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-9230ece52fa64552bf1644966d5a65b8 | COC(=O)c1cncc(OCc2ccccc2)c1>>OCc1cncc(OCc2ccccc2)c1 | C(C1=CC=CC=C1)OC=1C=NC=C(C(=O)OC)C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)OC=1C=C(C=NC1)CO | CO[C:2](=[O:1])[c:3]1[cH:4][n:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[OH:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | COC(=O)c1cncc(OCc2ccccc2)c1 | OCc1cncc(OCc2ccccc2)c1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2cccnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)OC=1C=C(C=NC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "C(C1=CC=CC=C1)OC=1C=C(C=NC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 55 | MINUTE | To a stirring solution of 363 mg (1.49 mmol) of methyl 5-(benzyloxy)nicotinate in 10 mL of THF at 0° C. was added 141 mg (3.71 mmol) of LiAlH4. The ice bath was removed, and after 55 min., 20.5 mg of LiAlH4 was added. After 40 min., the reaction was quenched by adding successively 160 μL of H2O, 160 μL of 15% aqueous N... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1.c1ccccc1 | Other | C1CCOC1 | null | 0.916667 | COC(=O)c1cncc(OCc2ccccc2)c1>C1CCOC1>OCc1cncc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e2dd2ec31054b9b81d7ac2d16cb3e32 | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1>>NCc1cncc(OCc2ccccc2)c1 | N(=[N+]=[N-])CC=1C=NC=C(C1)OCC1=CC=CC=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)OC=1C=C(C=NC1)CN | [N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[NH2:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1 | NCc1cncc(OCc2ccccc2)c1 | null | null | C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(COc2cccnc2)cc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[N;H0;D2;+0:5]=[N+]=[N-]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | To a stirring solution of 181 mg of 3-(azidomethyl)-5-(benzyloxy)pyridine in 6 mL of THF at 0° C. was added 80.6 mg (2.12 mmol) of LiAlH4. The ice bath was removed and stirring was continued with warming to r.t. After 30 min. the reaction was quenched by adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, an... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | C1CCOC1 | null | null | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1>C1CCOC1>NCc1cncc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5b51a862e25494ea7c5e2e8520f0ea2 | Cc1cncc(C(=O)O)c1>>Cc1cncc(CO)c1 | CC=1C=NC=C(C(=O)O)C1.FC=1C=C(C=C(C(=O)O)C1)C(=O)O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC=1C=C(C=NC1)CO | O=[C:7]([c:6]1[cH:5][n:4][cH:3][c:2]([CH3:1])[cH:9]1)[OH:8]>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]([CH2:7][OH:8])[cH:9]1 | Cc1cncc(C(=O)O)c1 | Cc1cncc(CO)c1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 41.6 | [{"value": 41.6, "product": "CC=1C=C(C=NC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 25 | MINUTE | To stirring solution of 233 mg (1.70 mmol) of 5-methylnicotinic acid (synthesized following the general procedure for 5-fluoro-isophthalic acid) in 30 mL of THF at 0° C. was added 181 mg (4.76 mmol) of LiAlH4. After 25 min., the reaction was quenched by adding successively 180 μL of H2O, 180 μL of 15% aqueous NaOH, and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 0.416667 | Cc1cncc(C(=O)O)c1>C1CCOC1>Cc1cncc(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab18c6ac634844d4a609487fa0e5d6d4 | COC(=O)c1cncc(N)c1.F>>COC(=O)c1cncc(F)c1 | NC=1C=NC=C(C(=O)OC)C1.N(=O)[O-].[Na+].C1=CC=NC=C1.F>>FC=1C=NC=C(C(=O)OC)C1 | N[c:9]1[cH:8][n:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:11]1.[FH:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([F:10])[cH:11]1 | COC(=O)c1cncc(N)c1.F | COC(=O)c1cncc(F)c1 | null | null | null | Miscellaneous | OtherReaction | 4a0d8ea4faae36ec8fa63572a55c4e62bf6204415ee06b3846ec397b4647428d | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:[c:9]:1.[FH;D0;+0:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[F;H0;D1;+0:10]):[c:9]:[#7;a:8]:[c:7]:1 | 56 | [{"value": 56.0, "product": "FC=1C=NC=C(C(=O)OC)C1", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | To a stirring solution of 243 mg (1.6 mmol) of methyl 5-aminonicotinate in 5 mL of HF-pyridine at 0° C. was added 119 mg (1.72 mmol) of NaNO2. The mixture was stirred at 0° C. for 30 min. and at 50° C. for 1 h. The reaction was quenched by ice and sat. NaHCO3 solution. The aqueous layer was extracted with CHCl3, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | 50 | 1 | COC(=O)c1cncc(N)c1.F>>COC(=O)c1cncc(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8235be2de36244b5931c0eec595e522e | Cc1ccc(F)cc1F.O=C(Cl)CCl>>Cc1cc(C(=O)CCl)c(F)cc1F | FC1=C(C=CC(=C1)F)C.[Al+3].[Cl-].[Cl-].[Cl-].ClCC(=O)Cl.Cl>>ClCC(=O)C1=C(C=C(C(=C1)C)F)F | [CH3:1][c:2]1[cH:3][cH:4][c:9]([F:10])[cH:11][c:12]1[F:13].Cl[C:5](=[O:6])[CH2:7][Cl:8]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[CH2:7][Cl:8])[c:9]([F:10])[cH:11][c:12]1[F:13] | Cc1ccc(F)cc1F.O=C(Cl)CCl | Cc1cc(C(=O)CCl)c(F)cc1F | null | null | O.CCOC(=O)C | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[F;D1;H0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[F;D1;H0:5]):[c:7] | null | [] | 0 | CELSIUS | 10 | MINUTE | To a stirring solution of 2,4-difluorotoluene was added 6.3 g (47.3 mmol) of AlCl3, and 3.4 mL (42.6 mmol) of chloroacetyl chloride at 0° C. After the mixture was stirred for 10 min. at 0° C. and then at 45° C. for 30 min. The mixture was allowed to cool to r.t., about 16 mL of conc. HCl, 25 mL of water, and 100 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.CCOC(=O)C | 0 | 0.166667 | Cc1ccc(F)cc1F.O=C(Cl)CCl>O.CCOC(=O)C>Cc1cc(C(=O)CCl)c(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ff14337d2df49888c63797f7b623921 | CC(C)O.COC(=O)c1cncc(O)c1>>COC(=O)c1cncc(OC(C)C)c1 | C1(CCCCC1)N=C=NC1CCCCC1.C(C)(C)O.COC(C1=CN=CC(=C1)O)=O.C1=CC=CC=C1>>C(C)(C)OC=1C=NC=C(C(=O)OC)C1 | O[CH:11]([CH3:12])[CH3:13].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([OH:10])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][CH:11]([CH3:12])[CH3:13])[cH:14]1 | CC(C)O.COC(=O)c1cncc(O)c1 | COC(=O)c1cncc(OC(C)C)c1 | null | Cl[Cu] | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | aee3d691a6dfc6c8223fef7b9bb4e58ec7e16fbc345d424207a131929cdf1d03 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccncc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 47 | [{"value": 47.0, "product": "C(C)(C)OC=1C=NC=C(C(=O)OC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.8, "product": "C(C)(C)OC=1C=NC=C(C(=O)OC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 13 | HOUR | A solution of 677 mg (3.28 mmol) of dicyclohexylcarbodiimide (DCC), 0.3 mL (3.92 mmol) of isopropanol, and 7.7 mg (0.078 mmol) of CuCl was heated at 60° C. After 13 h, 460 mg (3.0 mmol) of 5-hydroxynicotinic acid methyl ester and 10 mL of benzene were added and heated at 105° C. for 24.5 h. The mixture was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | null | null | c1ccncc1 | HO- | Cl[Cu].C(Cl)(Cl)Cl | 105 | 13 | CC(C)O.COC(=O)c1cncc(O)c1>Cl[Cu].C(Cl)(Cl)Cl>COC(=O)c1cncc(OC(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-058286c0a8fa43de95442814099db85b | C#CC(C)O.CC=NO>>Cc1cc(C(C)O)on1 | C(C)=NO.CC(C#C)O.CCN(CC)CC.[O-]Cl.[Na+]>>CC1=NOC(=C1)C(C)O | [CH:3]#[C:4][CH:5]([CH3:6])[OH:7].[CH3:1][CH:2]=[N:9][OH:8]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]([CH3:6])[OH:7])[o:8][n:9]1 | C#CC(C)O.CC=NO | Cc1cc(C(C)O)on1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 16b6cd102ecd71fbe2a5e7bfcc7c52ec8c6ac47b948d2e926aa77fed51055f5c | d59db5f5144aec61a5a64ca529856dc804630d654f00918274d989b69216eb79 | c1cnoc1 | [C;D1;H3:1]-[CH;D2;+0:2]=[N;H0;D2;+0:3]-[OH;D1;+0:4].[C;D1;H3:5]-[C:6](-[O;D1;H1:7])-[C;H0;D2;+0:8]#[CH;D1;+0:9]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:9]:[c;H0;D3;+0:8](-[C:6](-[C;D1;H3:5])-[O;D1;H1:7]):[o;H0;D2;+0:4]:[n;H0;D2;+0:3]:1 | 20.4 | [{"value": 20.0, "product": "CC1=NOC(=C1)C(C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.4, "product": "CC1=NOC(=C1)C(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirring solution of 5.2 mL (84.9 mmol) of acetaldehyde oxime, 6.7 mL (85.5 mmol) of 3-butyn-2-ol, and 1.2 mL (8.6 mmol) of Et3N in 20 mL of CH2Cl2 at 0° C. was added 275 mL of NaOCl over a period of 2 h 45 min. The ice bath was removed and stirring was continued at r.t. for 18 h. Chloroform was added, and the lay... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Oxime | null | null | c1cnoc1 | c1cnoc1 | null | C(Cl)Cl | null | 18 | C#CC(C)O.CC=NO>C(Cl)Cl>Cc1cc(C(C)O)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-899b98d2ab484400b7bea25123e46ab5 | COc1cc[n+]([O-])cc1>>COc1ccnc(C#N)c1 | C(=O)([O-])[O-].[K+].[K+].[Si](C)(C)(C)C#N.COC1=CC=[N+](C=C1)[O-].CN(C(=O)Cl)C>>COC1=CC(=NC=C1)C#N | [O-][n+:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:10][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([C:8]#[N:9])[cH:10]1 | COc1cc[n+]([O-])cc1 | COc1ccnc(C#N)c1 | null | null | C(Cl)(Cl)Cl.C(Cl)Cl | Miscellaneous | OtherReaction | c0c80df06675fdbdd79462aedc4dec8e941957e4eee3edebb6a9bcbeed226fe8 | 11eb82ea929cff4d1755ea39be3c9f0c09f93aea3fc48e5d62bd3dbda502eb7c | c1ccncc1 | [O-]-[n+;H0;D3:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1>>[N;D1;H0:7]#[C:8]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[c:2]:[n;H0;D2;+0:1]:1 | 73.2 | [{"value": 73.0, "product": "COC1=CC(=NC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "COC1=CC(=NC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a stirring mixture of 1.2 g (9.67 mmol) of 4-methoxypyridine-N-oxide in 18 mL of CH2Cl2 at r.t. was added 1.6 mL (12.0 mmol) of TMSCN. After 5 min. 0.9 mL (9.8 mmol) of dimethylcarbamoyl chloride. The solution was stirred at r.t. for 13 h and CHCl3 and 20 mL of 10% K2CO3 was added. The aqueous layer was extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | C(Cl)(Cl)Cl.C(Cl)Cl | null | 0.083333 | COc1cc[n+]([O-])cc1>C(Cl)(Cl)Cl.C(Cl)Cl>COc1ccnc(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bd222f064324e87951b60d63ae9570d | COc1ccnc(C#N)c1>>COc1ccnc(CN)c1 | [OH-].[Na+].O.COC1=CC(=NC=C1)C#N.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>COC1=CC(=NC=C1)CN | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([C:8]#[N:9])[cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][NH2:9])[cH:10]1 | COc1ccnc(C#N)c1 | COc1ccnc(CN)c1 | null | null | [Cl-].[Na+].O.C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccncc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 38.6 | [{"value": 38.6, "product": "COC1=CC(=NC=C1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 75 | MINUTE | To a stirring solution of 949 mg of 4-methoxypicolinonitrile in 15 mL of THF at 0° C. was added about 0.6 g of LiAlH4. The reaction became very exothermic. The mixture was allowed to warm to r.t. and after 40 min., the following were added in succession: 0.4 mL of H2O, 0.4 mL of 15% NaOH (aq.), and 1.2 mL of brine. The... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | [Cl-].[Na+].O.C1CCOC1 | null | 1.25 | COc1ccnc(C#N)c1>[Cl-].[Na+].O.C1CCOC1>COc1ccnc(CN)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7510fa7a762643ae9c45bf10b60c631c | COC(=O)c1cncc(N)c1>>COC(=O)c1cncc(N(C)C)c1 | NC=1C=NC=C(C(=O)OC)C1.[BH3-]C#N.[Na+].CCOC(=O)C.C(=O)(O)[O-].[Na+]>>CN(C=1C=NC=C(C(=O)OC)C1)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([NH2:10])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([N:10]([CH3:11])[CH3:12])[cH:13]1 | COC(=O)c1cncc(N)c1 | COC(=O)c1cncc(N(C)C)c1 | null | C(C)(=O)O | O.C=O.CC#N | Miscellaneous | OtherReaction | 0295391ed0de2e86c7e882f3199152884d99da63bc1b927b39500202e1a00977 | 98c3809a8b4046b29490f9afb6277ec8718e0550ab1278bc09b7f0dc821fa6fe | c1ccncc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[C;D1;H3:7]-[N;H0;D3;+0:1](-[C;D1;H3:8])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 37 | [{"value": 37.0, "product": "CN(C=1C=NC=C(C(=O)OC)C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18.5 | HOUR | To a stirring solution of 283 mg (1.86 mmol) of methyl 5-aminonicotinate in 19 mL of CH3CN and 19 mL of 37% formaldehyde in H2O was added 353 mg (5.62 mmol) of NaCNBH3, and 50 drops of acetic acid. The solution was stirred at r.t. for 18.5 h and 40 mL of EtOAc and 40 mL of sat. NaHCO3 solution was added. The layers wer... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Tertiary amine | null | null | c1ccncc1 | Other | C(C)(=O)O.O.C=O.CC#N | null | 18.5 | COC(=O)c1cncc(N)c1>C(C)(=O)O.O.C=O.CC#N>COC(=O)c1cncc(N(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2224827feb614d4dbaef6637acd0038d | CN(C)N.COC(=O)c1cccc(C(=O)O)c1>>COC(=O)c1cccc(C(=O)NN(C)C)c1 | CN(N)C.COC(=O)C=1C=C(C(=O)O)C=CC1.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O.CCN(C(C)C)C(C)C>>CN(NC(=O)C=1C=C(C(=O)OC)C=CC1)C | [NH2:12][N:13]([CH3:14])[CH3:15].O[C:10]([c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16]1)=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][N:13]([CH3:14])[CH3:15])[cH:16]1 | CN(C)N.COC(=O)c1cccc(C(=O)O)c1 | COC(=O)c1cccc(C(=O)NN(C)C)c1 | null | null | C(Cl)(Cl)Cl.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 60 | [{"value": 60.0, "product": "CN(NC(=O)C=1C=C(C(=O)OC)C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To the acid 3-(methoxycarbonyl)benzoic acid (253 mg, 1.40 mmol) in CH2Cl2 at rt, EDCI (312 mg, 1.64 mmol) and HOBT (189 mg, 1.40 mmol) were added and stirred at rt for 20 min. To that mixture, N,N-dimethyl hydrazine was added followed by DIPEA (404 mg, 14.0 mmol). Reaction mixture was stirred at rt for 16 h. Then react... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl.C(Cl)Cl | null | 0.333333 | CN(C)N.COC(=O)c1cccc(C(=O)O)c1>C(Cl)(Cl)Cl.C(Cl)Cl>COC(=O)c1cccc(C(=O)NN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1828696cbe48471ca423380990a521a1 | COC(=O)c1cccc(C(=O)NN(C)C)c1.Cc1csc(CBr)n1>>COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)N(C)C)c1 | CC=1N=C(SC1)CBr.[H-].[Na+].CN(NC(=O)C=1C=C(C(=O)OC)C=CC1)C>>CN(N(C(=O)C=1C=C(C(=O)OC)C=CC1)CC=1SC=C(N1)C)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][N:20]([CH3:21])[CH3:22])[cH:23]1.Br[CH2:13][c:14]1[n:15][c:16]([CH3:17])[cH:18][s:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][c:14]2[n:15][c:16]([CH3:17])[cH:18][s:19]2)[N:20]([CH3:21])[CH3:22])... | COC(=O)c1cccc(C(=O)NN(C)C)c1.Cc1csc(CBr)n1 | COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)N(C)C)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 955b062463d96a54b38789498cbcb3adc301ce67a58877702ec0a63ee9e0b888 | 75fa53fcea00b2bf91faff8a86bd2b4c6e278499b46cc76f6552f3496df57ac7 | O=C(NCc1nccs1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[c:13]>>[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1)-[C:11](=[O;D1;H0:12])-[c:13] | 70 | [{"value": 70.0, "product": "CN(N(C(=O)C=1C=C(C(=O)OC)C=CC1)CC=1SC=C(N1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 3.5 | CELSIUS | 10 | MINUTE | To the sodium hydride (16 mg, 0.68 mmol) in THF (3 ml) at 0° C., methyl 3-(2,2-dimethylhydrazinecarbonyl)benzoate (100 mg, 0.45 nmol) was added. After 10 min, 4-methyl-2-bromo methyl thiazole (103 mg, 0.54 mmol) was added and reaction mixture was stirred at 3-4° C. overnight. Reaction mixture was quenched with MeOH and... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine | null | null | c1ccccc1.c1cscn1 | HBr | C1CCOC1 | 3.5 | 0.166667 | COC(=O)c1cccc(C(=O)NN(C)C)c1.Cc1csc(CBr)n1>C1CCOC1>COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)N(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1d1ebcc11454a64b93acbc82c01bed0 | CC(=O)c1cccc(C#N)c1>>C=C(C)c1cccc(C#N)c1 | C(C)(=O)C=1C=C(C#N)C=CC1.[Li]CCCC>>C=C(C)C=1C=C(C#N)C=CC1 | O=[C:2]([CH3:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11]1>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11]1 | CC(=O)c1cccc(C#N)c1 | C=C(C)c1cccc(C#N)c1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | Functional Group Interconversion | OtherReaction | 77e55b8d58229cdaddbfef811692215b45ee4124fec87c1aa9c0e735816099ed | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | c1ccccc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[c:3](:[c:4]):[c:5] | 86 | [{"value": 86.0, "product": "C=C(C)C=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To the methyl triphenylphosphoniumbromide (4.3 grn, 12 mmol) in THF at 0° C., n-BuLi (1.6M, 7.5 ml, 12 mmol) was added and stirred for 30 min. Then 3-acetylbenzonitrile in THF was slowly added and the reaction mixture was stirred at 0° C. for further 3 h. Then reaction mixture was quenched with aqeous ammonium chloride... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | null | null | c1ccccc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | 0.5 | CC(=O)c1cccc(C#N)c1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>C=C(C)c1cccc(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1099a431d62f49558fafaed0b0376f72 | C=C(C)c1cccc(C#N)c1>>CC(C)c1cccc(C#N)c1 | C=C(C)C=1C=C(C#N)C=CC1>>C(C)(C)C=1C=C(C#N)C=CC1 | [CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11]1 | C=C(C)c1cccc(C#N)c1 | CC(C)c1cccc(C#N)c1 | null | null | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 16 | HOUR | To 3-(prop-1-en-2-yl)benzonitrile (1.2 gm, 8.3 mmol) in ethyl acetate (30 ml) 10% Pd/C (120 mg) was added and stirred under hydrogen atmosphere for 16 h. Then the reaction mixture was filtered and solvent evaporated to obtain 3-isopropylbenzonitrile in quantitative yield.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1 | null | C(C)(=O)OCC | null | 16 | C=C(C)c1cccc(C#N)c1>C(C)(=O)OCC>CC(C)c1cccc(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab97beeb08ef422c827061ccca03d900 | COc1cc(CO)ccc1C>>COc1cc(C=O)ccc1C | CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.COC=1C=C(C=CC1C)CO>>COC=1C=C(C=O)C=CC1C | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][cH:9][c:10]1[CH3:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[CH3:11] | COc1cc(CO)ccc1C | COc1cc(C=O)ccc1C | null | null | CCOCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 0.5 | HOUR | Dess-Martin periodinane (3 gm, 7.07 mmol) was added to (3-methoxy-4-methylphenyl)methanol (1 gm, 6.57 mmol) in CH2Cl2 (35 ml) at 0° C. After stirring at 0° C. for 0.5 h, some of the CH2Cl2 was removed, reaction mixture was diluted with ether, washed with sodium bicarbonate solution, sodium thiosulfate solution and wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | CCOCC.C(Cl)Cl | 0 | 0.5 | COc1cc(CO)ccc1C>CCOCC.C(Cl)Cl>COc1cc(C=O)ccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5fc16ce1d4c41b2a9a42a400362c159 | COc1cc(C=O)ccc1C.N#CC[PH](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1cc(C=CC#N)ccc1C | COC=1C=C(C=O)C=CC1C.C(#N)CP(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>COC=1C=C(C=CC1C)C=CC#N | O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12]([CH3:13])[cH:11][cH:10]1.c1ccc([PH](c2ccccc2)(c2ccccc2)[CH2:7][C:8]#[N:9])cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[CH:7][C:8]#[N:9])[cH:10][cH:11][c:12]1[CH3:13] | COc1cc(C=O)ccc1C.N#CC[PH](c1ccccc1)(c1ccccc1)c1ccccc1 | COc1cc(C=CC#N)ccc1C | null | null | null | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[PH](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;D1;H0:5]#[C:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77 | [{"value": 77.0, "product": "COC=1C=C(C=CC1C)C=CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Wittig reaction of 3-methoxy-4-methylbenzaldehyde with cyanomethyl triphenylphosphorane gave 3-(3-methoxy-4-methylphenyl)acrylonitrile in 77% yield which was further transformed to 3-(3-methoxy-4-methylphenyl)propan-1-amine using the above described procedures.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | COc1cc(C=O)ccc1C.N#CC[PH](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1cc(C=CC#N)ccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5eef4eb17fbb40088589f2c56bbf1698 | C#C[Si](C)(C)C.CC(C)(C)OC(=O)NCc1cccc(Br)c1>>CC(C)(C)OC(=O)NCc1cccc(C#C[Si](C)(C)C)c1 | BrC=1C=C(CNC(OC(C)(C)C)=O)C=CC1.C[Si](C)(C)C#C>>C[Si](C)(C)C#CC=1C=C(CNC(OC(C)(C)C)=O)C=CC1 | [CH:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20].Br[c:14]1[cH:13][cH:12][cH:11][c:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1 | C#C[Si](C)(C)C.CC(C)(C)OC(=O)NCc1cccc(Br)c1 | CC(C)(C)OC(=O)NCc1cccc(C#C[Si](C)(C)C)c1 | null | null | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67 | [{"value": 67.0, "product": "C[Si](C)(C)C#CC=1C=C(CNC(OC(C)(C)C)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | MINUTE | To tert-butyl 3-bromobenzylcarbamate (220 mg, 1 mmol) in triethylamine (3 ml), trimethylsilyl acetylene (147 mg, 1.5 mmol) was added followed by cuprous iodide (8 mg, 0.04 mmol). After stirring for 5 min, dichloro bis (triphenylphosphine) palladium (II) (35 mg, 0.05 mmol) was added and the reaction mixture was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)N(CC)CC | 90 | 0.083333 | C#C[Si](C)(C)C.CC(C)(C)OC(=O)NCc1cccc(Br)c1>C(C)N(CC)CC>CC(C)(C)OC(=O)NCc1cccc(C#C[Si](C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62eedefc3d194f2398d7a8f3f0424e2a | CC(C)(C)OC(=O)NC(Cc1ccccc1)C(O)CNCc1cccc(C#C[Si](C)(C)C)c1>>C#Cc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 | OC(C(CC1=CC=CC=C1)NC(OC(C)(C)C)=O)CNCC1=CC(=CC=C1)C#C[Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>>C(#C)C=1C=C(CNCC(C(CC2=CC=CC=C2)NC(OC(C)(C)C)=O)O)C=CC1 | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH:13]([CH2:14][c:... | CC(C)(C)OC(=O)NC(Cc1ccccc1)C(O)CNCc1cccc(C#C[Si](C)(C)C)c1 | C#Cc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 | null | null | CO.C1CCOC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc(CCCCNCc2ccccc2)cc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | 85 | [{"value": 85.0, "product": "C(#C)C=1C=C(CNCC(C(CC2=CC=CC=C2)NC(OC(C)(C)C)=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To tert-butyl 3-hydroxy-1-phenyl-4-(3-((trimethylsilyl)ethynyl)benzylamino)butan-2-ylcarbamate in a mixture of THF (2 ml) and MeOH (2 ml), 1M K2CO3 (0.25 ml) was added and the reaction mixture was stirred at rt for 18 h. Then solvent was removed, crude residue was redissolved in ethyl acetate, washed with water, brine ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.c1ccccc1 | Other | CO.C1CCOC1 | null | 18 | CC(C)(C)OC(=O)NC(Cc1ccccc1)C(O)CNCc1cccc(C#C[Si](C)(C)C)c1>CO.C1CCOC1>C#Cc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46c4bb24452e4994b14feba19b2a7e91 | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1.O=C(O)Cc1cccs1>>CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1 | S1C(=CC=C1)CC(=O)O.CC(C)OC(=O)/N=N/C(=O)OC(C)C.OCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(=O)SCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC | O[CH2:9][c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:21][c:15]([C:16](=[O:17])[O:18][CH2:19][CH3:20])[cH:14]1.OC([CH2:12][c:11]1ccc[s:10]1)=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][S:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]([C:16](=[O:17])[O:18][CH2:19][CH3:20])[cH:21]1 | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1.O=C(O)Cc1cccs1 | CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1 | null | null | C1CCOC1 | Protection | OtherReaction | 189263d4d19565b9c5c001a81e8abf2a60b1807919ec489920cd4293a1993653 | 7a83c40990eef465e85ff66652874583517e7c7b69d7750d5f2438fef535f94e | c1ccccc1 | O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[c;H0;D3;+0:3]1:[s;H0;D2;+0:4]:c:c:c:1.O-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[CH3;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[S;H0;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 95 | [{"value": 95.0, "product": "C(C)(=O)SCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To diethyl 5-(hydroxymethyl)isophthalate (2.52 gm, 10 mmol) in THF (30 ml), triphenyl phosphine (5.25 gm, 20 mmol) was added followed by thiolacetic acid (1.52 gm, 20 mmol) and Diisopropylazodicarboxylate (4.04 gm, 20 mmol) at 0° C. Reaction mixture was then allowed to come to rt and stirred for 2 h. Then solvent was r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Carbo-thioester | c1ccsc1 | null | c1ccccc1 | HO- | C1CCOC1 | null | 2 | CCOC(=O)c1cc(CO)cc(C(=O)OCC)c1.O=C(O)Cc1cccs1>C1CCOC1>CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-73a9c2b7f338443691adff10ef1e88f8 | CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1.CI>>CCOC(=O)c1cc(CSC)cc(C(=O)OCC)c1 | C(C)(=O)SCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC.C[O-].[Na+].CI>>CSCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC | CC(=O)[S:10][CH2:9][c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:19][c:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[cH:12]1.I[CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][S:10][CH3:11])[cH:12][c:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[cH:19]1 | CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1.CI | CCOC(=O)c1cc(CSC)cc(C(=O)OCC)c1 | null | null | CO.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 414ef9d7284b3a3a3ca4f3037df8885fc317c70df763f998bdece1a30f85b3fd | 950082924a0524bfc0063f92485d7f4b587dbc9668e1d8f834d8cda3a56bc402 | c1ccccc1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[c:3].I-[CH3;D1;+0:4]>>[CH3;D1;+0:4]-[S;H0;D2;+0:1]-[C:2]-[c:3] | 55 | [{"value": 55.0, "product": "CSCC=1C=C(C=C(C(=O)OCC)C1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To diethyl 5-(acetylthiomethyl)isophthalate (1.02 gm, 3.30 mmol) in THF (10 ml) and MeOH (10 ml), sodium methoxide (207 mg, 3.63 mmol) was added and stirred at rt for 2 h. Then methyl iodide (0.69 ml, 10.9 mmol) were added in two portions. After stirring at rt for 4 h, THF and MeOH were removed in vacuum and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Monosulfide | null | null | c1ccccc1 | HI | CO.C1CCOC1 | null | 2 | CCOC(=O)c1cc(CSC(C)=O)cc(C(=O)OCC)c1.CI>CO.C1CCOC1>CCOC(=O)c1cc(CSC)cc(C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e228e79404c4ec3899b5a1d1ae6ee4e | CC(C)I.Ic1cn[nH]c1>>CC(C)n1cc(I)cn1 | [H-].[Na+].IC=1C=NNC1.IC(C)C>>IC=1C=NN(C1)C(C)C | I[CH:2]([CH3:1])[CH3:3].[nH:4]1[cH:5][c:6]([I:7])[cH:8][n:9]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][c:6]([I:7])[cH:8][n:9]1 | CC(C)I.Ic1cn[nH]c1 | CC(C)n1cc(I)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16e7264339c5da2b038fe36dfca9cfcc21c80f0292d644875f157fe8da0791e0 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1cn[nH]c1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7;a:4]1:[c:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[n;H0;D3;+0:8]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1 | 66 | [{"value": 66.0, "product": "IC=1C=NN(C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "IC=1C=NN(C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a slurry of sodium hydride (95%, 0.58 g, 23 mmol) in DMF (20 mL) was added a solution of 4-Iodo-1H-pyrazole (2023A) (4.07 g, 21 mmol) in DMF (20 mL) and the resulting mixture was stirred at rt for 10 min. Then 2-iodopropane (2.52 mL, 25.2 mmol) was added dropwise and the resulting mixture was stirred at rt overnight... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1 | HI | CN(C)C=O | null | 0.166667 | CC(C)I.Ic1cn[nH]c1>CN(C)C=O>CC(C)n1cc(I)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c099c81471ed49b6a737d54bf864cdc4 | CC(C)[C@@H](N)C(=O)O.Cc1cc(S(=O)(=O)Cl)ccc1F>>Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F | Cl.C(=O)([O-])[O-].[K+].[K+].N[C@H](C(C)C)C(=O)O.FC1=C(C=C(C=C1)S(=O)(=O)Cl)C>>FC1=C(C=C(C=C1)S(=O)(=O)N[C@@H](C(=O)O)C(C)C)C | [NH2:8][C@@H:9]([C:10](=[O:11])[OH:12])[CH:13]([CH3:14])[CH3:15].Cl[S:5]([c:4]1[cH:3][c:2]([CH3:1])[c:18]([F:19])[cH:17][cH:16]1)(=[O:6])=[O:7]>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[NH:8][C@@H:9]([C:10](=[O:11])[OH:12])[CH:13]([CH3:14])[CH3:15])[cH:16][cH:17][c:18]1[F:19] | CC(C)[C@@H](N)C(=O)O.Cc1cc(S(=O)(=O)Cl)ccc1F | Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F | null | null | O1CCOCC1.C(C)OC(C)=O.O1CCOCC1.O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:7]-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | null | [] | null | null | 30 | MINUTE | D-Valine (1.39 g, 11.9 mmol) was dissolved in 80 ml of dioxane/water (1:1) containing K2CO3 (3.3 g, 24 mmol). A solution of 4-fluro-3-methylphenyl-sulfonylchloride (10 mmol) in dioxane (4 ml) was dropped in with good stirring. The reaction mixture was stirred at room temperature for 30 min. Ethylacetate (80 ml), 1N HCl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | O1CCOCC1.C(C)OC(C)=O.O1CCOCC1.O | null | 0.5 | CC(C)[C@@H](N)C(=O)O.Cc1cc(S(=O)(=O)Cl)ccc1F>O1CCOCC1.C(C)OC(C)=O.O1CCOCC1.O>Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05def82bb6244609805478b31b3662e3 | CC(C)(C)ON.Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F>>Cc1cc(S(=O)(=O)N[C@@H](C(=O)NOC(C)(C)C)C(C)C)ccc1F | CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.C(C)(C)(C)ON.FC1=C(C=C(C=C1)S(=O)(=O)N[C@@H](C(=O)O)C(C)C)C.C(CCl)Cl>>C(C)(C)(C)ONC([C@@H](C(C)C)NS(=O)(=O)C1=CC(=C(C=C1)F)C)=O | [NH2:12][O:13][C:14]([CH3:15])([CH3:16])[CH3:17].O[C:10]([C@H:9]([NH:8][S:5]([c:4]1[cH:3][c:2]([CH3:1])[c:23]([F:24])[cH:22][cH:21]1)(=[O:6])=[O:7])[CH:18]([CH3:19])[CH3:20])=[O:11]>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[NH:8][C@@H:9]([C:10](=[O:11])[NH:12][O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([CH3:... | CC(C)(C)ON.Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F | Cc1cc(S(=O)(=O)N[C@@H](C(=O)NOC(C)(C)C)C(C)C)ccc1F | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[NH2;D1;+0:11]>>[#7:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[#8:10]-[C:7](-[C;D1;H3:6])(-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | null | null | 30 | MINUTE | 2(R)-[(4-Fluoro-3-methylphenylsulfonyl)]amino-3-methylbutyric acid (2.64 g, 9.12 mmol) was dissolved in DCM (30 ml), followed by addition of DIEA (3.18 ml, 2 eq.) and O-t-butylhydroxylamine hydrochloride (2.3 g, 2 eq.). EDC.HCl (2.1 g, 1.2 eq.) was then added portionwise as solid. More EDC (0.6, 0.5 eq.) was added afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 0.5 | CC(C)(C)ON.Cc1cc(S(=O)(=O)N[C@@H](C(=O)O)C(C)C)ccc1F>C(Cl)Cl>Cc1cc(S(=O)(=O)N[C@@H](C(=O)NOC(C)(C)C)C(C)C)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db9b73dacfa84f6f8103b4b29ead54f9 | CC=CCO.COC(=O)CO>>CC=CCOC(=O)CO | C(CO)(=O)OC.C(=O)([O-])[O-].[K+].[K+].C(C=CC)O>>C(CO)(=O)OCC=CC | [CH3:1][CH:2]=[CH:3][CH2:4][OH:5].CO[C:6](=[O:7])[CH2:8][OH:9]>>[CH3:1][CH:2]=[CH:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][OH:9] | CC=CCO.COC(=O)CO | CC=CCOC(=O)CO | null | null | null | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4].[C;D1;H3:5]-[C:6]=[C:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:5]-[C:6]=[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4] | null | [] | null | null | null | null | Methyl glycolate (10.4 g, 114 mmol), crotyl alcohol (100 ml, excess), was refluxed in the presence of K2CO3 (0.8 g) for 1 hr, during which time about 10 ml of the condensate was removed through a Dean-Stock trap. After diluting with hexane (100 ml), the solid was filtered through a short silica gel column (50 g), washe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | null | HO- | null | null | null | CC=CCO.COC(=O)CO>>CC=CCOC(=O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13d30fe1be93481c9a591cd17820f840 | C[C@H](O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)OCc1ccccc1>>C[C@H]1[C@H](C(=O)OCc2ccccc2)N1C(c1ccccc1)(c1ccccc1)c1ccccc1 | C(C)OC(C)=O.C(C1=CC=CC=C1)OC([C@H](NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C@@H](O)C)=O.S(=O)(=O)(Cl)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1[C@H]([C@@H]1C)C(=O)OCC1=CC=CC=C1 | O[C@@H:2]([CH3:1])[C@H:3]([C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH:14][C:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)([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>>[CH3:1][C@H:2]1[C@H:3]([C:4](=[O:5])[O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:1... | C[C@H](O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)OCc1ccccc1 | C[C@H]1[C@H](C(=O)OCc2ccccc2)N1C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 2b8d3ae1cef67f4eac801b4420bb688b247ac9b1186de2c97cb925917621bd64 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | O=C(OCc1ccccc1)[C@H]1CN1C(c1ccccc1)(c1ccccc1)c1ccccc1 | O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3](-[NH;D2;+0:4]-[C:5](-[c:6])(-[c:7])-[c:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[C:3]1-[C@H;D3;+0:1](-[C;D1;H3:2])-[N;H0;D3;+0:4]-1-[C:5](-[c:6])(-[c:7])-[c:8] | null | [] | null | null | null | null | N-Trityl-D-threonine benzyl ester (2.5 g, 5.5 mmol), TEA (2.8 ml, 20 mmol) were dissolved in 100 ml of dry toluene at −50° C. A solution of sulfuryl chloride (800 ul, 8 mmol) in toluene (20 ml) was added in 15 min. The reaction was allowed to warm up to r.t. Ethylacetate (100 ml) was added and this was washed with sat.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | null | C1C[NH]1 | C1C[NH]1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | C[C@H](O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)OCc1ccccc1>C1(=CC=CC=C1)C>C[C@H]1[C@H](C(=O)OCc2ccccc2)N1C(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6608355280f42a3bd26ad96883a3177 | CN1C2CCC1CC(N)C2.ClC(Cl)(Cl)c1nc2ccccc2[nH]1>>CN1C2CCC1CC(NC(=O)c1nc3ccccc3[nH]1)C2 | ClC(C1=NC2=C(N1)C=CC=C2)(Cl)Cl.Cl.Cl.CN1C2CC(CC1CC2)N.O1CCCC1>>CN1C2CC(CC1CC2)NC(=O)C2=NC1=C(N2)C=CC=C1 | [CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([NH2:9])[CH2:21]2.Cl[C:10](Cl)(Cl)[c:12]1[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[nH:20]1>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([NH:9][C:10](=[O:11])[c:12]1[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]1)[CH2:21]2 | CN1C2CCC1CC(N)C2.ClC(Cl)(Cl)c1nc2ccccc2[nH]1 | CN1C2CCC1CC(NC(=O)c1nc3ccccc3[nH]1)C2 | null | null | null | Acylation | OtherReaction | 9a770d58124eb17b012a2cbd58c5527dfbcd7ab7cd2cd8def748b2211eaf51cb | ad3fc183ae5176823c40bc04c8aa28c8e790bb261043e2aca084d9053b9865e6 | O=C(NC1CC2CCC(C1)N2)c1nc2ccccc2[nH]1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:11])-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1)-[C:10] | 10 | [{"value": 10.0, "product": "CN1C2CC(CC1CC2)NC(=O)C2=NC1=C(N2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction was carried out as described in General Procedure 2 using 2-trichloromethyl-1H-benzoimidazole (Example 1, 100 mg, 0.42 mmol) and 8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine dihydrochloride (172 mg, 0.84 mmol) in tetrahydrofuran (THF, 3 mL). Purification afforded 10 mg (10%) of the title compound. MS (ESI): m... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Primary amine | Secondary amide | null | null | C1CC2CCC(C1)[NH]2.c1ccc2[nH]cnc2c1 | HCl | null | null | null | CN1C2CCC1CC(N)C2.ClC(Cl)(Cl)c1nc2ccccc2[nH]1>>CN1C2CCC1CC(NC(=O)c1nc3ccccc3[nH]1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bf372b83196459a83b8c596b56048fe | C1CNCCN1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1>>O=C(c1nc2cc(Cl)ccc2[nH]1)N1CCNCC1 | ClC1=CC2=C(NC(=N2)C(Cl)(Cl)Cl)C=C1.N1CCNCC1.C1CCOC1>>ClC1=CC2=C(NC(=N2)C(=O)N2CCNCC2)C=C1 | [NH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1.Cl[C:2](Cl)(Cl)[c:3]1[n:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[nH:12]1>>[O:1]=[C:2]([c:3]1[n:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[nH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1 | C1CNCCN1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1 | O=C(c1nc2cc(Cl)ccc2[nH]1)N1CCNCC1 | null | null | null | Acylation | OtherReaction | 431a3cd1ea547ffff42bbf82af8a724b0772256855bcf434d750615b52aa6b1d | b517a4c48f9c53e17674ed0ea66010e40eed76bba75af718a6c5b19a82250c12 | O=C(c1nc2ccccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:13]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 10 | [{"value": 10.0, "product": "ClC1=CC2=C(NC(=N2)C(=O)N2CCNCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction was carried out as described in General Procedure 2 with commercially available 5-chloro-2-trichloromethyl-1H-benzoimidazole (100 mg, 0.37 mmol) and piperazine (64 mg, 0.75 mmol) in THF (3 mL). Purification afforded 10 mg (10%) of the title compound. MS (ESI): mass calculated for C12H13ClN4O, 264.08; m/z f... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amine | Tertiary amide | C1CNCCN1 | C1C[NH]CCN1 | c1ccc2[nH]cnc2c1.C1C[NH]CCN1 | HCl | null | null | null | C1CNCCN1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1>>O=C(c1nc2cc(Cl)ccc2[nH]1)N1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e3a28d790714c6995672309acff838e | CCN1CCNCC1.Cc1cccc2[nH]c(C(Cl)(Cl)Cl)nc12>>CCN1CCN(C(=O)c2nc3c(C)cccc3[nH]2)CC1 | CC1=CC=CC=2NC(=NC21)C(Cl)(Cl)Cl.C(C)N1CCNCC1.C1CCOC1>>C(C)N1CCN(CC1)C(=O)C1=NC2=C(N1)C=CC=C2C | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:19][CH2:20]1.Cl[C:7](Cl)(Cl)[c:9]1[n:10][c:11]2[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]2[nH:18]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[n:10][c:11]3[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]3[nH:18]2)[CH2:19][CH2:20]1 | CCN1CCNCC1.Cc1cccc2[nH]c(C(Cl)(Cl)Cl)nc12 | CCN1CCN(C(=O)c2nc3c(C)cccc3[nH]2)CC1 | null | null | null | Acylation | OtherReaction | 036f61423714f200e062ddd740161f5b9b68a55e0b5115b18db716b23c133d37 | b517a4c48f9c53e17674ed0ea66010e40eed76bba75af718a6c5b19a82250c12 | O=C(c1nc2ccccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:13]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 62 | [{"value": 62.0, "product": "C(C)N1CCN(CC1)C(=O)C1=NC2=C(N1)C=CC=C2C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction was carried out as described in General Procedure 2 using 4-methyl-2-trichloromethyl-1H-benzoimidazole (Example 20, Step A, 100 mg, 0.40 mmol) and N-ethylpiperazine (0.10 mL, 0.80 mmol) in THF (3 mL). Purification afforded 67 mg (62%) of the title compound. MS (ESI): mass calculated for C15H20N4O, 272.16; ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1 | HCl | null | null | null | CCN1CCNCC1.Cc1cccc2[nH]c(C(Cl)(Cl)Cl)nc12>>CCN1CCN(C(=O)c2nc3c(C)cccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d98907bde2ad45d1b0f8b22747e034d8 | CN1CCNCC1.COC(=O)C(OC)(OC)OC.Nc1ccccc1O>>CN1CCN(C(=O)c2nc3ccccc3o2)CC1 | CN1CCNCC1.NC1=C(C=CC=C1)O.COC(C(=O)OC)(OC)OC.[O-]S(=O)(=O)C(F)(F)F.[Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.OC1=NC=CC=C1>>O1C(=NC2=C1C=CC=C2)C(=O)N2CCN(CC2)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:17][CH2:18]1.CO[C:6](=[O:7])[C:8](OC)(OC)OC.[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[OH:16]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[CH2:17][CH2:18]1 | CN1CCNCC1.COC(=O)C(OC)(OC)OC.Nc1ccccc1O | CN1CCN(C(=O)c2nc3ccccc3o2)CC1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | e17d614ed539e565d81ae0962263543a7e843c875afaafe64a497d6356ed0ec1 | 578784d43d65f73391dd45ff9b0389cb7892b0085fa8a8f37a33948346c348e9 | O=C(c1nc2ccccc2o1)N1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-O-C)(-O-C)-O-C.[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1)-[c;H0;D3;+0:3]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[o;H0... | 48 | [{"value": 48.0, "product": "O1C(=NC2=C1C=CC=C2)C(=O)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.4, "product": "O1C(=NC2=C1C=CC=C2)C(=O)N2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | 5 | HOUR | A stirred solution of 2-aminophenol (300 mg, 2.75 mmol), methyl 2,2,2-trimethoxyacetate (902 mg, 5.50 mmol), and ytterbium triflate (170 mg, 0.28 mmol) in toluene (10 mL) was heated to reflux. After 5 h, the mixture was cooled, and the precipitate was collected and dried. The crude solid was suspended in toluene (5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Ether.Aromatic alcohol.Primary amine.Secondary amine | Tertiary amide | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | 125 | 5 | CN1CCNCC1.COC(=O)C(OC)(OC)OC.Nc1ccccc1O>C1(=CC=CC=C1)C>CN1CCN(C(=O)c2nc3ccccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-687876fd9504433f8e40399fa283c6f1 | CN1CCN(C(=O)c2nc3c([N+](=O)[O-])cccc3[nH]2)CC1>>CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1 | CN1CCN(CC1)C(=O)C1=NC2=C(N1)C=CC=C2[N+](=O)[O-].[H][H]>>NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C | O=[N+:12]([O-])[c:11]1[c:10]2[n:9][c:8]([C:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:19][CH2:18]3)=[O:7])[nH:17][c:16]2[cH:15][cH:14][cH:13]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][c:10]3[c:11]([NH2:12])[cH:13][cH:14][cH:15][c:16]3[nH:17]2)[CH2:18][CH2:19]1 | CN1CCN(C(=O)c2nc3c([N+](=O)[O-])cccc3[nH]2)CC1 | CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1 | null | C1CCOC1.C(C)O.[Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1nc2ccccc2[nH]1)N1CCNCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6](-[C:7](-[#7:8])=[O;D1;H0:9]):[#7;a:10]:[c:11]:1>>[#7:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[#7;a:10]:[c:11]:[c:4](:[#7;a:5]:1):[c:2](-[NH2;D1;+0:1]):[c:3] | 91 | [{"value": 91.0, "product": "NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (4-methyl-piperazin-1-yl)-(4-nitro-1H-benzoimidazol-2-yl)-methanone (640 mg, 2.21 mmol) in 1:1 THF/ethanol (10 mL, with a few drops of ethyl acetate) was added 10% palladium on carbon (640 mg). The reaction mixture was placed under 1 atm hydrogen for 72 h. The resulting mixture was filtered through dia... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1 | Other | C1CCOC1.C(C)O.[Pd] | null | null | CN1CCN(C(=O)c2nc3c([N+](=O)[O-])cccc3[nH]2)CC1>C1CCOC1.C(C)O.[Pd]>CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b25c3dfbe1947958b939819f085e635 | CC(C)=O.CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1>>CC(C)Nc1cccc2[nH]c(C(=O)N3CCN(C)CC3)nc12 | NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C.CC(=O)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C | O=[C:2]([CH3:1])[CH3:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]3)[n:21][c:22]12>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]3)[n:21][c:22]1... | CC(C)=O.CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1 | CC(C)Nc1cccc2[nH]c(C(=O)N3CCN(C)CC3)nc12 | null | C(C)(=O)O | ClC(C)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(c1nc2ccccc2[nH]1)N1CCNCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[#7;a:8]:[c:9]:[c:10](:[#7;a:11]:1):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[#7;a:8]:[c:9]:[c:10](:[#7;a:11]:1):[c:12](-[NH;D2;+0:13]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:14] | 61.1 | [{"value": 60.0, "product": "C(C)(C)NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "C(C)(C)NC1=CC=CC=2NC(=NC21)C(=O)N2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of (4-amino-1H-benzoimidazol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 43; 50 mg, 0.19 mmol) in dichloroethane (10 mL), was added acetone (0.07 mL, 0.96 mmol) and acetic acid (10 drops), followed by NaBH(OAc)3 (203 mg, 0.96 mmol). The reaction mixture was stirred at room temperature for 16 h, and... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccc2[nH]cnc2c1.C1C[NH]CC[NH]1 | Other | C(C)(=O)O.ClC(C)Cl | null | 16 | CC(C)=O.CN1CCN(C(=O)c2nc3c(N)cccc3[nH]2)CC1>C(C)(=O)O.ClC(C)Cl>CC(C)Nc1cccc2[nH]c(C(=O)N3CCN(C)CC3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-684e4a3330224d4e9dccb562656e8dbc | CN1CCNCC1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1.[NH4+]>>CN1CCN(C(=N)c2nc3cc(Cl)ccc3[nH]2)CC1 | ClC1=CC2=C(NC(=N2)C(Cl)(Cl)Cl)C=C1.CN1CCNCC1.C(C)(=O)[O-].[NH4+]>>ClC1=CC2=C(NC(=N2)C(N2CCN(CC2)C)=N)C=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:18][CH2:19]1.Cl[C:6](Cl)(Cl)[c:8]1[n:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]2[nH:17]1.[NH4+:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[NH:7])[c:8]2[n:9][c:10]3[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]3[nH:17]2)[CH2:18][CH2:19]1 | CN1CCNCC1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1.[NH4+] | CN1CCN(C(=N)c2nc3cc(Cl)ccc3[nH]2)CC1 | null | null | C(C)#N.C(=O)(O)[O-].[Na+] | Functional Group Interconversion | OtherReaction | 6370db9971c1ac02df058708afde29206f0e61baae298df29ec5d0829169879e | e05e2344747dd96328a9ecb08fedf62cd3244b040cc6955de7b61639ba999820 | N=C(c1nc2ccccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1.[NH4+;D0:13]>>[NH;D1;+0:13]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 22.4 | [{"value": 22.0, "product": "ClC1=CC2=C(NC(=N2)C(N2CCN(CC2)C)=N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.4, "product": "ClC1=CC2=C(NC(=N2)C(N2CCN(CC2)C)=N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of 5-chloro-2-trichloromethyl-1H-benzoimidazole (100 mg, 0.37 mmol) in acetonitrile (4 mL) was added N-methylpiperazine (0.04 mL, 0.4 mmol). The mixture was stirred for 10 min then ammonium acetate (29 mg, 0.38 mmol) was added. After 18 h the reaction mixture was diluted with satd aq NaHCO3 (10 mL), and... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1 | HCl | C(C)#N.C(=O)(O)[O-].[Na+] | null | 0.166667 | CN1CCNCC1.Clc1ccc2[nH]c(C(Cl)(Cl)Cl)nc2c1.[NH4+]>C(C)#N.C(=O)(O)[O-].[Na+]>CN1CCN(C(=N)c2nc3cc(Cl)ccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07ffd95abc0343efb5b5937b13bb0a17 | CC(C)(C)c1ccc(N)c(C(C)(C)C)c1.NO.OC(O)C(Cl)(Cl)Cl>>CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1 | S(=O)(=O)([O-])[O-].[Na+].[Na+].ClC(C(O)O)(Cl)Cl.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)N.Cl.NO>>C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)NC(/C=N/O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1.[NH2:13][OH:14].O[CH:12]([C:10](Cl)(Cl)Cl)[OH:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])/[CH:12]=[N:13]/[OH:14])[c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1 | CC(C)(C)c1ccc(N)c(C(C)(C)C)c1.NO.OC(O)C(Cl)(Cl)Cl | CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1 | null | null | Cl.O | Acylation | OtherReaction | 945b0c41a86c791948d53e53b6060216294cdbc727563e10d955fcd0adda1c96 | ed66e3eedfeda41282995a3fcf8794b82675627b3c0201c4e47ec301ec6a89a1 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[CH;D3;+0:2](-O)-[OH;D1;+0:3].[NH2;D1;+0:4]-[O;D1;H1:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H1:5]/[N;H0;D2;+0:4]=[CH;D2;+0:2]/[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 25 | [{"value": 25.0, "product": "C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)NC(/C=N/O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.8, "product": "C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)NC(/C=N/O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Sodium sulfate (20.75 g, 146 mmol) and chloral hydrate (2.78 g, 17 mmol) were dissolved in water (30 mL). Then a solution of 2,4-di-tert-butyl-phenylamine [prepared according to P. D. Bartlett, M. Roha, R. M. Stiles, J. Am. Chem. Soc. 1954, 76, 2349-2353](3 g, 14.6 mmol) in water (6 mL), 25% HCl (1.9 mL), and a solutio... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary alcohol.Secondary alcohol.Primary amine.Primary amine | Secondary amide.Oxime | null | null | c1ccccc1 | HCl | Cl.O | 100 | null | CC(C)(C)c1ccc(N)c(C(C)(C)C)c1.NO.OC(O)C(Cl)(Cl)Cl>Cl.O>CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f8784a802314aa1a0ca0cfde41711cd | CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1>>CC(C)(C)c1cc2c(c(C(C)(C)C)c1)NC(=O)C2=O | C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)NC(/C=N/O)=O.S(O)(O)(=O)=O>>C(C)(C)(C)C=1C=C2C(C(NC2=C(C1)C(C)(C)C)=O)=O | N(=[CH:18]/[C:16]([NH:15][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:14][c:9]1[C:10]([CH3:11])([CH3:12])[CH3:13])=[O:17])\[OH:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]2[c:8]([c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]1)[NH:15][C:16](=[O:17])[C:18]2=[O:19] | CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1 | CC(C)(C)c1cc2c(c(C(C)(C)C)c1)NC(=O)C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 03e26bd863db1451489ee0f1368908e688e08d7fcfd1b579498bc95cc4edfd9e | ab4bf08516e66cf6fd8670ac9e8d4ecd074b35f40b66b51c2d0c9c0d98ab1c51 | O=C1Nc2ccccc2C1=O | [O;D1;H0:1]=[C:2](-[#7:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8])/[CH;D2;+0:9]=N/[OH;D1;+0:10]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](:[c:7]:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10] | 42 | [{"value": 42.0, "product": "C(C)(C)(C)C=1C=C2C(C(NC2=C(C1)C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | N-(2,4-Di-tert-butyl-phenyl)-2-[(E)-hydroxyimino]-acetamide (500 mg, 1.7 mmol) in concentrated sulfuric acid (3.8 mL) was heated at 90° C. for 2 h. This solution was cooled at 0° C. and slowly added to ice-water (15 mL), the brown precipitate was filtered off and purified by chromatography on silica gel with a gradient... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Ketone | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | null | 0 | null | CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1>>CC(C)(C)c1cc2c(c(C(C)(C)C)c1)NC(=O)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95541a6909a948f4a82c9ee7d9271731 | CC(C)(C)c1cc(C(C)(C)C)c2c(c1)[C@](O)(C(F)(F)F)C(=O)O2.C[C@@H](N=C=O)c1cccc2ccccc12>>C[C@H](c1cccc2ccccc12)N1C(=O)O[C@@](c2cc(C(C)(C)C)cc(C(C)(C)C)c2O)(C(F)(F)F)C1=O | C(C)(C)(C)C=1C=C(C2=C([C@@](C(O2)=O)(C(F)(F)F)O)C1)C(C)(C)C.C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=C=O>>C(C)(C)(C)C=1C(=C(C=C(C1)C(C)(C)C)[C@@]1(C(N(C(O1)=O)[C@H](C)C1=CC=CC2=CC=CC=C12)=O)C(F)(F)F)O | [OH:16][C@:17]1([C:33]([F:34])([F:35])[F:36])[c:18]2[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]([C:27]([CH3:28])([CH3:29])[CH3:30])[c:31]2[O:32][C:37]1=[O:38].[CH3:1][C@H:2]([c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[N:13]=[C:14]=[O:15]>>[CH3:1][C@H:2]([c:3]1[cH:4][cH:5][cH:6][... | CC(C)(C)c1cc(C(C)(C)C)c2c(c1)[C@](O)(C(F)(F)F)C(=O)O2.C[C@@H](N=C=O)c1cccc2ccccc12 | C[C@H](c1cccc2ccccc12)N1C(=O)O[C@@](c2cc(C(C)(C)C)cc(C(C)(C)C)c2O)(C(F)(F)F)C1=O | null | CN(C1=CC=NC=C1)C | C1(=CC=CC=C1)C | Protection | OtherReaction | ea88d100183af599edc7a9637231fdcbd79d3bdad759e6dec059ab78d75a6951 | 839ad78ca2d527e9137d226b0bb82fba3f84cea49dffccaff257c10250a58384 | O=C1OC(c2ccccc2)C(=O)N1Cc1cccc2ccccc12 | [C;D1;H3:1]-[C:2](-[c:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:11]1(-[OH;D1;+0:12])-[c:13]:[c:14](:[c:15])-[O;H0;D2;+0:16]-[C;H0;D3;+0:17]-1=[O;D1;H0:18]>>[C;D1;H3:1]-[C:2](-[c:3])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:12]-[C:11](-[c:13]:[c:14](-... | 37.9 | [{"value": 37.0, "product": "C(C)(C)(C)C=1C(=C(C=C(C1)C(C)(C)C)[C@@]1(C(N(C(O1)=O)[C@H](C)C1=CC=CC2=CC=CC=C12)=O)C(F)(F)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.9, "product": "C(C)(C)(C)C=1C(=C(C=C(C1)C(C)(C)C)[C@@]1(C(N(C(O1)=O)[C@H](C)C1=CC=CC2=CC=CC=C12)=O)C(F)(F)F)O", "details": "CALCULAT... | null | null | null | null | (R)-(+)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (100 mg, 0.3 mmol), (R)-(−)-1-(1-naphthyl)ethyl isocyanate (58 uL, 0.33 mmol), and 4-dimethylaminopyridine (3.7 mg, 0.03 mmol) were heated at reflux in toluene (1 mL) for 1 h under nitrogen. The resulting solution was evaporated to dryness and th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Tertiary alcohol | Carbamic ester.Ether.Substituted dicarboximide.Aromatic alcohol | c1ccc2c(c1)CCO2 | C1COC[NH]1 | c1ccc2ccccc2c1.C1COC[NH]1.c1ccccc1 | null | CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C | null | null | CC(C)(C)c1cc(C(C)(C)C)c2c(c1)[C@](O)(C(F)(F)F)C(=O)O2.C[C@@H](N=C=O)c1cccc2ccccc12>CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C>C[C@H](c1cccc2ccccc12)N1C(=O)O[C@@](c2cc(C(C)(C)C)cc(C(C)(C)C)c2O)(C(F)(F)F)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-266a053e03574460a841a0ad7cca8813 | BrCCC1CC1.O=Cc1ccc(OC(F)F)c(O)c1>>O=Cc1ccc(OC(F)F)c(OCC2CC2)c1 | FC(OC1=C(C=C(C=O)C=C1)O)F.C([O-])([O-])=O.[K+].[K+].BrCCC1CC1>>C1(CC1)COC=1C=C(C=O)C=CC1OC(F)F | BrC[CH2:13][CH:14]1[CH2:15][CH2:16]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([OH:12])[cH:17]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16]2)[cH:17]1 | BrCCC1CC1.O=Cc1ccc(OC(F)F)c(O)c1 | O=Cc1ccc(OC(F)F)c(OCC2CC2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CC2)cc1 | Br-C-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[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]1-[C:3]-[C:4]-1):[c:8] | 100 | [{"value": 100.0, "product": "C1(CC1)COC=1C=C(C=O)C=CC1OC(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "C1(CC1)COC=1C=C(C=O)C=CC1OC(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 1.5 | HOUR | To a mixture of 4-difluoromethoxy-3-hydroxy-benzaldehyde (5.0 g, 27 mmol) and potassium carbonate (5.5 g, 40 mmol) in dimethylformamide (30 ml) under inert atmosphere at 60° C. was added bromoethylcyclopropane (5 g, 37 mmol). The mixture was stirred and heated at 65° C. After 1.5 hour, the mixture was allowed to cool a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC1 | HBr | CN(C=O)C | 65 | 1.5 | BrCCC1CC1.O=Cc1ccc(OC(F)F)c(O)c1>CN(C=O)C>O=Cc1ccc(OC(F)F)c(OCC2CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-373bdf2a529045239c8931d5cc8fa60e | CC(=O)Nc1cccc2c1C(=O)OC2=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | NC(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1.C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1.C(C)(=O)[O-].[Na+]>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O | O1[C:11](=[O:12])[c:10]2[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][c:9]2[C:34]1=[O:35].[NH2:13][CH:14]([CH2:15][C:16](=[O:17])[OH:18])[c:19]1[cH:20][cH:21][c:22]([O:23][CH:24]([F:25])[F:26])[c:27]([O:28][CH2:29][CH:30]2[CH2:31][CH2:32]2)[cH:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[... | CC(=O)Nc1cccc2c1C(=O)OC2=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1cccc(OCC2CC2)c1 | [NH2;D1;+0:1]-[C:2](-[c:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:8]=[C;H0;D3;+0:9]1-[N;H0;D3;+0:1](-[C:2](-[c:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1:[c:15] | 147.4 | [{"value": 85.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 147.4, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-amino-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid (500 mg, 1.0 mmol) in acetic acid (10 ml) was added 3-acetamido-phthalic anhydride (390 mg, 1.9 mmol) and sodium acetate (160 mg, 1.9 mmol). The mixture was heated at reflux temperature overnight. The solvent was removed in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1CC1 | HO- | C(C)(=O)O | null | 2 | CC(=O)Nc1cccc2c1C(=O)OC2=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>C(C)(=O)O>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bae428cf047c495fb22a3970fa1f4943 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.CNC>>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | O.CNC.C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O | O[C:16]([CH2:15][CH:14]([N:13]1[C:11](=[O:12])[c:10]2[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][c:9]2[C:36]1=[O:37])[c:21]1[cH:22][cH:23][c:24]([O:25][CH:26]([F:27])[F:28])[c:29]([O:30][CH2:31][CH:32]2[CH2:33][CH2:34]2)[cH:35]1)=[O:17].[NH:18]([CH3:19])[CH3:20]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:... | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.CNC | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1c2ccccc2C(=O)N1Cc1cccc(OCC2CC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 30 | [{"value": 30.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 2 | HOUR | To a solution of 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid (470 mg, 1.04 mmol) in tetrahydrofurane (10 ml) was added carbonyldiimidazole (250 mg, 1.56 mmol) at room temperature. The solution was stirred at room temperature for 2 hours. To the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1CC1 | HO- | O1CCCC1 | null | 2 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.CNC>O1CCCC1>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-605cf8fd2ad9469187f7a3d6ea59f0ca | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.[NH4+]>>CC(=O)Nc1cccc2c1C(=O)N(C(CC(N)=O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | O.[OH-].[NH4+].C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O | O[C:16]([CH2:15][CH:14]([N:13]1[C:11](=[O:12])[c:10]2[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][c:9]2[C:34]1=[O:35])[c:19]1[cH:20][cH:21][c:22]([O:23][CH:24]([F:25])[F:26])[c:27]([O:28][CH2:29][CH:30]2[CH2:31][CH2:32]2)[cH:33]1)=[O:18].[NH4+:17]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[... | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.[NH4+] | CC(=O)Nc1cccc2c1C(=O)N(C(CC(N)=O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1c2ccccc2C(=O)N1Cc1cccc(OCC2CC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 81 | [{"value": 81.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid (100 mg, 0.22 mmol) in tetrahydrofurane was added carbonyldiimidazole (53 mg, 0.33 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1CC1 | HO- | O1CCCC1 | null | 2 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O.[NH4+]>O1CCCC1>CC(=O)Nc1cccc2c1C(=O)N(C(CC(N)=O)c1ccc(OC(F)F)c(OCC3CC3)c1)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c937f784f2a4ad3a097e16eab2582c2 | CCON1C(=O)C2=CC=CC(=C=O)C2C1=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>>O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O | NC(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1.C(C)ON1C(C=2C(C1=O)C(C=CC2)=C=O)=O.C([O-])([O-])=O.[Na+].[Na+].Cl>>C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=CC=CC=C2C1=O)=O | CCON1[C:22](=[O:23])[C:24]2=[CH:25][CH:26]=[CH:27][C:28](=C=O)[CH:29]2[C:30]1=[O:31].[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:13])[c:14]([O:15][CH2:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1)[NH2:21]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:13]... | CCON1C(=O)C2=CC=CC(=C=O)C2C1=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1 | O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O | null | null | O.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 2c9fd1473431d6610ae2271df4f3a7433a89b8c51d2cf99aa9f0244fdfd4c0c6 | 9585573d87159a707fa25d0a0d4067c835fe11982d5e0753013d0f1cb950abd4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OCC2CC2)c1 | C-C-O-N1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3]2=[CH;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[C;H0;D3;+0:7](=C=O)-[CH;D3;+0:8]-2-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[NH2;D1;+0:11]-[C:12](-[c:13])-[C:14]-[C:15](=[O;D1;H0:16])-[O;D1;H1:17]>>[O;D1;H0:16]=[C:15](-[O;D1;H1:17])-[C:14]-[C:12](-[c:13])-[N;H0;D3;+0:11]1-[C;H0;D3;+0:... | 91 | [{"value": 91.0, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 3-amino-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid (0.78 g, 2.9 mmol) and N-ethoxy-carbonyl-phthalimide (0.64 g, 2.9 mmol) in 30 ml of water and acetonitrile (1:1) was added sodium carbonate (0.33 g, 31 mmol). The mixture was stirred at room temperature for 5 hours. 1N HCl was add... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary amine.Conjugated diene | Substituted dicarboximide | C1=CCC2CNCC2=C1 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2 | HO- | O.C(C)#N | null | 5 | CCON1C(=O)C2=CC=CC(=C=O)C2C1=O.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>O.C(C)#N>O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa57a71b05ff4c5296aaee85066cc44b | NO.O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O>>O=C(CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O)NO | O.Cl.NO.C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=CC=CC=C2C1=O)=O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)NO)N1C(C2=CC=CC=C2C1=O)=O | [NH2:31][OH:32].O[C:2](=[O:1])[CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([F:11])[F:12])[c:13]([O:14][CH2:15][CH:16]2[CH2:17][CH2:18]2)[cH:19]1)[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]1=[O:30]>>[O:1]=[C:2]([CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([F:11])[F:12])[c:13]([O:14... | NO.O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O | O=C(CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O)NO | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OCC2CC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 68.2 | [{"value": 61.0, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)NO)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)NO)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid (1.1 g, 2.6 mmol) in tetrahydrofurane was added carbonyldiimidazole (0.73 g, 4.5 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture was added hydroxy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 2 | NO.O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O>O1CCCC1>O=C(CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1C(=O)c2ccccc2C1=O)NO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f51fc51a777b44369e3aaf741ad4562a | CC(=O)Cl.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>>COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1.Cl | NC(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1.C(C)(=O)Cl>>Cl.COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC1CC1)N)=O | C[C:1](=O)[Cl:23].[OH:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[c:16]([O:17][CH2:18][CH:19]2[CH2:20][CH2:21]2)[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[c:16]([O:17][CH2:18][CH:19]2[CH2:20][CH2:21]2)[c... | CC(=O)Cl.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1 | COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1.Cl | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | e4e418517831e68b0ae6eff0e20954e6373d72ef6db8a62429d10c826be6ea2e | b1bbfb03e48869c16300667505b58de6f6c5a435aa2a615a319deee7cf33326a | c1ccc(OCC2CC2)cc1 | C-[C;H0;D3;+0:1](=O)-[Cl;H0;D1;+0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1].[ClH;D0;+0:2] | 90.3 | [{"value": 90.0, "product": "Cl.COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC1CC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "Cl.COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC1CC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a stirred suspension of 3-amino-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid (500 mg, 1.7 mmol) in methanol (10 ml) was added dropwise acetyl chloride (0.3 ml, 4.3 mmol) under nitrogen atmosphere at 0° C. After the addition, the mixture was stirred at 0° C. for 15 min and the ice bath was removed... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid | Ester | null | null | c1ccccc1.C1CC1 | Other | CO | 0 | 0.25 | CC(=O)Cl.NC(CC(=O)O)c1ccc(OC(F)F)c(OCC2CC2)c1>CO>COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74fca55ed9ba45eb977de16add4474da | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1>>COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC1CC1)N)=O.C(C)N(CC)CC.C(C)OC(C1=C(C=CC=C1[N+](=O)[O-])CBr)=O>>COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O | CCO[C:33]([c:32]1[c:24]([CH2:23]Br)[cH:25][cH:26][cH:27][c:28]1[N+:29](=[O:30])[O-:31])=[O:34].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[c:15]([O:16][CH2:17][CH:18]2[CH2:19][CH2:20]2)[cH:21]1)[NH2:22]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH:8][cH:9][c:10]([O:... | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1 | COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | null | null | CN(C)C=O | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1c2ccccc2CN1Cc1cccc(OCC2CC2)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C-C):[c:7].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[NH2;D1;+0:13])-[c:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[c:14])-[N;H0;D3;+0:13]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 77 | [{"value": 75.0, "product": "COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 3-amino-3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-propionic acid methyl ester (490 mg, 1.5 mmol) and triethyl amine (0.43 ml, 3.1 mmol) in DMF (10 ml) was added 2-bromomethyl-6-nitro-benzoic acid ethyl ester (460 mg, 1.6 mmol). The mixture was heated at 90° C. under nitrogen atmosphere overnigh... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C)C=O | 90 | null | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].COC(=O)CC(N)c1ccc(OC(F)F)c(OCC2CC2)c1>CN(C)C=O>COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8a1cde0087248e48b1128b2f46f420e | COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O>>O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1)=O.[OH-].[Na+].Cl>>C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O | C[O:3][C:2](=[O:1])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:13])[c:14]([O:15][CH2:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1)[N:21]1[CH2:22][c:23]2[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[c:31]2[C:32]1=[O:33]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:1... | COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1c2ccccc2CN1Cc1cccc(OCC2CC2)c1 | 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] | 90 | [{"value": 90.0, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a suspension of 3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (550 mg, 1.2 mmol) in methanol (5 ml) was added dropwise 10 N NaOH (0.23 ml, 2.3 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour. Then it was allowed to warm up to room... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2 | Other | CO | 0 | 1 | COC(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O>CO>O=C(O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2492be98e06e40b8aafb94fbe685af1e | CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O>>CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc(N)c2C1=O | C1(CC1)COC=1C=C(C=CC1OC(F)F)C(CC(=O)N(C)C)N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O.[H][H]>>NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1 | O=[N+:30]([O-])[c:29]1[cH:28][cH:27][cH:26][c:25]2[c:31]1[C:32](=[O:33])[N:23]([CH:7]([CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[c:8]1[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[c:16]([O:17][CH2:18][CH:19]3[CH2:20][CH2:21]3)[cH:22]1)[CH2:24]2>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:1... | CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O | CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc(N)c2C1=O | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2CN1Cc1cccc(OCC2CC2)c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#7:7]>>[#7:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 97.4 | [{"value": 65.0, "product": "NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(3-cyclopropylmethoxy-4-difluoromethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-N,N-dimethyl-propionamide (330 mg, 0.67 mmol) in ethyl acetate (100 ml) was added 10% Pd on carbon (100 mg). The suspension was shaked under about 50 psi hydrogen atmosphere at room temperature overnight. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2 | Other | [Pd].C(C)(=O)OCC | null | null | CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc([N+](=O)[O-])c2C1=O>[Pd].C(C)(=O)OCC>CN(C)C(=O)CC(c1ccc(OC(F)F)c(OCC2CC2)c1)N1Cc2cccc(N)c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a667f61d6de44e47ba4dbe0f093a45f1 | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].CCOc1cc(C(N)CC(=O)OC)ccc1OC(F)F>>CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F | COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N)=O.C(C)OC(C1=C(C=CC=C1[N+](=O)[O-])CBr)=O.C(C)N(CC)CC>>COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC)=O | CCO[C:24]([c:23]1[c:15]([CH2:14]Br)[cH:16][cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22])=[O:25].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[NH2:13])[cH:26][cH:27][c:28]1[O:29][CH:30]([F:31])[F:32]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[N:13]... | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].CCOc1cc(C(N)CC(=O)OC)ccc1OC(F)F | CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F | null | null | CN(C)C=O | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1c2ccccc2CN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C-C):[c:7].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[NH2;D1;+0:13])-[c:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[c:14])-[N;H0;D3;+0:13]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 81 | [{"value": 81.0, "product": "COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester was prepared by the procedure of example 11 from 3-amino-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester (7.3 g, 0.025 mol), 2-bromomethyl-6-nitro-benzoic acid ethyl ester (7.6 g, 0.028 mol) a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C)C=O | null | null | CCOC(=O)c1c(CBr)cccc1[N+](=O)[O-].CCOc1cc(C(N)CC(=O)OC)ccc1OC(F)F>CN(C)C=O>CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-179ce012b91d4a62923b0b90fe099259 | CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F | COC(CC(N1C(C2=C(C=CC=C2C1)[N+](=O)[O-])=O)C1=CC(=C(C=C1)OC(F)F)OCC)=O>>COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)N)=O)=O | O=[N+:20]([O-])[c:19]1[cH:18][cH:17][cH:16][c:15]2[c:21]1[C:22](=[O:23])[N:13]([CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:26]([O:27][CH:28]([F:29])[F:30])[cH:25][cH:24]1)[CH2:8][C:9](=[O:10])[O:11][CH3:12])[CH2:14]2>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[N:13]2[CH2:14][c:... | CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2CN1Cc1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#7:7]>>[#7:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | 3-(7-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester was prepared by the procedure of example 14 from 3-(4-difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (9.1 g, 0.02 mol) and palladium on carbon under hyd... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | [Pd] | null | null | CCOc1cc(C(CC(=O)OC)N2Cc3cccc([N+](=O)[O-])c3C2=O)ccc1OC(F)F>[Pd]>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0b52d441dca482b899eecbf8aecbd4d | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F.O=C(Cl)C1CC1>>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)N)=O)=O.C1(CC1)C(=O)Cl>>COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[N:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([NH2:20])[c:26]3[C:27]2=[O:28])[cH:29][cH:30][c:31]1[O:32][CH:33]([F:34])[F:35].Cl[C:21](=[O:22])[CH:23]1[CH2:24][CH2:25]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[... | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F.O=C(Cl)C1CC1 | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:12] | 77 | [{"value": 77.0, "product": "COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To the THF solution of 3-(7-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester (2.8 g, 7 mmol) was added cyclopropanyl carbonyl chloride (0.72 ml, 8 mmol) dropwise. The reaction mixture was then heated to reflux for 1 hour. The solvent was removed under vacuo. The m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C1CCOC1 | null | 1 | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F.O=C(Cl)C1CC1>C1CCOC1>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b57c10312bc04da7920cf0ad8e3e8068 | CC(=O)Cl.CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)N)=O)=O.C(C)(=O)Cl>>COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(C)=O)=O)=O | Cl[C:21]([CH3:22])=[O:23].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[N:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([NH2:20])[c:24]3[C:25]2=[O:26])[cH:27][cH:28][c:29]1[O:30][CH:31]([F:32])[F:33]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[N:... | CC(=O)Cl.CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1c2ccccc2CN1Cc1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:10] | 81 | [{"value": 81.0, "product": "COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(C)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(7-Acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester was prepared by the procedure of example 20 from 3-(7-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester (2.8 g, 7 mmol) and acetyl chloride (0.57 ml,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HCl | C1CCOC1 | null | null | CC(=O)Cl.CCOc1cc(C(CC(=O)OC)N2Cc3cccc(N)c3C2=O)ccc1OC(F)F>C1CCOC1>CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f03e17d7059f44458a78494682eb5139 | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | COC(CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1C(C2=C(C=CC=C2C1)NC(C)=O)=O)=O.[OH-].[Na+]>>C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC | C[O:11][C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28]([O:29][CH:30]([F:31])[F:32])[cH:27][cH:26]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[c:23]2[C:24]1=[O:25])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[N:12]2[CH2:13][c:1... | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1c2ccccc2CN1Cc1ccccc1 | 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] | 96 | [{"value": 96.0, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the THF solution of 3-(7-acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester (2.5 g, 5.4 mmol) was added dropwise 10N NaOH (1 ml, 10 mmol) and was stirred at room temperature overnight. The resulted suspension was filtered and the solid was dissolved in wate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | C1CCOC1 | null | 8 | CCOc1cc(C(CC(=O)OC)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>C1CCOC1>CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9af0aea3a2945688050960a30fc418c | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+]>>CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | C1(CC1)C(=O)O.C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.[NH4+].[OH-]>>C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH:32]([F:33])[F:34])[cH:29][cH:28]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[CH:22]3[CH2:23][CH2:24]3)[c:25]2[C:26]1=[O:27])=[O:11].[NH4+:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:10])=[O:1... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+] | CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 70 | [{"value": 70.0, "product": "C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Cyclopropanecarboxylic acid {2-[2-carbamoyl-1′-(4-difluoromethoxy-3-ethoxy-phenyl)-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl)}-amide was prepared by the procedure of example 6 from 3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.8 g, 1.7 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+]>C1CCOC1>CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c2d73f64ee34fe7bf6f5170ad143543 | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.CNC>>CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.CNC>>FC(OC1=C(C=C(C=C1)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:32]([O:33][CH:34]([F:35])[F:36])[cH:31][cH:30]1)[N:14]1[CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[CH:24]3[CH2:25][CH2:26]3)[c:27]2[C:28]1=[O:29])=[O:10].[NH:11]([CH3:12])[CH3:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.CNC | CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 50 | [{"value": 50.0, "product": "FC(OC1=C(C=C(C=C1)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.9, "product": "FC(OC1=C(C=C(C=C1)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Cyclopropanecarboxylic acid {2-[1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-dimethylcarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide was prepared by the procedure of example 13 from 3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.8 g, 1.7 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.CNC>C1CCOC1>CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65e30e45fa2a46c68c81428d5358f201 | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.NO>>CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.Cl.NO>>FC(OC1=C(C=C(C=C1)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH:33]([F:34])[F:35])[cH:30][cH:29]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]1=[O:28])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.NO | CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 80 | [{"value": 80.0, "product": "FC(OC1=C(C=C(C=C1)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "FC(OC1=C(C=C(C=C1)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Cyclopropanecarboxylic acid {2-[1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide was prepared by the procedure of example 8 from 3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.8 g, 1.7 mm... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.NO>C1CCOC1>CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1cb7d322d184b009605a104f89bc80b | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+]>>CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.[NH4+].[OH-]>>C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28]([O:29][CH:30]([F:31])[F:32])[cH:27][cH:26]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[c:23]2[C:24]1=[O:25])=[O:11].[NH4+:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:10])=[O:11])[N:12]2[CH2:13... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+] | CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 73.9 | [{"value": 72.0, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(7-Acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionamide was prepared by the procedure of example 6 from 3-[7-(acetylamino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.6 g, 1.3 mmol), CDI (0.3 g, 2 mmol) and NH4OH (0.20 ml, 2.6 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+]>C1CCOC1>CCOc1cc(C(CC(N)=O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f7a60923c234611a8f7c9bda13f1297 | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC>>CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.CNC>>C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH:32]([F:33])[F:34])[cH:29][cH:28]1)[N:14]1[CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27])=[O:10].[NH:11]([CH3:12])[CH3:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[N:11](... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC | CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 50 | [{"value": 50.0, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(7-Acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-N,N-dimethyl-propionamide was prepared by the procedure of example 13 from 3-(7-acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.1 g, 0.22 mmol), CDI (0.05 g, 0.33 mmol) and dimeth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC>C1CCOC1>CCOc1cc(C(CC(=O)N(C)C)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d5377c1fd9b4284a22889a98815339f | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO>>CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.Cl.NO>>C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:29]([O:30][CH:31]([F:32])[F:33])[cH:28][cH:27]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]2[C:25]1=[O:26])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N... | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO | CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 40 | [{"value": 40.0, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.5, "product": "C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(7-Acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-N-hydroxy-propionamide was prepared by the procedure of example 8 from 3-(7-acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.6 g, 1.3 mmol), CDI (0.32 g, 2.0 mmol) and hydroxylamin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO>C1CCOC1>CCOc1cc(C(CC(=O)NO)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7ef466be18949bca94370676a24a86d | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CC(=O)O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | NC(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1.C(C)(=O)[O-].[Na+]>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O | O1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]2[C:25]1=[O:26].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[NH2:12])[cH:27][cH:28][c:29]1[O:30][CH:31]([F:32])[F:33]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[N:12]2[C:... | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CC(=O)O)ccc1OC(F)F | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [NH2;D1;+0:1]-[C:2](-[c:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[C:4]-[C:2](-[c:3])-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[c:14](:[c:15]):[c:12](:[c:13])-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | 45 | [{"value": 45.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.3, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid was prepared by the procedure of Example 4 from 3-amino-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (2.7 g, 13 mmol), 3-acetamido-phthalic anhydride (4.0 g, 14.5 mmol) and sodium acetate (1.2 g, 14.5 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)O | null | null | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CC(=O)O)ccc1OC(F)F>C(C)(=O)O>CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba163bbeb9dc48c29be801b1bb835a49 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+]>>CCOc1cc(C(CC(N)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O.C1=CN(C=N1)C(=O)N2C=CN=C2.[NH4+].[OH-]>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:29]([O:30][CH:31]([F:32])[F:33])[cH:28][cH:27]1)[N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]2[C:25]1=[O:26])=[O:11].[NH4+:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:10])=[O:11])[N:12]2... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+] | CCOc1cc(C(CC(N)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 80 | [{"value": 80.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionamide was prepared by the procedure of Example 6 from 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.5 g, 1.1 mmol), CDI (0.19 g, 1.2 mmol) and NH4OH (0.1 ml,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.[NH4+]>C1CCOC1>CCOc1cc(C(CC(N)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b4fb531082343fea372fd8b3eb17abf | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC>>CCOc1cc(C(CC(=O)N(C)C)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O.C1=CN(C=N1)C(=O)N2C=CN=C2.CNC>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH:33]([F:34])[F:35])[cH:30][cH:29]1)[N:14]1[C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[c:26]2[C:27]1=[O:28])=[O:10].[NH:11]([CH3:12])[CH3:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC | CCOc1cc(C(CC(=O)N(C)C)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 67 | [{"value": 67.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-N,N-dimethyl-propionamide was prepared by the procedure of example 13 from 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.5 g, 1.1 mmol), CDI (0.2 g, 0.1.3 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.CNC>C1CCOC1>CCOc1cc(C(CC(=O)N(C)C)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-523f5c9bddad4a31bde0b810e10c7b2a | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O.C1=CN(C=N1)C(=O)N2C=CN=C2.Cl.NO>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH:32]([F:33])[F:34])[cH:29][cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 50 | [{"value": 50.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.6, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)NO)C1=CC(=C(C=C1)OC(F)F)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-N-hydroxy-propionamide was prepared by the procedure of example 8 from 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.5 g, 1.1 mmol), CDI (0.2 g, 1.3 mmol) and hydro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F.NO>C1CCOC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44c5825a1a984ddc82117484029cae12 | CCOc1cc(C=O)ccc1OC(F)F.CS(C)(=O)=O.[Li][N]([Si](C)(C)C)[Si](C)(C)C>>CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F | C1CCOC1.FC(OC1=C(C=C(C=O)C=C1)OCC)F.[Li]N([Si](C)(C)C)[Si](C)(C)C.C1CCOC1.CS(=O)(=O)C.[Li]N([Si](C)(C)C)[Si](C)(C)C>>FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N)OCC)F | O=[CH:7][c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:16]([O:17][CH:18]([F:19])[F:20])[cH:15][cH:14]1.[CH3:9][S:10]([CH3:11])(=[O:12])=[O:13].[Li][N:8]([Si](C)(C)C)[Si](C)(C)C>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([NH2:8])[CH2:9][S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15][c:16]1[O:17][CH:18]([F:19])[F:20] | CCOc1cc(C=O)ccc1OC(F)F.CS(C)(=O)=O.[Li][N]([Si](C)(C)C)[Si](C)(C)C | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 618154013e24d9669ba7df9f8e7acde1fef6f7ec3c856cdef82bda134f4c3241 | 3fe2da536db38411cbae3d2f5c5613f71d964782a2cf29cab7c95c2d0f6c49d8 | c1ccccc1 | C-[Si](-C)(-C)-[N;H0;D3;+0:1](-[Li])-[Si](-C)(-C)-C.O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#16:7](-[CH3;D1;+0:8])(=[O;D1;H0:9])=[O;D1;H0:10]>>[C;D1;H3:6]-[#16:7](=[O;D1;H0:9])(=[O;D1;H0:10])-[CH2;D2;+0:8]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:3](:[c:4]):[c:5] | 10 | [{"value": 10.0, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.1, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To the THF solution (100 ml) of 4-difluoromethoxy-3-ethoxy-benzaldehyde (21.0 g, 0.1 mol) was added dropwise LiN(TMS)2 (1M in THF, 100 ml, 0.1 mol) at 0° C. After 15 minutes of stirring, BF3 THF complex (22 ml, 0.2 mol) was added to the reaction mixture (1). To the THF solution (100 ml) of methyl sulfone (9.4 g, 0.1 mo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amine.Silyl protective group.Silyl protective group | Primary amine | null | null | c1ccccc1 | HO-.Li | CO | null | 0.25 | CCOc1cc(C=O)ccc1OC(F)F.CS(C)(=O)=O.[Li][N]([Si](C)(C)C)[Si](C)(C)C>CO>CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-369d00d1b1a247dd9166d078e2cebea8 | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1>>CCOc1cc(C(CS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N)OCC)F.CCN(CC)CC.COC(C1=C(C=CC=C1NC(=O)C1CC1)CBr)=O>>FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[NH2:13])[cH:29][cH:30][c:31]1[O:32][CH:33]([F:34])[F:35].CO[C:27]([c:26]1[c:15]([CH2:14]Br)[cH:16][cH:17][cH:18][c:19]1[NH:20][C:21](=[O:22])[CH:23]1[CH2:24][CH2:25]1)=[O:28]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH... | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1 | CCOc1cc(C(CS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | CN(C)C=O | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[c:11])-[N;H0;D3;+0:10]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 30 | [{"value": 30.0, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.5, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To the DMF solution (20 ml) of 1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethylamine (0.80 g, 2.7 mmol) was added Et3N (1.6 ml, 12 mmol) followed by 2-bromomethyl-6-(cyclopropanecarbonyl-amino)-benzoic acid methyl ester (1.0 g, 3.2 mmol). The mixture was heated at 90° C. for 12 hours then cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | CN(C)C=O | 90 | null | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1>CN(C)C=O>CCOc1cc(C(CS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c83fbc343d5f4f7f87c0e5497d9d461c | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F>>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N)OCC)F.C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1.C(C)(=O)[O-].[Na+]>>FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F | O1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[NH2:13])[cH:28][cH:29][c:30]1[O:31][CH:32]([F:33])[F:34]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11... | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F | CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]-1:[c:12]>>[C:1]-[C:2](-[c:4])-[N;H0;D3;+0:3]1-[C;H0;D3;+0:6](=[O;D1;H0:5])-[c:11](:[c:12]):[c:9](:[c:10])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 402.8 | [{"value": 40.0, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 402.8, "product": "FC(OC1=C(C=C(C=C1)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-{2-[1-(4-Difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide was prepared by the procedure of example 4 from 1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethylamine (0.6 g, 0.2 mmol), 3-acetamido-phthalic anhydride (0.4 g, 0.2 mmol) and sodium acetate... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)O | null | null | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC(F)F>C(C)(=O)O>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10d0a8db4a35453e95ca9abc6f193d02 | CCOc1cc(C(CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+]>>CCOc1cc(C(CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C1=CN(C=N1)C(=O)N2C=CN=C2.[NH4+].[OH-]>>C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH:33]([F:34])[F:35])[cH:30][cH:29]1)[N:12]1[CH2:13][c:14]2[c:15]([Cl:16])[cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]1=[O:28])=[O:11].[NH4+:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:1... | CCOc1cc(C(CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+] | CCOc1cc(C(CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 20 | [{"value": 20.0, "product": "C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.9, "product": "C(N)(=O)CC(C1=CC(=C(C=C1)OC(F)F)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Cyclopropanecarboxylic acid {2-[2-carbamoyl-1-(4-difluoromethoxy-3-ethoxy-phenyl)-ethyl]-7-chloro-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide was prepared by the procedure of Example 6 from 3-[4-chloro-7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (0.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1CCOC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F.[NH4+]>C1CCOC1>CCOc1cc(C(CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b3ba999033c4e63acf2ce7a8ef5dff3 | C1COCCN1.CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)N2CCOCC2)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | O.N1CCOCC1.C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC)=O.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:34]([O:35][CH:36]([F:37])[F:38])[cH:33][cH:32]1)[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][c:24]([NH:25][C:26]([CH3:27])=[O:28])[c:29]2[C:30]1=[O:31])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]... | C1COCCN1.CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | CCOc1cc(C(CC(=O)N2CCOCC2)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CC(c1ccccc1)N1C(=O)c2ccccc2C1=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 44 | [{"value": 44.0, "product": "FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.5, "product": "FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (400 mg, 0.86 μmmol) in tetrahydrofurane was added carbonyldiimidazole (160 mg, 1 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture was added morp... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 2 | C1COCCN1.CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>O1CCCC1>CCOc1cc(C(CC(=O)N2CCOCC2)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3ae96d8307b418d8aef398a60f98e9f | C1COCCN1.CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>>CCOc1cc(C(CC(=O)N2CCOCC2)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | O.N1CCOCC1.C(C)(=O)NC=1C=CC=C2CN(C(C12)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OCC.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1CC2=CC=CC(=C2C1=O)NC(C)=O)OCC)F | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH:35]([F:36])[F:37])[cH:32][cH:31]1)[N:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([NH:24][C:25]([CH3:26])=[O:27])[c:28]2[C:29]1=[O:30])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8... | C1COCCN1.CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | CCOc1cc(C(CC(=O)N2CCOCC2)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CC(c1ccccc1)N1Cc2ccccc2C1=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 72.1 | [{"value": 72.0, "product": "FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1CC2=CC=CC(=C2C1=O)NC(C)=O)OCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "FC(OC1=C(C=C(C=C1)C(CC(=O)N1CCOCC1)N1CC2=CC=CC(=C2C1=O)NC(C)=O)OCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(7-acetylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid (300 mg, 0.67 mmol) in tetrahydrofurane was added carbonyldiimidazole (130 mg, 0.80 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture was added morpho... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 2 | C1COCCN1.CCOc1cc(C(CC(=O)O)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F>O1CCCC1>CCOc1cc(C(CC(=O)N2CCOCC2)N2Cc3cccc(NC(C)=O)c3C2=O)ccc1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c5180c44c8d4d3e9fc82971b7fbeea7 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O.CNC>>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O | O.CNC.C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)O)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O | O[C:16]([CH2:15][CH:14]([N:13]1[C:11](=[O:12])[c:10]2[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][c:9]2[C:35]1=[O:36])[c:21]1[cH:22][cH:23][c:24]([O:25][CH:26]([F:27])[F:28])[c:29]([O:30][CH:31]([F:32])[F:33])[cH:34]1)=[O:17].[NH:18]([CH3:19])[CH3:20]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:1... | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O.CNC | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O | null | null | O1CCCC1.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 55 | [{"value": 55.0, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "C(C)(=O)NC1=C2C(N(C(C2=CC=C1)=O)C(CC(=O)N(C)C)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 2 | HOUR | To a solution of 3-(4-acetylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(3,4-bis-difluoromethoxy-phenyl)-propionic acid (350 mg, 0.72 mmol) in tetrahydrofurane was added carbonyldiimidazole (175 mg, 1.08 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture was added dimet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | O1CCCC1.C1CCOC1 | null | 2 | CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)O)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O.CNC>O1CCCC1.C1CCOC1>CC(=O)Nc1cccc2c1C(=O)N(C(CC(=O)N(C)C)c1ccc(OC(F)F)c(OC(F)F)c1)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b8c45b165ab45dda851acf86774508c | COC(=O)CC(N)c1ccc(OC(F)F)c(OC(F)F)c1.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr>>COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2c(Cl)ccc(NC(=O)C3CC3)c2C1=O | COC(CC(C1=CC(=C(C=C1)OC(F)F)OC(F)F)N)=O.C(C)N(CC)CC.COC(C1=C(C(=CC=C1NC(=O)C1CC1)Cl)CBr)=O>>COC(CC(N1C(C2=C(C=CC(=C2C1)Cl)NC(=O)C1CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[c:15]([O:16][CH:17]([F:18])[F:19])[cH:20]1)[NH2:21].CO[C:36]([c:35]1[c:23]([CH2:22]Br)[c:24]([Cl:25])[cH:26][cH:27][c:28]1[NH:29][C:30](=[O:31])[CH:32]1[CH2:33][CH2:34]1)=[O:37]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH... | COC(=O)CC(N)c1ccc(OC(F)F)c(OC(F)F)c1.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr | COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2c(Cl)ccc(NC(=O)C3CC3)c2C1=O | null | null | CN(C)C=O | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[NH2;D1;+0:13])-[c:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[c:14])-[N;H0;D3;+0:13]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 17.2 | [{"value": 17.0, "product": "COC(CC(N1C(C2=C(C=CC(=C2C1)Cl)NC(=O)C1CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.2, "product": "COC(CC(N1C(C2=C(C=CC(=C2C1)Cl)NC(=O)C1CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 3-amino-3-(3,4-bis-difluoromethoxy-phenyl)-propionic acid methyl ester (50 mg, 0.16 mmol) and triethyl amine (0.09 ml, 3.1 mmol) in DMF (2 ml) was added 2-bromomethyl-3-chloro-6-(cyclopropanecarbonyl-amino)-benzoic acid methyl ester (67 mg, 0.19 mmol). The mixture was heated at 90° C. under nitrogen at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | CN(C)C=O | 90 | null | COC(=O)CC(N)c1ccc(OC(F)F)c(OC(F)F)c1.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr>CN(C)C=O>COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2c(Cl)ccc(NC(=O)C3CC3)c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-446fafb1ee064224abd7736ba3691682 | CNC.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>>CN(C)C(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | O.CNC.FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC(OC=1C=C(C=CC1OC(F)F)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F | [CH3:1][NH:2][CH3:3].O[C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[c:16]([O:17][CH:18]([F:19])[F:20])[cH:21]1)[N:22]1[CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]([NH:29][C:30](=[O:31])[CH:32]3[CH2:33][CH2:34]3)[c:35]2[C:36]1=[O:37]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH:7]([c:8... | CNC.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | CN(C)C(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | null | null | O1CCCC1.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 50 | [{"value": 50.0, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.2, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(N(C)C)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(3,4-bis-difluoromethoxy-phenyl)-3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-propionic acid (400 mg, 0.81 mmol) in tetrahydrofurane (10 ml) was added carbonyldiimidazole (200 mg, 1.21 mmol) at room temperature. The solution was stirred at room temperature for 2 hours. To the mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | O1CCCC1.C1CCOC1 | null | 2 | CNC.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>O1CCCC1.C1CCOC1>CN(C)C(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e62f2d29c07740cbae7255a825828135 | O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O.[NH4+]>>NC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | O.[OH-].[NH4+].FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC(OC=1C=C(C=CC1OC(F)F)C(CC(N)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F | O[C:2](=[O:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:13])[c:14]([O:15][CH:16]([F:17])[F:18])[cH:19]1)[N:20]1[CH2:21][c:22]2[cH:23][cH:24][cH:25][c:26]([NH:27][C:28](=[O:29])[CH:30]3[CH2:31][CH2:32]3)[c:33]2[C:34]1=[O:35].[NH4+:1]>>[NH2:1][C:2](=[O:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][C... | O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O.[NH4+] | NC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 57.3 | [{"value": 46.0, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(N)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(N)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(3,4-bis-difluoromethoxy-phenyl)-3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-propionic acid (400 mg, 0.81 mmol) in tetrahydrofurane was added carbonyldiimidazole (200 mg, 1.21 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | O1CCCC1 | null | 2 | O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O.[NH4+]>O1CCCC1>NC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fde2b0697e5940dfa135d2404847b75d | NO.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>>O=C(CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O)NO | O.NO.FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC(OC=1C=C(C=CC1OC(F)F)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F | [NH2:35][OH:36].O[C:2](=[O:1])[CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([F:11])[F:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18]1)[N:19]1[CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]3[CH2:30][CH2:31]3)[c:32]2[C:33]1=[O:34]>>[O:1]=[C:2]([CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([O:9][CH:1... | NO.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | O=C(CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O)NO | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 55.5 | [{"value": 46.0, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.5, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(3,4-bis-difluoromethoxy-phenyl)-3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-propionic acid (400 mg, 0.81 mmol) in tetrahydrofurane was added carbonyldiimidazole (200 mg, 1.21 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | O1CCCC1 | null | 2 | NO.O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>O1CCCC1>O=C(CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O)NO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0761fa093f24823a4245ebe120aca76 | COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>>O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | Cl.COC(CC(N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC(F)F)=O.[OH-].[Na+]>>FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F | C[O:3][C:2](=[O:1])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([F:12])[F:13])[c:14]([O:15][CH:16]([F:17])[F:18])[cH:19]1)[N:20]1[CH2:21][c:22]2[cH:23][cH:24][cH:25][c:26]([NH:27][C:28](=[O:29])[CH:30]3[CH2:31][CH2:32]3)[c:33]2[C:34]1=[O:35]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]... | COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | 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] | 70.5 | [{"value": 70.0, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "FC(OC=1C=C(C=CC1OC(F)F)C(CC(=O)O)N1C(C2=C(C=CC=C2C1)NC(=O)C1CC1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-(3,4-bis-difluoromethoxy-phenyl)-3-[7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-propionic acid methyl ester (2.0 g, 4 mmol) in tetrahydrofurane (20 ml) was added NaOH (0.8 ml of 10 N) at room temperature. The solution was stirred overnight at room temperature. The resulted suspens... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | Other | O1CCCC1.O | null | 8 | COC(=O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O>O1CCCC1.O>O=C(O)CC(c1ccc(OC(F)F)c(OC(F)F)c1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d66db81322d54060919d458613af4f4e | CCc1c(I)[nH]c(C=O)c1C(=O)OC.OB(O)c1ccc(F)cc1>>CCc1c(-c2ccc(F)cc2)[nH]c(C=O)c1C(=O)OC | C(C)C=1C(=C(NC1I)C=O)C(=O)OC.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].FC1=CC=C(C=C1)B(O)O>>FC1=CC=C(C=C1)C1=C(C(=C(N1)C=O)C(=O)OC)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH3:20])[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | CCc1c(I)[nH]c(C=O)c1C(=O)OC.OB(O)c1ccc(F)cc1 | CCc1c(-c2ccc(F)cc2)[nH]c(C=O)c1C(=O)OC | 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(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | 85 | CELSIUS | null | null | Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. To a solution of methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate (0.123 g, 0.40 mmol) in dimethoxyethane (4.0 mL) was added K3PO4 (0.426 g, 2.00 mmol), Pd(PPh3)4 (0.0463 g, 0.04 mmol), and 4-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(OC)COC | 85 | null | CCc1c(I)[nH]c(C=O)c1C(=O)OC.OB(O)c1ccc(F)cc1>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(OC)COC>CCc1c(-c2ccc(F)cc2)[nH]c(C=O)c1C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f56d8cdb74bd43b89e7e5dfe834e5229 | CCc1c(I)[nH]c(C=O)c1C(=O)OC.[Br][Zn][c]1cccs1>>CCc1c(-c2cccs2)[nH]c(C=O)c1C(=O)OC | C(C)C=1C(=C(NC1I)C=O)C(=O)OC.Br[Zn]C=1SC=CC1.CN1CCCC1>>C(C)C=1C(=C(NC1C=1SC=CC1)C=O)C(=O)OC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:14]([C:15](=[O:16])[O:17][CH3:18])[c:11]([CH:12]=[O:13])[nH:10]1.[Br][Zn][c:5]1[cH:6][cH:7][cH:8][s:9]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][s:9]2)[nH:10][c:11]([CH:12]=[O:13])[c:14]1[C:15](=[O:16])[O:17][CH3:18] | CCc1c(I)[nH]c(C=O)c1C(=O)OC.[Br][Zn][c]1cccs1 | CCc1c(-c2cccs2)[nH]c(C=O)c1C(=O)OC | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C | C1CCOC1 | C-C Coupling | Negishi coupling | d52f2edbc5daab81dce3af9a116562eb268929ce323f8b9094e4b472127d61ab | 2fa33fd5addc8f2395bff4f579b56f6ec2658c42e330172c5375bb77385dd09e | c1c[nH]c(-c2cccs2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].[Br]-[Zn]-[c;H0;D3;+0:12]1:[#16;a:13]:[c:14]:[c:15]:[c:16]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[#16;a:13]:[c:14]:[c:15]:[c:16]:2):[c:10]:1-[C:11] | null | [] | 100 | CELSIUS | null | null | Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. To a solution of methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate (0.123 g, 0.40 mmol) and bromo(thien-2-yl)zinc (0.1374 g, 0.60 mmol) in THF (2.0 mL) was added Pd(Pt-Bu3)2 (0.0123 g, 0.02 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Zinc halide | null | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1 | Br-.I-.Zn | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1CCOC1 | 100 | null | CCc1c(I)[nH]c(C=O)c1C(=O)OC.[Br][Zn][c]1cccs1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1CCOC1>CCc1c(-c2cccs2)[nH]c(C=O)c1C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f4d8741ddbd431a8594357909836278 | C#CC[Si](C)(C)C.CCc1c(I)[nH]c(C=O)c1C(=O)OC>>CCc1c(C#CC[Si](C)(C)C)[nH]c(C=O)c1C(=O)OC | CCN(C(C)C)C(C)C.C[Si](CC#C)(C)C.C(C)C=1C(=C(NC1I)C=O)C(=O)OC>>C(C)C=1C(=C(NC1C#CC[Si](C)(C)C)C=O)C(=O)OC | [CH:5]#[C:6][CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11].I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH3:20])[c:13]([CH:14]=[O:15])[nH:12]1>>[CH3:1][CH2:2][c:3]1[c:4]([C:5]#[C:6][CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11])[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | C#CC[Si](C)(C)C.CCc1c(I)[nH]c(C=O)c1C(=O)OC | CCc1c(C#CC[Si](C)(C)C)[nH]c(C=O)c1C(=O)OC | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[Cu]I | O1CCOCC1 | C-C Coupling | Sonogashira alkyne_aryl halide | 1533f4c85cc29a1add08a6b31ffb99d3f3e5a452d4488825854066d3a642b9b6 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cc[nH]c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].[C:12]-[C:13]#[CH;D1;+0:14]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:14]#[C:13]-[C:12]):[c:10]:1-[C:11] | null | [] | 80 | CELSIUS | 8 | HOUR | Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. Pd(Pt-Bu3)4 (18.4 mg, 0.040 mmol), Pd2(dba)3 (16.5 mg, 0.020 mmol), and CuI (4.6 mg, 0.020 mmol) were combined in a dry flask under N2 prior to evacuating the flask and refilling with argon. After the f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HI | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[Cu]I.O1CCOCC1 | 80 | 8 | C#CC[Si](C)(C)C.CCc1c(I)[nH]c(C=O)c1C(=O)OC>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[Cu]I.O1CCOCC1>CCc1c(C#CC[Si](C)(C)C)[nH]c(C=O)c1C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1121d71466f649fc845d9e78663978d0 | CC(C)(C)OC(=O)n1cccc1B(O)O.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2cccn2C(=O)OC(C)(C)C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C(C)(C)(C)OC(=O)N1C(=CC=C1)B(O)O>>C(C)C1=C(NC(=C1C(=O)OCC1=CC=CC=C1)C=O)C=1N(C=CC1)C(=O)OC(C)(C)C | OB(O)[c:5]1[cH:6][cH:7][cH:8][n:9]1[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].I[c:4]1[c:3]([CH2:2][CH3:1])[c:21]([C:22](=[O:23])[O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:18]([CH:19]=[O:20])[nH:17]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][n:9]2[C:10](=[O:11])[O:12][C:13]([CH3... | CC(C)(C)OC(=O)n1cccc1B(O)O.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1 | CCc1c(-c2cccn2C(=O)OC(C)(C)C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 039b811ef23d495da01184d6c5a30fbcde0426a5aabb14ba9b64e71653aecb29 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccc[nH]2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15]:[#7;a:16]:1-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20](-[C;D1;H3:21])(-[C;D1;H3:22])-[C;D1;H3:23]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid, the title compound was obtained. Proton NMR for the prod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc[nH]1.c1cc[nH]c1 | c1cc[nH]c1.c1ccc[nH]1 | c1cc[nH]c1.c1ccc[nH]1.c1ccccc1 | HI.B | null | null | null | CC(C)(C)OC(=O)n1cccc1B(O)O.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2cccn2C(=O)OC(C)(C)C)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2dc5bd1d16549e89b76f253ffe7b5ef | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1noc(C)c1B(O)O>>CCc1c(-c2c(C)noc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.CC1=NOC(=C1B(O)O)C>>CC1=NOC(=C1C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC)C | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[c:6]([CH3:7])[n:8][o:9][c:10]1[CH3:11]>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[c:6]([CH3:7])[n:8][o:9][c:10]2[CH3:11])[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1noc(C)c1B(O)O | CCc1c(-c2c(C)noc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | bbdd7f10acc6acad525e6606fb5b27d423aa7b051ba1677af511def6eb7b1b52 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2cnoc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[c:13](-[C;D1;H3:14]):[#8;a:15]:[#7;a:16]:[c:17]:1-[C;D1;H3:18]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[c:13](-[C;D1;H3:14]):[#... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3,5-dimethylisoxazol-4-ylboronic acid, the title compound was obtained. Proton NMR for the product was consi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1cnoc1 | c1cc[nH]c1.c1cnoc1 | c1cc[nH]c1.c1cnoc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1noc(C)c1B(O)O>>CCc1c(-c2c(C)noc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b32faa020ee47f284ec4b740507d9d3 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cc2ccccc2o1>>CCc1c(-c2cc3ccccc3o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.O1C(=CC2=C1C=CC=C2)B(O)O>>O1C(=CC2=C1C=CC=C2)C2=C(C(=C(N2)C=O)C(=O)OCC2=CC=CC=C2)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:18]([C:19](=[O:20])[O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:15]([CH:16]=[O:17])[nH:14]1.OB(O)[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[o:13]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[nH:14][c:15]([CH:16]=[O:17])[... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cc2ccccc2o1 | CCc1c(-c2cc3ccccc3o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 76deb476b47a61dff523ccb08a4d07b2dd91078d9338bcc7bf999c2d0f56be06 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2cc3ccccc3o2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[#8;a:13]:[c:14]:[c:15]:[c:16]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[#8;a:13]:[c:14]:[c:15]:[c:16]:2):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 1-benzofuran-2-ylboronic acid, the title compound was obtained. Proton NMR for the product was consistent wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccc2occc2c1 | c1cc[nH]c1.c1ccc2occc2c1 | c1cc[nH]c1.c1ccc2occc2c1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cc2ccccc2o1>>CCc1c(-c2cc3ccccc3o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e99f90fcbcd4a3bb1ebac1e8e78860e | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1cccc(B(O)O)c1>>CCc1c(-c2cccc([N+](=O)[O-])c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>C(C)C=1C(=C(NC1C1=CC(=CC=C1)[N+](=O)[O-])C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:18]([C:19](=[O:20])[O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:15]([CH:16]=[O:17])[nH:14]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]2)[nH:14][c:15]([CH:16]=... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1cccc(B(O)O)c1 | CCc1c(-c2cccc([N+](=O)[O-])c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-nitrophenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1cccc(B(O)O)c1>>CCc1c(-c2cccc([N+](=O)[O-])c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26361af314ce47278b8becb2705460fe | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccc(B(O)O)o1>>CCc1c(-c2ccc(C)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.CC1=CC=C(O1)B(O)O>>C(C)C=1C(=C(NC1C=1OC(=CC1)C)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:12]([CH:13]=[O:14])[nH:11]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([CH3:9])[o:10]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([CH3:9])[o:10]2)[nH:11][c:12]([CH:13]=[O:14])[c:15]1[C:16](=[O:17])[O:18][CH2:19][c:... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccc(B(O)O)o1 | CCc1c(-c2ccc(C)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 374151cd8562369a1eacee0395c9dc3923cf696b12fdea9ea1822d37a0f17591 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccco2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[#8;a:13]:[c:14]:[c:15]:[c:16]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[#8;a:13]:[c:14]:[c:15]:[c:16]:2):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 5-methyl-2-furylboronic acid, the title compound was obtained. Proton NMR for the product was consistent wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccoc1 | c1cc[nH]c1.c1ccoc1 | c1cc[nH]c1.c1ccoc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccc(B(O)O)o1>>CCc1c(-c2ccc(C)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54feba516f3c41c483dc887b65debd2c | CC(=O)Nc1cccc(B(O)O)c1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2cccc(NC(C)=O)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C(C)(=O)NC=1C=C(C=CC1)B(O)O>>C(C)(=O)NC=1C=C(C=CC1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14]1.I[c:4]1[c:3]([CH2:2][CH3:1])[c:19]([C:20](=[O:21])[O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:16]([CH:17]=[O:18])[nH:15]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14]2)[nH:15][... | CC(=O)Nc1cccc(B(O)O)c1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1 | CCc1c(-c2cccc(NC(C)=O)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-(acetylamino) phenylboronic acid, the title compound was obtained. Proton NMR for the product was consiste... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CC(=O)Nc1cccc(B(O)O)c1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2cccc(NC(C)=O)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef2f3a1ebf1c4899b9bf76d5b0421dab | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccncc1>>CCc1c(-c2ccncc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.N1=CC=C(C=C1)B(O)O>>C(C)C=1C(=C(NC1C1=CC=NC=C1)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:12]([CH:13]=[O:14])[nH:11]1.OB(O)[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[nH:11][c:12]([CH:13]=[O:14])[c:15]1[C:16](=[O:17])[O:18][CH2:19][c:20]1... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccncc1 | CCc1c(-c2ccncc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccncc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:2):[c:10]:... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with pyridin-4-ylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccncc1>>CCc1c(-c2ccncc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-620a021f7bc6475cbe5f1b7c69f198e9 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1>>CCc1c(-c2ccccc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C1(=CC=CC=C1)B(O)O>>C(C)C=1C(=C(NC1C1=CC=CC=C1)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:12]([CH:13]=[O:14])[nH:11]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[nH:11][c:12]([CH:13]=[O:14])[c:15]1[C:16](=[O:17])[O:18][CH2:19][c:20... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1 | CCc1c(-c2ccccc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with phenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with the titl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1>>CCc1c(-c2ccccc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d89e3ba291eb4e5abe388b511bd57ed3 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1cccc(B(O)O)c1>>CCc1c(-c2cccc(C#N)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C(#N)C=1C=C(C=CC1)B(O)O>>C(#N)C=1C=C(C=CC1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:14]([CH:15]=[O:16])[nH:13]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12]2)[nH:13][c:14]([CH:15]=[O:16])[c:17]1[C:18]... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1cccc(B(O)O)c1 | CCc1c(-c2cccc(C#N)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-cyanophenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1cccc(B(O)O)c1>>CCc1c(-c2cccc(C#N)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fb76d1d6aa24e4fa51edc2a01dff896 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1cccc(B(O)O)c1>>CCc1c(-c2cccc(OC)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.COC=1C=C(C=CC1)B(O)O>>C(C)C=1C(=C(NC1C1=CC(=CC=C1)OC)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:14]([CH:15]=[O:16])[nH:13]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12]2)[nH:13][c:14]([CH:15]=[O:16])[c:17]1[C:1... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1cccc(B(O)O)c1 | CCc1c(-c2cccc(OC)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-methoxyphenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1cccc(B(O)O)c1>>CCc1c(-c2cccc(OC)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbdd718c05dc4650abd401a673e26b63 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=Cc1ccc(B(O)O)o1>>CCc1c(-c2ccc(C=O)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C(=O)C1=CC=C(O1)B(O)O>>C(C)C=1C(=C(NC1C=1OC(=CC1)C=O)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[o:11]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([CH:9]=[O:10])[o:11]2)[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=Cc1ccc(B(O)O)o1 | CCc1c(-c2ccc(C=O)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 374151cd8562369a1eacee0395c9dc3923cf696b12fdea9ea1822d37a0f17591 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccco2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12]1:[#8;a:13]:[c:14](-[C:15]=[O;D1;H0:16]):[c:17]:[c:18]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[#8;a:13]:[c:14](-[C:15]=[O;D1;H0... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 5-formyl-2-furylboronic acid, the title compound was obtained. Proton NMR for the product was consistent wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccoc1 | c1cc[nH]c1.c1ccoc1 | c1cc[nH]c1.c1ccoc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=Cc1ccc(B(O)O)o1>>CCc1c(-c2ccc(C=O)o2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80261fd924414abf95d179aa81f56f3f | CC1(C)COB(c2ccccc2C#N)OC1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2ccccc2C#N)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.CC1(COB(OC1)C1=C(C#N)C=CC=C1)C>>C(#N)C1=C(C=CC=C1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | CC1(C)COB([c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]#[N:12])OC1.I[c:4]1[c:3]([CH2:2][CH3:1])[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:14]([CH:15]=[O:16])[nH:13]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]#[N:12])[nH:13][c:14]([CH:15]=[O:16])[c:17]1[... | CC1(C)COB(c2ccccc2C#N)OC1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1 | CCc1c(-c2ccccc2C#N)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 7c9717b7729071d12e25abaff1d8ae42c770ada58ba886a3864ee04298a7f2ec | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | C-C1(-C)-C-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7])-O-C-1.I-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13](-[C:14](-[#8:15])=[O;D1;H0:16]):[c:17]:1-[C:18]>>[#8:15]-[C:14](=[O;D1;H0:16])-[c:13]1:[c:10](-[C:11]=[O;D1;H0:12]):[#7;a:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the title compound was obtained. Proton NMR for the pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | B1OCCCO1.c1ccccc1.c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CC1(C)COB(c2ccccc2C#N)OC1.CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1>>CCc1c(-c2ccccc2C#N)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-184a1361dd3f491d84a315e3116c1f7b | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1ccc(B(O)O)cc1>>CCc1c(-c2ccc(C#N)cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.C(#N)C1=CC=C(C=C1)B(O)O>>C(#N)C1=CC=C(C=C1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:14]([CH:15]=[O:16])[nH:13]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]2)[nH:13][c:14]([CH:15]=[O:16])[c:17]1[C:18]... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1ccc(B(O)O)cc1 | CCc1c(-c2ccc(C#N)cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing of methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 4-cyanophenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.N#Cc1ccc(B(O)O)cc1>>CCc1c(-c2ccc(C#N)cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00101ddf8ec64b46b714b3e291d73cd7 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1ccc(B(O)O)cc1>>CCc1c(-c2ccc([N+](=O)[O-])cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>C(C)C=1C(=C(NC1C1=CC=C(C=C1)[N+](=O)[O-])C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:18]([C:19](=[O:20])[O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:15]([CH:16]=[O:17])[nH:14]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]2)[nH:14][c:15]([CH:16]=... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1ccc(B(O)O)cc1 | CCc1c(-c2ccc([N+](=O)[O-])cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 4-nitrophenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.O=[N+]([O-])c1ccc(B(O)O)cc1>>CCc1c(-c2ccc([N+](=O)[O-])cc2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3aa5289f9574daf9ff73783497d6299 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1ccccc1B(O)O>>CCc1c(-c2ccccc2OC)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.COC1=C(C=CC=C1)B(O)O>>C(C)C=1C(=C(NC1C1=C(C=CC=C1)OC)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:14]([CH:15]=[O:16])[nH:13]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH3:12]>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[O:11][CH3:12])[nH:13][c:14]([CH:15]=[O:16])[c:17]1[C:18](=... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1ccccc1B(O)O | CCc1c(-c2ccccc2OC)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[#8:16]):[c:17]>>[#8:16]-[c:15](:[c:17]):[c;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11]):[c:13]:... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 2-methoxyphenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.COc1ccccc1B(O)O>>CCc1c(-c2ccccc2OC)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-512f2c285af348039890eccf0d469ae4 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccccc1B(O)O>>CCc1c(-c2ccccc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.CC1=C(C=CC=C1)B(O)O>>C(C)C=1C(=C(NC1C1=C(C=CC=C1)C)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH3:11]>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH3:11])[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccccc1B(O)O | CCc1c(-c2ccccc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[C;D1;H3:16]):[c:17]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[C;D1;H3:16]):[c:17])... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 2-methylphenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1ccccc1B(O)O>>CCc1c(-c2ccccc2C)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64f79b0f235f498ba9e27323268453ee | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1cccc(B(O)O)c1>>CCc1c(-c2cccc(C)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.CC=1C=C(C=CC1)B(O)O>>C(C)C=1C(=C(NC1C1=CC(=CC=C1)C)C=O)C(=O)OCC1=CC=CC=C1 | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[cH:11]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[cH:11]2)[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1cccc(B(O)O)c1 | CCc1c(-c2cccc(C)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-methylphenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.Cc1cccc(B(O)O)c1>>CCc1c(-c2cccc(C)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1795a238ab044d039a53feaf0307ffc7 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1Cl>>CCc1c(-c2ccccc2Cl)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.ClC1=C(C=CC=C1)B(O)O>>ClC1=C(C=CC=C1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11]>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:19][... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1Cl | CCc1c(-c2ccccc2Cl)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[Cl;D1;H0:16]):[c:17]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[Cl;D1;H0:16]):[c:17... | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 2-chloro phenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1ccccc1Cl>>CCc1c(-c2ccccc2Cl)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9befa699efc4a7dbd35b8be590dfca5 | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cccc(Cl)c1>>CCc1c(-c2cccc(Cl)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | C(C)C=1C(=C(NC1I)C=O)C(=O)OCC1=CC=CC=C1.FC1=CC=C(C=C1)B(O)O.ClC=1C=C(C=CC1)B(O)O>>ClC=1C=C(C=CC1)C1=C(C(=C(N1)C=O)C(=O)OCC1=CC=CC=C1)CC | I[c:4]1[c:3]([CH2:2][CH3:1])[c:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:13]([CH:14]=[O:15])[nH:12]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[nH:12][c:13]([CH:14]=[O:15])[c:16]1[C:17](=[O:18])[O:... | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cccc(Cl)c1 | CCc1c(-c2cccc(Cl)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(OCc1ccccc1)c1c[nH]c(-c2ccccc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1-[C:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:3](-[C:4]=[O;D1;H0:5]):[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:10]:1-[C:11] | null | [] | null | null | null | null | Following the procedures described in Example 5, replacing methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate with benzyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate and 4-fluorophenylboronic acid with 3-chloro phenylboronic acid, the title compound was obtained. Proton NMR for the product was consistent with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CCc1c(I)[nH]c(C=O)c1C(=O)OCc1ccccc1.OB(O)c1cccc(Cl)c1>>CCc1c(-c2cccc(Cl)c2)[nH]c(C=O)c1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f997a64537a9492286b1717d5ad08c07 | O=P([O-])(O)O.O[C@H](CS)[C@H](O)CS.[Cl-].[K+]>>O=P([O-])(O)O.O=P([O-])([O-])O.[Cl-].[K+].[Na+].[Na+] | OP(=O)(O)[O-].[K+].[Na+].[Cl-].[Cl-].[K+].C([C@H]([C@@H](CS)O)O)S>>OP(=O)(O)[O-].OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Cl-].[K+].[K+] | [O:1]=[P:2]([O-:3])([OH:4])[OH:10].SC[C@H]([C@@H](CS)[OH:6])[OH:5].[Cl-:12].[K+:14]>>[O:1]=[P:2]([O-:3])([OH:4])[OH:5].[O:6]=[P:7]([O-:8])([O-:9])[OH:10].[Cl-:12].[K+:14].[Na+:16].[Na+:17] | O=P([O-])(O)O.O[C@H](CS)[C@H](O)CS.[Cl-].[K+] | O=P([O-])(O)O.O=P([O-])([O-])O.[Cl-].[K+].[Na+].[Na+] | null | null | null | Miscellaneous | OtherReaction | 0a63e9114770803282288223c11337ae7baf3adc31e7ceac59bd02ed19b8a7ad | 82b336b5814d8711671ec9af3a7734f888b7351ab18f076a5ea51b01bee25830 | null | S-C-[C@@H](-[OH;D1;+0:1])-[C@H](-[OH;D1;+0:2])-C-S.[O;-;D1;H0:3]-[P;H0;D4;+0:4](=[O;D1;H0:5])(-[O;D1;H1:6])-[OH;D1;+0:7]>>[O;-;D1;H0:8]-[#15:9](-[O;-;D1;H0:10])(=[O;H0;D1;+0:1])-[OH;D1;+0:7].[O;-;D1;H0:3]-[P;H0;D4;+0:4](=[O;D1;H0:5])(-[O;D1;H1:6])-[OH;D1;+0:2] | null | [] | null | null | null | null | 137 Mm NaCl, 2.6 mM KCl, 10 mM Na2HPO4, 1.8 mM KH2PO4, pH 7.4; 1 mM DTT; 1X protease inhibitor cocktail
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol.Aliphatic thiol.Aliphatic thiol | null | null | null | null | Other | null | null | null | O=P([O-])(O)O.O[C@H](CS)[C@H](O)CS.[Cl-].[K+]>>O=P([O-])(O)O.O=P([O-])([O-])O.[Cl-].[K+].[Na+].[Na+] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52b61003ae8d40ce80402b208ebd9ec3 | NC(=O)[C@@H](N)Cc1ccc(O)cc1>>c1ccc2[nH]cnc2c1 | N[C@@H](CC1=CC=C(C=C1)O)C(=O)N.Cl.C(C)N(CC)CC>>N1=CNC2=C1C=CC=C2 | O=[C:6]([C@H](C[c:1]1[cH:2][cH:3][c:4](O)[cH:8][cH:9]1)[NH2:5])[NH2:7]>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | NC(=O)[C@@H](N)Cc1ccc(O)cc1 | c1ccc2[nH]cnc2c1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 8122077837d574c1833e90acf44c3fd8221ff4c194f4f1f3e2c3974049e231a7 | 073fb5aa4cd15969a74799a193e5a035fb3eef58e311c8a52c655b67e20989e7 | c1ccc2[nH]cnc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-C-[C@H](-[NH2;D1;+0:5])-[C;H0;D3;+0:6](=O)-[NH2;D1;+0:7]):[c:8]:[cH;D2;+0:9]:1>>[c:3]1:[c:2]:[c;H0;D3;+0:1]2:[nH;D2;+0:5]:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[c;H0;D3;+0:9]:2:[c:8]:[cH;D2;+0:4]:1 | 72 | [{"value": 72.0, "product": "N1=CNC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a room temperature solution of intermediate 2 in anhydrous dioxane (200 mL) were added triethylamine (6 mL, 40 mmol) and tert-butyldimethylsilyltrifluoro methanesulfonate (8.6 g, 32 mmol). The resulting solution was then stirred overnight and quenched with saturated aqueous sodium bicarbonate solution. It was extrac... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | O1CCOCC1 | null | 8 | NC(=O)[C@@H](N)Cc1ccc(O)cc1>O1CCOCC1>c1ccc2[nH]cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9c1bce431ec4479a560518fb4274253 | N#CCN.O=C(c1ccccc1)c1ccccc1>>c1ccc2[nH]cnc2c1 | CCN(C(C)C)C(C)C.S(O)(O)(=O)=O.NCC#N.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1>>N1=CNC2=C1C=CC=C2 | [C:4](#[N:5])[CH2:8][NH2:7].O=[C:6](c1ccccc1)c1c[cH:3][cH:2][cH:1][cH:9]1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | N#CCN.O=C(c1ccccc1)c1ccccc1 | c1ccc2[nH]cnc2c1 | null | null | ClCCl | Miscellaneous | OtherReaction | b491fa558dc349d5b29598ff0bfa6d694df9fc42511902bdf0203eda9ea03e40 | 365be7bfd7417046e3b0e4817e7d90fe737a8d60cf7e6e5edfbdb62c2ea53baf | c1ccc2[nH]cnc2c1 | O=[C;H0;D3;+0:1](-c1:[cH;D2;+0:2]:[c:3]:[c:4]:[cH;D2;+0:5]:c:1)-c1:c:c:c:c:c:1.[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[CH2;D2;+0:8]-[NH2;D1;+0:9]>>[c:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:7]2:[nH;D2;+0:6]:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[c;H0;D3;+0:8]:2:[cH;D2;+0:2]:1 | 156,273.7 | [{"value": 82.0, "product": "N1=CNC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 156273.7, "product": "N1=CNC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of 2-aminoacetonitrile bisulfate (2.9 g, 0.013 mmol) in dichloromethane (50 mL) was added benzophenone (3.48 mL, 0.0208 mmol) followed by DIEA (4.53 mL, 0.026 mmol). After stirring 18 h, the dichloromethane solution was washed with water (50 mL), dried over sodium sulfate, filtered, and the filtra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine | null | c1ccccc1.c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | ClCCl | null | 18 | N#CCN.O=C(c1ccccc1)c1ccccc1>ClCCl>c1ccc2[nH]cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-013ab63fc14c465f86602ccbdd674b99 | CC(C)I.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.IC(C)C.C([O-])([O-])=O.[K+].[K+]>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | I[CH:10]([CH3:11])[CH3:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CC(C)I.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 100 | [{"value": 100.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of methyl 3-cyano-4-hydroxybenzoate (82 g, 463 mmol; J. Med. Chem, 2002, 45, 5769) in dimethylformamide (800 mL) was added 2-iodopropane (93 mL, 926 mmol) and potassium carbonate (190 g, 1.4 mol). The resulting mixture was heated at 50° C. for 16 h, at which time it was allowed to cool to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CN(C=O)C | 50 | null | CC(C)I.COC(=O)c1ccc(O)c(C#N)c1>CN(C=O)C>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69c03e72d9bd405aac2dea424d4025d4 | COC(=O)c1ccc(OC(C)C)c(C#N)c1>>CC(C)Oc1ccc(C(=O)O)cc1C#N | C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C.[OH-].[K+]>>C(#N)C=1C=C(C(=O)O)C=CC1OC(C)C | C[O:11][C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:13]([C:14]#[N:15])[cH:12]1)=[O:10]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]1[C:14]#[N:15] | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | CC(C)Oc1ccc(C(=O)O)cc1C#N | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 87 | [{"value": 87.0, "product": "C(#N)C=1C=C(C(=O)O)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "C(#N)C=1C=C(C(=O)O)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a cooled (0° C.) solution of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (100 g, 463 mmol) in tetrahydrofuran (500 mL) was added 10% potassium hydroxide (500 mL). The resulting solution was allowed to warm to room temperature and maintained for 16 h, at which time it was concentrated to remove the tetrahydrofuran.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O1CCCC1 | null | 2 | COC(=O)c1ccc(OC(C)C)c(C#N)c1>O1CCCC1>CC(C)Oc1ccc(C(=O)O)cc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35fbad4d62654a16af7fbd074cf502cf | CC(C)(C)OC(=O)N[C@H](CCO)Cc1ccc(Br)cc1>>N[C@H](CCO)Cc1ccc(Br)cc1 | BrC1=CC=C(C=C1)C[C@@H](CCO)NC(OC(C)(C)C)=O.Cl.O1CCOCC1>>Cl.N[C@H](CCO)CC1=CC=C(C=C1)Br | CC(C)(C)OC(=O)[NH:2][C@H:3]([CH2:4][CH2:5][OH:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[NH2:2][C@H:3]([CH2:4][CH2:5][OH:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CC(C)(C)OC(=O)N[C@H](CCO)Cc1ccc(Br)cc1 | N[C@H](CCO)Cc1ccc(Br)cc1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 94 | [{"value": 94.0, "product": "Cl.N[C@H](CCO)CC1=CC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1,1-Dimethylethyl {(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}carbamate (4.4 g, 12.8 mmol) was dissolved in 4N HCl/dioxane (20 mL). After 2 h, the reaction mixture was concentrated in vacuo to give 3.69 g (94%) of the title compound as a white solid. LC/MS (ES) m/e 244.0 (M+H)+.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | null | null | 2 | CC(C)(C)OC(=O)N[C@H](CCO)Cc1ccc(Br)cc1>>N[C@H](CCO)Cc1ccc(Br)cc1 |
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