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-c31cb9b44c404c10ba3aa533aa079e2b | ord-fac4a83c352644bd84e41f5061162643 | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1>>COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 | C=O.Cl.CN(C(OC1=CC(=CC=C1)C(CCC1=CC=C(C=C1)OC)NC)=O)C.[OH-].[Na+]>>CN(C(OC1=CC(=CC=C1)C(CCC1=CC=C(C=C1)OC)N(C)C)=O)C | O=[CH2:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21]2)[NH:22][CH3:24])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])... | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1 | COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CCCc2ccccc2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[c:4])-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:2]-[C:3](-[c:4])-[N;H0;D3;+0:5](-[C;D1;H3:6])-[CH3;D1;+0:1] | null | [] | 90 | CELSIUS | 2 | HOUR | Formic acid (10 ml) and 35% aqueous formaldehyde solution (10 ml) were added to 3-[3-(4-methoxyphenyl)-1-methylaminopropyl]phenyl dimethylcarbamate (500 mg, 1.4 mmol) obtained from Example 2 and the mixture was stirred at 90° C. for 2 hours. After cooling the reaction mixture to room temperature the mixture was neutral... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(=O)O | 90 | 2 | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1>C(=O)O>COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0219005098e64f6d8b20ac6a432dba0e | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1>>CNC(CC(=O)O)c1cccc(O)c1 | OC=1C=C(C=O)C=CC1.C(CC(=O)O)(=O)O.C(C)(=O)O.CN>>OC=1C=C(C=CC1)C(CC(=O)O)NC | [CH3:1][NH2:2].O=C(O)[CH2:4][C:5](=[O:6])[OH:7].O=[CH:3][c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1>>[CH3:1][NH:2][CH:3]([CH2:4][C:5](=[O:6])[OH:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1 | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1 | CNC(CC(=O)O)c1cccc(O)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 029574ef26de21f885bdd45bc4c594df31907abcec9280dfb6bae6d8c823e790 | b3ae5256a03516152477e54cb65b2c8ce8e6de1b7a097a5a730c0f14a2ab31ca | c1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[CH;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:6](:[c:7]):[c:8] | 58.8 | [{"value": 58.8, "product": "OC=1C=C(C=CC1)C(CC(=O)O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Hydroxybenzaldehyde (25.7 g, 210 mmol) was dissolved in ethanol (70 ml), and malonic acid (25.7 g) and the acetic acid salt of methylamine (38.6 g) were added to the solution. The resulting mixture was heated under reflux for 3 hours. Crystals which precipitated in the reaction mixture were collected by filtration to... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine | Secondary amine | null | null | c1ccccc1 | HO- | C(C)O | null | null | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1>C(C)O>CNC(CC(=O)O)c1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c444d6cd1494f348b8fe8d56c164586 | CCO.CNC(CC(=O)O)c1cccc(O)c1>>CCOC(=O)CC(NC)c1cccc(O)c1 | OC=1C=C(C=CC1)C(CC(=O)O)NC.C(C)O.S(O)(O)(=O)=O.C(O)([O-])=O.[Na+]>>OC=1C=C(C=CC1)C(CC(=O)OCC)NC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][CH:7]([NH:8][CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH:8][CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1 | CCO.CNC(CC(=O)O)c1cccc(O)c1 | CCOC(=O)CC(NC)c1cccc(O)c1 | 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;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5] | null | [] | null | null | null | null | 3-(3-Hydroxyphenyl)-3-methylaminopropionic acid (24.1 g) obtained from Example 7a was dissolved in ethanol (200 ml), and concentrated sulfuric acid (10 ml) was added dropwise to the solution. The resulting mixture was heated under reflux for 8 hours. The reaction mixture was neutralized with saturated aqueous sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.CNC(CC(=O)O)c1cccc(O)c1>>CCOC(=O)CC(NC)c1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d175929ad14c40eebb87c51e8c9d33b0 | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C>>CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | C(C1=CC=CC=C1)Br.C(C)(C)(C)OC(=O)N(C)C(CC(=O)OCC)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:20][cH:21]1)[N:22]([CH3:23])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:... | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 84.2 | [{"value": 84.2, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | N,N-Dimethylformamide and benzyl bromide (2.3 ml, 19 mmol) were added sequentially to ethyl 3-[N-(t-butoxy carbonyl)-N-methylamino]-3-(4-hydroxyphenyl)propionate (5.10 g, 16 mmol) obtained from Example 16a and potassium carbonate (3.27 g, 24 mmol) and the mixture was stirred at room temperature for 4 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 4 | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C>CN(C=O)C>CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05b22ece25a14d5396cd84f1b34ecfac | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C>>CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 | S(=O)(=O)([O-])[O-].[Mg+2].[OH-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C | CCO[C:12]([CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1)=[O:13]>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][OH:13])[c:14]1[cH:15][cH:16][c:17... | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 | null | null | O1CCCC1.O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Tetrahydrofuran (100 ml) was added to lithium aluminum hydride (1.02 g, 27 mmol) under an atmosphere of nitrogen, and a solution of ethyl 3-(4-benzyloxyphenyl)-3-[N-(t-butoxycarbonyl)-N-methylamino]propionate (5.56 g, 13 mmol) obtained from Example 115a in tetrahydrofuran was slowly added thereto at −78° C. After stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1.O | 0 | 0.5 | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C>O1CCCC1.O>CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70959b126ca245479646bacd142a7c3e | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N>>CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | C1COCCOCCOCCOCCO1.C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C.C(C)N(CC)CC.[C-]#N.[Na+].CS(=O)(=O)Cl>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C | O[CH2:12][CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[C-:13]#[N:14]>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][C:13]#[N:14])[c:15]1[cH:16]... | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | a1e85c1b3a4aa1231f3779c2baa8b6951b270c05216d065e2aa7ce489240e0a5 | 1d32632fcc69ac04f0b8d96dc5305dd07d5339ab86bfe9a364cefb5e65c6d5b1 | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[N;D1;H0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:4]#[N;D1;H0:5] | 92.6 | [{"value": 92.6, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | t-Butyl N-[1-(4-benzyloxyphenyl)-3-hydroxypropyl]-N-methylcarbamate (1.50 g, 4.0 mmol) obtained from Example 115b was dissolved in tetrahydrofuran (20 ml) under an atmosphere of nitrogen. To the solution was added triethylamine (0.84 ml, 6.0 mmol) and then methanesulfonyl chloride (0.37 ml, 4.8 mmol), in an ice bath. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Nitrile | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N>O1CCCC1>CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca7ab29d47cf47ccb109611ba5a06c28 | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1>>CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 | [H-].C(C(C)C)[Al+]CC(C)C.CCCCCC.[BH4-].[Na+].S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCCO)N(C(OC(C)(C)C)=O)C | N#[C:13][CH2:12][CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][CH2:13][OH:14])[c:15]1[cH:16][cH:17... | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 | null | null | ClCCl.O | Functional Group Interconversion | OtherReaction | dfa6aab906f1cce8c060c3454d617eee54109b7fbe31f54f7240a7e17e9d9a0b | cfcea505f43817e62057efa9fa83f3ef47a11a99a8a6ad13903bd9b247dfd586 | c1ccc(COc2ccccc2)cc1 | N#[C;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;D1;H1:4] | 82.8 | [{"value": 82.8, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCCO)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | t-Butyl N-[1-(4-benzyloxyphenyl)-3-cyanopropyl]-N-methylcarbamate (1.00 g, 2.6 mmol) obtained from Example 115c was dissolved in dichloromethane (20 ml) under an atmosphere of nitrogen. To the solution was added 0.95 M solution of diisobutylaluminum hydride in hexane (5.5 ml, 5.3 mmol) at −78° C. and the temperature wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | ClCCl.O | null | 2 | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1>ClCCl.O>CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d5e32cdc1a24053b189723a5d5a0dca | CCOC(=O)C=C1NCCc2cc(OC)ccc21>>CCOC(=O)CC1NCCc2cc(OC)ccc21 | COC=1C=C2CCNC(C2=CC1)=CC(=O)OCC.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2CCNC(C2=CC1)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[NH:8][CH2:9][CH2:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[NH:8][CH2:9][CH2:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21 | CCOC(=O)C=C1NCCc2cc(OC)ccc21 | CCOC(=O)CC1NCCc2cc(OC)ccc21 | null | [Pt]=O | C(C)(=O)O | Reduction | Hydrogenation (double to single) | a2a16c1a99dc53e406de229794c537c379a76e9a646517a7c8ab052fadff31d4 | b586296faf9080b398947dcba4825d3daf71a75997a309df19187f20bff3e49d | c1ccc2c(c1)CCNC2 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[C;H0;D3;+0:6](-[#7:7]-[C:8])-[c:9](:[c:10]):[c:11]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH;D3;+0:6](-[#7:7]-[C:8])-[c:9](:[c:10]):[c:11] | 64 | [{"value": 64.0, "product": "COC=1C=C2CCNC(C2=CC1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of ethyl (6-methoxy-3,4-dihydro-2H-isoquinolin-1-yliden)-acetate (7.56 g) obtained in step (b) of Example 187 in acetic acid (50 ml) was added platinum oxide (400 mg), and the resulting mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. After stirring, the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Ester | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | null | [Pt]=O.C(C)(=O)O | null | 3 | CCOC(=O)C=C1NCCc2cc(OC)ccc21>[Pt]=O.C(C)(=O)O>CCOC(=O)CC1NCCc2cc(OC)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8511ca8f99834023b6fd94eef48cd1be | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O>>CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | O.C(C)OC(=O)CC1N(CCC2=CC(=CC=C12)O)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].CN(C(=O)Cl)C>>CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[c:9]([cH:20][c:21]([OH:22])[cH:29][cH:30]2)[CH2:10][CH2:11][N:12]1[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].Cl[C:24](=[O:25])[N:26]([CH3:27])[CH3:28].[OH2:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[C:8]2=[C:9]([CH2:10][CH2:11][N:12]1[C:13](=[O:... | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | null | null | CN(C=O)C | Protection | OtherReaction | 6d2f16630df4090cd3c58cd2f34abacbdfcd8c38c0b22f845df91da04096e9d8 | 8113e1af9c36bbe7fed7499330e4e08640ab6a60502ef3feb1a2935ccf85500c | C1=CC2=C(CC1)CCNC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]1-[#7:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])-[C:19]-[C:20]-[c;H0;D3;+0:21]2:[cH;D2;+0:22]:[c;H0;D3;+0:23](-[O;D1;H1:24]):[cH;D2;+0:25]:[cH;D2;+0:26]:[c;H0;D3;+0:27]:2-1.... | 95 | [{"value": 95.0, "product": "CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of t-butyl 1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.70 g, 5.07 mmol) synthesized in step (d) of Example 187 in dimethylformamide (5 ml) were added potassium carbonate (1.03 g, 7.50 mmol) and N,N-dimethylcarbamoyl chloride (0.69 ml, 7.5 mmol), and the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester.Ether.Tertiary alcohol | c1ccc2c(c1)CC[NH]C2 | C1=CC2=C(CC1)CC[NH]C2 | C1=CC2=C(CC1)CC[NH]C2 | HCl | CN(C=O)C | null | 2.5 | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O>CN(C=O)C>CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49eed0ece98a4e43bb1fdcb2d99d8533 | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2>>CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO | CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C | CCO[C:25]([CH2:24][CH:23]1[C:10]2=[C:11]([CH2:12][C:7](O)([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[CH:8]=[CH:9]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:26]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][N:15]([C:16](=[O:17])[... | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO | null | null | O1CCCC1 | Reduction | OtherReaction | 3853f56c6f0ecde368d58bc22fc3494232d8f07bad3b0cd3580c749ca6f02671 | f97908a80f5a6be714b164c5d0248e40307dea320152935297423c15a42639b6 | c1ccc2c(c1)CCNC2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]1-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]-[C:14]-[C;H0;D3;+0:15]2=[C;H0;D3;+0:16]-1-[CH;D2;+0:17]=[CH;D2;+0:18]-[C;H0;D4;+0:19](-O)(-[#8:20]-[C:21](-[#7:22])=[O;D1;H0:23])-[CH2;D2;+0:24]-2>>[#7:22]-[C:21](=[O;D1;H0:23])... | 78.2 | [{"value": 78.0, "product": "CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To a solution of t-butyl 6-dimethylcarbamoyloxy-1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.97 g, 4.84 mmol) synthesized in step (e) of Example 187 in tetrahydrofuran (30 ml) was added lithium aluminum hydride (270 mg, 7.2 mmol) at −78° C., and the resulting mixture was stirred for 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Tertiary alcohol | Ether.Primary alcohol | C1=CC2=C(CC1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | HO- | O1CCCC1 | 0 | 0.333333 | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2>O1CCCC1>CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-810f16b7ef66497bb4aef6c797da3d2b | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C>>COc1ccc2c(c1)CCN[C@@H]2CCO | COC=1C=C2CCN[C@@H](C2=CC1)CCO[Si](C)(C)C(C)(C)C.FC(C(=O)N)(F)F.F.O.C(O)([O-])=O.[Na+]>>COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F | CC(C)(C)[Si](C)(C)[O:15][CH2:14][CH2:13][C@@H:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][NH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][C@@H:12]2[CH2:13][CH2:14][OH:15] | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C | COc1ccc2c(c1)CCN[C@@H]2CCO | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc2c(c1)CCNC2 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 79 | [{"value": 79.0, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-methoxy-1-(R)-(2-t-butyldimethylsilyloxyethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (1.14 g, 2.73 mmol) obtained in step (a) of Example 190 in acetonitrile (10 ml) was added dropwise 48% solution of hydrofluoric acid in water (0.5 ml, 13.67 mmol) gradually with stirring under cooling in a w... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccc2c(c1)CCNC2 | Other | C(C)#N | null | null | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C>C(C)#N>COc1ccc2c(c1)CCN[C@@H]2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04725603260849d48bb508a803e3335e | BrC(Br)(Br)Br.COc1ccc2c(c1)CCN[C@@H]2CCO>>COc1ccc2c(c1)CCN[C@@H]2CCBr | COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F | BrC(Br)(Br)[Br:15].O[CH2:14][CH2:13][C@@H:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][NH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][C@@H:12]2[CH2:13][CH2:14][Br:15] | BrC(Br)(Br)Br.COc1ccc2c(c1)CCN[C@@H]2CCO | COc1ccc2c(c1)CCN[C@@H]2CCBr | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccc2c(c1)CCNC2 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:3]-[CH2;D2;+0:2]-[Br;H0;D1;+0:1] | 98 | [{"value": 98.0, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-methoxy-1-(R)-(2-hydroxyethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (330 mg, 1.09 mmol) obtained in step (b) of Example 190 and carbon tetrabromide (542 mg, 1.63 mmol) in dichloromethane (5 ml) was added gradually triphenyl phosphine (343 mg, 1.31 mmol) with stirring under cooling in a wate... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccc2c(c1)CCNC2 | HBr | ClCCl | null | null | BrC(Br)(Br)Br.COc1ccc2c(c1)CCN[C@@H]2CCO>ClCCl>COc1ccc2c(c1)CCN[C@@H]2CCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65d431d7209b45498ff11f66c2e891a5 | COc1ccc2c(c1)CCN[C@@H]2CCBr>>Oc1ccc2c(c1)CCN[C@@H]2CCBr | C(O)([O-])=O.[Na+].COC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F.B(Br)(Br)Br>>OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F | C[O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][NH:17][C@@H:18]2[CH2:19][CH2:20][Br:21]>>[OH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][NH:17][C@@H:18]2[CH2:19][CH2:20][Br:21] | COc1ccc2c(c1)CCN[C@@H]2CCBr | Oc1ccc2c(c1)CCN[C@@H]2CCBr | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CCNC2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-methoxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (390 mg, 1.07 mmol) obtained in step (c) of Example 190 in dichloromethane (5 ml) was added 1M solution of boron tribromide in dichloromethane (2.14 ml, 2.14 mmol) gradually at −78° C. with stirring. The resulting mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCNC2 | Other | ClCCl | null | null | COc1ccc2c(c1)CCN[C@@H]2CCBr>ClCCl>Oc1ccc2c(c1)CCN[C@@H]2CCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55e5a9fd7546411f9c81bab5cdc86e74 | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr>>CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr | O.OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F.C([O-])([O-])=O.[K+].[K+].CN(C(=O)Cl)C>>CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][NH:15][C@@H:16]2[CH2:17][CH2:18][Br:19]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][NH:15][C@@H:16]2[CH2:17][CH2:18][Br:19] | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr | null | null | CN(C=O)C | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccc2c(c1)CCNC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 52 | [{"value": 52.0, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-hydroxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (270 mg, 0.77 mmol) obtained in step (d) of Example 190 and potassium carbonate (268 mg, 1.94 mmol) in dimethylformamide (3 ml) was added dimethylcarbamyl chloride (0.2 ml, 1.55 mmol) gradually with stirring under cooling in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccc2c(c1)CCNC2 | HCl | CN(C=O)C | null | null | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr>CN(C=O)C>CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf323f7afa53467cafe4b857cd8596b7 | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl>>Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl | C([O-])([O-])=O.[K+].[K+].[I-].[K+].ClC=1C(=CC(=CC1)O)C.CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F>>CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C.FC(C(=O)N)(F)F | Br[CH2:6][CH2:7][C@H:8]1[NH:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21][cH:22][c:23]21.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:24][cH:25][c:26]1[Cl:27]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][C@H:8]2[NH:9][CH2:10][CH2:11][c:12]3[cH:13][c:14]([O:15][C:16](=[O:17])[N:18]... | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl | Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC[C@H]2NCCc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#7:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 84 | [{"value": 84.0, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of potassium carbonate (115 mg, 0.83 mmol), potassium iodide (catalytic amount) and 4-chloro-m-cresol (65 mg, 0.46 mmol) in dimethylformamide (2 ml) was added a solution of 6-dimethylcarbamoyloxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (160 mg, 0.38 mmol) obtained in step (e) o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CCNC2 | HBr | O.CN(C=O)C | null | null | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl>O.CN(C=O)C>Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f82cb094b916404d816fa1996624d2f5 | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O>>CN(C)C(=O)Oc1ccc(C=O)c(O)c1 | [H-].[Na+].OC1=C(C=O)C=CC(=C1)O.CN(C(=O)Cl)C>>CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]([OH:14])[cH:15]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]([OH:14])[cH:15]1 | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O | CN(C)C(=O)Oc1ccc(C=O)c(O)c1 | null | null | O | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 30 | [{"value": 30.0, "product": "CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.7, "product": "CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of sodium hydride (5.74 g, 239 mmol), which was prepared free from mineral oil by washing with hexane, in dimethylformamide (100 ml) was added 2,4-dihydroxybenzaldehyde (15.0 g, 109 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. S... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccccc1 | HCl | O | null | null | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O>O>CN(C)C(=O)Oc1ccc(C=O)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ebe0a412cc846918196e16ac99face6 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1>>C=Cc1cc(OC(=O)N(C)C)ccc1C=O | [F-].[K+].FC(S(=O)(=O)OC1=C(C=CC(=C1)OC(N(C)C)=O)C=O)(F)F.[Cl-].[Li+].C(CCC)[Sn](C=C)(CCCC)CCCC>>CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].O=S(=O)(O[c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16])C(F)(F)F>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16] | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1 | C=Cc1cc(OC(=O)N(C)C)ccc1C=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O | O1CCOCC1 | C-C Coupling | Stille reaction_vinyl OTf | 19b30501d1aaa5f5dd56b13112130366c0e45d6c2d2ca2c3e4e656b3de7ef26d | 22963776d86934928a954d267e6c7c5a64095fcc3303c473fde6e3c4d4878a47 | c1ccccc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[C:7]=[O;D1;H0:8]):[c:9]>>[C;D1;H2:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[C:7]=[O;D1;H0:8]):[c:9] | 79.5 | [{"value": 79.0, "product": "CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-dimethylcarbamoyloxy-2-formyl-phenyl trifluoromethanesulfonate (4.13 g, 12.1 mmol) obtained in step (b) of Example 192 in 1,4-dioxane (15 ml) were added tetrakis(triphenylphosphine)palladium (693 mg, 0.600 mmol), 2,6-di-t-butylphenol (5 mg), lithium chloride (1.54 g, 36.4 mmol) and tributyl(vinyl)tin... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | TfOH.HO-.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O.O1CCOCC1 | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O.O1CCOCC1>C=Cc1cc(OC(=O)N(C)C)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa43c8d32bb7464c940f3914b41e2b99 | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li].CCCCCC.C(C)(=O)OCC>>CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16].[CH3:17][C:18](=[O:19])[O:20][CH2:21][CH3:22]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][C:18](=[O:19])[O:20][CH2:21][CH3:22] | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccccc1 | [C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7].[C:8]-[#8:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:12])-[CH2;D2;+0:11]-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:4](:[c:7]):[c:3]-[C:2]=[C;D1;H2:1] | 99.8 | [{"value": 99.0, "product": "CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of diisopropylamine (1.26 g, 12.5 mmol) in tetrahydrofuran (30 ml) was added 1.6M solution of n-butyllithium in hexane (7.20 ml, 11.5 mmol) at −20° C. with stirring, and the resulting mixture was stirred for 20 minutes at −20° C. under a nitrogen atmosphere. Subsequently, ethyl acetate (1.07 ml, 11.0 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1 | null | O1CCCC1 | null | null | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O>O1CCCC1>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fb639fd66584ac792fd3c6665db98e8 | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO | O.Cl.CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C.[BH4-].[Li+]>>CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C | CCO[C:18]([CH2:17][CH:15]([c:14]1[c:3]([CH:2]=[CH2:1])[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13]1)[OH:16])=[O:19]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][CH2:18][OH:19] | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO | 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:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 97.3 | [{"value": 97.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 3-(4-dimethylcarbamoyloxy-2-vinyl-phenyl)-3-hydroxy-propionate (5.28 g, 17.2 mmol) obtained in step (d) of Example 192 in tetrahydrofuran (50 ml) was added lithium tetrahydroborate (544 mg, 25.0 mmol) at −20° C. with stirring, and the reaction temperature was raised gradually to ambient temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | O1CCCC1 | null | null | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC>O1CCCC1>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa7e08c51f0d436a83a30c39cd26cb99 | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | O.CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C.C(C)N(CC)CC.C(C)(C)(C)[Si](Cl)(C)C>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][CH2:18][OH:19].Cl[Si:20]([CH3:21])([CH3:27])[C:33]([CH3:34])([CH3:35])[CH3:36].N([CH2:22][CH3:25])([CH2:29][CH3:30])[CH2:32][CH3:31]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[... | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | CN(C1=CC=NC=C1)C | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 500aab33a5fdae74a8362d9d6c793395a5801abb4ca2c4d3e1d2b2517e0a3aef | 9209b2acefe19f140772464284a8330dc3debcbdc34c49c2add1f0a0e951600b | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[CH3;D1;+0:8]-[CH2;D2;+0:9]-N(-[CH2;D2;+0:10]-[CH3;D1;+0:11])-[CH2;D2;+0:12]-[CH3;D1;+0:13].[C:14]-[C:15]-[OH;D1;+0:16]>>[C:14]-[C:15]-[O;H0;D2;+0:16]-[Si;H0;D4;+0:1](-[c;H0;D3;+0:2]1:[c:17]:[cH;D2;+0:8]:[c:18]:[c:19]:[cH;D... | 139.6 | [{"value": 70.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 139.6, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 4-(1,3-dihydroxy-propyl)-3-vinyl-phenyl dimethylcarbamate (4.44 g, 16.7 mmol) synthesized in step (e) of Example 192 in dichloromethane (40 ml) were added triethylamine (4.18 ml, 30.0 mmol), t-butyldimethylchlorosilane (4.67 g, 17.0 mmol) and a catalytic amount of 4-dimethylaminopyridine at −0° C. with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine.Silyl protective group | Silyl protective group | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 5 | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC>CN(C1=CC=NC=C1)C.ClCCl>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbad98721f0c4cb7b111c662fc92423b | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C | BrC(Br)(Br)[Br:17].[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:18][CH2:19][O:20][Si:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[C:34]([CH3:35])([CH3:36])[CH3:37]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:... | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | null | ClCCl | Functional Group Interconversion | Bromination | 9f0ae5e83907ecc1fcfb1d88ad36f98595319ee8517fc263e77784e52e82e13b | f5672e6730ea422d01df5937ff46c934f5dfdf1d4fbf514db56d670518e21c21 | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].[C:2]-[C:3]-[CH;D3;+0:4](-[O;D1;H1:5])-[c:6](:[c:7]):[c:8]-[C:9]=[C;D1;H2:10]>>[Br;H0;D1;+0:1]-[C;H0;D4;+0:4](-[O;D1;H1:5])(-[C:3]-[C:2])-[c:6](:[c:7]):[c:8]-[C:9]=[C;D1;H2:10] | 78 | [{"value": 78.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 1 | HOUR | To a solution of 4-[3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (3.00 g, 5.95 mmol) synthesized in step (f) of Example 192 and carbon tetrabromide (3.98 g, 12.0 mmol) in dichloromethane (20 ml) was added triphenyl phosphine (3.14 g, 12.0 mmol) at room temperature, and the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Secondary alcohol | Tertiary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | ClCCl | null | 1 | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>ClCCl>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61bb9b670573410ba6523b2a8e732d6d | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C.C(C=C)N>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C | [CH2:1]=[CH:2][CH2:3][NH2:4].Br[C:5]([OH:6])([CH2:7][CH2:8][O:9][Si:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]1[cH:28][cH:29][c:30]([O:31][C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][c:38]1[CH:39]=[CH2:40]>>[CH2:1]=[CH:2][CH2... | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 07af7d4c7984f572726ef942df12a89735b132164a86a1c8a3ba0c5326426194 | 1eca3e4a42a47a41a21e5d78efdcb9eebb24be6eecab751fa86ecd6c304b18a3 | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Br-[C;H0;D4;+0:1](-[O;D1;H1:2])(-[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[C:8]=[C;D1;H2:9].[C;D1;H2:10]=[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:4]-[C:3]-[C;H0;D4;+0:1](-[O;D1;H1:2])(-[NH;D2;+0:13]-[C:12]-[C:11]=[C;D1;H2:10])-[c:5](:[c:6]):[c:7]-[C:8]=[C;D1;H2:9] | 72 | [{"value": 72.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 8 | HOUR | To a solution of 4-[1-bromo-3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (2.62 g, 4.62 mmol) synthesized in step (g) of Example 192 in acetonitrile (20 ml) was added allylamine (1.87 ml, 25.0 mmol) at room temperature, and the resulting mixture was stirred at room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary alcohol.Primary amine | Tertiary alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | 8 | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>C(C)#N>C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31e19f1e653e4f18a99319eceab0f633 | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C>>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C(C=C)N(C(OC(C)(C)C)=O)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C1=C(C=C(C=C1)OC(N(C)C)=O)C=C>>C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2 | C=[CH:13][c:11]1[c:10]([CH:24]([N:16]([CH2:15][CH:14]=C)[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:25][CH2:26][O:27][Si:28]([c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[C:41]([CH3:42])([CH3:43])[CH3:44])[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O... | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl | ClCCl | C-C Coupling | OtherReaction | 234a9f25d5c12ce6762f8b70a6ea1ebc56ad581f8e23f3c9a3e6209e4c8c40c9 | 7cc827c291e2a977a7a91dfb00752230897a77bed46038b3e1551b560ca4b6fc | C1=Cc2ccccc2C(CCO[SiH](c2ccccc2)c2ccccc2)NC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10].C=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H0:5])-[#7:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 96 | [{"value": 96.0, "product": "C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERC... | 45 | CELSIUS | 3 | HOUR | To a solution of t-butyl allyl-[3-(t-butyl-diphenyl-silanyloxy)-1-(4-dimethylcarbamoyloxy-2-vinyl-phenyl) -propyl]-carbamate (360 mg, 0.56 mmol) synthesized in step (j) of Example 192 in dichloromethane (40 ml) was added tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]r... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Vinyl | null | null | C1=Cc2ccccc2C[NH]C1 | C1=Cc2ccccc2C[NH]C1.c1ccccc1.c1ccccc1 | Other | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl | 45 | 3 | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C>CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-372570775d5042a6837ac6872a7b4d7e | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO | O.C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:27][CH2:26][CH2:25][CH:24]1[c:10]2[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:12][c:11]2[CH:13]=[CH:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH:13]=[CH:... | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | C1=Cc2ccccc2CNC1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of t-butyl 1-[2-(t-butyl-diphenyl-silanyloxy)-ethyl]-7-dimethylcarbamoyloxy-1,3-dihydro-benzo[c]azepine-2-carboxylate (1.82 g, 2.96 mmol) synthesized in step (k) of Example 192 in tetrahydrofuran (10 ml) was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (6.0 ml, 6.0 mmol) at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | C1=Cc2ccccc2C[NH]C1 | Other | O1CCCC1 | null | 1 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>O1CCCC1>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9834969e46d8449ab85ba9d5b530563f | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO | C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2>>CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:27][CH2:26][CH2:25][CH:24]1[c:10]2[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:12][c:11]2[CH:13]=[CH:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2... | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO | null | [C].[Pd] | CO | Deprotection | OtherReaction | c2fff42fb9a693441092f85389941ed8df04d25c6eaadf1cc5d271208c6c87e1 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccc2c(c1)CCCNC2 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]1-[c:5]:[c:6](:[c:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-[#7:11]-1-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:16]-[C:15](-[C;D1;H3:17])(-[C;D1;H3:18])-[#8:14]-[C:12](=[O;D1;H0:13])-[#7:11]1-[C... | 91 | [{"value": 91.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of t-butyl 7-dimethylcarbamoyloxy-1-(2-hydroxyethyl)-1,3-dihydro-benzo[c]azepine-2-carboxylate (207 mg, 0.550 mmol) synthesized in step (k) of Example 192 in methanol (10 ml) was added 10% palladium carbon (27 mg), and the resulting mixture was stirred for 1 hour at room temperature. After stirring, the r... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1.C1=Cc2ccccc2C[NH]C1 | c1ccc2c(c1)CCC[NH]C2 | c1ccc2c(c1)CCC[NH]C2 | Other | [C].[Pd].CO | null | 1 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>[C].[Pd].CO>CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9cf3740ba6542ebacbe9a0806229494 | ClCc1ccccc1.O=Cc1ccc(O)cc1O>>O=Cc1ccc(OCc2ccccc2)cc1O | OC1=C(C=O)C=CC(=C1)O.C(O)([O-])=O.[Na+].[I-].[K+].C(C1=CC=CC=C1)Cl.Cl>>C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O | Cl[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][c:16]1[OH:17]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]1[OH:17] | ClCc1ccccc1.O=Cc1ccc(O)cc1O | O=Cc1ccc(OCc2ccccc2)cc1O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,4-dihydroxybenzaldehyde (50.0 g, 362 mmol) in acetonitrile (350 ml) were added sodium hydrogen carbonate (34.6 g, 412 mmol), potassium iodide (6.0 g, 36 mmol), and benzyl chloride (54.0 ml, 470 mmol), and the resulting mixture was refluxed for 24 hours under a nitrogen atmosphere. At the end of the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)#N | null | null | ClCc1ccccc1.O=Cc1ccc(O)cc1O>C(C)#N>O=Cc1ccc(OCc2ccccc2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92a02f518f58487c809bb5ec8470ed73 | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O>>COCOc1cc(OCc2ccccc2)ccc1C=O | O.C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O.C(C)(C)N(CC)C(C)C.COCCl>>C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC | Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17][c:18]1[CH:19]=[O:20]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17][c:18]1[CH:19]=[O:20] | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O | COCOc1cc(OCc2ccccc2)ccc1C=O | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 79 | [{"value": 79.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-benzyloxy-2-hydoxy-benzaldehyde (44.9 g, 197 mmol) synthesized in step (a) of Example 197 in dichloromethane (200 ml) were added diisopropylethylamine (52.0 ml, 300 mmol) and methoxymethyl chloride (20.5 ml, 270 mmol) at 0° C. with stirring, and the resulting mixture was stirred overnight at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O>ClCCl>COCOc1cc(OCc2ccccc2)ccc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfa6a4fe33564c42bbb76b0af6ce6fb0 | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O>>CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC | [H-].[Na+].C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC.O.C(C)OP(=O)(OCC)CC(=O)OCC>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[O:22][CH2:23][O:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c... | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O | CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(COc2ccccc2)cc1 | 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:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99.3 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 55% sodium hydride dispersion in mineral oil (1.57 g, 36.0 mmol) in tetrahydrofuran (100 ml) was added ethyl diethylphosphonoacetate (7.17 g, 32.0 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. Subsequently, a solution of 4-ben... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O>O1CCCC1>CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e7032211af346cab28f922d73f11869 | CCOC(=O)CC(=O)CCl.Nc1ccccn1>>O=c1cc(CCl)nc2ccccn12 | NC1=NC=CC=C1.C(C)OC(CC(=O)CCl)=O>>ClCC=1N=C2N(C(C1)=O)C=CC=C2 | CCO[C:2](=[O:1])[CH2:3][C:4](=O)[CH2:5][Cl:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][Cl:6])[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]12 | CCOC(=O)CC(=O)CCl.Nc1ccccn1 | O=c1cc(CCl)nc2ccccn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 18aaa9c9f1fc97f1276b7f3d8d51ea2f879273fca2a44162cb2a6bbc6598427f | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | O=c1ccnc2ccccn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[Cl;D1;H0:6]-[C:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[n;H0;D3;+0:10](:[c:11]:[c:12]):[c:8](:[c:9]):[n;H0;D2;+0:7]:1 | 99 | [{"value": 99.0, "product": "ClCC=1N=C2N(C(C1)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "ClCC=1N=C2N(C(C1)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 15 g (159.4 mmol) of 2-aminopyridine (10) was combined with approximately 80 g of polyphosphoric acid and heated to 120° C. to allow stirring. To the resulting solution was slowly added 30.5 mL (223.2 mmol) of ethyl-4-chloroacetoacetate and stirred at 120° C. under nitrogen for two hours. The hot reaction mixture was t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | c1ccncc1 | c1ccn2ccccc2n1 | c1ccn2ccccc2n1 | HO- | null | 120 | null | CCOC(=O)CC(=O)CCl.Nc1ccccn1>>O=c1cc(CCl)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad1e9031b79f410db9c8eca5f1bc3535 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12>>O=c1c(I)c(CCl)nc2ccccn12 | ClCC=1N=C2N(C(C1)=O)C=CC=C2.IN1C(CCC1=O)=O>>ClCC=1N=C2N(C(C1I)=O)C=CC=C2 | O=C1CCC(=O)N1[I:4].[O:1]=[c:2]1[cH:3][c:5]([CH2:6][Cl:7])[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]12>>[O:1]=[c:2]1[c:3]([I:4])[c:5]([CH2:6][Cl:7])[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]12 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12 | O=c1c(I)c(CCl)nc2ccccn12 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 1f06dfec407448bf0cc30da2662fcfbc61576861352771e24080279cb02cd786 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1ccnc2ccccn12 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[cH;D2;+0:10]:1>>[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:10]:1-[I;H0;D1;+0:1] | 83 | [{"value": 83.0, "product": "ClCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "ClCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A mixture of 21.9 g (112.5 mmol) of the product from Step 1 (11) and 38.9 g (168.8 mmol) of N-iodosuccinimide in 660 mL of acetonitrile was stirred at 80° C. under nitrogen for 16 hours. The reaction mixture was then allowed to cool to ambient temperature and the acetonitrile was removed in vacuo. The resulting solid w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccn2ccccc2n1 | c1cnc2ccccn2c1 | c1cnc2ccccn2c1 | HO- | C(C)#N | 80 | 16 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12>C(C)#N>O=c1c(I)c(CCl)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a3d0f6d29274e9ea7dca831a61f173c | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12>>CC(=O)OCc1nc2ccccn2c(=O)c1I | ClCC=1N=C2N(C(C1I)=O)C=CC=C2.C(C)(=O)[O-].[K+].O>>C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2 | [CH3:1][C:2](=[O:3])[O-:4].Cl[CH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[I:17]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[I:17] | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12 | CC(=O)OCc1nc2ccccn2c(=O)c1I | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | O=c1ccnc2ccccn12 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C;D1;H3:8]-[C:9](-[O-;H0;D1:10])=[O;D1;H0:11]>>[C;D1;H3:8]-[C:9](=[O;D1;H0:11])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 90.4 | [{"value": 90.0, "product": "C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | A mixture of 20.0 g (62.4 mmol) of the product from Step 2 (12) and 9.2 g (93.6 mmol) of potassium acetate in 200 mL DMF was stirred at 40° C. under nitrogen for three hours. The reaction mixture was allowed to cool to ambient temperature and the addition of excess water to the reaction solution caused the product to p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | c1cnc2ccccn2c1 | Other | CN(C)C=O | 40 | 3 | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12>CN(C)C=O>CC(=O)OCc1nc2ccccn2c(=O)c1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-465f2de5c44f4eafb490bd0a27c9b5c6 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1>>O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | OCC=1N=C2N(C(C1I)=O)C=CC=C2.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].[OH-].[Na+].OO.B1(C2CCCC1CCC2)CC3=CC=CC=C3>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO | I[c:3]1[c:2](=[O:1])[n:20]2[c:15]([n:14][c:11]1[CH2:12][OH:13])[cH:16][cH:17][cH:18][cH:19]2.C1CC2CCCC(C1)B2[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH2:12][OH:13])[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]12 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | null | C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe] | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | OtherReaction | f0be20dcbd3a5b120ffc0bdc604159d6719571a9db2f4d60ae9c44e29a64bcf5 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=c1c(Cc2ccccc2)cnc2ccccn12 | I-[c;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1=[O;D1;H0:9].[c:10]:[c:11](-[CH2;D2;+0:12]-B1-C2-C-C-C-C-1-C-C-C-2):[c:13]>>[C:3]-[c:2]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:1]:1-[CH2;D2;+0:12]-[c:11](:[c:10]):[c:13] | 91 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | A mixture of 4.0 g (13.24 mmol) of the product from Step 4 (14), 1.0 g (1.32 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene] palladium(II) dichloromethane adduct, and 8.4 g (39.72 mmol) of K3PO4 in 30 mL of DMF was heated to 80° C. To the resulting solution was added dropwise 40 mL (19.9 mmol) of B-Benzyl-9-BBN... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2ccccn2c1.B1C2CCCC1CCC2 | c1cnc2ccccn2c1 | c1ccccc1.c1cnc2ccccn2c1 | HI.B | C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O.C(C)(=O)OCC | 80 | 12 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1>C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O.C(C)(=O)OCC>O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-528b4a3f707542e9930cb18135cacbc2 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12>>O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | C(C)N(CC)CC.C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O | [OH:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2[c:11](=[O:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[CH:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2[c:11](=[O:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | null | null | ClCCl.O.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1c(Cc2ccccc2)cnc2ccccn12 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | 26.5 mL (53.0 mmol) of oxalyl chloride in 40 mL dichloromethane was cooled to −78° C. To the resulting solution was added a solution of 7.52 mL (105.9 mmol) of DMSO in 24 mL dichloromethane and stirred at −78° C. for one hour. Then was added a solution of 4.7 g (17.65 mmol) of the product from Step 5 (15) in 60 mL dich... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cnc2ccccn2c1.c1ccccc1 | null | ClCCl.O.C(C)(=O)OCC | -78 | 1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12>ClCCl.O.C(C)(=O)OCC>O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b3825057f854ccab44104ace7905bbb | C=[C](C)[Mg][Br].O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1>>C=C(C)C(O)c1nc2ccccn2c(=O)c1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O.C(=C)(C)[Mg]Br>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C(C(=C)C)O | [Br][Mg][C:2](=[CH2:1])[CH3:3].[CH:4](=[O:5])[c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH2:1]=[C:2]([CH3:3])[CH:4]([OH:5])[c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:... | C=[C](C)[Mg][Br].O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | C=C(C)C(O)c1nc2ccccn2c(=O)c1Cc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard from aldehyde to alcohol | d22306a6b4853561d9b1af524233a68c51df43b11c29a213ef7bf34e1cbc345b | ade448327e9ff2e4739cb0236a603ed53083987df6f7590d564d9a5dce0bda24 | O=c1c(Cc2ccccc2)cnc2ccccn12 | [Br]-[Mg]-[C;H0;D3;+0:1](=[C;D1;H2:2])-[C;D1;H3:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C;D1;H2:2]=[C;H0;D3;+0:1](-[C;D1;H3:3])-[CH;D3;+0:5](-[OH;D1;+0:4])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 106 | [{"value": 106.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C(C(=C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 105.3, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C(C(=C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | A mixture of 500 mg (1.9 mmol) of the product from Step 6 (16) in 15 ml THF was cooled to −78° C. To the resulting solution was added dropwise 7.6 ml (3.8 mmol) of isopropenylmagnesium bromide and stirred at −78° C. for 2 hours. The reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (2×). The c... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde.Vinyl | Secondary alcohol.Vinyl | null | null | c1cnc2ccccn2c1.c1ccccc1 | Br-.Mg | C1CCOC1 | -78 | 2 | C=[C](C)[Mg][Br].O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1>C1CCOC1>C=C(C)C(O)c1nc2ccccn2c(=O)c1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abdcff8565974421a008799f7eedc0ca | CC(C)C(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.O=C1NC(=O)c2ccccc21>>CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C(C)C)O.CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1(C=2C(C(N1)=O)=CC=CC2)=O>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C(C)C)N2C(C1=CC=CC=C1C2=O)=O | O[CH:4]([CH:2]([CH3:1])[CH3:3])[c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][CH2:21][CH2:22]2.[NH:23]1[C:24](=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]1=[O:33]>>[CH3:1][CH:2]([CH3:3])[CH:4]([c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:... | CC(C)C(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.O=C1NC(=O)c2ccccc21 | CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu_imide | 627f58d0e6226c1dbf2a932ee95739face3ceb0131e12fc74fabc98d7152eb3c | 7956e5ca56cf10b6e124d86d58ecab05b08a7230f12df133c0e18930774c5c47 | O=C1c2ccccc2C(=O)N1Cc1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | O-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1.[O;D1;H0:11]=[C:12]1-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])-[c:16]:[c:17]-1>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12](=[O;D1;H0:11])-[c:17]:[c:16]-[C:14]-1=[O;D1;H0:15])-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8... | 44 | [{"value": 44.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C(C)C)N2C(C1=CC=CC=C1C2=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A previous batch of the product from Step 8 (18) was combined with the above and 150 mg (0.48 mmol) of this crude material was dissolved in 3 ml of dry tetrahydrofuran then cooled to 0° C. Phthalimide 212 mg (1.4 mmol) was added to the cold solution followed by triphenylphosphine 189 mg (0.72 mmol) then DIAD 140 μl (0.... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Secondary alcohol | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1cnc2n(c1)CCCC2.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | 0 | null | CC(C)C(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.O=C1NC(=O)c2ccccc21>O1CCCC1>CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-052f3e5dd9644c4a82306ccb302e5a38 | CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O>>CC(C)C(N)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C(C)C)N2C(C1=CC=CC=C1C2=O)=O.NN>>NC(C(C)C)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2 | O=C1c2ccccc2C(=O)[N:5]1[CH:4]([CH:2]([CH3:1])[CH3:3])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[CH2:20][CH2:21][CH2:22][CH2:23]2>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[... | CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O | CC(C)C(N)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=c1c(Cc2ccccc2)cnc2n1CCCC2 | O=C1-[N;H0;D3;+0:1](-[C:2](-[C:3])-[c:4]:[#7;a:5])-C(=O)-c2:c:c:c:c:c:2-1>>[#7;a:5]:[c:4]-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | The product from Step 9 (19), 95 mg (0.22 mmol) was dissolved in 3 ml of dry ethanol then 50 μl (1.6 mmol) of hydrazine was added and the reaction was left to stir at room temperature for 1 h then heated to 40° C. for 2.5 h. The precipitate was removed by filtration and washed with ethyl acetate and the solvent evapora... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1cnc2n(c1)CCCC2 | HO- | C(C)O | null | 1 | CC(C)C(c1nc2n(c(=O)c1Cc1ccccc1)CCCC2)N1C(=O)c2ccccc2C1=O>C(C)O>CC(C)C(N)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-569b44ae1a804b5881ce58036529f28d | Cc1ccc(C(=O)N(CCCN2C(=O)c3ccccc3C2=O)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1>>Cc1ccc(C(=O)N(CCCN)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C(C)C)N(C(C2=CC=C(C=C2)C)=O)CCCN2C(C1=CC=CC=C1C2=O)=O.NN.C(=O)(C(F)(F)F)O>>NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2 | O=C1c2ccccc2C(=O)[N:12]1[CH2:11][CH2:10][CH2:9][N:8]([C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:36][cH:35]1)=[O:7])[CH:13]([c:14]1[n:15][c:16]2[n:17]([c:18](=[O:19])[c:20]1[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][CH2:29][CH2:30][CH2:31]2)[CH:32]([CH3:33])[CH3:34]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]... | Cc1ccc(C(=O)N(CCCN2C(=O)c3ccccc3C2=O)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1 | Cc1ccc(C(=O)N(CCCN)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(NCc1nc2n(c(=O)c1Cc1ccccc1)CCCC2)c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 2 | HOUR | The product from Step 12 (22), 50 mg (0.08 mmol) was dissolved in 1 ml of anhydrous ethanol. Hydrazine 18 μl (0.57 mmol) was added and the reaction stirred at room temperature for 2 h. The precipitate was filtered through a PTFE filter and washed with ethyl acetate. The solvent was evaporated and the crude material was... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccccc1.c1cnc2n(c1)CCCC2 | HO- | C(C)O | null | 2 | Cc1ccc(C(=O)N(CCCN2C(=O)c3ccccc3C2=O)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1>C(C)O>Cc1ccc(C(=O)N(CCCN)C(c2nc3n(c(=O)c2Cc2ccccc2)CCCC3)C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2853ad1b901c40ae80bafeada5c16e43 | CCOC(=O)CC(=O)CCl.Nc1ccccn1>>O=c1cc(CCl)nc2ccccn12 | NC1=NC=CC=C1.C(C)OC(CC(=O)CCl)=O>>ClCC=1N=C2N(C(C1)=O)C=CC=C2 | CCO[C:2](=[O:1])[CH2:3][C:4](=O)[CH2:5][Cl:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][Cl:6])[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]12 | CCOC(=O)CC(=O)CCl.Nc1ccccn1 | O=c1cc(CCl)nc2ccccn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 18aaa9c9f1fc97f1276b7f3d8d51ea2f879273fca2a44162cb2a6bbc6598427f | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | O=c1ccnc2ccccn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[Cl;D1;H0:6]-[C:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[n;H0;D3;+0:10](:[c:11]:[c:12]):[c:8](:[c:9]):[n;H0;D2;+0:7]:1 | 99 | [{"value": 99.0, "product": "ClCC=1N=C2N(C(C1)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "ClCC=1N=C2N(C(C1)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 15 g (159.4 mmol) of 2-aminopyridine (10) was combined with approximately 80 g of polyphosphoric acid and heated to 120° C. to allow stirring. To the resulting solution was added slowly 30.5 mL (223.2 mmol) of ethyl-4-chloroacetoacetate and stirred at 120° C. under nitrogen for two hours. The hot reaction mixture was t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | c1ccncc1 | c1ccn2ccccc2n1 | c1ccn2ccccc2n1 | HO- | null | 120 | null | CCOC(=O)CC(=O)CCl.Nc1ccccn1>>O=c1cc(CCl)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ca7ce72ffee42aaba2034928fa59554 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12>>O=c1c(I)c(CCl)nc2ccccn12 | ClCC=1N=C2N(C(C1)=O)C=CC=C2.IN1C(CCC1=O)=O>>ClCC=1N=C2N(C(C1I)=O)C=CC=C2 | O=C1CCC(=O)N1[I:4].[O:1]=[c:2]1[cH:3][c:5]([CH2:6][Cl:7])[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]12>>[O:1]=[c:2]1[c:3]([I:4])[c:5]([CH2:6][Cl:7])[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]12 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12 | O=c1c(I)c(CCl)nc2ccccn12 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 1f06dfec407448bf0cc30da2662fcfbc61576861352771e24080279cb02cd786 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1ccnc2ccccn12 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[cH;D2;+0:10]:1>>[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:10]:1-[I;H0;D1;+0:1] | 83 | [{"value": 83.0, "product": "ClCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "ClCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A mixture of 21.9 g (112.5 mmol) of the product from Step 1 (11) and 38.9 g (168.8 mmol) of N-iodosuccinimide in 660 mL of acetonitrile was stirred at 80° C. under nitrogen for 16 hours. The reaction mixture was then allowed to cool to ambient temperature and the acetonitrile was removed in vacuo. The resulting solid w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccn2ccccc2n1 | c1cnc2ccccn2c1 | c1cnc2ccccn2c1 | HO- | C(C)#N | 80 | 16 | O=C1CCC(=O)N1I.O=c1cc(CCl)nc2ccccn12>C(C)#N>O=c1c(I)c(CCl)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4de979b5d68b48d5b058edca74835037 | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12>>CC(=O)OCc1nc2ccccn2c(=O)c1I | ClCC=1N=C2N(C(C1I)=O)C=CC=C2.C(C)(=O)[O-].[K+].O>>C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2 | [CH3:1][C:2](=[O:3])[O-:4].Cl[CH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[I:17]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2[c:14](=[O:15])[c:16]1[I:17] | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12 | CC(=O)OCc1nc2ccccn2c(=O)c1I | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | O=c1ccnc2ccccn12 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C;D1;H3:8]-[C:9](-[O-;H0;D1:10])=[O;D1;H0:11]>>[C;D1;H3:8]-[C:9](=[O;D1;H0:11])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 90.4 | [{"value": 90.0, "product": "C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "C(C)(=O)OCC=1N=C2N(C(C1I)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | A mixture of 20.0 g (62.4 mmol) of the product from Step 2 (12) and 9.2 g (93.6 mmol) of potassium acetate in 200 mL DMF was stirred at 40° C. under nitrogen for three hours. The reaction mixture was allowed to cool to ambient temperature and the addition of excess water to the reaction solution caused the product to p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | c1cnc2ccccn2c1 | Other | CN(C)C=O | 40 | 3 | CC(=O)[O-].O=c1c(I)c(CCl)nc2ccccn12>CN(C)C=O>CC(=O)OCc1nc2ccccn2c(=O)c1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac6d2b19e39f44a79ff89c98a3a3cf91 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1>>O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | OCC=1N=C2N(C(C1I)=O)C=CC=C2.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].[OH-].[Na+].OO.B1(C2CCCC1CCC2)CC3=CC=CC=C3>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO | I[c:3]1[c:2](=[O:1])[n:20]2[c:15]([n:14][c:11]1[CH2:12][OH:13])[cH:16][cH:17][cH:18][cH:19]2.C1CC2CCCC(C1)B2[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH2:12][OH:13])[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]12 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | null | C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe] | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | OtherReaction | f0be20dcbd3a5b120ffc0bdc604159d6719571a9db2f4d60ae9c44e29a64bcf5 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=c1c(Cc2ccccc2)cnc2ccccn12 | I-[c;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1=[O;D1;H0:9].[c:10]:[c:11](-[CH2;D2;+0:12]-B1-C2-C-C-C-C-1-C-C-C-2):[c:13]>>[C:3]-[c:2]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:1]:1-[CH2;D2;+0:12]-[c:11](:[c:10]):[c:13] | 91 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | A mixture of 4.0 g (13.24 mmol) of the product from Step 4 (14), 1.0 g (1.32 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene] palladium(II) dichloromethane adduct, and 8.4 g (39.72 mmol) of K3PO4 in 30 mL of DMF was heated to 80° C. To the resulting solution was added dropwise 40 mL (19.9 mmol) of B-Benzyl-9-BBN... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2ccccn2c1.B1C2CCCC1CCC2 | c1cnc2ccccn2c1 | c1ccccc1.c1cnc2ccccn2c1 | HI.B | C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O.C(C)(=O)OCC | 80 | 12 | O=c1c(I)c(CO)nc2ccccn12.c1ccc(CB2C3CCCC2CCC3)cc1>C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O.C(C)(=O)OCC>O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a97bb4ce85649a495a0d4155a9906fc | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12>>O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | C(C)N(CC)CC.C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)CO.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O | [OH:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2[c:11](=[O:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[CH:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2[c:11](=[O:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12 | O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | null | null | ClCCl.O.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1c(Cc2ccccc2)cnc2ccccn12 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | 26.5 mL (53.0 mmol) of oxalyl chloride in 40 mL dichloromethane was cooled to −78° C. To the resulting solution was added a solution of 7.52 mL (105.9 mmol) of DMSO in 24 mL dichloromethane and stirred at −78° C. for one hour. Then was added a solution of 4.7 g (17.65 mmol) of product from Step 5 (15) in 60 mL dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cnc2ccccn2c1.c1ccccc1 | null | ClCCl.O.C(C)(=O)OCC | -78 | 1 | O=c1c(Cc2ccccc2)c(CO)nc2ccccn12>ClCCl.O.C(C)(=O)OCC>O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8395e7f2660426fb4fea0f25dd79e4e | O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1>>C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)C=CC=C2)C=O.C(=C)[Mg]Br>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C=C)O | [CH:3](=[O:4])[c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[cH:19][cH:20][cH:21][cH:22]2>>[CH2:1]=[CH:2][CH:3]([OH:4])[c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][CH2:21][CH2:22]2 | O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1 | C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 21fe27eeafdcabda4c34bca4f02b73f86e41d44a0c003f40b099db641d94d557 | 1cfdacde78204b273e664dc0eb50ffc4dc70522ea435514fcadd01e492b9b547 | O=c1c(Cc2ccccc2)cnc2n1CCCC2 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[#7;a:10]:2:[c:11]:[c:12]:1>>[C;D1;H2:13]=[C:14]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3]1:[#7;a:4]:[c:5]2:[#7;a:10](:[c:11]:[c:12]:1)-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-2 | 104.8 | [{"value": 104.8, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C=C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 3 | HOUR | A mixture of 2.5 g (9.5 mmol) of the product from Step 6 (16) in 35 mL THF was cooled to −78° C. To the resulting solution was added dropwise 11.4 mL (11.4 mmol) of vinyl magnesium bromide and stirred at −78° C. for 3 hours. The reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (4×). The combi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Vinyl | c1cnc2ccccn2c1 | c1cnc2n(c1)CCCC2 | c1ccccc1.c1cnc2n(c1)CCCC2 | Other | C1CCOC1 | -78 | 3 | O=Cc1nc2ccccn2c(=O)c1Cc1ccccc1>C1CCOC1>C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b09930744d88424abcededd998256f5f | C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2>>CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(C=C)O.[H][H]>>C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)O | [CH2:1]=[CH:2][CH:3]([OH:4])[c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][CH2:21][CH2:22]2>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[n:6][c:7]2[n:8]([c:9](=[O:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][CH2:21][CH2:22]2 | C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | O=c1c(Cc2ccccc2)cnc2n1CCCC2 | [#7;a:1]:[c:2]-[C:3](-[O;D1;H1:4])-[CH;D2;+0:5]=[CH2;D1;+0:6]>>[#7;a:1]:[c:2]-[C:3](-[O;D1;H1:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6] | 85 | [{"value": 85.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of 0.097 g (0.33 mmol) of the product from Step 7 (23) and 0.02 g of Palladium on activated carbon was stirred in 5 mL of ethyl acetate. The flask was equipped with a balloon containing hydrogen gas and the reaction mixture was stirred at ambient temperature for 3 days. The reaction mixture was then filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1cnc2n(c1)CCCC2 | null | [Pd].C(C)(=O)OCC | null | 72 | C=CC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2>[Pd].C(C)(=O)OCC>CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b32bd64ddf9145fab0ed069dc7d2ce92 | CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.CS(=O)(=O)Cl>>CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC(CC)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2 | [CH3:1][CH2:2][CH:3]([OH:4])[c:9]1[n:10][c:11]2[n:12]([c:13](=[O:14])[c:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:23][CH2:24][CH2:25][CH2:26]2.Cl[S:5]([CH3:6])(=[O:7])=[O:8]>>[CH3:1][CH2:2][CH:3]([O:4][S:5]([CH3:6])(=[O:7])=[O:8])[c:9]1[n:10][c:11]2[n:12]([c:13](=[O:14])[c:15]1[CH2:16][c:17]1[cH:18][... | CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.CS(=O)(=O)Cl | CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | O=c1c(Cc2ccccc2)cnc2n1CCCC2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[OH;D1;+0:9]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 100 | [{"value": 100.0, "product": "CS(=O)(=O)OC(CC)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "CS(=O)(=O)OC(CC)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of 0.084 g (0.28 mmol) of the product (24) from Step 8 and 0.08 mL (0.56 mmol) of triethylamine in 2.5 mL of anhydrous DCM was cooled to 0° C. Then was added dropwise 0.03 mL (0.34 mmol) of methanesulfonyl chloride and the resulting mixture was allowed to warm to ambient temperature under nitrogen. Excess DCM... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1cnc2n(c1)CCCC2 | HCl | C(Cl)Cl | 0 | null | CCC(O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.CS(=O)(=O)Cl>C(Cl)Cl>CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42dac9e0cc2e438baefdc9be2c640253 | CC(C)(C)OC(=O)NCCCN.CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2>>CCC(NCCCNC(=O)OC(C)(C)C)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.N | CS(=O)(=O)OC(CC)C=1N=C2N(C(C1CC1=CC=CC=C1)=O)CCCC2.NCCCNC(OC(C)(C)C)=O.[I-].[K+].CO>>N.C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)NCCCNC(OC(C)(C)C)=O | [NH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].CS(=O)(=O)O[CH:3]([CH2:2][CH3:1])[c:16]1[n:17][c:18]2[n:19]([c:20](=[O:21])[c:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:30][CH2:31][CH2:32][CH2:33]2>>[CH3:1][CH2:2][CH:3]([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[... | CC(C)(C)OC(=O)NCCCN.CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2 | CCC(NCCCNC(=O)OC(C)(C)C)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.N | null | null | C(Cl)Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=c1c(Cc2ccccc2)cnc2n1CCCC2 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 28.6 | [{"value": 0.1, "product": "N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.0, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)NCCCNC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.6, "product": "C(C1=CC=CC=C1)C1=C(N=C2N(C1=O)CCCC2)C(CC)NCCCNC(OC(C)(C)C)=O", "details... | 60 | CELSIUS | 24 | HOUR | A mixture of 0.106 g (0.28 mmol) of the product from Step 9 (25), 0.15 g (0.84 mmol) of tert-butyl 3-aminopropylcarbamate, and 0.005 g (0.03 mmol) of potassium iodide in 5 mL of DMF was stirred at 60° C. under nitrogen for 24 hours. The reaction was quenched with water, extracted with ethyl acetate (4×) and the combine... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccccc1.c1cnc2n(c1)CCCC2 | HO- | C(Cl)Cl.CN(C)C=O | 60 | 24 | CC(C)(C)OC(=O)NCCCN.CCC(OS(C)(=O)=O)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2>C(Cl)Cl.CN(C)C=O>CCC(NCCCNC(=O)OC(C)(C)C)c1nc2n(c(=O)c1Cc1ccccc1)CCCC2.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c7803fc28434ac2bf2d75784aa563f6 | CI.N#Cc1ccc(OCc2ccccc2)cc1O>>COc1cc(OCc2ccccc2)ccc1C#N | C(C1=CC=CC=C1)OC1=CC(=C(C#N)C=C1)O.IC.[H-].[Na+]>>C(C1=CC=CC=C1)OC1=CC(=C(C#N)C=C1)OC | I[CH3:1].[OH:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17]#[N:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17]#[N:18] | CI.N#Cc1ccc(OCc2ccccc2)cc1O | COc1cc(OCc2ccccc2)ccc1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(COc2ccccc2)cc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | To a magnetically stirred solution of 4-benzyloxy-2-hydroxybenzonitrile (1-A, WO 00/69841) (7.95 g, 35.3 mmol) and iodomethane (5.43 mL, 87.2 mmol) in DMF (90 mL) cooled to −5° was added all at once sodium hydride (60% dispersion, 2.17 g, 54.2 mmol). The mixture was stirred for 30 min, warmed to room temperature and st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | CN(C)C=O | null | 0.5 | CI.N#Cc1ccc(OCc2ccccc2)cc1O>CN(C)C=O>COc1cc(OCc2ccccc2)ccc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a8d3389992248d6944aa2c1b72ed972 | COc1cc(OCc2ccccc2)ccc1C#N.[N-]=[N+]=[N-]>>COc1cc(OCc2ccccc2)ccc1-c1nn[nH]n1 | O.C(C1=CC=CC=C1)OC1=CC(=C(C#N)C=C1)OC.[N-]=[N+]=[N-].[Na+].Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=1N=NNN1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17]#[N:18].[N+:19](=[N-:20])=[N-:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1-[c:17]1[n:18][n:19][nH:20][n:21]1 | COc1cc(OCc2ccccc2)ccc1C#N.[N-]=[N+]=[N-] | COc1cc(OCc2ccccc2)ccc1-c1nn[nH]n1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(COc2ccc(-c3nn[nH]n3)cc2)cc1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7]:[c:8].[N-;H0;D1:9]=[N+;H0;D2:10]=[N-;H0;D1:11]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[n;H0;D2;+0:10]:[nH;D2;+0:9]:[n;H0;D2;+0:11]:1):[c:7]:[c:8] | null | [] | null | null | 30 | MINUTE | A vigorously stirred suspension of 4-benzyloxy-2-methoxybenzonitrile (1-B) (1.20 g, 5.0 mmol), sodium azide (732 mg, 11.3 mmol), and triethylamine hydrochloride (1.54 g, 11.3 mmol) in toluene (6 mL) was heated at 110° for 48 h. The brown suspension was cooled, water (15 mL) was added, and the mixture stirred for 30 min... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | null | C1(=CC=CC=C1)C | null | 0.5 | COc1cc(OCc2ccccc2)ccc1C#N.[N-]=[N+]=[N-]>C1(=CC=CC=C1)C>COc1cc(OCc2ccccc2)ccc1-c1nn[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ba94315f74a4f3da82902ec1853775e | CCCCCC12CCC(c3nnc(-c4ccc(OCc5ccccc5)cc4OC)n3C)(CC1)CC2>>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4OC)n3C)(CC1)CC2 | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)OC>>COC=1C=C(C=CC1C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)O | c1ccc(C[O:18][c:17]2[cH:16][cH:15][c:14](-[c:13]3[n:12][n:11][c:10]([C:9]45[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:26][CH2:25]4)[CH2:28][CH2:27]5)[n:23]3[CH3:24])[c:20]([O:21][CH3:22])[cH:19]2)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([c:10]3[n:11][n:12][c:13](-[c:14]4[cH:... | CCCCCC12CCC(c3nnc(-c4ccc(OCc5ccccc5)cc4OC)n3C)(CC1)CC2 | CCCCCC12CCC(c3nnc(-c4ccc(O)cc4OC)n3C)(CC1)CC2 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | A solution of 3-[4-(benzyloxy)-2-methoxyphenyl]-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (1-E) (272 mg, 0.572 mmol) in MeOH (8 mL) was hydrogenated for 19 h with 10% Pd/C catalyst (27 mg) at room temperature and atmospheric pressure. The catalyst was filtered and washed with MeOH. The MeOH was remo... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | Other | [Pd].CO | null | null | CCCCCC12CCC(c3nnc(-c4ccc(OCc5ccccc5)cc4OC)n3C)(CC1)CC2>[Pd].CO>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4OC)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4b83e628e09444daa2f0b9b64e2c1d2 | CCCCCC12CCC(C(=O)O)(CC1)CC2.C[Si](C)(C)C=[N+]=[N-]>>CCCCCC12CCC(C(=O)OC)(CC1)CC2 | C[Si](C)(C)C=[N+]=[N-].C(CCCC)C12CCC(CC1)(CC2)C(=O)O>>C(CCCC)C12CCC(CC1)(CC2)C(=O)OC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10](=[O:11])[OH:12])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2.C[Si](C)(C)[CH:13]=[N+]=[N-]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10](=[O:11])[O:12][CH3:13])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | CCCCCC12CCC(C(=O)O)(CC1)CC2.C[Si](C)(C)C=[N+]=[N-] | CCCCCC12CCC(C(=O)OC)(CC1)CC2 | null | null | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | C1CC2CCC1CC2 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | 10 | MINUTE | (Trimethylsilyl)diazomethane (2M/hexane, 53 mL, 106 mmol) was added slowly to a solution of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (2-A) (20.3 g, 90.6 mmol) in methylene chloride (100 mL) and methanol (40 mL) until the yellow color persisted. After stirring for 10 min at room temperature, the solution was conce... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | C1CC2CCC1CC2 | Other | CO.C(Cl)Cl | null | 0.166667 | CCCCCC12CCC(C(=O)O)(CC1)CC2.C[Si](C)(C)C=[N+]=[N-]>CO.C(Cl)Cl>CCCCCC12CCC(C(=O)OC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6f2bd4daaeb4b90bd37aa6b589eab91 | CCCCCC12CCC(C(=O)OC)(CC1)CC2.NN>>CCCCCC12CCC(C(=O)NN)(CC1)CC2 | NN.C(CCCC)C12CCC(CC1)(CC2)C(=O)OC.O>>C(CCCC)C12CCC(CC1)(CC2)C(=O)NN | CO[C:10]([C:9]12[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:15][CH2:14]1)[CH2:17][CH2:16]2)=[O:11].[NH2:12][NH2:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10](=[O:11])[NH:12][NH2:13])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | CCCCCC12CCC(C(=O)OC)(CC1)CC2.NN | CCCCCC12CCC(C(=O)NN)(CC1)CC2 | null | null | C(CO)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | C1CC2CCC1CC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7])(-[C:5])-[C:6] | null | [] | null | null | null | null | Hydrazine (anhydrous, 103 mL, 88.7 mmol) was added to a solution of methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate (2-B) in ethylene glycol (180 mL) and the mixture was stirred under reflux for 17 h. After cooling to room temperature, the mixture was poured into water (1500 mL) and extracted with methylene chloride ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1CC2CCC1CC2 | HO- | C(CO)O | null | null | CCCCCC12CCC(C(=O)OC)(CC1)CC2.NN>C(CO)O>CCCCCC12CCC(C(=O)NN)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d12e7d0d4e094acc9af766b376f160b5 | CCCCCC12CCC(C(=O)NN)(CC1)CC2.COc1ccc(C(=O)O)c(C)c1>>CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2 | C(C)N(CC)CC.[Cl-].ClC=1N(CC[N+]1C)C.CC1=C(C(=O)O)C=CC(=C1)OC.C(CCCC)C12CCC(CC1)(CC2)C(=O)NN>>COC1=CC(=C(C=C1)C=1OC(=NN1)C12CCC(CC1)(CC2)CCCCC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10]([NH:11][NH2:12])=[O:23])([CH2:24][CH2:25]1)[CH2:26][CH2:27]2.O=[C:13](O)[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([c:10]3[n:11][n:12][c:13](-[c:14]4[cH:15][cH:16][c... | CCCCCC12CCC(C(=O)NN)(CC1)CC2.COc1ccc(C(=O)O)c(C)c1 | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 9cd47482aac10ef536f59b494c104bc8c3ef635f3c5e7f741b0b8d333620cea9 | 6a0a64dedea322c67c78c82295ab9f68e41acfdbf703e197b4f985a15274c989 | c1ccc(-c2nnc(C34CCC(CC3)CC4)o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C;D1;H3:6]):[c:7].[C:8]-[C:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[NH;D2;+0:12]-[NH2;D1;+0:13])(-[C:14])-[C:15]>>[C:8]-[C:9](-[c;H0;D3;+0:10]1:[n;H0;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C;D1;H3:6]):[c:7]):[o;H0;D2;+0:11]:... | null | [] | null | null | 48 | HOUR | 2-Chloro-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium chloride (5.07 g, 30.0 mmol) was added to a solution of 2-methyl-4-methoxybenzoic acid (2-D) (856 mg, 5.0 mmol) and 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide (2-C) (1.25 g, 5.25 mmol) in methylene chloride (60 mL) followed by triethylamine (8.36 mL, 60 mmol) and t... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC2CCC1CC2 | HO- | C(Cl)Cl | null | 48 | CCCCCC12CCC(C(=O)NN)(CC1)CC2.COc1ccc(C(=O)O)c(C)c1>C(Cl)Cl>CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e941c7d8cd1b44b5a5fdf3c2ebce4d19 | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2.CN>>CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2 | COC1=CC(=C(C=C1)C=1OC(=NN1)C12CCC(CC1)(CC2)CCCCC)C.FC(C(=O)[O-])(F)F.C[NH3+].CN>>COC1=CC(=C(C=C1)C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)C | o1[c:10]([C:9]23[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:26][CH2:25]2)[CH2:28][CH2:27]3)[n:11][n:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[CH3:22].[NH2:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([c:10]3[n:11][n:12][c:13](-[c:14]4[cH:15][cH:... | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2.CN | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2 | null | null | null | Miscellaneous | OtherReaction | 06fefb205a4853de5c4e4a339b564c57a94b95a37d2e8ba13cde385235751498 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | [C;D1;H3:1]-[NH2;D1;+0:2].[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):o:1)(-[C:12])-[C:13]>>[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):[n;H0;D3;+0:2]:1-[C;D1;H3:1])(-[C:12])-[C:13] | null | [] | null | null | null | null | 2-(4-Methoxy-2-methylphenyl)-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole (2-E) (988 mg, 2.68 mmol), methylammonium trifluoroacetate (9.72 g, 67 mmol, prepared by combining equimolar amounts of methylamine and trifluoroacetic acid in ether followed by concentration in vacuo), and methylamine (2M/MeOH, 33 mL, 67 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nnco1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | HO- | null | null | null | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)o3)(CC1)CC2.CN>>CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1c506f5bd4a4f69afabbbdda5d1ebd2 | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2>>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4C)n3C)(CC1)CC2 | B(Br)(Br)Br.COC1=CC(=C(C=C1)C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)C>>CC=1C=C(C=CC1C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)O | C[O:18][c:17]1[cH:16][cH:15][c:14](-[c:13]2[n:12][n:11][c:10]([C:9]34[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:25][CH2:24]3)[CH2:27][CH2:26]4)[n:22]2[CH3:23])[c:20]([CH3:21])[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([c:10]3[n:11][n:12][c:13](-[c:14]4[cH:15][cH:16][c:17]... | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2 | CCCCCC12CCC(c3nnc(-c4ccc(O)cc4C)n3C)(CC1)CC2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | Boron tribromide (1M/CH2Cl2, 3.21 mL, 3.21 mmol) was added to a solution of 3-(4-methoxy-2-methylphenyl)4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (2-F) (410 mg, 1.07 mmol) in methylene chloride (6 mL) at 0° C. The mixture was stirred at room temperature for 2 h. The solution was washed with water, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | Other | C(Cl)Cl | null | 2 | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4C)n3C)(CC1)CC2>C(Cl)Cl>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4C)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-592291b2ec824fb19d6e2d104fb4ea04 | CCCCCC12CCC(C(=O)O)(CC1)CC2.O=C(Cl)C(=O)Cl>>CCCCCC12CCC(C(=O)Cl)(CC1)CC2 | C(C(=O)Cl)(=O)Cl.C(CCCC)C12CCC(CC1)(CC2)C(=O)O>>C(CCCC)C12CCC(CC1)(CC2)C(=O)Cl | O[C:10]([C:9]12[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:14][CH2:13]1)[CH2:16][CH2:15]2)=[O:11].O=C(Cl)C(=O)[Cl:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10](=[O:11])[Cl:12])([CH2:13][CH2:14]1)[CH2:15][CH2:16]2 | CCCCCC12CCC(C(=O)O)(CC1)CC2.O=C(Cl)C(=O)Cl | CCCCCC12CCC(C(=O)Cl)(CC1)CC2 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | C1CC2CCC1CC2 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])(-[C:6])-[C:7]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])(-[C:6])-[C:7] | null | [] | null | null | 3 | HOUR | Oxalyl chloride (505 μL, 5.79 mmol) was added dropwise to a mixture of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (3-A) in methylene chloride (10 mL). The solution was stirred at room temperature for 3 h and then concentrated in vacuo to give 4-pentylbicyclo[2.2.2]octane-1-carbonyl chloride (3-B). 1H NMR (500 MHz, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | C1CC2CCC1CC2 | HCl | C(Cl)Cl | null | 3 | CCCCCC12CCC(C(=O)O)(CC1)CC2.O=C(Cl)C(=O)Cl>C(Cl)Cl>CCCCCC12CCC(C(=O)Cl)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-030e66c4db174e88a95a86231066a60a | CCCCCC12CCC(C(=O)O)(CC1)CC2.CN>>CCCCCC12CCC(C(=O)NC)(CC1)CC2 | C(C)(C)N(C(C)C)CC.C(CCCC)C12CCC(CC1)(CC2)C(=O)O.Cl.CN>>CNC(=O)C12CCC(CC1)(CC2)CCCCC | O[C:10]([C:9]12[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:15][CH2:14]1)[CH2:17][CH2:16]2)=[O:11].[NH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10](=[O:11])[NH:12][CH3:13])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | CCCCCC12CCC(C(=O)O)(CC1)CC2.CN | CCCCCC12CCC(C(=O)NC)(CC1)CC2 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CC2CCC1CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])(-[C:5])-[C:6] | null | [] | null | null | 18 | HOUR | N,N-Diisopropylethylamine (1.44 mL, 11.1 mmol) was added to a mixture of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (3-A) (1.09 g, 4.45 mmol) and methylamine hydrochloride (1.5 g, 22.3 mmol) in methylene chloride (10 mL) was added and the mixture stirred at room temperature for 18 h. After diluting with methylene c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC2CCC1CC2 | HO- | C(Cl)Cl | null | 18 | CCCCCC12CCC(C(=O)O)(CC1)CC2.CN>C(Cl)Cl>CCCCCC12CCC(C(=O)NC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbb6f3573a304c5fbaff1f0b87a49bad | CCCCCC12CCC(C(=O)NC)(CC1)CC2.O=C(Cl)C(=O)Cl>>CCCCCC12CCC(C(Cl)=NC)(CC1)CC2 | C(C(=O)Cl)(=O)Cl.CNC(=O)C12CCC(CC1)(CC2)CCCCC>>CN=C(C12CCC(CC1)(CC2)CCCCC)Cl | O=[C:10]([C:9]12[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:15][CH2:14]1)[CH2:17][CH2:16]2)[NH:12][CH3:13].O=C(Cl)C(=O)[Cl:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:10]([Cl:11])=[N:12][CH3:13])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | CCCCCC12CCC(C(=O)NC)(CC1)CC2.O=C(Cl)C(=O)Cl | CCCCCC12CCC(C(Cl)=NC)(CC1)CC2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | dc7791bfee84cf66a1b8f977acbd29af2e1941d3332cba18b7c3de6672d67f79 | f77e7aabb720174699de30170bf16b12e447d00eff20d5f78e7a23cf128bc822 | C1CC2CCC1CC2 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[C;D1;H3:4])-[C:5](-[C:6])(-[C:7])-[C:8]>>[C:6]-[C:5](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[N;H0;D2;+0:3]-[C;D1;H3:4])(-[C:7])-[C:8] | null | [] | null | null | 4 | HOUR | Oxalyl chloride (846 μL, 9.7 mmol) was added dropwise to a solution of N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboxamide (3-C) (230 mg, 0.97 mmol) in methylene chloride (2.0 mL) and the mixture stirred at room temperature for 4 h. The solvent and excess reagent were removed in vacuo to provide N-methyl-4-pentylbicycl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary amide | Alkenyl halide | null | null | C1CC2CCC1CC2 | HCl | C(Cl)Cl | null | 4 | CCCCCC12CCC(C(=O)NC)(CC1)CC2.O=C(Cl)C(=O)Cl>C(Cl)Cl>CCCCCC12CCC(C(Cl)=NC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e64f2088409c4f1e9e76aba2dff66a1b | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2>>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | B(Br)(Br)Br.ClC1=C(C=CC(=C1)OC)C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC>>ClC=1C=C(C=CC1C1=NN=C(N1C)C12CCC(CC1)(CC2)CCCCC)O | C[O:18][c:17]1[cH:16][cH:15][c:14](-[c:13]2[n:12][n:11][c:10]([C:9]34[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:25][CH2:24]3)[CH2:27][CH2:26]4)[n:22]2[CH3:23])[c:20]([Cl:21])[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([c:10]3[n:11][n:12][c:13](-[c:14]4[cH:15][cH:16][c:17](... | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2 | CCCCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2.5 | HOUR | Boron tribromide (135 μL, 1.43 mmol) was added dropwise to a solution of 3-(2-chloro-4-methoxyphenyl)-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazole (3-F) (287 mg, 0.714 mmol) in methylene chloride (5 mL) at 0° C. The mixture was stirred at room temperature for 2.5 h. The solution was washed with water, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | Other | C(Cl)Cl | null | 2.5 | CCCCCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2>C(Cl)Cl>CCCCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd451761a0974684be9fdb908b83999c | COC(=O)C12CCC(/C=C/CC3(C)OCCO3)(CC1)CC2>>COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2 | CC1(OCCO1)C/C=C/C12CCC(CC1)(CC2)C(=O)OC.[H][H]>>CC1(OCCO1)CCCC12CCC(CC1)(CC2)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8](/[CH:9]=[CH:10]/[CH2:11][C:12]3([CH3:13])[O:14][CH2:15][CH2:16][O:17]3)([CH2:18][CH2:19]1)[CH2:20][CH2:21]2>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([CH2:9][CH2:10][CH2:11][C:12]3([CH3:13])[O:14][CH2:15][CH2:16][O:17]3)([CH2:18][CH2:19]1)[CH2:20][CH2:21]2 | COC(=O)C12CCC(/C=C/CC3(C)OCCO3)(CC1)CC2 | COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2 | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C(CC1OCCO1)CC12CCC(CC1)CC2 | [#8:1]-[C:2](-[C:3]/[CH;D2;+0:4]=[CH;D2;+0:5]/[C:6](-[C:7])(-[C:8])-[C:9])-[#8:10]>>[#8:1]-[C:2](-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C:6](-[C:7])(-[C:8])-[C:9])-[#8:10] | null | [] | null | null | 3 | HOUR | Methyl 4-[(1E)-3-(2-methyl-1,3-dioxolan-2-yl)prop-1-enyl]bicyclo[2.2.2]octane-1-carboxylate (4-B) (1.1 g) was stirred in ethanol (75 mL). A spatula tip scoop of 10% Pd on carbon (150 mg) was added. A hydrogen balloon was added and the mixture was stirred under hydrogen atmosphere for 3 h. The palladium-on-carbon was fi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCO1.C1CC2CCC1CC2 | null | [Pd].C(C)O | null | 3 | COC(=O)C12CCC(/C=C/CC3(C)OCCO3)(CC1)CC2>[Pd].C(C)O>COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-459c5cfb913d41c4829308c412ec545b | COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2>>CC1(CCCC23CCC(C(=O)O)(CC2)CC3)OCCO1 | Cl.CC1(OCCO1)CCCC12CCC(CC1)(CC2)C(=O)OC.CO.[OH-].[K+]>>CC1(OCCO1)CCCC12CCC(CC1)(CC2)C(=O)O | C[O:12][C:10]([C:9]12[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][C:2]3([CH3:1])[O:17][CH2:18][CH2:19][O:20]3)([CH2:14][CH2:13]1)[CH2:16][CH2:15]2)=[O:11]>>[CH3:1][C:2]1([CH2:3][CH2:4][CH2:5][C:6]23[CH2:7][CH2:8][C:9]([C:10](=[O:11])[OH:12])([CH2:13][CH2:14]2)[CH2:15][CH2:16]3)[O:17][CH2:18][CH2:19][O:20]1 | COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2 | CC1(CCCC23CCC(C(=O)O)(CC2)CC3)OCCO1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(CC1OCCO1)CC12CCC(CC1)CC2 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | Methyl 4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]octane-1-carboxylate (4-C) (1.0 g, 3.38 mmol) was stirred in a solution of 90% methanol and 10% water (50 mL). Excess potassium hydroxide (2.0 g) was added. The mixture was refluxed overnight. The cooled mixture was acidified with 1N hydrochloric acid (100 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1COCO1.C1CC2CCC1CC2 | Other | O | null | null | COC(=O)C12CCC(CCCC3(C)OCCO3)(CC1)CC2>O>CC1(CCCC23CCC(C(=O)O)(CC2)CC3)OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84fb52185c774a5eb874f0bf0248d023 | CC1(CCCC23CCC(c4nnc(-c5ccccc5C(F)(F)F)o4)(CC2)CC3)OCCO1>>CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 | CC1(OCCO1)CCCC12CCC(CC1)(CC2)C=2OC(=NN2)C2=C(C=CC=C2)C(F)(F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC(C1=C(C=CC=C1)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)=O)(F)F | C1C[O:3][C:2]([CH3:1])([CH2:4][CH2:5][CH2:6][C:7]23[CH2:8][CH2:9][C:10]([c:11]4[n:12][n:13][c:14](-[c:15]5[cH:16][cH:17][cH:18][cH:19][c:20]5[C:21]([F:22])([F:23])[F:24])[o:25]4)([CH2:26][CH2:27]2)[CH2:28][CH2:29]3)O1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12][n:13][c:14](-[c:15... | CC1(CCCC23CCC(c4nnc(-c5ccccc5C(F)(F)F)o4)(CC2)CC3)OCCO1 | CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | c1ccc(-c2nnc(C34CCC(CC3)CC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-[C;D1;H3:4])-O-C-C-[O;H0;D2;+0:5]-1>>[C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5] | null | [] | null | null | null | null | 2-{4-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazole (4-G) (0.158 g) was stirred in a mixure of 90% acetone/10% water (20 mL). p-Toluenesulfonic acid (10 mg) was added to the solution. The reaction was heated to reflux for 1 h. The volume was reduced by evapo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1nnco1.c1ccccc1.C1CC2CCC1CC2 | HO- | CC(=O)C | null | null | CC1(CCCC23CCC(c4nnc(-c5ccccc5C(F)(F)F)o4)(CC2)CC3)OCCO1>CC(=O)C>CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dbe3666ed85f447b85d247ea660ecf59 | CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2>>CC(O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 | O.[BH4-].[Na+].FC(C1=C(C=CC=C1)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)=O)(F)F.C(C)(=O)OCC>>FC(C1=C(C=CC=C1)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)O)(F)F | [CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12][n:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[C:21]([F:22])([F:23])[F:24])[o:25]3)([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12][n:13][c:14](-[c:15]4[cH... | CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 | CC(O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2nnc(C34CCC(CC3)CC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5]>>[C:1]-[C:2]-[CH;D3;+0:3](-[C;D1;H3:4])-[OH;D1;+0:5] | null | [] | null | null | null | null | 5-(4-{5-[2-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo[2.2.2]oct-1-yl)pentan-2-one (4-H) (0.072 g) was stirred in methanol (2 mL) at 0° C. Sodium borohydride (20 mg) was added. The reaction was allowed to stir to room temperature. The mixture was then layered with ethyl acetate (15 mL) and water (15 mL). The ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1nnco1.c1ccccc1.C1CC2CCC1CC2 | null | CO | null | null | CC(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2>CO>CC(O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)o3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58f158a836644cc2bae7cfd18667abfe | COc1ccc(-c2nnc(C34CCC(CCCC5(C)OCCO5)(CC3)CC4)o2)c(Cl)c1>>COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1 | ClC1=C(C=CC(=C1)OC)C=1OC(=NN1)C12CCC(CC1)(CC2)CCCC2(OCCO2)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC1=C(C=CC(=C1)OC)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)=O | C1C[O:20][C:18]([CH2:17][CH2:16][CH2:15][C:14]23[CH2:13][CH2:12][C:11]([c:10]4[n:9][n:8][c:7](-[c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][c:26]5[Cl:27])[o:25]4)([CH2:22][CH2:21]2)[CH2:24][CH2:23]3)([CH3:19])O1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([C:11]34[CH2:12][CH2:13][C:14]([CH2:15][CH2:16]... | COc1ccc(-c2nnc(C34CCC(CCCC5(C)OCCO5)(CC3)CC4)o2)c(Cl)c1 | COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | c1ccc(-c2nnc(C34CCC(CC3)CC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-[C;D1;H3:4])-O-C-C-[O;H0;D2;+0:5]-1>>[C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5] | null | [] | null | null | null | null | 2-(2-Chloro-4-methoxyphenyl)-5-{4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-1,3,4-oxadiazole (5-G) (0.200 g) was stirred in a mixure of 90% acetone/10% water (20 mL). p-Toluenesulfonic acid (15 mg) was added to the solution. The reaction was heated to reflux for 1 h. The volume was reduced by evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1nnco1.c1ccccc1.C1CC2CCC1CC2 | HO- | CC(=O)C | null | null | COc1ccc(-c2nnc(C34CCC(CCCC5(C)OCCO5)(CC3)CC4)o2)c(Cl)c1>CC(=O)C>COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4d247fa61c34f7fb684e5173dbc37e3 | COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1>>COc1ccc(-c2nnc(C34CCC(CCCC(C)O)(CC3)CC4)o2)c(Cl)c1 | O.[BH4-].[Na+].ClC1=C(C=CC(=C1)OC)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)=O.C(C)(=O)OCC>>ClC1=C(C=CC(=C1)OC)C1=NN=C(O1)C12CCC(CC1)(CC2)CCCC(C)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([C:11]34[CH2:12][CH2:13][C:14]([CH2:15][CH2:16][CH2:17][C:18]([CH3:19])=[O:20])([CH2:21][CH2:22]3)[CH2:23][CH2:24]4)[o:25]2)[c:26]([Cl:27])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([C:11]34[CH2:12][CH2:13][C:14]([CH2:15][CH2:16][CH2... | COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1 | COc1ccc(-c2nnc(C34CCC(CCCC(C)O)(CC3)CC4)o2)c(Cl)c1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2nnc(C34CCC(CC3)CC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5]>>[C:1]-[C:2]-[CH;D3;+0:3](-[C;D1;H3:4])-[OH;D1;+0:5] | null | [] | null | null | null | null | 5-{4-[5-(2-Chloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one (5-H) (0.150 g, 0.373 mmol) was stirred in methanol (5 mL) at 0° C. Sodium borohydride (0.0169 g, 0.448 mmol) was added. The reaction was allowed to stir to room temperature. The mixture was then layered with ethyl acetate (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1nnco1.c1ccccc1.C1CC2CCC1CC2 | null | CO | null | null | COc1ccc(-c2nnc(C34CCC(CCCC(C)=O)(CC3)CC4)o2)c(Cl)c1>CO>COc1ccc(-c2nnc(C34CCC(CCCC(C)O)(CC3)CC4)o2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df60b65268cd4187bb8abcd94d317da8 | COc1ccc(-c2nc(C34CCC(CCCC(C)O)(CC3)CC4)nn2C)c(Cl)c1>>CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2 | ClC1=C(C=CC(=C1)OC)C1=NC(=NN1C)C12CCC(CC1)(CC2)CCCC(C)O.C(C)[S-].[Na+].C(C)[S-].[Na+]>>ClC=1C=C(C=CC1C1=NN(C(=N1)C12CCC(CC1)(CC2)CCCC(C)O)C)O | C[O:18][c:17]1[cH:16][cH:15][c:14](-[c:13]2[n:12][c:11]([C:10]34[CH2:9][CH2:8][C:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[OH:3])([CH2:26][CH2:25]3)[CH2:28][CH2:27]4)[n:23][n:22]2[CH3:24])[c:20]([Cl:21])[cH:19]1>>[CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12][c:13](-[c:14]4[cH:15][cH:... | COc1ccc(-c2nc(C34CCC(CCCC(C)O)(CC3)CC4)nn2C)c(Cl)c1 | CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | af85e5faa5666fd77c1191cff8da8aae98340ec9be0b0764ad456817ff08d81a | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | c1ccc(-c2n[nH]c(C34CCC(CC3)CC4)n2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8](-[c:9]):[n;H0;D3;+0:10](-[CH3;D1;+0:11]):[n;H0;D2;+0:12]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8](-[c:9]):[n;H0;D2;+0:10]:[n;H0;D3;+0:12]:1-[CH3;D1;+0:11].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 5-{4-[5-(2-Chloro-4-methoxyphenyl)-1-methyl-1-H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-ol (5-J) (0.036 g, 0.086 mmol) was placed in a small vial with 0.5 mL of DMF. Sodium ethanethiolate (0.0218 g, 0.260 mmol) was added to the solution. The vial was sealed and heated to 1000 C for 1.5 h. The incomplete reac... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1.C1CC2CCC1CC2 | Other | CN(C)C=O | null | null | COc1ccc(-c2nc(C34CCC(CCCC(C)O)(CC3)CC4)nn2C)c(Cl)c1>CN(C)C=O>CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53742d0c5eb54af9bba80ba6264ee456 | CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2>>CC(=O)CCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | ClC=1C=C(C=CC1C1=NN(C(=N1)C12CCC(CC1)(CC2)CCCC(C)O)C)O.C[N+]1(CCOCC1)[O-]>>ClC1=C(C=CC(=C1)O)C=1N(C(=NN1)C12CCC(CC1)(CC2)CCCC(C)=O)C | [CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12]([CH3:24])[n:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]4[Cl:22])[n:23]3)([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([c:11]3[n:12][n:13][c:14](-[c:15]4[cH:16... | CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2 | CC(=O)CCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(Cl)Cl | Miscellaneous | OtherReaction | 5a0da850c5eca3182a8f1192617bc4ffa6221f660a8f48206d6fcbb187f9d1d9 | ef59ba7fad669d0d82c4daf03280dc0366c9a31cf6192836b4997e72f66f9d7c | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3](-[C;D1;H3:4])-[OH;D1;+0:5].[C:6]-[c:7]1:[n;H0;D2;+0:8]:[c:9](-[c:10]):[#7;a:11]:[n;H0;D3;+0:12]:1-[CH3;D1;+0:13]>>[C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5].[C:6]-[c:7]1:[n;H0;D2;+0:12]:[#7;a:11]:[c:9](-[c:10]):[n;H0;D3;+0:8]:1-[CH3;D1;+0:13] | null | [] | null | null | 15 | MINUTE | 3-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]4-methyl-4H-1,2,4-triazol-3-yl}phenol (5-K) (0.0035 g, 0.00869 mmol) was stirred in 0.5 mL of dry methylene chloride over activated 4 Å sieves. N-methylmorpholine N-oxide (0.0015 g, 0.013 mmol) was added. The mixture was allowed to stir under N2 for 15 min. Tetra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl | null | 0.25 | CC(O)CCCC12CCC(c3nc(-c4ccc(O)cc4Cl)nn3C)(CC1)CC2>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl>CC(=O)CCCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc0de27bcbc34212928ebda73822b8e1 | COC(=O)C12CCC(C(=O)O)(CC1)CC2.NC(=NO)c1ccc(F)cc1>>COC(=O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 | COC(=O)C12CCC(CC1)(CC2)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1.FC1=CC=C(C(N)=NO)C=C1>>FC1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C(=O)OC | O=[C:9](O)[C:8]12[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH2:22][CH2:21]1)[CH2:24][CH2:23]2.[NH2:10][C:11]([c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)=[N:19][OH:20]>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]4)[n:19][o:20]3)(... | COC(=O)C12CCC(C(=O)O)(CC1)CC2.NC(=NO)c1ccc(F)cc1 | COC(=O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | a2ae31d0a4419b2c5154a805176ea647c4ecfa171a098253676fdd25dd7bb0eb | 125aa09f13da5a63d8a4326b5eb28b82ab752c0f025e52bd5183605dc71565a2 | c1ccc(-c2noc(C34CCC(CC3)CC4)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])(-[C:4])-[C:5].[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[N;H0;D2;+0:8]-[OH;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[n;H0;D2;+0:8]:[o;H0;D2;+0:9]:1)(-[C:4])-[C:5] | null | [] | null | null | 1 | HOUR | To a suspension of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (7-A) (0.906 g, 4.27 mmol) in dichloromethane (20 mL) was added 1,1′-carbonyldiimidazole (1.04 g, 6.41 mmol). The reaction turned into a clear solution instantly with evolving of gas. After the mixture was stirred at room temperature for 1 h, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Oxime | null | null | c1ncon1 | c1ncon1.c1ccccc1.C1CC2CCC1CC2 | HO- | ClCCl | null | 1 | COC(=O)C12CCC(C(=O)O)(CC1)CC2.NC(=NO)c1ccc(F)cc1>ClCCl>COC(=O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09ebaf0ff92f45e8b1338251305a7176 | NNC(=O)c1ccccc1C(F)(F)F.O=C(O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2>>Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1 | C(C)N(CC)CC.FC1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C(=O)O.FC(C1=C(C(=O)NN)C=CC=C1)(F)F.[Cl-].ClC1[NH+](CCN1C)C>>FC1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C=2OC(=NN2)C2=C(C=CC=C2)C(F)(F)F | [NH2:15][NH:16][C:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24]([F:25])([F:26])[F:27])=[O:28].O=[C:14](O)[C:13]12[CH2:12][CH2:11][C:10]([c:9]3[o:8][n:7][c:6](-[c:5]4[cH:4][cH:3][c:2]([F:1])[cH:35][cH:34]4)[n:33]3)([CH2:30][CH2:29]1)[CH2:32][CH2:31]2>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9]([C:10]34[C... | NNC(=O)c1ccccc1C(F)(F)F.O=C(O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 | Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1 | null | null | ClCCl.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 9cd47482aac10ef536f59b494c104bc8c3ef635f3c5e7f741b0b8d333620cea9 | 6a0a64dedea322c67c78c82295ab9f68e41acfdbf703e197b4f985a15274c989 | c1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6)o5)(CC3)CC4)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])(-[C:4])-[C:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[c:10](:[c:11]):[c;H0;D3;+0:12](-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[NH;D2;+0:15]-[NH2;D1;+0:16]):[c:17]:[c:18]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:16]:[n;H0;D2;+0:15]:[c;H0;D3;+0:13](-[c;H0;D3;+0:12](:[c:17]:[c:18]):[c:... | null | [] | null | null | 48 | HOUR | A mixture of the acid (7-C) (138.9 mg, 0.439 mmol) and 2-(trifluoromethyl)benzoic hydrazide (7-D) (89.7 mg, 0.439 mmol) was first co-evaporated with toluene three times. Dichloromethane (7 mL) was added to the mixture as solvent. To the resulting suspension was added 2-chloro-1,3-dimethylimidazolinium chloride (743 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | null | null | c1nnco1 | c1ncon1.c1nnco1.c1ccccc1.c1ccccc1.C1CC2CCC1CC2 | HO- | ClCCl.C1(=CC=CC=C1)C | null | 48 | NNC(=O)c1ccccc1C(F)(F)F.O=C(O)C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2>ClCCl.C1(=CC=CC=C1)C>Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ffb1b09c9654cf0ab8b97de94dde1ea | CN.Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1>>Cn1c(-c2ccccc2C(F)(F)F)nnc1C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 | FC(C(=O)O)(F)F.CN.CN.FC1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C=2OC(=NN2)C2=C(C=CC=C2)C(F)(F)F>>FC1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C2=NN=C(N2C)C2=C(C=CC=C2)C(F)(F)F | [CH3:1][NH2:2].o1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]([F:11])([F:12])[F:13])[n:14][n:15][c:16]1[C:17]12[CH2:18][CH2:19][C:20]([c:21]3[n:22][c:23](-[c:24]4[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]4)[n:31][o:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[... | CN.Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1 | Cn1c(-c2ccccc2C(F)(F)F)nnc1C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 | null | null | CO | Miscellaneous | OtherReaction | 053ee3bc6819a903779afeaa459454f2cedeb9dc8ad12dec15fa99d829cab5ff | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6)[nH]5)(CC3)CC4)n2)cc1 | [C;D1;H3:1]-[NH2;D1;+0:2].[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):o:1)(-[C:12])-[C:13]>>[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):[n;H0;D3;+0:2]:1-[C;D1;H3:1])(-[C:12])-[C:13] | null | [] | null | null | null | null | A mixture of above 1,2,4-oxadiazole (7-E) (115.2 mg, 0.238 mmol) and the trifluoroacetic acid salt of methylamine (1.73 g, 11.9 mmol) in a 2M solution of methylamine in methanol (4 mL) was heated at 150° C. in a sealed tube for 48 h. The mixture was then concentrated, and the residue was taken up in dichloromethane, wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nnco1 | c1nnc[nH]1 | c1nnc[nH]1.c1ncon1.c1ccccc1.c1ccccc1.C1CC2CCC1CC2 | HO- | CO | null | null | CN.Fc1ccc(-c2noc(C34CCC(c5nnc(-c6ccccc6C(F)(F)F)o5)(CC3)CC4)n2)cc1>CO>Cn1c(-c2ccccc2C(F)(F)F)nnc1C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff54322d153a4dc4b467848c1630342a | NNC(=O)c1ccc(OCc2ccccc2)cc1C(F)(F)F.O=C(O)C12CCC(c3ccccc3)(CC1)CC2>>O=C(NNC(=O)C12CCC(c3ccccc3)(CC1)CC2)c1ccc(OCc2ccccc2)cc1C(F)(F)F | C(C1=CC=CC=C1)OC1=CC(=C(C(=O)NN)C=C1)C(F)(F)F.C1(=CC=CC=C1)C12CCC(CC1)(CC2)C(=O)O.C(C(=O)Cl)(=O)Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC1=CC(=C(C(=O)NNC(=O)C23CCC(CC2)(CC3)C3=CC=CC=C3)C=C1)C(F)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:21]1[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33][c:34]1[C:35]([F:36])([F:37])[F:38].O[C:5](=[O:6])[C:7]12[CH2:8][CH2:9][C:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)([CH2:17][CH2:18]1)[CH2:19][CH2:20]2>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[O:6])[C:7... | NNC(=O)c1ccc(OCc2ccccc2)cc1C(F)(F)F.O=C(O)C12CCC(c3ccccc3)(CC1)CC2 | O=C(NNC(=O)C12CCC(c3ccccc3)(CC1)CC2)c1ccc(OCc2ccccc2)cc1C(F)(F)F | null | CN(C)C=O | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | O=C(NNC(=O)C12CCC(c3ccccc3)(CC1)CC2)c1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[NH2;D1;+0:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[c:11])(-[C:5])-[C:6] | null | [] | null | null | 30 | MINUTE | To a magnetically stirred solution of 4-phenylbicyclo[2.2.2]octane-1-carboxylic acid (8-A) (70 mg, 0.30 mmol) in methylene chloride (1 mL) at room temperature was added 2 M oxalyl chloride in methylene chloride (0.61 mL, 1.22 mmol). Two drops of catalytic DMF were added to catalyze the reaction. The reaction was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC2CCC1CC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 0.5 | NNC(=O)c1ccc(OCc2ccccc2)cc1C(F)(F)F.O=C(O)C12CCC(c3ccccc3)(CC1)CC2>CN(C)C=O.C(Cl)Cl>O=C(NNC(=O)C12CCC(c3ccccc3)(CC1)CC2)c1ccc(OCc2ccccc2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8685a6eac8ea44819f3c9fe05917060f | CN.FC(F)(F)c1cc(OCc2ccccc2)ccc1-c1nnc(C23CCC(c4ccccc4)(CC2)CC3)o1>>Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 | CO.FC(C(=O)[O-])(F)F.CN.CN.C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=1OC(=NN1)C12CCC(CC1)(CC2)C2=CC=CC=C2)C(F)(F)F>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C1=NN=C(N1C)C12CCC(CC1)(CC2)C2=CC=CC=C2)C(F)(F)F | [CH3:1][NH2:2].o1[c:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][c:17]2[C:18]([F:19])([F:20])[F:21])[n:22][n:23][c:24]1[C:25]12[CH2:26][CH2:27][C:28]([c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)([CH2:35][CH2:36]1)[CH2:37][CH2:38]2>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][c:... | CN.FC(F)(F)c1cc(OCc2ccccc2)ccc1-c1nnc(C23CCC(c4ccccc4)(CC2)CC3)o1 | Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 | null | null | null | Miscellaneous | OtherReaction | 053ee3bc6819a903779afeaa459454f2cedeb9dc8ad12dec15fa99d829cab5ff | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(COc2ccc(-c3nnc(C45CCC(c6ccccc6)(CC4)CC5)[nH]3)cc2)cc1 | [C;D1;H3:1]-[NH2;D1;+0:2].[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):o:1)(-[C:12])-[C:13]>>[C:3]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c:9](:[c:10]):[c:11]):[n;H0;D3;+0:2]:1-[C;D1;H3:1])(-[C:12])-[C:13] | null | [] | 150 | CELSIUS | null | null | The trifluoroacetate salt of methylamine (380 mg, 2.61 mmol) and 2-[4-(benzyloxy)-2-(trifluoromethyl)phenyl]-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole (8-D) were suspended in a 2 M solution of methylamine in methanol (1.3 mL, 2.61 mmol) and heated at 150° C. overnight. After being-cooled to room temperature, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nnco1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC2CCC1CC2 | HO- | null | 150 | null | CN.FC(F)(F)c1cc(OCc2ccccc2)ccc1-c1nnc(C23CCC(c4ccccc4)(CC2)CC3)o1>>Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0c56182eea249c29f1d65743d49bf35 | Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2>>Cn1c(-c2ccc(O)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C1=NN=C(N1C)C12CCC(CC1)(CC2)C2=CC=CC=C2)C(F)(F)F>>CN1C(=NN=C1C12CCC(CC1)(CC2)C2=CC=CC=C2)C2=C(C=C(C=C2)O)C(F)(F)F | c1ccc(C[O:8][c:7]2[cH:6][cH:5][c:4](-[c:3]3[n:2]([CH3:1])[c:17]([C:18]45[CH2:19][CH2:20][C:21]([c:22]6[cH:23][cH:24][cH:25][cH:26][cH:27]6)([CH2:28][CH2:29]4)[CH2:30][CH2:31]5)[n:16][n:15]3)[c:10]([C:11]([F:12])([F:13])[F:14])[cH:9]2)cc1>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:9][c:10]2[C:11]([F:12])([F... | Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 | Cn1c(-c2ccc(O)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 | null | [Pd] | C(C)(=O)OCC.CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnc(C34CCC(c5ccccc5)(CC3)CC4)[nH]2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 3 | HOUR | The 3-[4-(Benzyloxy)-2-(trifluoromethyl)phenyl]-4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazole (8-E) (27 mg, 0.05 mmol) was dissolved in ethyl acetate/methanol (1:1, 4 mL) to which 10% palladium-on-carbon (4 mg) was added. The reaction was then placed under hydrogen atmosphere and stirred for 3 h at room ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1nnc[nH]1.c1ccccc1.c1ccccc1.C1CC2CCC1CC2 | Other | [Pd].C(C)(=O)OCC.CO | null | 3 | Cn1c(-c2ccc(OCc3ccccc3)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2>[Pd].C(C)(=O)OCC.CO>Cn1c(-c2ccc(O)cc2C(F)(F)F)nnc1C12CCC(c3ccccc3)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a286d955ac0a41d1a41f20d217b5c249 | CCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2>>CCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | ClC1=C(C=CC(=C1)OC)C1=NN=C(N1C)C12CCC(CC1)(CC2)CC.B(Br)(Br)Br>>ClC=1C=C(C=CC1C1=NN=C(N1C)C12CCC(CC1)(CC2)CC)O | C[O:15][c:14]1[cH:13][cH:12][c:11](-[c:10]2[n:9][n:8][c:7]([C:6]34[CH2:5][CH2:4][C:3]([CH2:2][CH3:1])([CH2:22][CH2:21]3)[CH2:24][CH2:23]4)[n:19]2[CH3:20])[c:17]([Cl:18])[cH:16]1>>[CH3:1][CH2:2][C:3]12[CH2:4][CH2:5][C:6]([c:7]3[n:8][n:9][c:10](-[c:11]4[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]4[Cl:18])[n:19]3[CH3:20])([... | CCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2 | CCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | 2 | HOUR | Triazole 9-D (30 mg, 0.08 mmol) was dissolved in 0.5 mL of dry methylene chloride, placed under an inert atmosphere, and cooled to 0° C. To this solution was added BBr3 (1 M in CH2Cl2, 0.25 mL, 0.25 mmol) and the cooling bath was immediately removed. The reaction was stirred for 2 h then diluted with 20 mL of methylene... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | Other | C(Cl)Cl | 0 | 2 | CCC12CCC(c3nnc(-c4ccc(OC)cc4Cl)n3C)(CC1)CC2>C(Cl)Cl>CCC12CCC(c3nnc(-c4ccc(O)cc4Cl)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c3871ec9b5e41f59191396ebbd8a2c1 | CCS(=O)(=O)CCC12CCC(C(=O)OC)(CC1)CC2>>CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2 | C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C(=O)OC.[OH-].[K+]>>C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C(=O)O | C[O:14][C:12]([C:11]12[CH2:10][CH2:9][C:8]([CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:16][CH2:15]1)[CH2:18][CH2:17]2)=[O:13]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][C:11]([C:12](=[O:13])[OH:14])([CH2:15][CH2:16]1)[CH2:17][CH2:18]2 | CCS(=O)(=O)CCC12CCC(C(=O)OC)(CC1)CC2 | CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CC2CCC1CC2 | 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 | Ester 10-3 (880 mg, 3 mmol) was dissolved in 10% water/methanol solution (100 mL) and treated with 1 g of potassium hydroxide. The reaction was heated at 60° C. for 1 h then at 45° C. overnight. The mixture was concentrated in vacuo then acidified to pH 2 with 1M HCl and extracted with three portions of methylene chlor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC2CCC1CC2 | Other | O.CO | 60 | null | CCS(=O)(=O)CCC12CCC(C(=O)OC)(CC1)CC2>O.CO>CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e706c624ca62436c8ab912eeec11dc73 | CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2.CN>>CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2 | C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C(=O)O.C(C(=O)Cl)(=O)Cl.CN>>C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C(=O)NC | O[C:12]([C:11]12[CH2:10][CH2:9][C:8]([CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:17][CH2:16]1)[CH2:19][CH2:18]2)=[O:13].[NH2:14][CH3:15]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][C:11]([C:12](=[O:13])[NH:14][CH3:15])([CH2:16][CH2:17]1)[CH2:18][CH2:19]2 | CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2.CN | CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2 | null | CN(C)C=O | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CC2CCC1CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])(-[C:5])-[C:6] | null | [] | null | null | 90 | MINUTE | Carboxylic acid 10-4 (810 mg, 2.96 mmol) was dissolved in 12 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with oxalyl chloride (2M in methylene chloride, 4.4 mL, 8.8 mmol) and subsequently with 5 drops of DMF. The reaction was stirred at room temperature under nitrogen atmosphere for 90 min, th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC2CCC1CC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 1.5 | CCS(=O)(=O)CCC12CCC(C(=O)O)(CC1)CC2.CN>CN(C)C=O.C(Cl)Cl>CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef748dab2bdd4380ac279454e952a728 | CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1>>CCS(=O)(=O)CCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 | C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C(=O)NC.C(C(=O)Cl)(=O)Cl.FC(C1=C(C=CC=C1)C1=NN=NN1)(F)F>>C(C)S(=O)(=O)CCC12CCC(CC1)(CC2)C2=NN=C(N2C)C2=C(C=CC=C2)C(F)(F)F | O=[C:12]([C:11]12[CH2:10][CH2:9][C:8]([CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:29][CH2:28]1)[CH2:31][CH2:30]2)[NH:26][CH3:27].n1[nH][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]([F:23])([F:24])[F:25])[n:14][n:13]1>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][C:11]([... | CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1 | CCS(=O)(=O)CCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 | null | CN(C)C=O | C(Cl)Cl | Miscellaneous | OtherReaction | 3b312fb2388e7c8a48dfc5e29439e6c80b8d8c210e1557d48baa2e24b968f478 | a267a1d067671b1e552868d2a160d189ea3d111697964c07c12357f5fdb70c13 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C;D1;H3:3])-[C:4](-[C:5])(-[C:6])-[C:7].[c:8]:[c:9](-[c;H0;D3;+0:10]1:[#7;a:11]:[n;H0;D2;+0:12]:n:[nH]:1):[c:13]>>[C:5]-[C:4](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:12]:[#7;a:11]:[c;H0;D3;+0:10](-[c:9](:[c:8]):[c:13]):[n;H0;D3;+0:2]:1-[C;D1;H3:3])(-[C:6])-[C:7] | null | [] | null | null | 1 | HOUR | Methyl amide 10-5 (220 mg, 0.77 mmol) was dissolved in anhydrous methylene chloride (2 mL) and treated with oxalyl chloride (2M in methylene chloride, 0.77 mL, 1.54 mmol) and DMF (2 drops). The solution was stirred at room temperature for 1 h, then solvent removed by evaporation under diminished pressure. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1nnn[nH]1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 1 | CCS(=O)(=O)CCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1>CN(C)C=O.C(Cl)Cl>CCS(=O)(=O)CCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d661520c8654c8b94727f04b623984e | COC(=O)C12CCC(/C=C/C(=O)OCc3ccccc3)(CC1)CC2>>COC(=O)C12CCC(CCC(=O)O)(CC1)CC2 | C(C)(=O)O.C(C1=CC=CC=C1)OC(/C=C/C12CCC(CC1)(CC2)C(=O)OC)=O>>COC(=O)C12CCC(CC1)(CC2)CCC(=O)O | c1ccc(C[O:13][C:11](/[CH:10]=[CH:9]/[C:8]23[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH2:15][CH2:14]2)[CH2:17][CH2:16]3)=[O:12])cc1>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([CH2:9][CH2:10][C:11](=[O:12])[OH:13])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | COC(=O)C12CCC(/C=C/C(=O)OCc3ccccc3)(CC1)CC2 | COC(=O)C12CCC(CCC(=O)O)(CC1)CC2 | null | [Pd] | C(C)(=O)OCC.CO | Deprotection | OtherReaction | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CC2CCC1CC2 | [C:1]-[C:2](/[CH;D2;+0:3]=[CH;D2;+0:4]/[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1)(-[C:8])-[C:9]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7])(-[C:8])-[C:9] | null | [] | null | null | 2 | HOUR | Diester 11-2 (0.625 g, 1.90 mmol) was dissolved in a 1:1 mixture of ethyl acetate/methanol (30 mL), placed under nitrogen atmosphere, then treated with 10% Pd/C (500 mg) and 0.1 mL of acetic acid. The reaction was placed under hydrogen atmosphere and stirred vigorously for 2 hr. The resulting solution was filtered thro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CC2CCC1CC2 | Other | [Pd].C(C)(=O)OCC.CO | null | 2 | COC(=O)C12CCC(/C=C/C(=O)OCc3ccccc3)(CC1)CC2>[Pd].C(C)(=O)OCC.CO>COC(=O)C12CCC(CCC(=O)O)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9617c9127714410590c90029d8cad091 | COC(=O)C12CCC(CCC(=O)O)(CC1)CC2>>COC(=O)C12CCC(CCCO)(CC1)CC2 | COC(=O)C12CCC(CC1)(CC2)CCC(=O)O.B.Cl>>OCCCC12CCC(CC1)(CC2)C(=O)OC | O=[C:11]([CH2:10][CH2:9][C:8]12[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH2:14][CH2:13]1)[CH2:16][CH2:15]2)[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([CH2:9][CH2:10][CH2:11][OH:12])([CH2:13][CH2:14]1)[CH2:15][CH2:16]2 | COC(=O)C12CCC(CCC(=O)O)(CC1)CC2 | COC(=O)C12CCC(CCCO)(CC1)CC2 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | C1CC2CCC1CC2 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | null | null | null | null | Carboxylic acid 11-3 (400 mg, 1.67 mmol) was dissolved in tetrahydrofuran (5 mL) and borane (1 M solution in THF, 2.17 mL, 1.3 eq.) was added dropwise at room temperature. After 2 h the reaction was added to 50 mL of 1 N HCl and then extracted three times with 50 mL of methylene chloride. The combined organic layers we... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC2CCC1CC2 | Other | O1CCCC1 | null | null | COC(=O)C12CCC(CCC(=O)O)(CC1)CC2>O1CCCC1>COC(=O)C12CCC(CCCO)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d49a63409384c689980b386e7f611d6 | COC(=O)C12CCC(CCCO)(CC1)CC2.CS(=O)(=O)Cl>>COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2 | OCCCC12CCC(CC1)(CC2)C(=O)OC.N1=CC=CC=C1.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCC12CCC(CC1)(CC2)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([CH2:9][CH2:10][CH2:11][OH:12])([CH2:17][CH2:18]1)[CH2:19][CH2:20]2.Cl[S:13]([CH3:14])(=[O:15])=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([CH2:9][CH2:10][CH2:11][O:12][S:13]([CH3:14])(=[O:15])=[O:16])([CH2:17][CH2:18]1)[CH2:19][CH2:20]2 | COC(=O)C12CCC(CCCO)(CC1)CC2.CS(=O)(=O)Cl | COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CC2CCC1CC2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 4 | HOUR | Hydroxyester 11-4 (430 mg, 1.9 mmol) was dissolved in 2.5 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with pyridine (0.5 mL) and methanesulfonyl chloride (0.368 mL, 4.8 mmol) and stirred for 4 h at room temperature. The mixture was diluted with 100 mL of ethyl acetate and washed with 1N aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC2CCC1CC2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 4 | COC(=O)C12CCC(CCCO)(CC1)CC2.CS(=O)(=O)Cl>C(Cl)Cl.C(C)(=O)OCC>COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af2cecdb19664bf285599a4ff49c08f1 | CC[S-].COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2>>CCSCCCC12CCC(C(=O)OC)(CC1)CC2 | CS(=O)(=O)OCCCC12CCC(CC1)(CC2)C(=O)OC.C(C)[S-].[Na+]>>C(C)SCCCC12CCC(CC1)(CC2)C(=O)OC | [CH3:1][CH2:2][S-:3].CS(=O)(=O)O[CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([C:11](=[O:12])[O:13][CH3:14])([CH2:15][CH2:16]1)[CH2:17][CH2:18]2>>[CH3:1][CH2:2][S:3][CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][C:10]([C:11](=[O:12])[O:13][CH3:14])([CH2:15][CH2:16]1)[CH2:17][CH2:18]2 | CC[S-].COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2 | CCSCCCC12CCC(C(=O)OC)(CC1)CC2 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4ce663f1d715457759f86c3a689fb26031b2c96ac82d1a129bc4ad678e13b486 | 38c56b8cb3a8c00dfe37ecf8d5a5d7b7efcdb1e68a885b3435776031eb2535b7 | C1CC2CCC1CC2 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5]-[S-;H0;D1:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[C:5]-[C;D1;H3:4] | null | [] | 45 | CELSIUS | 3 | HOUR | Mesylate 11-5 (3.30 g, 10.9 mmol) was dissolved in DMF (20 mL) and treated with sodium ethanethiolate (1.82 g, 21.7 mmol). The solution was stirred at 45° C. for 3 h, then the mixture was diluted with 100 mL of ethyl acetate and washed twice with 1N aqueous HCl, then with saturated aqueous sodium bicarbonate, and brine... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Monosulfide | null | null | C1CC2CCC1CC2 | MsOH.HO- | CN(C)C=O.C(C)(=O)OCC | 45 | 3 | CC[S-].COC(=O)C12CCC(CCCOS(C)(=O)=O)(CC1)CC2>CN(C)C=O.C(C)(=O)OCC>CCSCCCC12CCC(C(=O)OC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ce4bb22dcce4c04888f87d4df956e15 | CCS(=O)(=O)CCCC12CCC(C(=O)OC)(CC1)CC2>>CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2 | C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C(=O)OC.[OH-].[K+].Cl>>C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C(=O)O | C[O:15][C:13]([C:12]12[CH2:11][CH2:10][C:9]([CH2:8][CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:17][CH2:16]1)[CH2:19][CH2:18]2)=[O:14]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][CH2:8][C:9]12[CH2:10][CH2:11][C:12]([C:13](=[O:14])[OH:15])([CH2:16][CH2:17]1)[CH2:18][CH2:19]2 | CCS(=O)(=O)CCCC12CCC(C(=O)OC)(CC1)CC2 | CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CC2CCC1CC2 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | Sulfone 11-7 (3.1 g, 10 mmol) was dissolved in 9:1 MeOH/water (50 mL) and treated with potassium hydroxide (3 g). The solution was stirred at room temperature overnight, then the mixture was acidified with 1 N HCl and extracted four times with 50 mL of methylene chloride. The organic layer was dried over anhydrous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC2CCC1CC2 | Other | CO.O | null | 8 | CCS(=O)(=O)CCCC12CCC(C(=O)OC)(CC1)CC2>CO.O>CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14428e54e0524b8d822981d4378a9abf | CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2.CN>>CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2 | CN.C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C(=O)O.C(C(=O)Cl)(=O)Cl.CN>>C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C(=O)NC | O[C:13]([C:12]12[CH2:11][CH2:10][C:9]([CH2:8][CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:18][CH2:17]1)[CH2:20][CH2:19]2)=[O:14].[NH2:15][CH3:16]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][CH2:8][C:9]12[CH2:10][CH2:11][C:12]([C:13](=[O:14])[NH:15][CH3:16])([CH2:17][CH2:18]1)[CH2:19][CH2:20]2 | CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2.CN | CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2 | null | CN(C)C=O | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CC2CCC1CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])(-[C:5])-[C:6] | null | [] | null | null | 90 | MINUTE | Carboxylic acid 11-8 (3.0 g, 11 mmol) was dissolved in 50 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with oxalyl chloride (2 M in methylene chloride, 16.2 mL, 32.4 mmol) and subsequently with 5 drops of DMF. The reaction was stirred at room temperature under nitrogen atmosphere for 90 min, th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC2CCC1CC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 1.5 | CCS(=O)(=O)CCCC12CCC(C(=O)O)(CC1)CC2.CN>CN(C)C=O.C(Cl)Cl>CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dbb478b35b94176bb360da1ffb6b9df | CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1>>CCS(=O)(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 | C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C(=O)NC.C(C(=O)Cl)(=O)Cl.FC(C1=C(C=CC=C1)C1=NN=NN1)(F)F>>C(C)S(=O)(=O)CCCC12CCC(CC1)(CC2)C2=NN=C(N2C)C2=C(C=CC=C2)C(F)(F)F | O=[C:13]([C:12]12[CH2:11][CH2:10][C:9]([CH2:8][CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])([CH2:30][CH2:29]1)[CH2:32][CH2:31]2)[NH:27][CH3:28].n1[nH][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[C:23]([F:24])([F:25])[F:26])[n:15][n:14]1>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][CH2:8][C:9]12[CH2:10]... | CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1 | CCS(=O)(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 | null | CN(C)C=O | C(Cl)Cl | Miscellaneous | OtherReaction | 3b312fb2388e7c8a48dfc5e29439e6c80b8d8c210e1557d48baa2e24b968f478 | a267a1d067671b1e552868d2a160d189ea3d111697964c07c12357f5fdb70c13 | c1ccc(-c2nnc(C34CCC(CC3)CC4)[nH]2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C;D1;H3:3])-[C:4](-[C:5])(-[C:6])-[C:7].[c:8]:[c:9](-[c;H0;D3;+0:10]1:[#7;a:11]:[n;H0;D2;+0:12]:n:[nH]:1):[c:13]>>[C:5]-[C:4](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:12]:[#7;a:11]:[c;H0;D3;+0:10](-[c:9](:[c:8]):[c:13]):[n;H0;D3;+0:2]:1-[C;D1;H3:3])(-[C:6])-[C:7] | null | [] | null | null | 1 | HOUR | Methyl amide 11-9 (0.470 g, 1.56 mmol) was dissolved in anhydrous methylene chloride (5 mL) and treated with oxalyl chloride (2M in methylene chloride, 1.56 mL, 3.12 mmol) and DMF (2 drops). The solution was stirred at room temperature for 1 h, then solvent removed by evaporation under reduced pressure. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1nnn[nH]1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.C1CC2CCC1CC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 1 | CCS(=O)(=O)CCCC12CCC(C(=O)NC)(CC1)CC2.FC(F)(F)c1ccccc1-c1nnn[nH]1>CN(C)C=O.C(Cl)Cl>CCS(=O)(=O)CCCC12CCC(c3nnc(-c4ccccc4C(F)(F)F)n3C)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25cc8f7fb801465897a61ea3c50f29e0 | COC(=O)C12CCC(C=O)(CC1)CC2.C[Si](C)(C)[N-][Si](C)(C)C>>C=CC12CCC(C(=O)OC)(CC1)CC2 | C(=O)C12CCC(CC1)(CC2)C(=O)OC.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>>C(=C)C12CCC(CC1)(CC2)C(=O)OC | O=[CH:2][C:3]12[CH2:4][CH2:5][C:6]([C:7](=[O:8])[O:9][CH3:10])([CH2:11][CH2:12]1)[CH2:13][CH2:14]2.C[Si](C)(C)[N-][Si](C)(C)[CH3:1]>>[CH2:1]=[CH:2][C:3]12[CH2:4][CH2:5][C:6]([C:7](=[O:8])[O:9][CH3:10])([CH2:11][CH2:12]1)[CH2:13][CH2:14]2 | COC(=O)C12CCC(C=O)(CC1)CC2.C[Si](C)(C)[N-][Si](C)(C)C | C=CC12CCC(C(=O)OC)(CC1)CC2 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CCOC(=O)C.C1CCOC1 | C-C Coupling | OtherReaction | 65846b40393caf810f4a2d80980311afbe6a487d5b2731f135215f55a25e4832 | 37f02ff997533d11a1e569347ef78cf65235ab0024b34a145afdaafd2d3d15ac | C1CC2CCC1CC2 | C-[Si](-C)(-C)-[N-]-[Si](-C)(-C)-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[C:3](-[C:4])(-[C:5])-[C:6]>>[C:4]-[C:3](-[CH;D2;+0:2]=[CH2;D1;+0:1])(-[C:5])-[C:6] | null | [] | null | null | 5 | MINUTE | To a stirred solution of methyltriphenylphosphonium bromide (9.1 g, 12.8 mmol) in THF (50 ml) at 0° C. was added potassium hexamethyldisilazide (0.5M in toluene, 48.6 ml), dropwise over 5 min. The resulting mixture was allowed to warm up to room temperature over 1 h, then cooled again to 0° C. and treated with methyl 4... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Silyl protective group.Silyl protective group | Vinyl | null | null | C1CC2CCC1CC2 | HO- | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C.C1CCOC1 | null | 0.083333 | COC(=O)C12CCC(C=O)(CC1)CC2.C[Si](C)(C)[N-][Si](C)(C)C>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C.C1CCOC1>C=CC12CCC(C(=O)OC)(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4524a489f9b44534838f0c7596a9c754 | CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)O)cc1Br.NCCCCc1ccccc1>>CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)NCCCCc2ccccc2)cc1Br | BrC=1C=C(C(=O)O)C=CC1C(F)(F)P(=O)(OCC)OCC.BrC=1C=C(C(=O)O)C=CC1C(F)(F)P(=O)(OCC)OCC.C(CCCC1=CC=CC=C1)N>>C(C)OP(OCC)(=O)C(F)(F)C1=C(C=C(C=C1)C(NCCCCC1=CC=CC=C1)=O)Br | O[C:16]([c:15]1[cH:14][cH:13][c:12]([C:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])([F:10])[F:11])[c:30]([Br:31])[cH:29]1)=[O:17].[NH2:18][CH2:19][CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[C:9]([F:10])([F:11])[c:12]1[cH:13][cH:... | CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)O)cc1Br.NCCCCc1ccccc1 | CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)NCCCCc2ccccc2)cc1Br | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The 3-bromo-4-[(diethoxyphosphoryl)difluoromethyl)benzoic acid (Compound 35) was coupled to phenbutyl amine following the procedures of Example 39 to give {[2-bromo-4-(4-phenylbutylcarbamoyl)phenyl]difluoromethyl}-phosphonic acid diethyl ester which was treated in a manner similar to Example 40 to give Compound 62. MS ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)O)cc1Br.NCCCCc1ccccc1>>CCOP(=O)(OCC)C(F)(F)c1ccc(C(=O)NCCCCc2ccccc2)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2403a85443ef411082748b0d1bf65b55 | CCOP([O-])OCC.O=Cc1ccc2ccccc2c1Br>>CCOP(=O)(OCC)C(O)c1ccc2ccccc2c1Br | C(C)OP(OCC)[O-].BrC1=C(C=CC2=CC=CC=C12)C=O.C(C)N(CC)CC>>C(C)OP(OCC)(=O)C(O)C1=C(C2=CC=CC=C2C=C1)Br | [CH3:1][CH2:2][O:3][P:4]([O-:5])[O:6][CH2:7][CH3:8].[CH:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[c:20]1[Br:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([OH:10])[c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[c:20]1[Br:21] | CCOP([O-])OCC.O=Cc1ccc2ccccc2c1Br | CCOP(=O)(OCC)C(O)c1ccc2ccccc2c1Br | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc2ccccc2c1 | [C:1]-[#8:2]-[P;H0;D3;+0:3](-[O-;H0;D1:4])-[#8:5]-[C:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:1]-[#8:2]-[P;H0;D4;+0:3](=[O;H0;D1;+0:4])(-[#8:5]-[C:6])-[CH;D3;+0:8](-[OH;D1;+0:7])-[c:9](:[c:10]):[c:11] | 250.6 | [{"value": 250.6, "product": "C(C)OP(OCC)(=O)C(O)C1=C(C2=CC=CC=C2C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 1-bromo-2-naphthaldehyde (0.740 g, 0.001 mole) in tetrahydofuran (10 mL) was added triethylamine (0.150 mL, 0.001 mole) followed by diethylphosphite (0.330 mL, 0.002 mole). The reaction mixture was then stirred at room temperature under nitrogen gas for 18 hours. The volatiles then evaporated in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccc2ccccc2c1 | null | O1CCCC1 | null | 18 | CCOP([O-])OCC.O=Cc1ccc2ccccc2c1Br>O1CCCC1>CCOP(=O)(OCC)C(O)c1ccc2ccccc2c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c53421942780463f9b28d93d665c9e04 | Cc1ccc(Br)c(C(=O)O)c1.O=C(Cl)C(=O)Cl>>Cc1ccc(Br)c(C(=O)Cl)c1 | BrC1=C(C(=O)O)C=C(C=C1)C.C(C(=O)Cl)(=O)Cl>>BrC1=C(C(=O)Cl)C=C(C=C1)C | O[C:8]([c:7]1[c:5]([Br:6])[cH:4][cH:3][c:2]([CH3:1])[cH:11]1)=[O:9].O=C(Cl)C(=O)[Cl:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]([C:8](=[O:9])[Cl:10])[cH:11]1 | Cc1ccc(Br)c(C(=O)O)c1.O=C(Cl)C(=O)Cl | Cc1ccc(Br)c(C(=O)Cl)c1 | null | CN(C=O)C | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | To a suspension of 2-bromo-5-methyl benzoic acid (1.0 g, 0.00465 mole) in dry dichloromethane (10 mL ) was added oxalylchloride (1.22 mL, 0.013 mole) dropwise at 0° C. followed by 1-2 drops of N,N-dimethyl formamide. The reaction mixture was then stirred for 2 hours at room temperature and the solvents were evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C.ClCCl | null | 2 | Cc1ccc(Br)c(C(=O)O)c1.O=C(Cl)C(=O)Cl>CN(C=O)C.ClCCl>Cc1ccc(Br)c(C(=O)Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5e975d5ff7f4aa3ae29321d95a6db35 | CCI.O=Cc1cc(O)ccc1Br>>CCOc1ccc(Br)c(C=O)c1 | C(=O)([O-])[O-].[Cs+].[Cs+].ICC.C(=O)([O-])[O-].[Cs+].[Cs+].BrC1=C(C=O)C=C(C=C1)O>>BrC1=C(C=O)C=C(C=C1)OCC | I[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([CH:10]=[O:11])[cH:12]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([CH:10]=[O:11])[cH:12]1 | CCI.O=Cc1cc(O)ccc1Br | CCOc1ccc(Br)c(C=O)c1 | null | null | O.CS(=O)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 98.2 | [{"value": 98.2, "product": "BrC1=C(C=O)C=C(C=C1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 2-Bromo-5-hydroxybenzaldehyde (0.96 g, 4.8 mmol) was dissolved in anhydrous DMSO (10 mL). Iodoethane (0.50 mL, 6.2 mmol) and Cs2CO3 (1.9 g, 6.3 mmol) were added and the mixture stirred at room temperature for 1.5 hours. Additional Cs2CO3 (1.45 g, 4.8 mmol) was added to the reaction mixture and then was stirred for 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | O.CS(=O)C.CCOC(=O)C | null | 1.5 | CCI.O=Cc1cc(O)ccc1Br>O.CS(=O)C.CCOC(=O)C>CCOc1ccc(Br)c(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d79908969d25494b9bc412519485110e | CCOP(OCC)OCC.O=C(O)c1cc(I)ccc1Br>>CCOP(=O)(OCC)C(=O)c1cc(I)ccc1Br | BrC1=C(C(=O)O)C=C(C=C1)I.BrC1=C(C(=O)Cl)C=C(C=C1)I.BrC1=C(C(=O)Cl)C=C(C=C1)I.P(OCC)(OCC)OCC>>BrC1=C(C=C(C=C1)I)C(=O)P(OCC)(OCC)=O | CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:6][CH2:7][CH3:8].O[C:9](=[O:10])[c:11]1[cH:12][c:13]([I:14])[cH:15][cH:16][c:17]1[Br:18]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[C:9](=[O:10])[c:11]1[cH:12][c:13]([I:14])[cH:15][cH:16][c:17]1[Br:18] | CCOP(OCC)OCC.O=C(O)c1cc(I)ccc1Br | CCOP(=O)(OCC)C(=O)c1cc(I)ccc1Br | null | null | null | Miscellaneous | OtherReaction | 3c53722c63fd30e780f359165c19bae99608549d2498be52386c63534c90fc74 | 2464b583d940c451c00c1488740fdde63610bb85f8f9a614db893662c6ccb8a2 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[P;H0;D3;+0:2](-[#8:3]-[C:4])-[#8:5]-[C:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]>>[C:4]-[#8:3]-[P;H0;D4;+0:2](=[O;H0;D1;+0:1])(-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | 2-Bromo-5-iodobenzoic acid was converted to 2-bromo-5-iodobenzoyl chloride following procedures similar to those in Example 82A. The 2-bromo-5-iodobenzoyl chloride was reacted with triethyl phosphite following procedures similar to those in Example 82 to give diethyl (2-bromo-5-iodophenyl)oxomethylphosphonate. The diet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1 | HO- | null | null | null | CCOP(OCC)OCC.O=C(O)c1cc(I)ccc1Br>>CCOP(=O)(OCC)C(=O)c1cc(I)ccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d941f1079a7d416380c18f33a1dec18c | CCOP(=O)(OCC)C(F)(F)Br.Cc1ccc(I)c([N+](=O)[O-])c1>>CCOP(=O)(OCC)C(F)(F)c1ccc(C)cc1[N+](=O)[O-] | IC1=C(C=C(C=C1)C)[N+](=O)[O-].BrC(F)(F)P(OCC)(OCC)=O>>CC1=CC(=C(C=C1)C(F)(F)P(OCC)(OCC)=O)[N+](=O)[O-] | Br[C:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])([F:10])[F:11].I[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[C:9]([F:10])([F:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | CCOP(=O)(OCC)C(F)(F)Br.Cc1ccc(I)c([N+](=O)[O-])c1 | CCOP(=O)(OCC)C(F)(F)c1ccc(C)cc1[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | a9360a3749745f33ebc314f70b8e3a6a8dc1dd58b5ad0c0de648021793b38e59 | 7f4a56339ba18973720dd4919f75a8d70f3626ae8993e1433a8be25e2d9363c5 | c1ccccc1 | Br-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[#15:4](-[#8:5])(-[#8:6])=[O;D1;H0:7].I-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#7;+:12]):[c:13]>>[#7;+:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[#15:4](-[#8:5])(-[#8:6])=[O;D1;H0:7]):[c:9]:[c:10] | null | [] | null | null | null | null | Commercially available 4-iodo-3-nitrotoluene was reacted with diethyl bromodifluoromethylphosphonate under Cd coupling conditions using Example 25 to yield diethyl (4-methyl-2-nitrophenyl)difluoromethylphosphonate. The diethyl (4-methyl-2-nitrophenyl)difluoromethylphosphonate (500 mg, 1.55 mmol) was dissolved in EtOAc ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br-.I- | null | null | null | CCOP(=O)(OCC)C(F)(F)Br.Cc1ccc(I)c([N+](=O)[O-])c1>>CCOP(=O)(OCC)C(F)(F)c1ccc(C)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bacd7e94c6644747b69497e12a174d52 | Cc1ccc([N+](=O)[O-])c(Br)c1C>>Cc1ccc(N)c(Br)c1C | C(=O)(O)[O-].[Na+].O.BrC1=C(C=CC(=C1C)C)[N+](=O)[O-].O.O.Cl[Sn]Cl>>BrC1=C(N)C=CC(=C1C)C | O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:9]([CH3:10])[c:7]1[Br:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:7]([Br:8])[c:9]1[CH3:10] | Cc1ccc([N+](=O)[O-])c(Br)c1C | Cc1ccc(N)c(Br)c1C | null | null | CN(C)C=O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 2-bromo-3,4-dimethylnitrobenzene (1.0 g, 4.35 mmole) in 10 mL DMF was added SnCl2.2H2O (4.92 g, 21.8 mmole). This solution was stirred overnight at room temperature 50 mL of H2O was added and the pH was adjusted to 8 with the addition of sat. NaHCO3 and extracted with 150 mL of EtOAC. The organic layer... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CN(C)C=O | null | null | Cc1ccc([N+](=O)[O-])c(Br)c1C>CN(C)C=O>Cc1ccc(N)c(Br)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-900acc20278b45259bc9294c07deb951 | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+]>>CCOC(=O)c1cnc(SC)nc1N | [NH4+].[OH-].ClC1=NC(=NC=C1C(=O)OCC)SC>>NC1=NC(=NC=C1C(=O)OCC)SC | Cl[c:13]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([S:10][CH3:11])[n:12]1.[NH4+:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([S:10][CH3:11])[n:12][c:13]1[NH2:14] | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+] | CCOC(=O)c1cnc(SC)nc1N | null | null | CCO | Functional Group Interconversion | OtherReaction | 1b077d7db1392b159d0fd0777de714d1fad7ef0bbe69adc404d2d103f4416610 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH4+;D0:12]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:12]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | null | [] | 20 | CELSIUS | 20 | HOUR | 140 ml of a 20% NH4OH solution are added, in 20 minutes, and while maintaining the temperature at around 20° C., to a suspension of 50.7 g of ethyl 4-chloro-2-(methylthio)pyrimidin-5-carboxylate in 400 ml of EtOH. After stirring at ambient temperature for 20 hours, the reaction medium is concentrated under vacuum almos... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | CCO | 20 | 20 | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+]>CCO>CCOC(=O)c1cnc(SC)nc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-721a486c34364a8f81627403375be008 | NCC1CC1.O=C(O)CCNC(=O)OCC1c2ccccc2-c2ccccc21>>NCCC(=O)NCC1CC1 | Cl.C1(CC1)CN.C(C)N(CC)CC.N(CCC(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12.C(C(=O)Cl)(=O)Cl>>C1(CC1)CNC(CCN)=O | [NH2:6][CH2:7][CH:8]1[CH2:9][CH2:10]1.O=C(OCC1c2ccccc2-c2ccccc21)[NH:1][CH2:2][CH2:3][C:4](O)=[O:5]>>[NH2:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][CH:8]1[CH2:9][CH2:10]1 | NCC1CC1.O=C(O)CCNC(=O)OCC1c2ccccc2-c2ccccc21 | NCCC(=O)NCC1CC1 | null | CN(C=O)C | ClCCl | Acylation | OtherReaction | 0bc677927bc73bcc6d2500d048a7a3157f92a18691a47f58331e9c6c64cbafa4 | 337ca72c0bb1979769aac1fc7825c6586b8e75bbb5702fd9212c320d1f1752db | C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[NH;D2;+0:5]-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[NH2;D1;+0:5] | 57.4 | [{"value": 57.0, "product": "C1(CC1)CNC(CCN)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "C1(CC1)CNC(CCN)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To solution of Fmoc-β-Ala-OH (1.0 g, 3.212 mmol) and oxalyl chloride (0.428 g, 0.29 mL, 3.373 mmol) in dichloromethane (20.0 mL) was added a few drops of N,N-dimethylformamide at 0° C. The mixture was stirred at room temperature for 1 hr followed by addition of cyclopropylmethylamine (0.229 g, 0.28 mL, 3.212 mmol) and ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine | Secondary amide.Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | C1CC1 | HO- | CN(C=O)C.ClCCl | null | 1 | NCC1CC1.O=C(O)CCNC(=O)OCC1c2ccccc2-c2ccccc21>CN(C=O)C.ClCCl>NCCC(=O)NCC1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36a7c0faa6814c2c9f73edb4f607b7fd | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-]>>Cc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F | [OH-].[K+].Cl.ClC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F.C(C)(C)(C)[O-].[K+].C(CC(=O)OCC)(=O)OCC>>CC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F | Cl[c:2]1[cH:3][c:4]([NH2:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-] | Cc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F | null | null | O.CS(=O)C | Functional Group Interconversion | OtherReaction | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9]>>[C;D1;H3:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9] | 91 | [{"value": 91.0, "product": "CC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "CC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 20 | HOUR | Under argon atmosphere, a suspension of potassium tert-butanolate (71.6 g, 625 mmol) in DMSO (150 mL) was placed in a 1.5 L flask, fitted with a mechanical stirrer. Then diethyl malonate (97.9 mL, 625 mmol) was added drop wise at 20-30° C. under ice bath cooling. To the thick white suspension was the added solid commer... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O.CS(=O)C | 60 | 20 | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-]>O.CS(=O)C>Cc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9add6480315e46a98a360293a6be148f | Cc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F>>Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | BrC1=C(C=C(C(=C1)C)C(F)(F)F)[N+](=O)[O-].[Cu]C#N.Cl>>CC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F | Br[c:4]1[cH:3][c:2]([CH3:1])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][c:7]1[N+:8](=[O:9])[O-:10]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | Cc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F | Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | null | null | CN1C(CCC1)=O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 88.1 | [{"value": 88.0, "product": "CC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "CC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 30 | MINUTE | A mixture of 1-bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene from step 2 (49.80 g, 175 mmol) and copper(I) cyanide (16.5 g, 184 mmol) in 1-methyl-2-pyrrolidone (NMP) (180 mL) was heated up to 150° C. and stirred for 30 min under nitrogen atmosphere. The mixture was cooled to 23° C. and poured into 1 N HCl, extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CN1C(CCC1)=O | 150 | 0.5 | Cc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F>CN1C(CCC1)=O>Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-730d320a85e34d6b847c29289fba94a2 | Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F>>Cc1cc(C#N)c(N)cc1C(F)(F)F | CC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F.C(C)O>>NC1=C(C#N)C=C(C(=C1)C(F)(F)F)C | O=[N+:8]([O-])[c:7]1[c:4]([C:5]#[N:6])[cH:3][c:2]([CH3:1])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:9]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[c:7]([NH2:8])[cH:9][c:10]1[C:11]([F:12])([F:13])[F:14] | Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | Cc1cc(C#N)c(N)cc1C(F)(F)F | null | [Fe] | Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78.4 | [{"value": 78.0, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | Iron powder (37.42 g, 670 mmol) was added in small portions to a stirred suspension of finely grinded 5-methyl-2-nitro-4-trifluoromethyl-benzonitrile from step 3 (34.58 g, 150 mmol) in methanol (75 mL) and 37% HCl (93 mL). The internal temperature was kept between 40 and 60° C. by external water bath cooling. The resul... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].Cl.CO | 50 | 1 | Cc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F>[Fe].Cl.CO>Cc1cc(C#N)c(N)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2dad9ca12f0a4cdebbe56d3a67afacc9 | Cc1cc(C#N)c(N)cc1C(F)(F)F>>Cc1cc(C#N)ccc1C(F)(F)F | N(=O)OCCC(C)C.NC1=C(C#N)C=C(C(=C1)C(F)(F)F)C.N(=O)OCCC(C)C>>CC=1C=C(C#N)C=CC1C(F)(F)F | N[c:7]1[c:4]([C:5]#[N:6])[cH:3][c:2]([CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13] | Cc1cc(C#N)c(N)cc1C(F)(F)F | Cc1cc(C#N)ccc1C(F)(F)F | null | null | CC(C)(C)OC.C1CCOC1 | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | 92.8 | [{"value": 92.8, "product": "CC=1C=C(C#N)C=CC1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | null | null | To a solution of 2-amino-5-methyl-4-trifluoromethyl-benzonitrile from step 4 (23.34 g, 117 mmol) in dry THF (350 mL) was added isoamyl nitrite (34.3 mL, 257 mmol) and the mixture was refluxed for 20 h. Additional isoamyl nitrite (16.6 mL, 129 mmol) was added and the mixture was refluxed for further 20 h. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CC(C)(C)OC.C1CCOC1 | 23 | null | Cc1cc(C#N)c(N)cc1C(F)(F)F>CC(C)(C)OC.C1CCOC1>Cc1cc(C#N)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d44c2f7f507240709e8ec1b0f10585dd | Cc1cc(C#N)ccc1C(F)(F)F.[OH-]>>Cc1cc(C(=O)O)ccc1C(F)(F)F | CC=1C=C(C#N)C=CC1C(F)(F)F.[OH-].[Na+].O1CCOCC1.Cl>>CC=1C=C(C(=O)O)C=CC1C(F)(F)F | N#[C:5][c:4]1[cH:3][c:2]([CH3:1])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:9][cH:8]1.[OH-:7]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14] | Cc1cc(C#N)ccc1C(F)(F)F.[OH-] | Cc1cc(C(=O)O)ccc1C(F)(F)F | null | null | CC(C)(C)OC | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccccc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH-;D0:5]>>[O;D1;H0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | null | [] | 23 | CELSIUS | null | null | A mixture of 3-methyl-4-trifluoromethyl-benzonitrile from step 5 (16.25 g, 88 mmol) and 3 N NaOH (88 mL, 264 mmol) in dioxane (90 mL) was refluxed for 18 h. The mixture was cooled to 23° C., diluted with TBME, acidified with 1 N HCl to pH 1 and extracted twice with TBME. The combined organic layers were washed with bri... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccccc1 | null | CC(C)(C)OC | 23 | null | Cc1cc(C#N)ccc1C(F)(F)F.[OH-]>CC(C)(C)OC>Cc1cc(C(=O)O)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fae13e3e41e4091b3c9f1fcfac1c4e2 | CNOC.Cc1cc(C(=O)O)ccc1C(F)(F)F>>CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1 | CC=1C=C(C(=O)O)C=CC1C(F)(F)F.Cl.CNOC.CN1CCOCC1.Cl.CN(CCCN=C=NCC)C>>CON(C(C1=CC(=C(C=C1)C(F)(F)F)C)=O)C | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]([CH3:16])[cH:17]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]([CH3:16])[cH:17]1 | CNOC.Cc1cc(C(=O)O)ccc1C(F)(F)F | CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1 | null | CN(C)C=1C=CN=CC1 | CC(C)(C)OC.CN(C)C=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:6]-[#8:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 23 | CELSIUS | 18 | HOUR | To a suspension of 3-methyl-4-trifluoromethyl-benzoic acid from step 6 (14.1 g, 69.1 mmol), N,O-dimethylhydroxylamine hydrochloride (10.78 g, 111 mmol), N-methylmorpholine (12.14 mL, 111 mmol) and 4-DMAP (844 mg, 691 mmol) in DCM (230 mL) at 0° C. were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.CC(C)(C)OC.CN(C)C=O.C(Cl)Cl | 23 | 18 | CNOC.Cc1cc(C(=O)O)ccc1C(F)(F)F>CN(C)C=1C=CN=CC1.CC(C)(C)OC.CN(C)C=O.C(Cl)Cl>CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07273519cc5a420d9b55a2a52a879b30 | CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1>>CC(=O)c1ccc(C(F)(F)F)c(C)c1 | Cl.CON(C(C1=CC(=C(C=C1)C(F)(F)F)C)=O)C.C[Mg]Br.C(C)OCC>>CC=1C=C(C=CC1C(F)(F)F)C(C)=O | CON(C)[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([CH3:13])[cH:14]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([CH3:13])[cH:14]1 | CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1 | CC(=O)c1ccc(C(F)(F)F)c(C)c1 | null | null | CCOC(=O)C.C1CCOC1 | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of N-methoxy-3,N-dimethyl-4-trifluoromethyl-benzamide from step 7 (16.90 g, 68.36 mmol) in THF (280 mL) at −5° C. was added a 3 M methylmagnesium bromide solution in diethyl ether (45.6 mL, 136.7 mmol). The mixture was stirred at 0° C. for 1 h, then was warmed up to 23° C. and stirring was continued at 23... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | CCOC(=O)C.C1CCOC1 | 0 | 1 | CON(C)C(=O)c1ccc(C(F)(F)F)c(C)c1>CCOC(=O)C.C1CCOC1>CC(=O)c1ccc(C(F)(F)F)c(C)c1 |
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