]#[C:15]-[c;H0;D3;+0:16]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:9](:[c:10]:[c:... | null | [] | 95 | CELSIUS | null | null | A solution of (E)-3-(dimethylamino)-1-phenyl-2-p-tolylprop-2-en-1-one (Compound 113, 500 mg, 1.9 mmol), cyanoacetamide (175 mg, 2.1 mmol) and MeOH (0.2 ml, 2.2 mmol) in DMF (4 ml) was cannulated into a suspension of NaH (119 mg, 4.7 mmol, 95% in mineral oil) in DMF (2 ml) at room temperature. After the addition was com... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amide | Aromatic alcohol | null | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | CN(C)C=O | 95 | null | Cc1ccc(/C(=C\N(C)C)C(=O)c2ccccc2)cc1.N#CCC(N)=O>CN(C)C=O>Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c9aa8d926b9e4d48be5d60afa1a929ff | Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1.O=P(Cl)(Cl)Cl>>Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1 | OC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C.OC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C.O=P(Cl)(Cl)Cl>>ClC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C | O[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:13]1.O=P(Cl)(Cl)[Cl:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([Cl:12])[n:13][c:14]2-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1 | Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1.O=P(Cl)(Cl)Cl | Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8] | null | [] | null | null | null | null | A solution of 2-hydroxy-6-phenyl-5-p-tolylnicotinonitrile (Compound 114, 528 mg, 1.9 mmol) in POCl3 (5 ml) was heated to 110° C. overnight. POCl3 was removed and the residue was purified by MPLC column chromatography (silica gel, 10% ethyl acetate in hexane) to obtain the title compound as an oil-foam.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | null | null | null | Cc1ccc(-c2cc(C#N)c(O)nc2-c2ccccc2)cc1.O=P(Cl)(Cl)Cl>>Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e4e6c63a3c704d84b663b5daf5e4cb4e | C1COCCN1.Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1>>Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1 | ClC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C.ClC1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C.N1CCOCC1>>O1CCN(CC1)C1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C | [NH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.Cl[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[n:18... | C1COCCN1.Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1 | Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2ccc(N3CCOCC3)nc2-c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | A solution of 2-chloro-6-phenyl-5-p-tolylnicotinonitrile (Compound 115, 124 mg, 0.4 mmol) and morpholine (36 mg, 0.4 mmol) in DMF (2 ml) was heated at 150° C. for 2 hours. The solvents was removed and the residue was purified by MPLC column chromatography (silica gel, 10% ethyl acetate in hexane) to obtain the title co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccccc1.c1ccncc1.C1COCC[NH]1.c1ccccc1 | HCl | CN(C)C=O | null | null | C1COCCN1.Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccccc2)cc1>CN(C)C=O>Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2ecc3c987ef342dcaf56a896c2b14bed | Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1>>Cc1ccc(-c2ccc(N3CCOCC3)nc2-c2ccccc2)cc1 | O1CCN(CC1)C1=C(C#N)C=C(C(=N1)C1=CC=CC=C1)C1=CC=C(C=C1)C>>C1(=CC=CC=C1)C1=C(C=CC(=N1)N1CCOCC1)C1=CC=C(C=C1)C | N#C[c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:25][cH:24]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:16][c:9]1[N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[n:16][c:17]2-[c:18]2[cH:19][cH:20]... | Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1 | Cc1ccc(-c2ccc(N3CCOCC3)nc2-c2ccccc2)cc1 | null | null | O.OS(=O)(=O)O | Miscellaneous | OtherReaction | 2782d5e71efdd4476422244c4ad577379d0202dc54aae59c8e088483d6c84377 | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | c1ccc(-c2ccc(N3CCOCC3)nc2-c2ccccc2)cc1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | A solution of 2-morpholino-6-phenyl-5-p-tolylnicotinonitrile (Compound 116,120 mg, 0.3 mmol) in 50% H2SO4 (5 ml) was heated at 140° C. overnight. The mixture was cooled down to room temperature and diluted with water, extracted with CH2Cl2. The organic layer was washed with water and brine, dried over MgSO4, concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.C1COCC[NH]1.c1ccccc1 | Other | O.OS(=O)(=O)O | null | null | Cc1ccc(-c2cc(C#N)c(N3CCOCC3)nc2-c2ccccc2)cc1>O.OS(=O)(=O)O>Cc1ccc(-c2ccc(N3CCOCC3)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ddefdcac9e5747c6b7cfd8a0a67b1f46 | CCCCCCCOc1ccc(CC[C@]2(C)COS(=O)(=O)N2C(=O)OC(C)(C)C)cc1.[C-]#N>>CCCCCCCOc1ccc(CC[C@](C)(CC#N)NC(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(=O)N1S(OC[C@@]1(C)CCC1=CC=C(C=C1)OCCCCCCC)(=O)=O.[C-]#N.[Na+].CCOC(=O)C.C(=O)(O)[O-].[Na+].[C-]#N.[Na+]>>C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)CC#N)=O | O=S1(=O)O[CH2:17][C@:15]([CH2:14][CH2:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:29][cH:28]2)([CH3:16])[N:20]1[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].[C-:18]#[N:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH... | CCCCCCCOc1ccc(CC[C@]2(C)COS(=O)(=O)N2C(=O)OC(C)(C)C)cc1.[C-]#N | CCCCCCCOc1ccc(CC[C@](C)(CC#N)NC(=O)OC(C)(C)C)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | f57541a7f6a3d74a6d321498ba1b15bbb05b3fa0a67ba536f11ac19dc39432ba | eb88cb07aac17cb12e0a138ed8fa1d1b035456016e1feeb4cc2967f1b56aa938 | c1ccccc1 | O=S1(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[N;H0;D3;+0:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C-;H0;D1:13]#[N;D1;H0:14]>>[C:3]-[C:2](-[C;D1;H3:4])(-[CH2;D2;+0:1]-[C;H0;D2;+0:13]#[N;D1;H0:14])-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])... | null | [] | null | null | 25 | HOUR | To a stirred solution of (R)-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-2,2-dioxo-2λ*6*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (174 mg, 0.40 mMol) in DMF (5 ml) is added sodium cyanide (94 mg, 1.91 mMol). The mixture is stirred at RT for 25 hours. Additional sodium cyanide (37 mg, 0.76 mMol) is added ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Sulfamate | Carbamic ester.Nitrile | C1COS[NH]1 | null | c1ccccc1 | Other | CN(C)C=O | null | 25 | CCCCCCCOc1ccc(CC[C@]2(C)COS(=O)(=O)N2C(=O)OC(C)(C)C)cc1.[C-]#N>CN(C)C=O>CCCCCCCOc1ccc(CC[C@](C)(CC#N)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a5a2fe0492d94de8b066ceb11f7807be | CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1.O=S(Cl)Cl>>CCCCCCCOc1ccc(CCC2(C)CO[S@@](=O)N2C(=O)OC(C)(C)C)cc1 | Cl.C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)CO)=O.N1=CC=CC=C1.S(=O)(Cl)Cl>>C(C)(C)(C)OC(=O)N1[S@@](OCC1(C)CCC1=CC=C(C=C1)OCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@:15]([CH3:16])([CH2:17][OH:18])[NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]1.Cl[S:19](Cl)=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13]... | CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1.O=S(Cl)Cl | CCCCCCCOc1ccc(CCC2(C)CO[S@@](=O)N2C(=O)OC(C)(C)C)cc1 | null | null | CCOC(=O)C.C(C)#N | Acylation | OtherReaction | 0772ead6d6c4a73abc768614b9a548144ff3a8ce311783c4120a9053dfbc740e | 15374908571cf37cd8e0e59b02bd756d6e6b28f11089be06518fb705c56ce79e | O=[S@]1NC(CCc2ccccc2)CO1 | Cl-[S;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C:3]-[C:4]-[C@;H0;D4;+0:5](-[C;D1;H3:6])(-[C:7]-[OH;D1;+0:8])-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[C:3]-[C:4]-[C;H0;D4;+0:5]1(-[C;D1;H3:6])-[C:7]-[O;H0;D2;+0:8]-[S@@;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]-1-[C:10](=[O;D1;H0:... | null | [] | -10 | CELSIUS | null | null | A stirred solution of thionyl chloride (0.14 ml, 1.91 mMol) in acetonitril (10 ml) is cooled to −40° C. At this temperature, a solution of [(R)-3-(4-heptyloxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester (300 mg, 0.76 mMol) in acetonitril (5 ml), and pyridine (0.31 ml, 3.81 mMol) are added su... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Primary alcohol | Carbamic ester.Sulfinate | null | C1COS[NH]1 | c1ccccc1.C1COS[NH]1 | HCl | CCOC(=O)C.C(C)#N | -10 | null | CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1.O=S(Cl)Cl>CCOC(=O)C.C(C)#N>CCCCCCCOc1ccc(CCC2(C)CO[S@@](=O)N2C(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-70054e6b95a147cabccc72cb3935270a | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1.CCCCCCCOS(C)(=O)=O>>CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1 | Cl.C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)O)(C)CO)=O.C([O-])([O-])=O.[K+].[K+].C(CCCCCC)OS(=O)(=O)C>>C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)CO)=O | [OH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@:15]([CH3:16])([CH2:17][OH:18])[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][cH:28]1.CS(=O)(=O)O[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14... | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1.CCCCCCCOS(C)(=O)=O | CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1 | null | null | CCOC(=O)C.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 6 | HOUR | To a stirred solution of [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (2.06 g, 6.98 mMol) in ethanol (100 ml) is added potassium carbonate (2.90 g, 20.8 mMol) and methanesulfonic acid heptyl ester (2.04 g, 10.5 mMol). The mixture is heated to reflux temperature and stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | c1ccccc1 | MsOH.HO- | CCOC(=O)C.C(C)O | null | 6 | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1.CCCCCCCOS(C)(=O)=O>CCOC(=O)C.C(C)O>CCCCCCCOc1ccc(CC[C@](C)(CO)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dc96f4ef043c40f5b91e8bb96a45a857 | CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1>>CCCCCCCOc1ccc(CC[C@@](C)(N)C(=O)O)cc1 | C(C)(C)(C)OC(=O)N[C@@](C(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C.FC(C(=O)O)(F)F>>N[C@@](C(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C | CC(C)(C)OC(=O)[NH:17][C@@:15]([CH2:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:22][cH:21]1)([CH3:16])[C:18](=[O:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@@:15]([CH3:16])([NH2:17])[C:18](=[O:19])[O... | CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1 | CCCCCCCOc1ccc(CC[C@@](C)(N)C(=O)O)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[C:3]-[C:2](-[C;D1;H3:4])(-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | 8 | HOUR | To a stirred solution of (R)-2-tert-butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid (43 mg, 0.11 mMol) in CH2Cl2 (2 ml) is added trifluoroacetic acid (0.1 ml). The mixture is stirred at RT for 8 hours. After that time, the reaction mixture is concentrated under reduced pressure. Column chromatography e... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1>C(Cl)Cl>CCCCCCCOc1ccc(CC[C@@](C)(N)C(=O)O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ed19de40aa354320974dd94b4cf5e358 | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1>>CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1 | C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)C=O)=O.CC(C)=CC.Cl(=O)[O-].[Na+].Cl>>C(C)(C)(C)OC(=O)N[C@@](C(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@@:15]([CH3:16])([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:25]=[O:26])[cH:28][cH:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@@:15]([CH... | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1 | CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1 | null | null | OP(=O)(O)[O-].[K+].CCOC(=O)C.C(C)(C)(C)O | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | c1ccccc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH;D2;+0:12]=[O;D1;H0:13]>>[C:1]-[C:2](-[C;D1;H3:3])(-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C;H0;D3;+0:12](=[O;D1;H0:13])-[O;D1;H1:14] | null | [] | null | null | 1 | HOUR | To a stirred solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (103 mg, 0.26 mMol) in tert-butanol (1 ml) and 10% aqueous KH2PO4 (1 ml) is added 2-methyl-2-butene (0.66 ml, 5.27 mMol) and sodium chlorite (59 mg, 0.52 mMol). The mixture is stirred at RT for 1 hour. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ccccc1 | Other | OP(=O)(O)[O-].[K+].CCOC(=O)C.C(C)(C)(C)O | null | 1 | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1>OP(=O)(O)[O-].[K+].CCOC(=O)C.C(C)(C)(C)O>CCCCCCCOc1ccc(CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-651db5982fa74a0abf2ef00d192ec652 | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1>>CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)O)(C)CO)=O>>C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)C=O)=O | [CH3:1][C:23]([CH3:5])([CH3:7])[O:22][C:20]([NH:19][C@@:15]([CH2:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([OH:8])[cH:28][cH:27]1)([CH3:16])[CH2:17][OH:18])=[O:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@:15]([CH3:16])([CH:17]=[O:18])[NH:19][C:20](=[O:21])[O:22][... | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1 | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(Cl)Cl | Miscellaneous | OtherReaction | d9daff346ad4d767a9a64e8a5f37e0597f3f7676fef1882c7a3b53fc0a4a92b7 | f87267d5b81fc94c38102237cbfa3eb7eda0cc732d3c41cd91572caa89ba83f2 | c1ccccc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;H0;D4;+0:8](-[CH3;D1;+0:9])(-[CH3;D1;+0:10])-[CH3;D1;+0:11])-[CH2;D2;+0:12]-[OH;D1;+0:13].[OH;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[CH3;D1;+0:9]-[C:18]-[C:19]-[C:20]-[CH2;D2;+0:10]-[C:21]-[CH2;D2;+0:11]-[O;H0;D2;+0:14]-[c:15](:[c:16]):[c:17].[C:1]-[C:2](-[C;D... | null | [] | null | null | 1 | HOUR | To a stirred solution of [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (1.98 g, 5.03 mMol) in CH2Cl2 (20 ml) is added N-morpholine-N-oxide (884 mg, 7.54 mMol) and tetra-n-propylammonium perruthenate (177 mg, 0.50 mMol). The mixture is stirred at RT for 1 hour. The mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Aromatic alcohol.Boc | Aldehyde.Ether.Ether.Boc | null | null | c1ccccc1 | Other | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl | null | 1 | CC(C)(C)OC(=O)N[C@@](C)(CO)CCc1ccc(O)cc1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl>CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0013bc2581a94e40a5eb4281af024df5 | CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1>>CCCCCCCOc1ccc(CC[C@@](C)(N)CCC(=O)O)cc1 | C(C)(C)(C)OC(=O)N[C@@](CCC(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C.FC(C(=O)O)(F)F>>N[C@@](CCC(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C | CC(C)(C)OC(=O)[NH:17][C@@:15]([CH2:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:24][cH:23]1)([CH3:16])[CH2:18][CH2:19][C:20](=[O:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@@:15]([CH3:16])([NH2:17])[... | CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1 | CCCCCCCOc1ccc(CC[C@@](C)(N)CCC(=O)O)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | 6.5 | HOUR | To a stirred solution of (R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hexanoic acid (24 mg, 0.06 mMol) in CH2Cl2 (2 ml) is added trifluoroacetic acid (0.1 ml). The mixture is stirred at RT for 6.5 hours. After that time, the reaction mixture is concentrated under reduced pressure to give the title com... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 6.5 | CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1>C(Cl)Cl>CCCCCCCOc1ccc(CC[C@@](C)(N)CCC(=O)O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a9f79f4a19f0430b8d7025cea73829d7 | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1>>CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(=O)N[C@@](/C=C/C(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C>>C(C)(C)(C)OC(=O)N[C@@](CCC(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C@:15]([CH3:16])(/[CH:17]=[CH:18]/[C:19](=[O:20])[OH:21])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2... | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1 | CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1 | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])/[CH;D2;+0:12]=[CH;D2;+0:13]/[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[C:1]-[C:2](-[C;D1;H3:3])(-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[C:14]... | null | [] | null | null | 17 | HOUR | To a stirred solution of (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid (53 mg, 0.12 mMol) in AcOEt (10 ml) is added palladium on charcoal (10 mg, 10%). The reaction is stirred under a H2-atmosphere at RT for 17 hours. The reaction mixture is filtered over Celite and the filtrate is... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | [Pd].CCOC(=O)C | null | 17 | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1>[Pd].CCOC(=O)C>CCCCCCCOc1ccc(CC[C@](C)(CCC(=O)O)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-91458b10ebb940e4819c2a5ed4ed83e3 | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1>>CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1 | C(C)OC(\C=C\[C@](CCC1=CC=C(C=C1)OCCCCCCC)(C)NC(=O)OC(C)(C)C)=O.[OH-].[Li+].CCOC(=O)C.Cl>>C(C)(C)(C)OC(=O)N[C@@](/C=C/C(=O)O)(CCC1=CC=C(C=C1)OCCCCCCC)C | CC[O:21][C:19](/[CH:18]=[CH:17]/[C@:15]([CH2:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:31][cH:30]1)([CH3:16])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH... | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1 | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1 | null | null | CO.C1CCOC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]/[C:6]>>[C:6]/[C:5]=[C:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 3.5 | HOUR | To a stirred solution of (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid ethyl ester (56 mg, 0.12 mMol) in methanol (0.5 ml), THF (0.5 ml) and water (0.5 ml) is added lithium hydroxide (14 mg, 0.61 mMol). The mixture is stirred at RT for 3.5 hours. The reaction mixture is then poured... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.C1CCOC1.O | null | 3.5 | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1>CO.C1CCOC1.O>CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)O)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e219271ff5654914b84b2a1a70a9aa35 | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1.CCOC(=O)CP(=O)(OCC)OCC>>CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1 | C(=O)(O)[O-].[Na+].C(C)(C)(C)OC(N[C@@](CCC1=CC=C(C=C1)OCCCCCCC)(C)C=O)=O.C(C)OC(CP(=O)(OCC)OCC)=O.C(CCC)[Li]>>C(C)OC(\C=C\[C@](CCC1=CC=C(C=C1)OCCCCCCC)(C)NC(=O)OC(C)(C)C)=O | O=[CH:17][C@:15]([CH2:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:33][cH:32]1)([CH3:16])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].CCOP(=O)(OCC)[CH2:18][C:19](=[O:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c... | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1.CCOC(=O)CP(=O)(OCC)OCC | CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[CH;D2;+0:6]-[C:7](-[C:8])(-[C;D1;H3:9])-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:8]-[C:7](-[C;D1;H3:9])(-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])/[CH;D... | null | [] | -78 | CELSIUS | 1 | HOUR | To a stirred solution of (diethoxy-phosphoryl)-acetic acid ethyl ester (429 mg, 1.92 mMol) in dry THF (7 ml) is added n-butyllithium (0.66 ml, 2.5M in hexane, 1.66 mMol) at −78° C. The mixture was stirred at −78° C. for 1 hour. After that time, a solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbami... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1 | HO- | C1CCOC1.CCOC(=O)C | -78 | 1 | CCCCCCCOc1ccc(CC[C@](C)(C=O)NC(=O)OC(C)(C)C)cc1.CCOC(=O)CP(=O)(OCC)OCC>C1CCOC1.CCOC(=O)C>CCCCCCCOc1ccc(CC[C@](C)(/C=C/C(=O)OCC)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5759d37bf2144098891bfd299ba656fc | CC(C)[C@H](N)C(=O)O.Cc1ccc(S(=O)(=O)[O-])cc1.[Br-]>>CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O | C1(=CC=C(C=C1)S(=O)(=O)[O-])C.N[C@@H](C(C)C)C(=O)O.C(C)(C)N(CC)C(C)C.[Br-].C[Si](N[Si](C)(C)C)(C)C>>BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH2:5])[C:14](=[O:15])[OH:16].O=S(=O)([O-])[c:10]1[cH:9][cH:8][c:7]([CH3:6])[cH:13][cH:12]1.[Br-:11]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[C:14](=[O:15])[OH:16] | CC(C)[C@H](N)C(=O)O.Cc1ccc(S(=O)(=O)[O-])cc1.[Br-] | CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | bd5126b16127e76becb744f051b270fbdaf9bb35bf82bd45a8eaf2ac5fe2568e | 150d19ed45d0eaa38177d3f86903c657a113d723a24ccdeb7f6cedc10a23b711 | c1ccccc1 | O=S(=O)(-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH3;D1;+0:5]):[c:6]:[c:7]:1.[Br-;H0;D0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[Br;H0;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]):[c:6]:[c:7]:1 | 89 | [{"value": 89.0, "product": "BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | 1 | HOUR | To a suspension of 10 g (34.6 mmol) of p-toluenesulphonate of L-valine in 100 mL of CH2Cl2 is added at 20-25° C. and under nitrogen atmosphere 8.0 mL (38 mmol) of 1,1,1,3,3,3-hexamethyldisilazane. After shaking the mixture at 20-25° C. for one hour, 13.2 mL (76 mmol) of diisopropylethylamine and 8.64 g (34.6 mmol) of 4... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine | Aromatic halide.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(Cl)Cl | 22.5 | 1 | CC(C)[C@H](N)C(=O)O.Cc1ccc(S(=O)(=O)[O-])cc1.[Br-]>C(Cl)Cl>CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-145a239c04c24a43b4d3485f843fcd6d | CC(C)[C@H](N)C(=O)O.CCN(C(C)C)C(C)C.[Br-]>>CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O | [OH-].[Na+].C(C)(C)N(CC)C(C)C.[Br-].N[C@@H](C(C)C)C(=O)O>>BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH2:5])[C:14](=[O:15])[OH:16].C[CH:10](N([CH:6]([CH3:7])[CH3:13])[CH2:8][CH3:9])[CH3:12].[Br-:11]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[C:14](=[O:15])[OH:16] | CC(C)[C@H](N)C(=O)O.CCN(C(C)C)C(C)C.[Br-] | CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O | null | null | O.CN(C)C=O.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 4d53f11fdf00bc732f2e5025e1637dfb8b67a80335622e7f11cf8c0fad2cbfbf | 9cda39025b7943c5d62a8ccedbc8cd6c465a80735eda4de2f1f137bae9f6d974 | c1ccccc1 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH;D3;+0:5](-[CH3;D1;+0:6])-[CH3;D1;+0:7].[Br-;H0;D0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[Br;H0;D1;+0:8]-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[CH2;D2;+0:5]-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12](=[O;D1;H0:... | 153.4 | [{"value": 76.5, "product": "BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 153.4, "product": "BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | 1 | HOUR | 52 mL (0.21 mol) of N,O-bistrimethylsilylacetamide is added under nitrogen atmosphere to a mixture made up of 23.5 g (0.20 mol) of L-valine and 38.5 mL (0.22 mol) of diisopropylethylamine in 12.5 mL of DMF. After 1 h at 80° C. the suspension changes to a clear solution. Then, in portions and controlling exothermy, 50 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Aromatic halide.Secondary amine | null | c1ccccc1 | c1ccccc1 | Other | O.CN(C)C=O.C1(=CC=CC=C1)C | 22.5 | 1 | CC(C)[C@H](N)C(=O)O.CCN(C(C)C)C(C)C.[Br-]>O.CN(C)C=O.C1(=CC=CC=C1)C>CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e01ec6a0314544228d23b8e21d159f26 | CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O.CCCCC(=O)Cl>>CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C | O.BrC1=CC=C(CN[C@@H](C(C)C)C(=O)O)C=C1.C([O-])(O)=O.[Na+].C(CCCC)(=O)Cl>>BrC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1 | [NH:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1)[C@H:16]([C:17](=[O:18])[OH:19])[CH:20]([CH3:21])[CH3:22].Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1)[C@H:16]([C:17](=[O:18])[OH:19])[CH:20]([CH3:21... | CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O.CCCCC(=O)Cl | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C | null | null | C1CCOC1 | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH;D2;+0:7]-[C:8]-[c:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:5]-[C:6](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[N;H0;D3;+0:7](-[C:8]-[c:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 91.2 | [{"value": 91.2, "product": "BrC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "BrC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A mixture made up of 5 g (17.47 mmol) of N-(4-bromobenzyl)-L-valine and 5.9 g (70.24 mmol) of sodium bicarbonate in 50 mL of dry THF is left under stirring and under nitrogen atmosphere for one hour. The preceding suspension is cooled to 0° C. and to it is added over a period of 15 min. 4.2 mL (35.41 mmol) of valeroyl ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HCl | C1CCOC1 | 0 | 1 | CC(C)[C@H](NCc1ccc(Br)cc1)C(=O)O.CCCCC(=O)Cl>C1CCOC1>CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-193ceffdbb5248e78d55572665c91315 | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | BrC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1.C[O-].[Na+].N1N=NN=C1C1=C(C=CC=C1)B(O)O>>CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O | Br[c:12]1[cH:11][cH:10][c:9]([CH2:8][N:7]([C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[C@H:26]([C:27](=[O:28])[OH:29])[CH:30]([CH3:31])[CH3:32])[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-[c:19]1[n:20][n:21][n:22][nH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][c:12... | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1 | CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | CO | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]):[c:4]:[c:5] | 55.6 | [{"value": 55.6, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | MINUTE | Nitrogen is bubbled for 5 min. To a mixture made up of 0.50 g (1.35 mmol) of N-(4-bromobenzyl)-N-valeryl-L-valine, 0.308 g (1.52 mmol) of 2-(1H-tetrazol-5-yl)phenylboronic acid, 0.0028 g (0.016 mmol) of palladium chloride and 0.0084 g (0.032 mmol) of triphenylphosphine in a solution of 2.06 mL (13.0 mmol) of sodium met... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | HBr.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CO | 70 | 0.25 | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CO>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2c34eba3d0b341ddb43c12b392296d96 | CCCCC(=O)N(Cc1ccc(I)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | IC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1.N1N=NN=C1C1=C(C=CC=C1)B(O)O.[OH-].[Na+]>>CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O | I[c:12]1[cH:11][cH:10][c:9]([CH2:8][N:7]([C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[C@H:26]([C:27](=[O:28])[OH:29])[CH:30]([CH3:31])[CH3:32])[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-[c:19]1[n:20][n:21][n:22][nH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]... | CCCCC(=O)N(Cc1ccc(I)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1 | CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CO.O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]):[c:4]:[c:5] | 85.1 | [{"value": 85.0, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Nitrogen is bubbled for 5 min. To a mixture made up of 0.20 g (0.48 mmol) of N-(4-iodobenzyl)-N-valeryl-L-valine, 0.115 g (0.61 mmol) of 2-(1H-tetrazol-5-yl)phenylboronic acid, 0.017 g (0.024 mmol) of bis(triphenylphosphine)palladium chloride and 0.115 g (2.87 mmol) of NaOH in 2.4 mL of methanol and 0.7 mL of water are... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | HI.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.O | 70 | null | CCCCC(=O)N(Cc1ccc(I)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.O>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7b8ab9258581450a8bc951e07b1b819c | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | BrC1=CC=C(CN([C@@H](C(C)C)C(=O)O)C(CCCC)=O)C=C1.C[O-].[Na+].N1N=NN=C1C1=C(C=CC=C1)B(O)O>>CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O | Br[c:12]1[cH:11][cH:10][c:9]([CH2:8][N:7]([C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[C@H:26]([C:27](=[O:28])[OH:29])[CH:30]([CH3:31])[CH3:32])[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-[c:19]1[n:20][n:21][n:22][nH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][c:12... | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1 | CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C | null | [Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | CO | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]1:[#7;a:11]:[#7;a:12]:[#7;a:13]:[#7;a:14]:1):[c:15]):[c:4]:[c:5] | 58.1 | [{"value": 58.0, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "CCCCC(=O)N(CC=1C=CC(=CC1)C=2C=CC=CC2C=3NN=NN3)[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture made up of 1 g (2.70 mmol) of (4-bromobenzyl)-N-valeryl-L-valine, 0.513 g (2.70 mmol) of 2-(1H-tetrazol-5-yl)phenylboronic acid, 0.120 g of 5% Pd/C in paste (0.028 mmol of palladium) and 0.0084 g (0.032 mmol) of triphenylphosphine in a solution of 4.1 mL (21.5 mmol) of sodium methoxide in 30% methanol and 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | HBr.B | [Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CO | 70 | null | CCCCC(=O)N(Cc1ccc(Br)cc1)[C@H](C(=O)O)C(C)C.OB(O)c1ccccc1-c1nnn[nH]1>[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CO>CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-945f48425f244a0f908f48acbe24b21e | CCCC(=O)c1ccc(C(F)(F)F)cc1.NO>>CCCC(N)c1ccc(C(F)(F)F)cc1 | FC(C1=CC=C(C=C1)C(CCC)=O)(F)F.Cl.NO>>FC(C1=CC=C(C=C1)C(CCC)N)(F)F | O=[C:4]([CH2:3][CH2:2][CH3:1])[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1.O[NH2:5]>>[CH3:1][CH2:2][CH2:3][CH:4]([NH2:5])[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1 | CCCC(=O)c1ccc(C(F)(F)F)cc1.NO | CCCC(N)c1ccc(C(F)(F)F)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b3b7f77639b5887eb01ca3993741cdf8449b0bba226b4062e2af88eca5bc2340 | 152739a554e3dfe142780f62e93c3937034728a057c1d7df6cf14c157c162e6c | c1ccccc1 | O-[NH2;D1;+0:1].O=[C;H0;D3;+0:2](-[C:3]-[C:4])-[c:5](:[c:6]):[c:7]>>[C:4]-[C:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:5](:[c:6]):[c:7] | 83 | [{"value": 83.0, "product": "FC(C1=CC=C(C=C1)C(CCC)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "FC(C1=CC=C(C=C1)C(CCC)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 1-[4-(trifluoromethyl)phenyl]butan-1-one (6 g, 27.8 mmol) in ethanol (60 ml) was added hydroxylamine hydrochloride (5.79 g, 83.3 mmol) and the reaction heated to reflux and stirred for 16 h. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was taken up in... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | 16 | CCCC(=O)c1ccc(C(F)(F)F)cc1.NO>C(C)O>CCCC(N)c1ccc(C(F)(F)F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e38829eb64e348e38ddd3c72f10e5bc3 | NO.O=C(CCc1ccccc1)c1ccc(C(F)(F)F)cc1>>NC(CCc1ccccc1)c1ccc(C(F)(F)F)cc1 | Cl.NO.C1(=CC=CC=C1)CCC(=O)C1=CC=C(C=C1)C(F)(F)F>>C1(=CC=CC=C1)CCC(N)C1=CC=C(C=C1)C(F)(F)F | O[NH2:1].O=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[NH2:1][CH:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | NO.O=C(CCc1ccccc1)c1ccc(C(F)(F)F)cc1 | NC(CCc1ccccc1)c1ccc(C(F)(F)F)cc1 | null | [Ni] | CCO | Heteroatom Alkylation and Arylation | OtherReaction | b3b7f77639b5887eb01ca3993741cdf8449b0bba226b4062e2af88eca5bc2340 | 152739a554e3dfe142780f62e93c3937034728a057c1d7df6cf14c157c162e6c | c1ccc(CCCc2ccccc2)cc1 | O-[NH2;D1;+0:1].O=[C;H0;D3;+0:2](-[C:3]-[C:4])-[c:5](:[c:6]):[c:7]>>[C:4]-[C:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:5](:[c:6]):[c:7] | 28 | [{"value": 28.0, "product": "C1(=CC=CC=C1)CCC(N)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Hydroxylamine hydrochloride (2.1 g, 0.03 mol) was added to a solution of 3-phenyl-1-[4-(trifluoromethyl)phenyl]propan-1-one (Journal of the American Chemical Society 1994, 116(6), 2312-17, 2.8 g, 0.01 mol) in EtOH (30 ml). The solution was heated to reflux temperature for 18 hours. After cooling to RT, the solvent was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Ni].CCO | null | 48 | NO.O=C(CCc1ccccc1)c1ccc(C(F)(F)F)cc1>[Ni].CCO>NC(CCc1ccccc1)c1ccc(C(F)(F)F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-eaef31384a664eadb0c135127658cd34 | CC(C)(C)/C=C/C=O.CC(C)(C)S(N)=O>>CC(C)(C)/C=C/C=N/S(=O)C(C)(C)C | CC(C)(C)S(=O)N.CC(/C=C/C=O)(C)C>>CC(/C=C/C=N/S(=O)C(C)(C)C)(C)C | O=[CH:7]/[CH:6]=[CH:5]/[C:2]([CH3:1])([CH3:3])[CH3:4].[NH2:8][S:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH3:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])/[CH:5]=[CH:6]/[CH:7]=[N:8]/[S:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH3:14] | CC(C)(C)/C=C/C=O.CC(C)(C)S(N)=O | CC(C)(C)/C=C/C=N/S(=O)C(C)(C)C | null | [O-]S(=O)(=O)[O-].[Cu+2] | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | null | O=[CH;D2;+0:1]/[C:2]=[C:3]/[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[#16:9](-[NH2;D1;+0:10])=[O;D1;H0:11]>>[C:8]-[#16:9](=[O;D1;H0:11])/[N;H0;D2;+0:10]=[CH;D2;+0:1]/[C:2]=[C:3]/[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 58 | [{"value": 58.0, "product": "CC(/C=C/C=N/S(=O)C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "CC(/C=C/C=N/S(=O)C(C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-methylpropane-2-sulfinamide (3.08 g, 0.025 mol) in dichloromethane (10 ml) was added CuSO4 (5.42 g, 0.034 mol) followed by (2E)-4,4-dimethylpent-2-enal (Journal of Organic Chemistry 1993, 58(9), 2517-22, 1.9 g, 0.017 mol) in dichloromethane (60 ml). The reaction mixture was stirred at RT overnight un... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | null | HO- | [O-]S(=O)(=O)[O-].[Cu+2].ClCCl | null | 8 | CC(C)(C)/C=C/C=O.CC(C)(C)S(N)=O>[O-]S(=O)(=O)[O-].[Cu+2].ClCCl>CC(C)(C)/C=C/C=N/S(=O)C(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d8a15633b09740b3a83773b2d22693a7 | CC(C)(C)S(N)=O.O=Cc1ccc(C(F)(F)F)cc1C(F)(F)F>>CC(C)(C)S(=O)/N=C/c1ccc(C(F)(F)F)cc1C(F)(F)F | FC(C1=C(C=O)C=CC(=C1)C(F)(F)F)(F)F.C(C)(C)(C)S(=O)N>>FC(C1=C(C=CC(=C1)C(F)(F)F)\C=N\S(=O)C(C)(C)C)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])[NH2:7].O=[CH:8][c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])/[N:7]=[CH:8]/[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | CC(C)(C)S(N)=O.O=Cc1ccc(C(F)(F)F)cc1C(F)(F)F | CC(C)(C)S(=O)/N=C/c1ccc(C(F)(F)F)cc1C(F)(F)F | null | [O-]S(=O)(=O)[O-].[Cu+2] | O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#16:6](-[NH2;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[#16:6](=[O;D1;H0:8])/[N;H0;D2;+0:7]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2,4-bis trifluoromethyl benzaldehyde (10.0 g, 41.3 mmol), tert butyl sulfinamide (4.5 g, 37.2 mmol) and anhydrous CuSO4 (13.1 g, 82.6 mmol) in DCM (100 ml) was stirred at room temperature overnight. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1 | HO- | [O-]S(=O)(=O)[O-].[Cu+2].O.C(Cl)Cl | null | 8 | CC(C)(C)S(N)=O.O=Cc1ccc(C(F)(F)F)cc1C(F)(F)F>[O-]S(=O)(=O)[O-].[Cu+2].O.C(Cl)Cl>CC(C)(C)S(=O)/N=C/c1ccc(C(F)(F)F)cc1C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bcbee99499544c32b5f10b72d55104b4 | CC(C)(C)S(N)=O.O=Cc1cc(C(F)(F)F)ccc1C(F)(F)F>>CC(C)(C)S(=O)/N=C/c1cc(C(F)(F)F)ccc1C(F)(F)F | FC(C1=C(C=O)C=C(C=C1)C(F)(F)F)(F)F.C(C)(C)(C)S(=O)N>>FC(C1=C(C=C(C=C1)C(F)(F)F)\C=N\S(=O)C(C)(C)C)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])[NH2:7].O=[CH:8][c:9]1[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])/[N:7]=[CH:8]/[c:9]1[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | CC(C)(C)S(N)=O.O=Cc1cc(C(F)(F)F)ccc1C(F)(F)F | CC(C)(C)S(=O)/N=C/c1cc(C(F)(F)F)ccc1C(F)(F)F | null | [O-]S(=O)(=O)[O-].[Cu+2] | O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#16:6](-[NH2;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[#16:6](=[O;D1;H0:8])/[N;H0;D2;+0:7]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "FC(C1=C(C=C(C=C1)C(F)(F)F)\\C=N\\S(=O)C(C)(C)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "FC(C1=C(C=C(C=C1)C(F)(F)F)\\C=N\\S(=O)C(C)(C)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 2,5-bis trifluoromethyl benzaldehyde (21.5 g, 88.8 mmol), tert butyl sulfinamide (16.1 g, 133 mmol) and anhydrous CuSO4 (16.5 g, 103 mmol) in DCM (94 ml) was stirred at room temperature for 16 hours and at reflux for 3 days. The fine suspension was diluted with water and extracted with DCM. The extracts we... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1 | HO- | [O-]S(=O)(=O)[O-].[Cu+2].O.C(Cl)Cl | null | 16 | CC(C)(C)S(N)=O.O=Cc1cc(C(F)(F)F)ccc1C(F)(F)F>[O-]S(=O)(=O)[O-].[Cu+2].O.C(Cl)Cl>CC(C)(C)S(=O)/N=C/c1cc(C(F)(F)F)ccc1C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8a2d937961c84f83bb3d0b101579b0e6 | CCO.O=C(O)/C=C/c1ccc(Cl)cc1Cl>>CCOC(=O)/C=C/c1ccc(Cl)cc1Cl | ClC1=C(C=CC(=C1)Cl)/C=C/C(=O)O.OS(=O)(=O)O.C(C)O>>ClC1=C(C=CC(=C1)Cl)/C=C/C(=O)OCC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15] | CCO.O=C(O)/C=C/c1ccc(Cl)cc1Cl | CCOC(=O)/C=C/c1ccc(Cl)cc1Cl | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | To a stirred solution of (2E)-3-(2,4-Dichlorophenyl)acrylic acid (10 g, 46 mmol) in ethanol (60 ml) was added conc. H2SO4 (2.5 ml). The mixture was heated to reflux and for 48 H, then allowed to cool, concentrated in vacuo, dissolved in ethyl acetate, washed three times with 4N NaOH, dried over sodium sulfate and conce... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)/C=C/c1ccc(Cl)cc1Cl>>CCOC(=O)/C=C/c1ccc(Cl)cc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-917ece0eec46449d9168e8c7c7e43f66 | CCOC(=O)/C=C/c1ccc(Cl)cc1Cl>>OC/C=C/c1ccc(Cl)cc1Cl | [Cl-].[NH4+].CO.ClC1=C(C=CC(=C1)Cl)/C=C/C(=O)OCC.[H-].C(C(C)C)[Al+]CC(C)C>>ClC1=C(C=CC(=C1)Cl)/C=C/CO | CCO[C:2](=[O:1])/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12]>>[OH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12] | CCOC(=O)/C=C/c1ccc(Cl)cc1Cl | OC/C=C/c1ccc(Cl)cc1Cl | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | 83.5 | [{"value": 83.5, "product": "ClC1=C(C=CC(=C1)Cl)/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | O1CCCC1 | -78 | 0.25 | CCOC(=O)/C=C/c1ccc(Cl)cc1Cl>O1CCCC1>OC/C=C/c1ccc(Cl)cc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7c2786f87aa442578313278254796421 | CCCC(Br)c1ccc(C(F)(F)F)cc1.NN>>CCCC(NN)c1ccc(C(F)(F)F)cc1 | O.NN.BrC(CCC)C1=CC=C(C=C1)C(F)(F)F>>FC(C1=CC=C(C=C1)C(CCC)NN)(F)F | Br[CH:4]([CH2:3][CH2:2][CH3:1])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1.[NH2:5][NH2:6]>>[CH3:1][CH2:2][CH2:3][CH:4]([NH:5][NH2:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1 | CCCC(Br)c1ccc(C(F)(F)F)cc1.NN | CCCC(NN)c1ccc(C(F)(F)F)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 3d6a0fb7692357cd3b01a8550f26a3d32cd2f5bbbcecf29a7c61d058336d3455 | 726ecae32562749f86242fa3f594278651834eef7e324f8996c8ee29abff92ee | c1ccccc1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[C:3]-[C:2]-[CH;D3;+0:1](-[NH;D2;+0:8]-[N;D1;H2:7])-[c:4](:[c:5]):[c:6] | null | [] | 70 | CELSIUS | 16 | HOUR | Hydrazine monohydrate (8.9 g) was dissolved in isopropanol (25 ml) and 1-(1-bromobutyl)-4-(trifluoromethyl)benzene (as prepared in WO 2005013985, 2.0 g, 7.12 mmol) added. The mixture was heated to 70° C. and stirred for 16 h. After this time the solvent was removed and the residue taken up in ethyl acetate and washed t... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Secondary halide | Hydrazine | null | null | c1ccccc1 | HBr | C(C)(C)O | 70 | 16 | CCCC(Br)c1ccc(C(F)(F)F)cc1.NN>C(C)(C)O>CCCC(NN)c1ccc(C(F)(F)F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c54bbd9f8a764e4e9a0add2e75bf4c31 | CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)OCC)CCC2>>CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)O)CCC2 | C1(=CC=CC=C1)C1=CN(C=2C(CCCC12)CC(=O)OCC)C(CCC)C1=CC=C(C=C1)C(F)(F)F.[OH-].[Li+].Cl>>C1(=CC=CC=C1)C1=CN(C=2C(CCCC12)CC(=O)O)C(CCC)C1=CC=C(C=C1)C(F)(F)F | CC[O:30][C:28]([CH2:27][CH:26]1[c:25]2[n:15]([CH:4]([CH2:3][CH2:2][CH3:1])[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]2[CH2:33][CH2:32][CH2:31]1)=[O:29]>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:1... | CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)OCC)CCC2 | CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)O)CCC2 | null | null | C(C)(=O)OCC.O.O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2cc(-c3ccccc3)c3c2CCCC3)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 55 | [{"value": 55.0, "product": "C1(=CC=CC=C1)C1=CN(C=2C(CCCC12)CC(=O)O)C(CCC)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.5, "product": "C1(=CC=CC=C1)C1=CN(C=2C(CCCC12)CC(=O)O)C(CCC)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of ethyl (3-phenyl-1-{1-[4-(trifluoromethyl)phenyl]butyl}-4,5,6,7-tetrahydro-1H-indol-7-yl)acetate (107 mg, 2.2 mmol) in dioxane (5 ml) and water (0.5 ml) was added lithium hydroxide (900 mg, 22.0 mmol) and the reaction heated to reflux for 16 h. After cooling, the reaction was diluted with ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2c1CCC[CH]2 | Other | C(C)(=O)OCC.O.O1CCOCC1 | null | null | CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)OCC)CCC2>C(C)(=O)OCC.O.O1CCOCC1>CCCC(c1ccc(C(F)(F)F)cc1)n1cc(-c2ccccc2)c2c1C(CC(=O)O)CCC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0407c9fe77f041d9bd525224435cc5c6 | CCC[C@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2>>CCC[C@@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2.CO.O=C=O | ClC1=C(C=CC(=C1)Cl)C1=CN(C=2[C@H](CCCC12)CC(=O)O)[C@H](CCC)C1=CC=C(C=C1)C(F)(F)F.ClC1=C(C=CC(=C1)Cl)C1=CN(C=2[C@@H](CCCC12)CC(=O)O)[C@H](CCC)C1=CC=C(C=C1)C(F)(F)F>>C(=O)=O.CO.ClC1=C(C=CC(=C1)Cl)C1=CN(C=2[C@H](CCCC12)CC(=O)O)[C@@H](CCC)C1=CC=C(C=C1)C(F)(F)F.ClC1=C(C=CC(=C1)Cl)C1=CN(C=2[C@@H](CCCC12)CC(=O)O)[C@H](CCC)C1=... | [CH3:1][CH2:2][CH2:3][C@H:4]([c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1)[n:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]2[Cl:25])[c:26]2[c:27]1[C@@H:28]([CH2:29][C:30](=[O:31])[OH:32])[CH2:33][CH2:34][CH2:35]2>>[CH3:1][CH2:2][CH2:3][C@@H:4]([c:5]1[cH:6][cH:7][c:8]([C:9]([... | CCC[C@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2 | CCC[C@@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2.CO.O=C=O | null | null | null | Functional Group Addition | OtherReaction | 0568bfa101e7b7815d8146be4ac22be4c88e59ce699e2b995b4efb8663abdc27 | a937da46e6f225bcb02dbd2ad7da2a85f9370a425c5efcbdc38ccfcfc915d0c8 | c1ccc(Cn2cc(-c3ccccc3)c3c2CCCC3)cc1 | null | null | [] | null | null | null | null | Prepared as described for Example 1, using 2,4-dichloro-beta-nitrostyrene in Step 2 with heating at 200° C. in a microwave apparatus; m/z (ES−) 522 (M−H+). The enantiomers and diastereomers could be separated by supercritical fluid chromatography. A CHIRALPAK AD-H column 250×10 mm (5μ) Column temperature 40° C., Mobile... | 10.6084/m9.figshare.5104873.v1 | null | null | Carbon dioxide.Methanol | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2c1CCCC2 | Other | null | null | null | CCC[C@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2>>CCC[C@@H](c1ccc(C(F)(F)F)cc1)n1cc(-c2ccc(Cl)cc2Cl)c2c1[C@@H](CC(=O)O)CCC2.CO.O=C=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6954c721ef9f486e9691b22e474bc1ae | CCOC(C)=O.O.O=C(CBr)c1ccccc1>>CCOC(=O)CC1CCCC(CC(=O)c2ccccc2)C1=O | O.C(C)(=O)OCC.BrCC(=O)C1=CC=CC=C1>>O=C1C(CCCC1CC(C1=CC=CC=C1)=O)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].[OH2:22].Br[CH2:12][C:13](=[O:14])[c:15]1[cH:7][cH:19][cH:18][cH:17][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:21]1=[O:22] | CCOC(C)=O.O.O=C(CBr)c1ccccc1 | CCOC(=O)CC1CCCC(CC(=O)c2ccccc2)C1=O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 8d3b6a1bba42ef0b89ec88de94d7085f571244747ad5f26c97b1216b2409b302 | 90399ff7a9ad36387fad356b2ffa56f0a83d14d1335bf666ef3601a9c7f0302c | O=C(CC1CCCCC1=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1.[C:10]-[#8:11]-[C:12](-[CH3;D1;+0:13])=[O;D1;H0:14].[OH2;D0;+0:15]>>[C:10]-[#8:11]-[C:12](=[O;D1;H0:14])-[CH2;D2;+0:13]-[CH;D3;+0:9]1-[C:16]-[C:17]-[C:18]-[C:19](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]2:[c:5]:[c... | 50 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "O=C1C(CCCC1CC(C1=CC=CC=C1)=O)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Intermediate 2 (667 mg, 2.81 mmol) was dissolved in dimethylformamide (14 ml), 2-bromo-1-phenylethanone (560 mg, 2.81 mmol) was added and the reaction stirred for 24 h at room temperature. Water (5 ml) was added and the reaction allowed to stir for a further 24 h. The mixture was then diluted with ethyl acetate (100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone.Ketone.Ester | c1ccccc1 | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | Br- | CN(C=O)C | null | 24 | CCOC(C)=O.O.O=C(CBr)c1ccccc1>CN(C=O)C>CCOC(=O)CC1CCCC(CC(=O)c2ccccc2)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-edb649375269480abe9d8dfb97e80e8b | C/C=C/CC1CCCC(CC(=O)OCC)C1=O.OO>>CCOC(=O)CC1CCCC2CC(CC)OC12O | [OH-].[Na+].OO.C(\C=C\C)C1C(C(CCC1)CC(=O)OCC)=O.B>>C(C)C1OC2(C(C1)CCCC2CC(=O)OCC)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH:11]([CH2:12]/[CH:13]=[CH:14]/[CH3:15])[C:17]1=[O:18].O[OH:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([CH2:14][CH3:15])[O:16][C:17]12[OH:18] | C/C=C/CC1CCCC(CC(=O)OCC)C1=O.OO | CCOC(=O)CC1CCCC2CC(CC)OC12O | null | null | [Cl-].[Na+].O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1ed3b95020184a8a5989f044919a19aa817b658fd58e181aaea5379e25d0c35e | 30e7d6dd3b75353e5aacdad5f96f7c994f109bfa2fba8da6b5ab6bc218a7ed06 | C1CCC2OCCC2C1 | O-[OH;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](-[C:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10](-[C:11]/[CH;D2;+0:12]=[CH;D2;+0:13]/[C;D1;H3:14])-[C:15]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](-[C:7])-[C;H0;D4;+0:8]1(-[OH;D1;+0:9])-[O;H0;D2;+0:1]-[CH;D3;+0:12](-[CH2;D2;+0:13]-[C;D1;H3:14])-[C:11]-[C:10]-1-[C:15] | null | [] | 0 | CELSIUS | 35 | MINUTE | To a stirred solution of ethyl {3-[(2E)-but-2-en-1-yl]-2-oxocyclohexyl}acetate (565 mg, 2.37 mmol) in tetrahydrofuran (20 ml) at 0° C. was added borane.tetrahydrofuran complex (1 M in tetrahydrofuran, 3.56 ml, 3.56 mmol) and the reaction allowed to stir at 0° C. for 35 min. Sodium hydroxide (4N, 5.6 ml) and hydrogen pe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Ether.Tertiary alcohol | C1CCCCC1 | C1CCC2OCCC2C1 | C1CCC2OCCC2C1 | Other | [Cl-].[Na+].O.O1CCCC1 | 0 | 0.583333 | C/C=C/CC1CCCC(CC(=O)OCC)C1=O.OO>[Cl-].[Na+].O.O1CCCC1>CCOC(=O)CC1CCCC2CC(CC)OC12O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2be744609e3544b888297354be76dc9a | CCOC(=O)CBr.O=C1C=CCCC1>>CCOC(=O)CC1CCC=CC1=O | BrCC(=O)OCC.C1(C=CCCC1)=O.C(C)(C)[N-]C(C)C.[Li+]>>O=C1C(CCC=C1)CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:7]1[CH2:8][CH2:9][CH:10]=[CH:11][C:12]1=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]=[CH:11][C:12]1=[O:13] | CCOC(=O)CBr.O=C1C=CCCC1 | CCOC(=O)CC1CCC=CC1=O | null | null | O1CCCC1 | C-C Coupling | OtherReaction | f8d19cb0663cf5fc97b54d8c9ce649320dc8385e26cbf2d3227726fa074d8ce2 | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | O=C1C=CCCC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]1-[C:8]=[C:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[CH;D3;+0:12]1-[C:11]-[C:10]-[C:9]=[C:8]-[C:7]-1=[O;D1;H0:6] | null | [] | null | null | 20 | MINUTE | A solution of 2-cyclohexen-1-one (20 g, 0.208 mmol) in tetrahydrofuran (250 ml) was added to a preformed lithium diisopropylamide solution (prepared from diisopropylamine (31 ml) and n-butyllithium (140 ml, 1.6M solution) at −70° C.) over 20 minutes and stirred for a further 20 minutes. Ethyl bromoacetate (25 ml, 0.228... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | HBr | O1CCCC1 | null | 0.333333 | CCOC(=O)CBr.O=C1C=CCCC1>O1CCCC1>CCOC(=O)CC1CCC=CC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2d4777b6081240f594287e9174a72b72 | CCOC(=O)CC1CCC=CC1=O.Fc1cc[c]([Mg][Br])cc1>>CCOC(=O)CC1CCC(c2ccc(F)cc2)CC1=O | O=C1C(CCC=C1)CC(=O)OCC.FC1=CC=C(C=C1)[Mg]Br>>FC1=CC=C(C=C1)C1CC(C(CC1)CC(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]=[CH:18][C:19]1=[O:20].[Br][Mg][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][C:19]1=[O:20] | CCOC(=O)CC1CCC=CC1=O.Fc1cc[c]([Mg][Br])cc1 | CCOC(=O)CC1CCC(c2ccc(F)cc2)CC1=O | null | null | O1CCCC1.CSC | C-C Coupling | OtherReaction | b8beabd2dbc6a254ca24780c737c5463d8f6016f5fc49a6e23a39f215d151113 | 135f2ea95ad9a9b731f59e3aadf4d42e0f9aa41135665e9340592661a7692c1c | O=C1CCCC(c2ccccc2)C1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10]-[CH;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[CH2;D2;+0:12]-1 | null | [] | null | null | 20 | MINUTE | This ester (4 g, 0.022 mmol), copper (I) bromide-dimethyl sulfide complex (4.88 g, 0.023 mmol) in dimethyl sulfide (20 ml) and tetrahydrofuran (120 ml) was cooled to −40° C. under nitrogen and treated dropwise with 4-fluorophenylmagnesium bromide (1M solution in THF, 43.9 ml) so that the temperature did not rise above ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Ketone | C1=CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | Br-.Mg | O1CCCC1.CSC | null | 0.333333 | CCOC(=O)CC1CCC=CC1=O.Fc1cc[c]([Mg][Br])cc1>O1CCCC1.CSC>CCOC(=O)CC1CCC(c2ccc(F)cc2)CC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f60a963a40874eb2bc297b9753793e5a | CCOC(=O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21>>O=C(O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21 | ClC1=C(C=CC(=C1)Cl)C1=CN(C=2C(CCCC12)CC(=O)OCC)C(CCC1=CC=CC=C1)C1=CC=C(C=C1)C(F)(F)F.[Li+].[OH-]>>ClC1=C(C=CC(=C1)Cl)C1=CN(C=2C(CCCC12)CC(=O)O)C(CCC1=CC=CC=C1)C1=CC=C(C=C1)C(F)(F)F | CC[O:3][C:2](=[O:1])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[cH:19][n:20]([CH:21]([CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[c:30]3[cH:31][cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38][cH:39]3)[c:40]21>>[O:1]=[C:2]([OH:3])[CH2:4][C... | CCOC(=O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21 | O=C(O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21 | null | null | CCOC(=O)C.O.O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCC(c2ccccc2)n2cc(-c3ccccc3)c3c2CCCC3)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 60 | CELSIUS | null | null | The ester from the foregoing step (0.03 g, 0.05 mmol) was dissolved in a mixture of dioxane (7 ml)/water (2 ml). Then LiOH (12 mg, 0.5 mmol) was added and the solution heated to 60° C. for 14 h. The reaction mixture was then diluted with AcOEt (20 ml), washed with 2.0N HCl (20 ml), brine (20 ml), dried over Na2SO4 and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1c[nH]c2c1CCC[CH]2.c1ccccc1.c1ccccc1 | Other | CCOC(=O)C.O.O1CCOCC1 | 60 | null | CCOC(=O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21>CCOC(=O)C.O.O1CCOCC1>O=C(O)CC1CCCc2c(-c3ccc(Cl)cc3Cl)cn(C(CCc3ccccc3)c3ccc(C(F)(F)F)cc3)c21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e96109b552dd4f269eee287f5bebff85 | CCN(CC)CC.CCOC(C)=O.O=C(Cl)c1ccc(Cl)cc1Cl>>CCOC(=O)CC1CCCC(C(=O)c2ccc(Cl)cc2Cl)C1=O | C(C)(=O)OCC.C(C)N(CC)CC.ClC1=C(C(=O)Cl)C=CC(=C1)Cl>>ClC1=C(C(=O)C2C(C(CCC2)CC(=O)OCC)=O)C=CC(=C1)Cl | N([CH2:7][CH3:22])([CH2:8][CH3:9])[CH2:10][CH3:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]1[Cl:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]2[Cl:21])[C:2... | CCN(CC)CC.CCOC(C)=O.O=C(Cl)c1ccc(Cl)cc1Cl | CCOC(=O)CC1CCCC(C(=O)c2ccc(Cl)cc2Cl)C1=O | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | 966ef46f65e2d9d537f4dbf2bb16da9933f09f55de9a5caf6cd1fceeed2b9c62 | 5e69199b3713f19cb9321bf63be9b683f2c26f18dd2a3521343582a461cebafe | O=C1CCCCC1C(=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[CH2;D2;+0:7]-N(-[CH2;D2;+0:8]-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[CH3;D1;+0:11].[C:12]-[#8:13]-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16]>>[C:12]-[#8:13]-[C:14](=[O;D1;H0:16])-[CH2;D2;+0:15]-[CH;D3;+0:8]1-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:7]-[CH;D3;+0:6](-[... | null | [] | null | null | null | null | Intermediate 2 (2 g, 8.44 mmol) was dissolved in dioxane (50 ml) and triethylamine (1.18 ml, 8.44 mmol) and 2,4-dichlorobenzoyl chloride (1.76 g, 844 mmol) added. The reaction mixture was stirred at reflux for 16 h. The mixture was then allowed to cool and diluted with ethyl acetate and washed with saturated sodium bic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Tertiary amine | Ketone.Ketone.Ester | null | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HCl | O1CCOCC1 | null | null | CCN(CC)CC.CCOC(C)=O.O=C(Cl)c1ccc(Cl)cc1Cl>O1CCOCC1>CCOC(=O)CC1CCCC(C(=O)c2ccc(Cl)cc2Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b898882e96cb45c1803327a8130cdd74 | CO.O=Cc1c[nH]c2cccc(Br)c12>>COC(=O)c1c[nH]c2cccc(Br)c12 | CO.BrC1=C2C(=CNC2=CC=C1)C=O.[C-]#N.[Na+]>>BrC1=C2C(=CNC2=CC=C1)C(=O)OC | [CH3:1][OH:2].[CH:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([Br:13])[c:14]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([Br:13])[c:14]12 | CO.O=Cc1c[nH]c2cccc(Br)c12 | COC(=O)c1c[nH]c2cccc(Br)c12 | null | [O-2].[O-2].[Mn+4] | C(C)(=O)OCC | Acylation | Oxidation of alcohol and aldehyde to ester | 6c2cf9780d2b06093c0103c8dd3456912317575c5e7e70f8999846e7a24bbf0c | df63d853b69ab8d080a5e6aeacb0edaa9eaa2dd261e6fc3594fda9a1c296389c | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[OH;D1;+0:2].[O;D1;H0:3]=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[C;H0;D3;+0:4](=[O;D1;H0:3])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | 8 | HOUR | To a methanol (40 mL) solution of 4-bromo-1H-indole-3-carboaldehyde [Chem. Pharm. Bull. 33,3696 (1985)] (395 mg), sodium cyanide (432 mg) and manganese dioxide (15.3 g) were sequentially added and the mixture was stirred overnight at room temperature. To the reaction mixture, ethyl acetate (50 mL) was added and insolub... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Methanol | Ester | null | null | c1ccc2[nH]ccc2c1 | null | [O-2].[O-2].[Mn+4].C(C)(=O)OCC | null | 8 | CO.O=Cc1c[nH]c2cccc(Br)c12>[O-2].[O-2].[Mn+4].C(C)(=O)OCC>COC(=O)c1c[nH]c2cccc(Br)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-670c665077724bca8cf125a62ee6991a | O=C(O)Cc1c[nH]c2cccc(Br)c12>>CC(C(=O)O)c1c[nH]c2cccc(Br)c12 | BrC1=C2C(=CNC2=CC=C1)CC(=O)O.S(=O)(Cl)Cl.C(O)([O-])=O.[Na+]>>CC(C(=O)O)C1=CNC2=CC=CC(=C12)Br | [CH2:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Br:14])[c:15]12>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Br:14])[c:15]12 | O=C(O)Cc1c[nH]c2cccc(Br)c12 | CC(C(=O)O)c1c[nH]c2cccc(Br)c12 | null | null | CO | Miscellaneous | Methylation | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2[nH]ccc2c1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1>>[C;D1;H3:10]-[CH;D3;+0:4](-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | 30 | MINUTE | To methanol (10 mL), thionyl chloride (0.76 mL) was added dropwise at −15 to −10° C., followed by stirring for 30 minutes. To the mixture, (4-bromo-1H-indol-3-yl)acetic acid (Chemical and Pharmaceutical Bulletin, 33(9), 3696-3708 (1985), 1.32 g) was added, followed by stifling at room temperature for 2 hours. To the re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1 | Other | CO | null | 0.5 | O=C(O)Cc1c[nH]c2cccc(Br)c12>CO>CC(C(=O)O)c1c[nH]c2cccc(Br)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e993f9013eb04841a817eda50d228980 | Brc1cccc2cc[nH]c12.CCOC(=O)CCC(=O)O>>CCOC(=O)CCC(=O)c1c[nH]c2c(Br)cccc12 | BrC=1C=CC=C2C=CNC12.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].C(C)OC(CCC(=O)O)=O>>BrC=1C=CC=C2C(=CNC12)C(CCC(=O)OCC)=O | [cH:10]1[cH:11][nH:12][c:13]2[c:14]([Br:15])[cH:16][cH:17][cH:18][c:19]12.O[C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][nH:12][c:13]2[c:14]([Br:15])[cH:16][cH:17][cH:18][c:19]12 | Brc1cccc2cc[nH]c12.CCOC(=O)CCC(=O)O | CCOC(=O)CCC(=O)c1c[nH]c2c(Br)cccc12 | null | null | C(C)(=O)OCC | C-C Coupling | Friedel-Crafts acylation | 643dd2526887f35e47a621da873d478d9a850a82a4a035ba34c578de251cf299 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | c1ccc2[nH]ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | 30 | MINUTE | To a dichloromethane (50 mL) solution of aluminum chloride (6.80 g), succinic acid monoethyl ester chloride (8.39 g) was added under ice cooling and the mixture was stirred for 30 minutes. To the mixture, 7-bromoindole (5.0 g) was added, followed by stirring at room temperature for 5 hours. To the reaction mixture, ice... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)(=O)OCC | null | 0.5 | Brc1cccc2cc[nH]c12.CCOC(=O)CCC(=O)O>C(C)(=O)OCC>CCOC(=O)CCC(=O)c1c[nH]c2c(Br)cccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-89b9fac623f644f58e5b221f3871bc84 | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12.CSSC>>CCOC(=O)CCCc1c(SC)n(CC(=O)OCC)c2c(Br)cccc12 | BrC=1C=CC=C2C(=CN(C12)CC(=O)OCC)CCCC(=O)OCC.CSSC.S(=O)(=O)(Cl)Cl.C(O)([O-])=O.[Na+]>>BrC=1C=CC=C2C(=C(N(C12)CC(=O)OCC)SC)CCCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][n:13]([CH2:14][C:15](=[O:16])[O:17][CH2:18][CH3:19])[c:20]2[c:21]([Br:22])[cH:23][cH:24][cH:25][c:26]12.CS[S:11][CH3:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[c:10]([S:11][CH3:12])[n:13]([CH2:14][C:15](=[O:16])[O:17][CH2:18][CH3:1... | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12.CSSC | CCOC(=O)CCCc1c(SC)n(CC(=O)OCC)c2c(Br)cccc12 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | ad248cf111f817c98ea46473689eb96090b66a2ca74be4a4f40e2c225f4226c5 | 19099c5abc7af7f1b3d32ffaaaa6b84236f3e8c2bf9cb204008fe61bb9aa47e2 | c1ccc2[nH]ccc2c1 | C-S-[S;H0;D2;+0:1]-[C;D1;H3:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10](-[C:11]):[cH;D2;+0:12]:1>>[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10](-[C:11]):[c;H0;D3;+0:12]:1-[S;H0;D2;+0:1]-[C;D1;H3:2] | null | [] | -5 | CELSIUS | 1.5 | HOUR | To a chloroform (0.8 mL) solution of dimethyl disulfide (30 mg), sulfuryl chloride (34 mg) was added at −15° C. and the mixture was stirred at −5° C. for 1.5 hours. To the reaction mixture, a chloroform (0.5 mL) solution of the compound prepared in Example 43, namely, ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-ind... | 10.6084/m9.figshare.5104873.v1 | null | Disulfide | Monosulfide | c1c[nH]c2ccccc12 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | Other | C(Cl)(Cl)Cl | -5 | 1.5 | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12.CSSC>C(Cl)(Cl)Cl>CCOC(=O)CCCc1c(SC)n(CC(=O)OCC)c2c(Br)cccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0c8396c2e311451a90052e3059475ff1 | CC(C)(C)OC(=O)n1cc(CC#N)c2c(Br)cccc21.CI>>CC(C#N)c1c[nH]c2cccc(Br)c12 | CI.O1CCCC1.BrC1=C2C(=CN(C2=CC=C1)C(=O)OC(C)(C)C)CC#N.C(C)(C)[N-]C(C)C.[Li+]>>BrC1=C2C(=CNC2=CC=C1)C(C#N)C | CC(C)(C)OC(=O)[n:7]1[cH:6][c:5]([CH2:2][C:3]#[N:4])[c:14]2[c:8]1[cH:9][cH:10][cH:11][c:12]2[Br:13].I[CH3:1]>>[CH3:1][CH:2]([C:3]#[N:4])[c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([Br:13])[c:14]12 | CC(C)(C)OC(=O)n1cc(CC#N)c2c(Br)cccc21.CI | CC(C#N)c1c[nH]c2cccc(Br)c12 | null | null | CO.O | C-C Coupling | OtherReaction | 07049849031e3a31f966459abf4e157571e058dc660d9b7a1bcc5af2de911b16 | 46639df34c39bd91d429c22b8aea37df20d44d8a45c388ab04087f5136adf0a7 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2]:[c:3](-[CH2;D2;+0:4]-[C:5]#[N;D1;H0:6]):[c:7]:[c:8]:1:[c:9].I-[CH3;D1;+0:10]>>[CH3;D1;+0:10]-[CH;D3;+0:4](-[C:5]#[N;D1;H0:6])-[c:3]1:[c:7]:[c:8](:[c:9]):[nH;D2;+0:1]:[c:2]:1 | null | [] | null | null | 1 | HOUR | To a tetrahydrofuran solution (10 mL) of 1, -dimethylethyl 4-bromo-3-(cyanomethyl)-1H-indole-1-carboxylate [CAS registration number 151726-05-5, Organic Letters 2003, 5(19), 3519-3522] (1.0 g), lithium diisopropylamide (2M tetrahydrofuran solution; 3.4 mL) was added dropwise at −78° C. and the mixture was stirred at th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HI | CO.O | null | 1 | CC(C)(C)OC(=O)n1cc(CC#N)c2c(Br)cccc21.CI>CO.O>CC(C#N)c1c[nH]c2cccc(Br)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-18c7108f9b7b495bb89c863858504bb5 | CC(C#N)c1c[nH]c2cccc(Br)c12.CCO.[OH-]>>CC(C(=O)O)c1c[nH]c2cccc(Br)c12 | Cl.BrC1=C2C(=CNC2=CC=C1)C(C#N)C.C(C)O.[OH-].[K+]>>BrC1=C2C(=CNC2=CC=C1)C(C(=O)O)C | N#[C:3][CH:2]([CH3:1])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Br:14])[c:15]12.CC[OH:5].[OH-:4]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Br:14])[c:15]12 | CC(C#N)c1c[nH]c2cccc(Br)c12.CCO.[OH-] | CC(C(=O)O)c1c[nH]c2cccc(Br)c12 | null | null | C(CO)O | Acylation | OtherReaction | e41cdaf6ecb9257286a05c8e01433d124042c5939fb4d758964487a1f4637b56 | e38d1b350c527156572f58ef95bb65354ed43ce776b83f166b6fd042d5d9aca9 | c1ccc2[nH]ccc2c1 | C-C-[OH;D1;+0:1].N#[C;H0;D2;+0:2]-[C:3](-[C;D1;H3:4])-[c:5]:[c:6]:[#7;a:7].[OH-;D0:8]>>[#7;a:7]:[c:6]:[c:5]-[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:2](=[O;H0;D1;+0:8])-[OH;D1;+0:1] | null | [] | 120 | CELSIUS | 8 | HOUR | The compound prepared in Example 51, namely, 2-(4-bromo-1H-indol-3-yl)propanenitrile (184 mg) was dissolved in a mixture of ethanol (1 mL) and ethylene glycol (1 mL) and an aqueous 20% potassium hydroxide solution (0.5 mL) was added, and then the mixture was stirred overnight at 120° C. The reaction mixture was ice-coo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | C(CO)O | 120 | 8 | CC(C#N)c1c[nH]c2cccc(Br)c12.CCO.[OH-]>C(CO)O>CC(C(=O)O)c1c[nH]c2cccc(Br)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3e013e4fe1c942929986588c683791e1 | C=O.CNC.Cc1cc2c([N+](=O)[O-])cccc2[nH]1>>Cc1[nH]c2cccc([N+](=O)[O-])c2c1CN(C)C | [OH-].[Na+].CC=1NC2=CC=CC(=C2C1)[N+](=O)[O-].C=O.CNC>>CN(CC1=C(NC2=CC=CC(=C12)[N+](=O)[O-])C)C | O=[CH2:17].[CH3:14][NH:15][CH3:16].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]2[cH:13]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]2[c:13]1[CH2:14][N:15]([CH3:16])[CH3:17] | C=O.CNC.Cc1cc2c([N+](=O)[O-])cccc2[nH]1 | Cc1[nH]c2cccc([N+](=O)[O-])c2c1CN(C)C | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 14f2bfa3d907d463fab4dfc74293051dd668edd77fb6e0a45ccb47b35b91e990 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2[nH]ccc2c1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[CH3;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[c:10](:[c:11]):[cH;D2;+0:12]:1>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[CH3;D1;+0:1])-[CH2;D2;+0:4]-[c;H0;D3;+0:12]1:[c:10](:[c:11]):[c:8](:[c:9]):[#7;a:7]:[c:6]:1-[C;D1;H3:5] | null | [] | null | null | 30 | MINUTE | To an acetic acid (5 mL) solution of an aqueous 370% formaldehyde solution (271 mg), an aqueous 50% dimethylamine solution (317 mg) was slowly added dropwise under ice cooling and the mixture was stirred at room temperature for 30 minutes. Furthermore, an acetic acid (1 mL) solution of 2-methyl-4-nitro-1H-indole [Tetra... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)(=O)O | null | 0.5 | C=O.CNC.Cc1cc2c([N+](=O)[O-])cccc2[nH]1>C(C)(=O)O>Cc1[nH]c2cccc([N+](=O)[O-])c2c1CN(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-effc2502315540b28200c0e001c18674 | Cn1c(C(=O)O)cc2cccc(Br)c21.O=C(Cl)C(=O)Cl>>Cn1c(C(=O)Cl)cc2cccc(Br)c21 | ClCCl.BrC=1C=CC=C2C=C(N(C12)C)C(=O)O.C(C(=O)Cl)(=O)Cl>>BrC=1C=CC=C2C=C(N(C12)C)C(=O)Cl | O[C:4]([c:3]1[n:2]([CH3:1])[c:14]2[c:8]([cH:7]1)[cH:9][cH:10][cH:11][c:12]2[Br:13])=[O:5].O=C(Cl)C(=O)[Cl:6]>>[CH3:1][n:2]1[c:3]([C:4](=[O:5])[Cl:6])[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([Br:13])[c:14]12 | Cn1c(C(=O)O)cc2cccc(Br)c21.O=C(Cl)C(=O)Cl | Cn1c(C(=O)Cl)cc2cccc(Br)c21 | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2[nH]ccc2c1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6](-[C;D1;H3:7]):[c:8]>>[C;D1;H3:7]-[#7;a:6](:[c:8]):[c:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3]):[c:5] | null | [] | null | null | 2 | HOUR | To a dichloromethane (2 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid (200 mg), oxalyl dichloride (0.10 mL) and N,N-dimethylformamide (5 mL) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, azeotroped twice with toluene to obtain a crude produ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc2ccccc2[nH]1 | HCl | CN(C=O)C | null | 2 | Cn1c(C(=O)O)cc2cccc(Br)c21.O=C(Cl)C(=O)Cl>CN(C=O)C>Cn1c(C(=O)Cl)cc2cccc(Br)c21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-757e66c04e504a789c6f1879b02fcaff | C[Si](C)(C)C=[N+]=[N-].Cn1c(C(=O)Cl)cc2cccc(Br)c21>>Cn1c(C(=O)/C=N/N)cc2cccc(Br)c21 | [Cl-].[NH4+].BrC=1C=CC=C2C=C(N(C12)C)C(=O)Cl.C[Si](C)(C)C=[N+]=[N-].CN(C)C>>BrC=1C=CC=C2C=C(N(C12)C)C(/C=N/N)=O | C[Si](C)(C)[CH:6]=[N+:7]=[N-:8].Cl[C:4]([c:3]1[n:2]([CH3:1])[c:16]2[c:10]([cH:9]1)[cH:11][cH:12][cH:13][c:14]2[Br:15])=[O:5]>>[CH3:1][n:2]1[c:3]([C:4](=[O:5])/[CH:6]=[N:7]/[NH2:8])[cH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([Br:15])[c:16]12 | C[Si](C)(C)C=[N+]=[N-].Cn1c(C(=O)Cl)cc2cccc(Br)c21 | Cn1c(C(=O)/C=N/N)cc2cccc(Br)c21 | null | null | O1CCCC1.C(C)#N | C-C Coupling | OtherReaction | 0eb9be582b4171e98855756865423597104bc4b70df5314952b9e9075be4f11d | c805d004663bed78868aa4a8654ca69ef2c416641e3fb5c93f35d7da53258a43 | c1ccc2[nH]ccc2c1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[#7;a:8](-[C;D1;H3:9]):[c:10]>>[C;D1;H3:9]-[#7;a:8](:[c:10]):[c:6](-[C;H0;D3;+0:4](=[O;D1;H0:5])/[CH;D2;+0:1]=[N;H0;D2;+0:2]/[NH2;D1;+0:3]):[c:7] | null | [] | null | null | 4 | HOUR | To a dichloromethane (2 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid (200 mg), oxalyl dichloride (0.10 mL) and N,N-dimethylformamide (5 mL) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, azeotroped twice with toluene to obtain a crude produ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Diazo.Silyl protective group | Hydrazone.Ketone | null | null | c1cc2ccccc2[nH]1 | HCl | O1CCCC1.C(C)#N | null | 4 | C[Si](C)(C)C=[N+]=[N-].Cn1c(C(=O)Cl)cc2cccc(Br)c21>O1CCCC1.C(C)#N>Cn1c(C(=O)/C=N/N)cc2cccc(Br)c21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-27fdefc4bc05481e8d695825b2e4ecdb | Brc1cccc2cc[nH]c12.N#CCCCCl>>N#CCCCc1c[nH]c2c(Br)cccc12 | [Cl-].[NH4+].BrC=1C=CC=C2C=CNC12.ClCCCC#N.C(C)[Mg]Br>>BrC=1C=CC=C2C(=CNC12)CCCC#N | [cH:6]1[cH:7][nH:8][c:9]2[c:10]([Br:11])[cH:12][cH:13][cH:14][c:15]12.Cl[CH2:5][CH2:4][CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][c:9]2[c:10]([Br:11])[cH:12][cH:13][cH:14][c:15]12 | Brc1cccc2cc[nH]c12.N#CCCCCl | N#CCCCc1c[nH]c2c(Br)cccc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Friedel-Crafts alkylation with halide | 4d207e3c16b48cdb1b200abcc5d949fb598eca99a1ea70eadeb1706cdf73ce8c | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:1:[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](:[c:4]):[c:9]:1:[c:10] | null | [] | null | null | null | null | To an anhydrous toluene (12 mL) solution of 7-bromoindole (1.0 g) and 4-chlorobutyronitrile (0.26 g), ethylmagnesium bromide (3.0M diethyl ether solution; 1.7 mL) was added dropwise under ice cooling and the mixture was heated to reflux for 4.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | C1(=CC=CC=C1)C | null | null | Brc1cccc2cc[nH]c12.N#CCCCCl>C1(=CC=CC=C1)C>N#CCCCc1c[nH]c2c(Br)cccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2d289fed0e074cd691f580ff0c9eda52 | BrBr.COC(=O)Cc1c(C)[nH]c2ccc(OC)cc12>>COC(=O)Cc1c(C)[nH]c2ccc(OC)c(Br)c12 | C(C)(=O)O.CC=1NC2=CC=C(C=C2C1CC(=O)OC)OC.BrBr.C(O)([O-])=O.[Na+]>>BrC1=C2C(=C(NC2=CC=C1OC)C)CC(=O)OC | Br[Br:17].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[c:7]([CH3:8])[nH:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[c:7]([CH3:8])[nH:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([Br:17])[c:18]12 | BrBr.COC(=O)Cc1c(C)[nH]c2ccc(OC)cc12 | COC(=O)Cc1c(C)[nH]c2ccc(OC)c(Br)c12 | null | null | O | Functional Group Interconversion | Bromination | 5f4e3ce42c7a2194af7c1cddbdb297d0a7498335a4f1fa479422f2b4e9c014a9 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2[nH]ccc2c1 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3]1:[c:4]:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:[cH;D2;+0:11]:1>>[#8:2]-[c:3]1:[c:4]:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:[c;H0;D3;+0:11]:1-[Br;H0;D1;+0:1] | null | [] | null | null | 1 | HOUR | To an acetic acid (12 mL) solution of methyl [2-methyl-5-(methyloxy)-1H-indol-3-yl]acetate (300 mg), bromine (206 mg) was added and the mixture was stirred at room temperature for one hour. To the reaction mixture, water and an aqueous saturated sodium hydrogen carbonate solution were added, followed by extraction with... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | O | null | 1 | BrBr.COC(=O)Cc1c(C)[nH]c2ccc(OC)cc12>O>COC(=O)Cc1c(C)[nH]c2ccc(OC)c(Br)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-502f3206842346ae9fee5bc68ef8a314 | CCOC(=O)c1cc2cccc(Br)c2n1C>>Cn1c(CO)cc2cccc(Br)c21 | BrC=1C=CC=C2C=C(N(C12)C)C(=O)OCC.[BH4-].[Li+].[Cl-].[NH4+]>>BrC=1C=CC=C2C=C(N(C12)C)CO | CCO[C:4]([c:3]1[n:2]([CH3:1])[c:13]2[c:7]([cH:6]1)[cH:8][cH:9][cH:10][c:11]2[Br:12])=[O:5]>>[CH3:1][n:2]1[c:3]([CH2:4][OH:5])[cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([Br:12])[c:13]12 | CCOC(=O)c1cc2cccc(Br)c2n1C | Cn1c(CO)cc2cccc(Br)c21 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2[nH]ccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5](-[C;D1;H3:6]):[c:7]>>[C;D1;H3:6]-[#7;a:5](:[c:7]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 5 | HOUR | To a tetrahydrofuran (40 mL) solution of ethyl 7-bromo-1-methyl-1H-indole-2-carboxylate (1.99 g), lithium tetrahydroborate (463 mg) was added at 0° C., followed by stirring at room temperature for 5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, followed by extraction with et... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc2ccccc2[nH]1 | HO- | O1CCCC1 | null | 5 | CCOC(=O)c1cc2cccc(Br)c2n1C>O1CCCC1>Cn1c(CO)cc2cccc(Br)c21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-84f48ebed0bb446fb2cd7436530f7815 | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12>>C#Cc1cccc2c(CCCC(=O)OCC)cn(CC(=O)OCC)c12 | C(C)O.C(C)OC(CN1C=C(C2=CC=CC(=C12)C#C[Si](C)(C)C)CCCC(=O)OCC)=O.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C=C(C2=CC=CC(=C12)C#C)CCCC(=O)OCC)=O | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH3:16])[cH:17][n:18]([CH2:19][C:20](=[O:21])[O:22][CH2:23][CH3:24])[c:25]12>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH3:16])[cH:17][n:18]([CH2:19]... | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12 | C#Cc1cccc2c(CCCC(=O)OCC)cn(CC(=O)OCC)c12 | null | null | O | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2[nH]ccc2c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]:[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]:[c:3]-[C:2]#[CH;D1;+0:1] | null | [] | null | null | 3 | HOUR | To an ethanol (2 mL) solution of ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-[(trimethylsilyl)ethynyl]-1H-indol-3-yl}butanoate (98 mg), potassium carbonate (50 mg) was added and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1c[nH]c2ccccc12 | Other | O | null | 3 | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12>O>C#Cc1cccc2c(CCCC(=O)OCC)cn(CC(=O)OCC)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-34274aba76f546ffba4485ff08e92631 | C#C[Si](C)(C)C.CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12>>CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12 | BrC=1C=CC=C2C(=CN(C12)CC(=O)OCC)CCCC(=O)OCC.C(#C)[Si](C)(C)C>>C(C)OC(CN1C=C(C2=CC=CC(=C12)C#C[Si](C)(C)C)CCCC(=O)OCC)=O | [CH:20]#[C:21][Si:22]([CH3:23])([CH3:24])[CH3:25].Br[c:19]1[c:18]2[n:11]([CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:10][c:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:29]2[cH:28][cH:27][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][n:11]([CH2:12][C:13](=[O:14])[O:15][... | C#C[Si](C)(C)C.CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12 | CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12 | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | a1410a6c5f23eac1c4ad4220ff842029c2836b214e978253716a6ba5113e3720 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2[nH]ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11].[C;D1;H3:12]-[#14:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C:16]#[CH;D1;+0:17]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7;a:6](:[c:11]):[c:4](:[c:5]):[c;H0;D3;+0:1](-[C;H0;D2;+0:17]#[C:16]-[#14:13](-[C;D1;H3:12])(-[C;D1;H3:14])-[C;D... | null | [] | null | null | null | null | To an ethanol (2 mL) solution of ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-[(trimethylsilyl)ethynyl]-1H-indol-3-yl}butanoate (98 mg), potassium carbonate (50 mg) was added and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1c[nH]c2ccccc12 | c1c[nH]c2ccccc12 | c1c[nH]c2ccccc12 | HBr | null | null | null | C#C[Si](C)(C)C.CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(Br)cccc12>>CCOC(=O)CCCc1cn(CC(=O)OCC)c2c(C#C[Si](C)(C)C)cccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fcbf6697cd884c5cb752fd15782067cc | C=Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)CCCS(=O)(=O)c1cn(CC(=O)OC)c2c(Br)cccc12>>O=C(O)CCCS(=O)(=O)c1cn(CC(=O)O)c2c(/C=C/c3ccc(OCCCCOc4ccccc4)cc3)cccc12 | BrC=1C=CC=C2C(=CN(C12)CC(=O)OC)S(=O)(=O)CCCC(=O)OC.C(=C)C1=CC=C(C=C1)OCCCCOC1=CC=CC=C1>>C(=O)(O)CN1C=C(C2=CC=CC(=C12)\C=C\C1=CC=C(C=C1)OCCCCOC1=CC=CC=C1)S(=O)(=O)CCCC(=O)O | [CH2:19]=[CH:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38]1.C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][n:12]([CH2:13][C:14](=[O:15])[O:16]C)[c:17]2[c:18](Br)[cH:39][cH:40][cH:41][c:42]12>>[O:1]=[C:2]... | C=Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)CCCS(=O)(=O)c1cn(CC(=O)OC)c2c(Br)cccc12 | O=C(O)CCCS(=O)(=O)c1cn(CC(=O)O)c2c(/C=C/c3ccc(OCCCCOc4ccccc4)cc3)cccc12 | null | null | null | C-C Coupling | OtherReaction | 4387b7436ab7a423e67708d45ebe8dc2c1af1523c11184decc19ed58624dc736 | be2bfc00bc9d3c502291c9bc6801d9a586862814583043779054eac086f1a966 | C(=C/c1cccc2cc[nH]c12)\c1ccc(OCCCCOc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C):[c:11].C-[O;H0;D2;+0:12]-[C:13](-[C:14])=[O;D1;H0:15].[CH2;D1;+0:16]=[C:17]-[c:18]>>[C:14]-[C:13](=[O;D1;H0:15])-[OH;D1;+0:12].[O;D1;H0:9]=[C:8](-[OH;D1;+0:10])-[C:7]-[#7;a:6](:[c:11]):[c:4](:[c:5]):[c;H0;D3;+0:1](/[CH;... | null | [] | null | null | null | null | Except for using the compound prepared in Example 103 in place of the compound prepared in Example 2 and 1-ethenyl-4-{[4-(phenyloxy)butyl]oxy}benzene in place of 4-vinylphenyl acetate, the same operation as in Example 3→Example 6 was conducted to obtain the titled compound having the following physical properties.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Vinyl | Carboxylic acid.Carboxylic acid | c1c[nH]c2ccccc12 | c1c[nH]c2ccccc12 | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HBr | null | null | null | C=Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)CCCS(=O)(=O)c1cn(CC(=O)OC)c2c(Br)cccc12>>O=C(O)CCCS(=O)(=O)c1cn(CC(=O)O)c2c(/C=C/c3ccc(OCCCCOc4ccccc4)cc3)cccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bb62d166589e47b08bd5708375452f37 | Brc1cccc2cc[nH]c12.Cc1ccccc1.[NH4+]>>N#CCC1(Cc2c[nH]c3c(Br)cccc23)CC1 | [Cl-].[NH4+].C(C)[Mg]Br.C1(=CC=CC=C1)C.BrC=1C=CC=C2C=CNC12>>BrC=1C=CC=C2C(=CNC12)CC1(CC1)CC#N | [cH:6]1[cH:7][nH:8][c:9]2[c:10]([Br:11])[cH:12][cH:13][cH:14][c:15]12.c1c[c:4]([CH3:5])[cH:16][cH:17]c1.[NH4+:1]>>[N:1]#[C:2][CH2:3][C:4]1([CH2:5][c:6]2[cH:7][nH:8][c:9]3[c:10]([Br:11])[cH:12][cH:13][cH:14][c:15]23)[CH2:16][CH2:17]1 | Brc1cccc2cc[nH]c12.Cc1ccccc1.[NH4+] | N#CCC1(Cc2c[nH]c3c(Br)cccc23)CC1 | null | null | C(C)OCC.C(C)#N | C-C Coupling | OtherReaction | 6416aba81bbecae357140f2939a749a32f766386d533b7e0f3c587fafd6c33f6 | b8bacb90390718f4555f6dee24489036b4f724075b0543a5a9bf8e9abad9b32c | c1ccc2c(CC3CC3)c[nH]c2c1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:c:c:c:1.[NH4+;D0:5].[c:6]:[c:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[N;H0;D1;+0:5]#[C:13]-[C:14]-[C;H0;D4;+0:2]1(-[CH2;D2;+0:1]-[c;H0;D3;+0:10]2:[c:9]:[#7;a:8]:[c:7](:[c:6]):[c:11]:2:[c:12])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1 | null | [] | null | null | null | null | To a toluene (12 mL) solution of 7-bromoindole (1.00 g), [1-bromomethyl)cyclopropyl]acetonitrile (444 mg) was added and a diethyl ether solution (1.7 mL) of 3M ethylmagnesium bromide was added dropwise under ice cooling, and then the mixture was refluxed for 2.5 hours. To the reaction mixture, an aqueous saturated ammo... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.C1CC1 | c1ccc2[nH]ccc2c1.C1CC1 | Other | C(C)OCC.C(C)#N | null | null | Brc1cccc2cc[nH]c12.Cc1ccccc1.[NH4+]>C(C)OCC.C(C)#N>N#CCC1(Cc2c[nH]c3c(Br)cccc23)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9c25fc59113f4ee5ad6fdc1b8bb23676 | CC(C)(NC(=O)OCc1ccccc1)C(=O)O.NC(=O)c1cccc(N)c1N>>CC(C)(NC(=O)OCc1ccccc1)C(=O)Nc1cccc(C(N)=O)c1N | N.C(C1=CC=CC=C1)OC(=O)NC(C(=O)O)(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.NC1=C(C(=O)N)C=CC=C1N>>NC1=C(C=CC=C1C(=O)N)NC(C(C)(C)NC(OCC1=CC=CC=C1)=O)=O | O[C:15]([C:2]([CH3:1])([CH3:3])[NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]([C:23]([NH2:24])=[O:25])[c:26]1[NH2:27]>>[CH3:1][C:2]([CH3:3])([NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[NH:17][c:18... | CC(C)(NC(=O)OCc1ccccc1)C(=O)O.NC(=O)c1cccc(N)c1N | CC(C)(NC(=O)OCc1ccccc1)C(=O)Nc1cccc(C(N)=O)c1N | null | null | CN(C)C=O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)OCc1ccccc1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[#7:6]-[C:7]=[O;D1;H0:8])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | 40 | CELSIUS | 8 | HOUR | 2-{[(Benzyloxy)carbonyl]amino}-2-methylpropanoic acid (5.18 g, 21.83 mmol) in a mixture of pyridine (25 mL) and DMF (25 mL) was treated with 1,1′-carbonyldiimidazole (3.72 g, 22.92 mmol) and heated at 40° C. for 2 hours. 2,3-Diaminobenzamide dihydrochlolide (4.89 g, 21.83 mmol), prepared as described in WO0026192, was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.N1=CC=CC=C1 | 40 | 8 | CC(C)(NC(=O)OCc1ccccc1)C(=O)O.NC(=O)c1cccc(N)c1N>CN(C)C=O.N1=CC=CC=C1>CC(C)(NC(=O)OCc1ccccc1)C(=O)Nc1cccc(C(N)=O)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5afe6e66a8f74511804c82406d689f87 | O=C(Cl)OCc1ccccc1.O=C(OCc1ccccc1)C1CCN1>>O=C(OCc1ccccc1)C1CCN1C(=O)OCc1ccccc1 | N1C(CC1)C(=O)OCC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].ClC(=O)OCC1=CC=CC=C1>>N1(C(CC1)C(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1 | Cl[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][NH:14]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:... | O=C(Cl)OCc1ccccc1.O=C(OCc1ccccc1)C1CCN1 | O=C(OCc1ccccc1)C1CCN1C(=O)OCc1ccccc1 | null | N1CCNCC1 | O.O1CCOCC1 | Protection | N-alkylation of secondary amines with alkyl halides | ab1f56f9799c3dc66e341c4a2c7ef981d06caa71d9d93c0206f4ac6c4c804b86 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)C1CCN1C(=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[C:9]-1-[C:7](=[O;D1;H0:8])-[#8:6]-[C:5] | 99.5 | [{"value": 96.0, "product": "N1(C(CC1)C(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "N1(C(CC1)C(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | Benzyl azetidine-2-carboxylate (4.0 g, 21 mmol) and potassium carbonate (5 g, 36 mmol) in a mixture of 1,4-dioxane (25 ml) and water (30 ml) was treated with benzyl chloroformate (3 ml, 21 mmol) at room temperature for 6 hours. Piperazine (5 drops) was added and the mixture was stirred for additional 0.5 hour. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | HCl | N1CCNCC1.O.O1CCOCC1 | null | 0.5 | O=C(Cl)OCc1ccccc1.O=C(OCc1ccccc1)C1CCN1>N1CCNCC1.O.O1CCOCC1>O=C(OCc1ccccc1)C1CCN1C(=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-caab6c8690124ab0a60e8c9035a4719f | NC(=O)c1cccc([N+](=O)[O-])c1N.O=C1CCC(=O)N1Cl>>NC(=O)c1cc(Cl)cc([N+](=O)[O-])c1N | NC1=C(C(=O)N)C=CC=C1[N+](=O)[O-].ClN1C(CCC1=O)=O>>NC1=C(C(=O)N)C=C(C=C1[N+](=O)[O-])Cl | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[NH2:14].O=C1CCC(=O)N1[Cl:7]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[NH2:14] | NC(=O)c1cccc([N+](=O)[O-])c1N.O=C1CCC(=O)N1Cl | NC(=O)c1cc(Cl)cc([N+](=O)[O-])c1N | null | null | C(C)#N | Functional Group Interconversion | Chlorination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:6]:[c:5]-[C:3](-[N;D1;H2:2])=[O;D1;H0:4]):[c:8]:[c:9] | 84 | [{"value": 84.0, "product": "NC1=C(C(=O)N)C=C(C=C1[N+](=O)[O-])Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "NC1=C(C(=O)N)C=C(C=C1[N+](=O)[O-])Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino-3-nitrobenzamide (4.0 g) in warm anhydrous acetonitrile (1.25 L) was treated with N-chlorosuccinimide (3.1 g) at 60° C. under nitrogen for 20 hours. The mixture was allowed to cool to room temperature and filtered. The filter cake was washed with acetonitrile and dried to provide the title compound (3.98 g, 84%... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | C(C)#N | null | null | NC(=O)c1cccc([N+](=O)[O-])c1N.O=C1CCC(=O)N1Cl>C(C)#N>NC(=O)c1cc(Cl)cc([N+](=O)[O-])c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3c7f730b94f942349c7865919bff10b4 | NC(=O)c1cccc(N)c1N.O=C(NC1(C(=O)O)CCCCC1)OCC1c2ccccc2-c2ccccc21>>NC(=O)c1cccc(NC(=O)C2(NC(=O)OCC3c4ccccc4-c4ccccc43)CCCCC2)c1N | C(C)(C)O.C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)NC1(CCCCC1)C(=O)O.C(=O)(C=1NC=CN1)C=1NC=CN1.Cl.Cl.NC1=C(C(=O)N)C=CC=C1N>>C1=CC=CC=2C3=CC=CC=C3C(C12)COC(NC1(CCCCC1)C(NC1=C(C(=CC=C1)C(N)=O)N)=O)=O | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[c:36]1[NH2:37].O[C:10](=[O:11])[C:12]1([NH:13][C:14](=[O:15])[O:16][CH2:17][CH:18]2[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3-[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8... | NC(=O)c1cccc(N)c1N.O=C(NC1(C(=O)O)CCCCC1)OCC1c2ccccc2-c2ccccc21 | NC(=O)c1cccc(NC(=O)C2(NC(=O)OCC3c4ccccc4-c4ccccc43)CCCCC2)c1N | null | null | CN(C)C=O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1(C(=O)Nc2ccccc2)CCCCC1)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])(-[C:7])-[C:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:7]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:8] | null | [] | 40 | CELSIUS | 1 | HOUR | A solution of 1-(9H-fluoren-9-ylmethoxycarbonyl amino)-cyclohexanecarboxylic acid (0.326 g, 0.9 mmol) in pyridine (1 mL) and DMF (1 ml) was heated to 40° C. for 30 min. Carbonyl diimidazole (0.15 g, 0.9 mmol) was added and the mixture was stirred at 40° C. for 1 hour then treated with 2,3-diamino-benzamide dihydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=O.N1=CC=CC=C1 | 40 | 1 | NC(=O)c1cccc(N)c1N.O=C(NC1(C(=O)O)CCCCC1)OCC1c2ccccc2-c2ccccc21>CN(C)C=O.N1=CC=CC=C1>NC(=O)c1cccc(NC(=O)C2(NC(=O)OCC3c4ccccc4-c4ccccc43)CCCCC2)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a092888c86624ae681dbaa94eb001e74 | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12>>NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCNCC3)nc12 | NC(=O)C1=CC=CC=2NC(=NC21)C2(CCN(CC2)C(=O)OCC2=CC=CC=C2)NC(=O)OCC2C1=CC=CC=C1C=1C=CC=CC21>>NC(=O)C1=CC=CC=2NC(=NC21)C2(CCNCC2)NC(OCC2C1=CC=CC=C1C=1C=CC=CC21)=O | O=C(OCc1ccccc1)[N:32]1[CH2:31][CH2:30][C:11]([c:10]2[nH:9][c:8]3[cH:7][cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:36]3[n:35]2)([NH:12][C:13](=[O:14])[O:15][CH2:16][CH:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3-[c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[CH2:34][CH2:33]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][... | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12 | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCNCC3)nc12 | null | [Pd] | CO.C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(NC1(c2nc3ccccc3[nH]2)CCNCC1)OCC1c2ccccc2-c2ccccc21 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 69 | [{"value": 69.0, "product": "NC(=O)C1=CC=CC=2NC(=NC21)C2(CCNCC2)NC(OCC2C1=CC=CC=C1C=1C=CC=CC21)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "NC(=O)C1=CC=CC=2NC(=NC21)C2(CCNCC2)NC(OCC2C1=CC=CC=C1C=1C=CC=CC21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of Example 49A (0.175 g, 0.3 mmol) and 10% Pd/C (0.015 g) in MeOH (5 ml) and acetic acid (0.2 ml), was stirred overnight under a H2 atmosphere at room temperature. The mixture was filtered through a pad of silica then concentrated under vacuum. The residue was purified by HPLC on a C18 column with 0-100% CH3C... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccc2[nH]cnc2c1.C1CCNCC1.c1ccc2c(c1)Cc1ccccc12 | HO- | [Pd].CO.C(C)(=O)O | null | null | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12>[Pd].CO.C(C)(=O)O>NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCNCC3)nc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0e6f6c0cbc074aa498a506bae30807b8 | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12>>NC(=O)c1cccc2[nH]c(C3(N)CCN(C(=O)OCc4ccccc4)CC3)nc12 | NC(=O)C1=CC=CC=2NC(=NC21)C2(CCN(CC2)C(=O)OCC2=CC=CC=C2)NC(=O)OCC2C1=CC=CC=C1C=1C=CC=CC21>>NC1(CCN(CC1)C(=O)OCC1=CC=CC=C1)C1=NC2=C(N1)C=CC=C2C(=O)N | O=C(OCC1c2ccccc2-c2ccccc21)[NH:12][C:11]1([c:10]2[nH:9][c:8]3[cH:7][cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:29]3[n:28]2)[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][c:10]([C:11]3([NH2:12])[CH2... | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12 | NC(=O)c1cccc2[nH]c(C3(N)CCN(C(=O)OCc4ccccc4)CC3)nc12 | null | null | CN(C)C=O.N1CCCCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(OCc1ccccc1)N1CCC(c2nc3ccccc3[nH]2)CC1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[c:3](:[#7;a:4]):[#7;a:5])(-[C:6])-[C:7]>>[#7;a:4]:[c:3](-[C:2](-[NH2;D1;+0:1])(-[C:6])-[C:7]):[#7;a:5] | 64 | [{"value": 64.0, "product": "NC1(CCN(CC1)C(=O)OCC1=CC=CC=C1)C1=NC2=C(N1)C=CC=C2C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.6, "product": "NC1(CCN(CC1)C(=O)OCC1=CC=CC=C1)C1=NC2=C(N1)C=CC=C2C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of Example 49A (0.035 g, 0.1 mmol) in DMF (2 ml) and piperidine (0.5 ml), was stirred at room temperature for 2 h. The mixture was concentrated under vacuum then crystallized from MeOH to provide 0.014 g (64%) of the desired product. MS (ESI) m/e 416 (M+Na)+. 1H NMR (DMSO-D6) δ ppm 8.14 (s, 1H), 7.84 (d, J=7.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccc2[nH]cnc2c1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O.N1CCCCC1 | null | null | NC(=O)c1cccc2[nH]c(C3(NC(=O)OCC4c5ccccc5-c5ccccc54)CCN(C(=O)OCc4ccccc4)CC3)nc12>CN(C)C=O.N1CCCCC1>NC(=O)c1cccc2[nH]c(C3(N)CCN(C(=O)OCc4ccccc4)CC3)nc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3e319cf58227442f8278995f7f7a352a | CCOC(=O)C1CCC2(CC1)OCCO2>>O=CC1CCC2(CC1)OCCO2 | [H-].C(C(C)C)[Al+]CC(C)C.C(C)OC(=O)C1CCC2(OCCO2)CC1>>O1CCOC12CCC(CC2)C=O | CCO[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>>[O:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2 | CCOC(=O)C1CCC2(CC1)OCCO2 | O=CC1CCC2(CC1)OCCO2 | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | C1CCC2(CC1)OCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH;D2;+0:1]=[O;D1;H0:2])-[C:5] | null | [] | null | null | 30 | MINUTE | Diisobutyl aluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmole) was added dropwise to a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester 4 (32.13 g, 150 mmole) in absolute toluene (160 ml) at −70° to −65° C. under argon and stirred for 30 minutes. The reaction mixture was then quenched a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | C1CCC2(CC1)OCCO2 | HO- | C1(=CC=CC=C1)C | null | 0.5 | CCOC(=O)C1CCC2(CC1)OCCO2>C1(=CC=CC=C1)C>O=CC1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-68c8ac8859e74626b8a337ceb841d865 | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N>>CN(C)C(C#N)C1CCC2(CC1)OCCO2 | CNC.O1CCOC12CCC(CC2)C=O.[C-]#N.[K+].Cl>>CN(C)C(C#N)C1CCC2(OCCO2)CC1 | [CH3:1][NH:2][CH3:3].O=[CH:4][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2.[C-:5]#[N:6]>>[CH3:1][N:2]([CH3:3])[CH:4]([C:5]#[N:6])[CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2 | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N | CN(C)C(C#N)C1CCC2(CC1)OCCO2 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 65895308b5f67b585ddaa37f306e495e36985cf3c70224ad6c8aa7852833472c | 860dd54cb9329ea0e96b0cf04a71152378c5b5aab7f54c5a6ec1d7b1b585ad63 | C1CCC2(CC1)OCCO2 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C-;H0;D1:5]#[N;D1;H0:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C:3]-[C:2](-[CH;D3;+0:1](-[C;H0;D2;+0:5]#[N;D1;H0:6])-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9])-[C:4] | null | [] | null | null | 4 | DAY | 40% aqueous dimethylamine solution (85 ml, 0.67 mole), 1,4-dioxa-spiro-[4.5]decane-8-carbaldehyde 5 (240 g, 0.141 mole) and potassium cyanide (22.05 g, 0.338 mole) were added while cooling with ice to a mixture of 4N hydrochloric acid (37 ml) and methanol (22 ml). The mixture was stirred for four days at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Nitrile.Tertiary amine | null | null | C1CCC2(CC1)OCCO2 | HO- | CO | null | 96 | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N>CO>CN(C)C(C#N)C1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bc612dc3b5e34a4491165424b9751861 | CN(C)CC1CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CN(C)CC1CCC(C=O)CC1 | O.CC(C)(C)[O-].[K+].[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)CC1CCC(CC1)=O.O>>CN(C)CC1CCC(CC1)C=O | O=[C:8]1[CH2:7][CH2:6][CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:12][CH2:11]1.C[O:10][CH2:9][P+](c1ccccc1)(c1ccccc1)c1ccccc1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH:9]=[O:10])[CH2:11][CH2:12]1 | CN(C)CC1CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CN(C)CC1CCC(C=O)CC1 | null | null | C1CCOC1 | Acylation | OtherReaction | 2752826963694d37119202b8c1f3995e9aecbc40e62730be90bd02ffe6d6fb4e | 43cbfec1f077c493b72a12008b2b079b7808ea096be066fc071cb46dfa7e38c3 | C1CCCCC1 | C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[C;H0;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7]>>[C:5]-[C:4]-[CH;D3;+0:3](-[CH;D2;+0:2]=[O;H0;D1;+0:1])-[C:6]-[C:7] | null | [] | 0 | CELSIUS | 15 | MINUTE | (Methoxymethyl)triphenylphosphonium chloride (25.7 g, 75 mmole) was suspended in absolute THF (100 ml) under argon, potassium tert-butylate (8.42 g, 75 mmole) dissolved in absolute THF (70 ml) was added dropwise, and then stirred for 15 minutes at 0° C. The corresponding 4-[dimethylaminomethyl]-cyclohexanone 8 (50 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aldehyde | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CCCCC1 | C1CCCCC1 | HO- | C1CCOC1 | 0 | 0.25 | CN(C)CC1CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>CN(C)CC1CCC(C=O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cf51c88887784dd4a140c68d1eeaed7a | CCOC(=O)C1CCC(=O)CC1.OCCO>>CCOC(=O)C1CCC2(CC1)OCCO2 | C(C)OCC.C(C)OC(=O)C1CCC(CC1)=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)OC(=O)C1CCC2(OCCO2)CC1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1.O[CH2:13][CH2:14][OH:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2 | CCOC(=O)C1CCC(=O)CC1.OCCO | CCOC(=O)C1CCC2(CC1)OCCO2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 87830b95e8a201d62318c70ccec6a054912fe58024d4e2b4b3794a96ad0f84ae | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | C1CCC2(CC1)OCCO2 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[C:9]>>[C:4]-[C:5]-[C;H0;D4;+0:6]1(-[C:8]-[C:9])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | null | [] | null | null | null | null | 4-oxo-cyclohexanecarboxylic acid ethyl ester (52.8 g, 0.31 mole, Merck, Order No. 814249), ethylene glycol (67.4 g, 1.08 mole) and p-toluenesulfonic acid (0.7 g) in toluene (160 ml) were stirred for 20 hours at RT, and the reaction solution was poured into diethyl ether (300 ml) and washed with water, sodium hydrogen c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | C1CCCCC1 | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)C1CCC(=O)CC1.OCCO>C1(=CC=CC=C1)C>CCOC(=O)C1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b0fe6a54e5da4524a2476d0387d80fda | CCOC(=O)C1CCC2(CC1)OCCO2>>O=CC1CCC2(CC1)OCCO2 | [H-].C(C(C)C)[Al+]CC(C)C.C(C)OC(=O)C1CCC2(OCCO2)CC1>>O1CCOC12CCC(CC2)C=O | CCO[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>>[O:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2 | CCOC(=O)C1CCC2(CC1)OCCO2 | O=CC1CCC2(CC1)OCCO2 | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | C1CCC2(CC1)OCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH;D2;+0:1]=[O;D1;H0:2])-[C:5] | null | [] | null | null | 30 | MINUTE | Diisobutyl aluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmole) was added dropwise at −70° to −65° C. under argon to a solution of 1,4-dioxaspior[4.5]decane-8-carboxylic acid ethyl ester 4 (32.13 g, 150 mmole) in absolute toluene (160 ml), and stirred for 30 minutes. The reaction mixture was then quenched a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | C1CCC2(CC1)OCCO2 | HO- | C1(=CC=CC=C1)C | null | 0.5 | CCOC(=O)C1CCC2(CC1)OCCO2>C1(=CC=CC=C1)C>O=CC1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-85f0a1c8da154ceeb53790dd29fb205d | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N>>CN(C)C(C#N)C1CCC2(CC1)OCCO2 | CNC.O1CCOC12CCC(CC2)C=O.[C-]#N.[K+].Cl>>CN(C)C(C#N)C1CCC2(OCCO2)CC1 | [CH3:1][NH:2][CH3:3].O=[CH:4][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2.[C-:5]#[N:6]>>[CH3:1][N:2]([CH3:3])[CH:4]([C:5]#[N:6])[CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2 | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N | CN(C)C(C#N)C1CCC2(CC1)OCCO2 | null | null | CO.O | Heteroatom Alkylation and Arylation | OtherReaction | 65895308b5f67b585ddaa37f306e495e36985cf3c70224ad6c8aa7852833472c | 860dd54cb9329ea0e96b0cf04a71152378c5b5aab7f54c5a6ec1d7b1b585ad63 | C1CCC2(CC1)OCCO2 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C-;H0;D1:5]#[N;D1;H0:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C:3]-[C:2](-[CH;D3;+0:1](-[C;H0;D2;+0:5]#[N;D1;H0:6])-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9])-[C:4] | null | [] | null | null | 4 | DAY | 40% aqueous dimethylamine solution (85 ml, 0.67 mole), 1,4-dioxa-spiro-[4.5]decane-8-carbaldehyde 5 (240 g, 0.141 mole) and potassium cyanide (22.05 g, 0.338 mole) were added while cooling with ice to a mixture of 4N hydrochloric acid (37 ml) and methanol (22 ml). The mixture was stirred for four days at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Nitrile.Tertiary amine | null | null | C1CCC2(CC1)OCCO2 | HO- | CO.O | null | 96 | CNC.O=CC1CCC2(CC1)OCCO2.[C-]#N>CO.O>CN(C)C(C#N)C1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-097883a3d0c64666940e3a5bdb9d6657 | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Fc1cc[c]([Mg][Br])cc1>>CN(C)C(c1ccc(F)cc1)C1CCC2(CC1)OCCO2 | [Cl-].[NH4+].FC1=CC=C(C=C1)[Mg]Br.CN(C)C(C#N)C1CCC2(OCCO2)CC1.O>>O1CCOC12CCC(CC2)C(C2=CC=C(C=C2)F)N(C)C | N#C[CH:4]([N:2]([CH3:1])[CH3:3])[CH:12]1[CH2:13][CH2:14][C:15]2([CH2:16][CH2:17]1)[O:18][CH2:19][CH2:20][O:21]2.[Br][Mg][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[CH:12]1[CH2:13][CH2:14][C:15]2([CH2:16][CH2:17]1)[O:18][CH2:19][CH2:20][O:21]2 | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Fc1cc[c]([Mg][Br])cc1 | CN(C)C(c1ccc(F)cc1)C1CCC2(CC1)OCCO2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 444c91293579a60209413501331234346535ff4ac3991b7e2904e204c2c70a4f | b7d29fa9e0a7d9ae2f2a2797da751d9d03a466b58f528baa09db504746325a44 | c1ccc(CC2CCC3(CC2)OCCO3)cc1 | N#C-[CH;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:5](-[C:6])-[C:7].[Br]-[Mg]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C:6]-[C:5](-[CH;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[C:7] | null | [] | null | null | 20 | HOUR | A solution of the aminonitrile 6 (19.89 g 88 mmole) in absolute THF (160 ml) was added dropwise under argon and cooling with ice to a 1M solution of 4-fluorophenyl magnesium bromide in THF (220 ml, 220 mmole) and stirred for 20 hours at RT. To work up the reaction mixture, saturated ammonium chloride solution (100 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCC2(CC1)OCCO2 | Br-.Mg | C1CCOC1 | null | 20 | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Fc1cc[c]([Mg][Br])cc1>C1CCOC1>CN(C)C(c1ccc(F)cc1)C1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b624ee5bc34e462b952ecc7a6393457b | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Clc1cc[c]([Mg][Br])cc1>>CN(Cc1ccc(Cl)cc1)C1CCC2(CC1)OCCO2 | [Cl-].[NH4+].CN(C)C(C#N)C1CCC2(OCCO2)CC1.ClC1=CC=C(C=C1)[Mg]Br.CCOCC.CCOCC.O>>ClC1=CC=C(C=C1)CN(C)C1CCC2(OCCO2)CC1 | C[N:2]([CH3:1])[CH:3](C#N)[CH:11]1[CH2:12][CH2:13][C:14]2([CH2:15][CH2:16]1)[O:17][CH2:18][CH2:19][O:20]2.[Br][Mg][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][C:14]2([CH2:15][CH2:16]1)[O:17][CH2:18][CH2:19][O:20]2 | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Clc1cc[c]([Mg][Br])cc1 | CN(Cc1ccc(Cl)cc1)C1CCC2(CC1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d7b5456c9955ffc875c62f984d5816fddaced2b9c719ee131b26ce373c71d55d | 582b1fa3957cd7f0262eb4576eaa346ef29166033eba11f6e738184ab300e163 | c1ccc(CNC2CCC3(CC2)OCCO3)cc1 | C-[N;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-C#N)-[CH;D3;+0:4](-[C:5]-[C:6])-[C:7]-[C:8].[Br]-[Mg]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:6]-[C:5]-[CH;D3;+0:4](-[N;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])-[C:7]-[C:8] | null | [] | null | null | 20 | HOUR | A solution of the aminonitrile 6 (22.43 g, 100 mmole) in absolute ether (100 ml) was added to a 1M solution of 4-chlorophenyl magnesium bromide in ether (200 ml, 200 mmole) under argon and while cooling with ice, and stirred for 20 hours at RT. To work up the reaction mixture, saturated ammonium chloride solution (100 ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile.Tertiary amine | Tertiary amine | C1CCC2(CC1)OCCO2.c1ccccc1 | c1ccccc1.C1CCC2(CC1)OCCO2 | c1ccccc1.C1CCC2(CC1)OCCO2 | HBr.Mg | null | null | 20 | CN(C)C(C#N)C1CCC2(CC1)OCCO2.Clc1cc[c]([Mg][Br])cc1>>CN(Cc1ccc(Cl)cc1)C1CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ffdc3e8a32ea49aaa4d8e260f3fbe86b | CN(C)C(CCc1ccccc1)C1CCC2(CC1)OCCO2>>CN(C)C(CCc1ccccc1)C1CCC(=O)CC1 | C(C)OCC.O1CCOC12CCC(CC2)C(CCC2=CC=CC=C2)N(C)C.[OH-].[Na+].Cl>>CN(C(CCC1=CC=CC=C1)C1CCC(CC1)=O)C | C1C[O:17][C:16]2(O1)[CH2:15][CH2:14][CH:13]([CH:4]([N:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:19][CH2:18]2>>[CH3:1][N:2]([CH3:3])[CH:4]([CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]1[CH2:14][CH2:15][C:16](=[O:17])[CH2:18][CH2:19]1 | CN(C)C(CCc1ccccc1)C1CCC2(CC1)OCCO2 | CN(C)C(CCc1ccccc1)C1CCC(=O)CC1 | null | null | O | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(CCCc2ccccc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | 20 | HOUR | The crude product of the ketal 7e (29.6 g, 97 mmole) was dissolved in water (44 ml), concentrated hydrochloric acid (64 ml) was added, and the mixture was stirred for 20 hours at RT. The reaction mixture was shaken with diethyl ether (2×100 ml), the aqueous phase was made alkaline with 5N NaOH while cooling with ice, a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | O | null | 20 | CN(C)C(CCc1ccccc1)C1CCC2(CC1)OCCO2>O>CN(C)C(CCc1ccccc1)C1CCC(=O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cd99407096e045d89a559822721c434e | CN(C)C(c1cccc(F)c1)C1CCC(C=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CN(C)C(c1cccc(F)c1)C1CCC(CC=O)CC1 | [Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)C(C1CCC(CC1)C=O)C1=CC(=CC=C1)F.Cl.CC(C)(C)[O-].[K+]>>CN(C)C(C1CCC(CC1)CC=O)C1=CC(=CC=C1)F | [CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1)[CH:12]1[CH2:13][CH2:14][CH:15]([CH:16]=[O:18])[CH2:19][CH2:20]1.CO[CH2:17][P+](c1ccccc1)(c1ccccc1)c1ccccc1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1)[CH:12]1[CH2:13][CH2:14][CH:15]([CH2:16][CH:17]=[O:18])[CH2:19]... | CN(C)C(c1cccc(F)c1)C1CCC(C=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CN(C)C(c1cccc(F)c1)C1CCC(CC=O)CC1 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 2afb3562bb5aba232b59538ac0a4194e60937df147c098cfc4dd7756c37b1dba | d26c7fb089b1337ec3c452f64a4b1f3cc9b8182a0bcee67ce09960f96bf796bd | c1ccc(CC2CCCCC2)cc1 | C-O-[CH2;D2;+0:1]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C:2]-[C:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6]>>[C:2]-[C:3](-[CH2;D2;+0:4]-[CH;D2;+0:1]=[O;H0;D1;+0:5])-[C:6] | null | [] | 0 | CELSIUS | 15 | MINUTE | (Methoxymethyl)triphenylphosphonium chloride (26.73 g, 78 mmole) was suspended in absolute THF (90 ml) under argon, potassium tert-butylate (8.75 g, 78 mmole), dissolved in absolute THF (90 ml), was added dropwise at 0° C., and the mixture was then stirred for 15 minutes at 0° C. The aldehyde 9b (13.69 g, 52 mmole), di... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Aldehyde | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.C1CCCCC1 | HO- | C1CCOC1.O | 0 | 0.25 | CN(C)C(c1cccc(F)c1)C1CCC(C=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1.O>CN(C)C(c1cccc(F)c1)C1CCC(CC=O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ef3281565b4e4622afcb19c9b901291b | Nc1ccc(C(F)(F)F)cc1.O=C1C=CC(=O)N1>>O=C1C=C(c2ccc(C(F)(F)F)cc2)C(=O)N1 | C1(C=CC(N1)=O)=O.FC(C1=CC=C(N)C=C1)(F)F.N(=O)[O-].[Na+].C(C)(=O)[O-].[Na+].Cl>>FC(C1=CC=C(C=C1)C=1C(NC(C1)=O)=O)(F)F | N[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1.[O:1]=[C:2]1[CH:3]=[CH:4][C:15](=[O:16])[NH:17]1>>[O:1]=[C:2]1[CH:3]=[C:4]([c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[C:15](=[O:16])[NH:17]1 | Nc1ccc(C(F)(F)F)cc1.O=C1C=CC(=O)N1 | O=C1C=C(c2ccc(C(F)(F)F)cc2)C(=O)N1 | null | [Cu](Cl)Cl | CC(=O)C.O | C-C Coupling | OtherReaction | 432869ddc01840d151f905c3fda680901ff00f566aad506d1ad2c5f4a7eff23c | b4142dbc8aebf8ea5ecf50af61f2215c729ea5a2dcf1f9e7fd52e13ad01c499d | O=C1C=C(c2ccccc2)C(=O)N1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]=[C;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 69 | [{"value": 69.0, "product": "FC(C1=CC=C(C=C1)C=1C(NC(C1)=O)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of hydrochloric acid (37% in water, 285 mL) and water (190 mL) was added to 4-(trifluoromethyl)aniline (150 g, 116 mL) at room temperature with vigorous stirring and the formed precipitate was allowed to stir for further 30 minutes. Temperature was reduced to 0° C. and sodium nitrite (70.6 g) in 180 mL of wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1.C1=CCNC1 | C1=CCNC1.c1ccccc1 | C1=CCNC1.c1ccccc1 | Other | [Cu](Cl)Cl.CC(=O)C.O | null | null | Nc1ccc(C(F)(F)F)cc1.O=C1C=CC(=O)N1>[Cu](Cl)Cl.CC(=O)C.O>O=C1C=C(c2ccc(C(F)(F)F)cc2)C(=O)N1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9b7f790f5e6545a49cac5475acb2be1c | C1CCOC1.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1>>OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1 | FC(C1=CC=C(C=C1)[C@]12CNC[C@@H]2C1)(F)F.C1CCOC1>>FC(C1=CC=C(C=C1)[C@]12CN(C[C@@H]2C1)CCCO)(F)F | C1[O:1][CH2:2][CH2:3][CH2:4]1.[NH:5]1[CH2:6][C@@H:7]2[CH2:8][C@:9]2([c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[CH2:20]1>>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][C@@H:7]2[CH2:8][C@:9]2([c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[CH2:20]1 | C1CCOC1.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1 | OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1 | null | null | BrCCCO | Heteroatom Alkylation and Arylation | OtherReaction | e0a0331ae8f609a37725fb0a9c5f73c3c0420d619f168b82ddae1ae7fc24a548 | 128400f60196a90df2be08c769daa326293f26a6f70a086568a2c266322e372f | c1ccc([C@@]23CNC[C@@H]2C3)cc1 | C1-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-1.[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[OH;D1;+0:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (Prep4, 151 mg) in dry THF (3.3 mL), TEA (0.112 mL) and 3-bromo-1-propanol (0.073 mL) were added and the resulting mixture was heated at reflux for 4 hours. After cooling at room temperature it was diluted with EtAcO (20 mL), washed with w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary alcohol.Tertiary amine | C1CCOC1.C1NC[C@H]2C[C@@H]12 | C1[NH]C[C@H]2C[C@@H]12 | C1[NH]C[C@H]2C[C@@H]12.c1ccccc1 | Other | BrCCCO | null | null | C1CCOC1.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1>BrCCCO>OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-41e3223279b340a3bb76d5a9cf5a22f9 | Cc1c[nH]c(=O)[nH]c1=O.ClCCCCBr>>Cc1cn(CCCCCl)c(=O)[nH]c1=O | O.CC=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCCl>>ClCCCCN1C(NC(C(=C1)C)=O)=O | [CH3:1][c:2]1[cH:3][nH:4][c:10](=[O:11])[nH:12][c:13]1=[O:14].Br[CH2:5][CH2:6][CH2:7][CH2:8][Cl:9]>>[CH3:1][c:2]1[cH:3][n:4]([CH2:5][CH2:6][CH2:7][CH2:8][Cl:9])[c:10](=[O:11])[nH:12][c:13]1=[O:14] | Cc1c[nH]c(=O)[nH]c1=O.ClCCCCBr | Cc1cn(CCCCCl)c(=O)[nH]c1=O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1cc[nH]c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | null | null | 20 | HOUR | A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg, commercially available from Aldrich) and K2CO3 (546 mg) in dry DMSO (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chlorobutane (0.46 mL) was then added and the mixture was stirred at room temperature for 20 hours. Water was then added an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | CS(=O)C | null | 20 | Cc1c[nH]c(=O)[nH]c1=O.ClCCCCBr>CS(=O)C>Cc1cn(CCCCCl)c(=O)[nH]c1=O |
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