dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7c3fa07821a4acd950e43369bfa1625 | COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1C=NC=CC1)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O.Cl>>N1=CC(=CC=C1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]1[C:18](=[O:19])[O:20]C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]1[C:18](=[O:19])[OH:20] | COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC | O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2cccnc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-[(Pyridin-3-ylmethyl)-amino]-phthalic acid dimethyl ester (0.91 g, 3.03 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid except the pH of crude reaction mixture was adjusted to 2–3 by dropwise addition of concentrated HCl. The solvent was then evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | null | null | null | COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80159be2392144d09e216792dc61590b | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4cccnc4)c3C2=O)C(=O)N1 | N1=CC(=CC=C1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1C=NC=CC1)=O)=O | COCCNc1cccc2c1C(=O)[N:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:27][C:25]1=[O:26])C2=O.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[c:22]1[C:23](O)=[O:24]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O | O=C1CCC(N2C(=O)c3cccc(NCc4cccnc4)c3C2=O)C(=O)N1 | null | null | CO.C(C)(=O)OCC | Acylation | OtherReaction | 5b97b2716363c7d076f525a81453119f9bd234e3df60a591fce8a07715532192 | b34812891aa4b14ae9732f1e94ebf3683240312475d27c2db2c5e5699f26030f | O=C1CCC(N2C(=O)c3cccc(NCc4cccnc4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]=[O;D1;H0:8])-C-2=O.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](-[C;H0;D3;+0:14](-O)=[O;D1;H0:15]):[c:16]>>[C:3]-[C:2](-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:16])-[C;H0;D3;+0:14]-1... | 46 | [{"value": 46.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1C=NC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[(Pyridin-3-ylmethyl)-amino]-phthalic acid (3.03 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was slurried in 50% methanol/ethyl acetate (20 ml) for 18 h to give 0.50 g (46%) of product ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HO- | CO.C(C)(=O)OCC | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccnc2)c1C(=O)O>CO.C(C)(=O)OCC>O=C1CCC(N2C(=O)c3cccc(NCc4cccnc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfdcbcc015a04d30a1e301c24a11ffe6 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(C(=O)O)o1>>COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC | C(=O)C1=CC=C(O1)C(=O)O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O.C(=O)(O)[O-].[Na+]>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)C(=O)O)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]1[C:21](=[O:22])[O:23][CH3:24].O=[CH:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[o:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[o:19]2)[c:20]1[C:21](=[O... | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(C(=O)O)o1 | COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2ccco2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]):[c:3] | null | [] | null | null | null | null | 5-Formyl-furan-2-carboxylic acid (1 g, 7.14 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester except the combined aqueous NaHCO3 extracts were washed with methylene chloride (1×70 ml) and the pH adjusted to 2–3 by dropwise addition of concentrated HC... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccoc1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(C(=O)O)o1>>COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a080fa42b94c4d4aa5467f846ef27407 | COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC>>O=C(O)c1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)C(=O)O)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>C(=O)(O)C1=CC=C(O1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:17][C:15]([c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][CH2:8][c:7]2[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[o:22]2)[c:18]1[C:19](=[O:20])[O:21]C)=[O:16]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[c:18]2[C:19](=[O:20])[OH:21])[o:22]1 | COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC | O=C(O)c1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2ccco2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-[(5-Carboxy-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.90 g, 2.70 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purifica... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccoc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cccc(NCc2ccc(C(=O)O)o2)c1C(=O)OC>>O=C(O)c1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b56ed8791a944129a68e40b13317ed46 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.Cc1cc(C=O)oc1C>>COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC | CC=1C=C(OC1C)C=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=C(C1)C)C)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:19]1[C:20](=[O:21])[O:22][CH3:23].O=[CH:11][c:12]1[cH:13][c:14]([CH3:15])[c:16]([CH3:17])[o:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][c:14]([CH3:15])[c:16]([CH3:17])[o:18]2)[c:19]1[C:20](=[O:21])[O:22... | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.Cc1cc(C=O)oc1C | COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2ccco2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]):[c:3] | 75 | [{"value": 75.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=C(C1)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4,5-Dimethyl-furan-2-carbaldehyde (0.98 ml, 8 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by chromatography (SiO2, 10% ethyl acetate/hexanes) to give 0.95 g (75%) of product as a yellow oil: 1H NMR (CDCl3) δ 7.32... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccoc1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.Cc1cc(C=O)oc1C>>COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cfa84e91e6c94d06b8e67c3313c14f77 | COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC>>Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=C(C1)C)C)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>CC=1C=C(OC1C)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:14][C:12]([c:11]1[cH:10][cH:9][cH:8][c:7]([NH:6][CH2:5][c:4]2[cH:3][c:2]([CH3:1])[c:20]([CH3:21])[o:19]2)[c:15]1[C:16](=[O:17])[O:18]C)=[O:13]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[c:15]2[C:16](=[O:17])[OH:18])[o:19][c:20]1[CH3:21] | COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC | Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2ccco2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-[(4,5-Dimethyl-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.95 g, 3 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purifica... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccoc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cccc(NCc2cc(C)c(C)o2)c1C(=O)OC>>Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c6b1c3d12724d2c8737b896e74c04dc | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C>>Cc1cc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)oc1C | CC=1C=C(OC1C)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>CC=1C=C(OC1C)CNC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | COCCNc1cccc2c1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25].O=C(O)[c:11]1[cH:10][cH:9][cH:8][c:7]([NH:6][CH2:5][c:4]2[cH:3][c:2]([CH3:1])[c:27]([CH3:28])[o:26]2)[c:12]1C(=O)O>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[C:13](=[O:14])... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C | Cc1cc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)oc1C | null | null | null | C-C Coupling | OtherReaction | e01b406c4bd6fd113e0f2e1f0fbdfa1994fad43c14b9a159b5c537e52be3a29d | 47dba274a38dfe0abc81230fe8a80653f556b2eb304748f9abffbd031c5d793d | O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7])-[C;H0;D3;+0:8]-2=[O;D1;H0:9].O-C(=O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14](-[#7:15]):[c;H0;D3;+0:16]:1-C(-O)=O>>[#7:7]-[C:5](=[O;D1;H0:6])-[C:4]-[#7:3]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:16]2:[c:14](-[#7:15]):... | 22 | [{"value": 22.0, "product": "CC=1C=C(OC1C)CNC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[(4,5-Dimethyl-furan-2-ylmethyl)-amino]-phthalic acid (3 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was purified by preparative HPLC (Symmetry C18, isocratic, 40% acetonitrile/water) t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2.c1ccccc1 | c1ccc2c(c1)C[NH]C2 | c1ccoc1.c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | null | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1cc(CNc2cccc(C(=O)O)c2C(=O)O)oc1C>>Cc1cc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)oc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-824e5a7e96704e8592397388d933559a | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cc2ccccc2o1>>COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC | O1C(=CC2=C1C=CC=C2)C=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC2=C(C1)C=CC=C2)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:21]1[C:22](=[O:23])[O:24][CH3:25].O=[CH:11][c:12]1[cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[o:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[c:21]1... | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cc2ccccc2o1 | COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2cc3ccccc3o2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]):[c:3] | 83 | [{"value": 83.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC2=C(C1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzofuran-2-carbaldehyde (1.17 ml, 8 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by chromatography (SiO2, 50% methylene chloride/hexane) to give 1.12 g (83%) of product as a yellow oil: 1H NMR (CDCl3) δ 7.50–7.4... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccc2occc2c1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cc2ccccc2o1>>COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bf4a66bcb92491d9327c32bce841ed3 | COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC2=C(C1)C=CC=C2)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>O1C(=CC2=C1C=CC=C2)CNC2=C(C(C(=O)O)=CC=C2)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[o:19]2)[c:20]1[C:21](=[O:22])[O:23]C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[o:19]2)[c:20]1[C:21](=[O:22])[OH:23] | COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC | O=C(O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2cc3ccccc3o2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 3-[(Benzofuran-2-ylmethyl)-amino]-phthalic acid dimethyl ester (1.12 g, 3.3 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purification.
... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccc2occc2c1 | Other | null | null | null | COC(=O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cc3ccccc3o2)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50cf84589f7c499782957520107cf0c1 | CC1(N)CCC(=O)NC1=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O>>CC1(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O | ClC=1C=C(CNC2=C(C(C(=O)O)=CC=C2)C(=O)O)C=CC1.Cl.NC1(C(NC(CC1)=O)=O)C>>ClC=1C=C(CNC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1 | [CH3:1][C:2]1([NH2:3])[CH2:23][CH2:24][C:25](=[O:26])[NH:27][C:28]1=[O:29].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]2)[c:20]1[C:21](O)=[O:22]>>[CH3:1][C:2]1([N:3]2[C:4](=[O:5])[c:6]3[cH:7][cH:8][cH:9][c:10]([NH:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][... | CC1(N)CCC(=O)NC1=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O | CC1(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 03989296fe7fd00d3061010c1aadbbfb4b9eaa9ca91856790fffb1e1bf4b4c50 | b7eb222f11e89f2ccff57aab9a5106ae4173f0ba94ac518e1a9f3b22a378531d | O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8].[C:9]-[C:10](-[C;D1;H3:11])(-[NH2;D1;+0:12])-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16]=[O;D1;H0:17]>>[C:9]-[C:10](-[C;D1;H3:11])(-[N;H0;D3;+0:12]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[... | 41 | [{"value": 41.0, "product": "ClC=1C=C(CNC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "ClC=1C=C(CNC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 3-(3-Chloro-benzylamino)-phthalic acid (4 mmol) in pyridine (50 ml) was added 3-amino-3-methyl-piperidine-2,6-dione hydrochloride (0.71 g, 4 mmol). The reaction mixture was heated to reflux for 18 h. The solvent was evaporated in vacuo and the residue dissolved in methylene chloride (150 ml). T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1CCNCC1 | HO- | N1=CC=CC=C1 | null | null | CC1(N)CCC(=O)NC1=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O>N1=CC=CC=C1>CC1(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1cc65329f18949559358be5e5faca254 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1cccc(Cl)c1>>O=C1CCC(N2Cc3c(NCc4cccc(Cl)c4)cccc3C2=O)C(=O)N1 | C(Cl)Cl.CO.ClC=1C=C(C=O)C=CC1.NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC=1C=C(CNC2=C3CN(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)C=CC1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH2:10])[cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[C:25](=[O:26])[NH:27]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH:10][CH2:11][c:12]4[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]4... | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1cccc(Cl)c1 | O=C1CCC(N2Cc3c(NCc4cccc(Cl)c4)cccc3C2=O)C(=O)N1 | null | null | C(C)(=O)O.C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2Cc3c(NCc4ccccc4)cccc3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 31.3 | [{"value": 31.0, "product": "ClC=1C=C(CNC2=C3CN(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.3, "product": "ClC=1C=C(CNC2=C3CN(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-(4-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (1.04 g, 4 mmol) was dissolved in acetic acid (7 ml) with heat. The mixture was cooled slightly and methylene chloride (50 ml) was added slowly followed by 3-chlorobenzaldehyde (0.91 ml, 8 mmol) and sodium triacetoxyborohydride (2.54 g, 12 mmol). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCNCC1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | C(C)(=O)O.C(Cl)Cl | null | 2 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1cccc(Cl)c1>C(C)(=O)O.C(Cl)Cl>O=C1CCC(N2Cc3c(NCc4cccc(Cl)c4)cccc3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-285cbc720c8f452cbfe1d2b20c8ade69 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CCCC1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCC4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.[N+](=O)([O-])C1=CC=C(C=C1)N(C([O-])=O)C1CCCC1>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.O=[N+]([O-])c1ccc([N:18]([C:16]([O-])=[O:17])[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)cc1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12]... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CCCC1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCC4)c3C2=O)C(=O)N1 | null | null | C(C)#N | Acylation | OtherReaction | c544444e833963de17b7285ecf254c119edba4524de2ca959e1686976f0aeaf8 | 75a79f455fef00f73470f8263f7f62d9ceebfd06076631fa20de1d0098d3252f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCC4)c3C2=O)C(=O)N1 | O=[N+](-[O-])-c1:c:c:c(-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4])-[C;H0;D3;+0:5](-[O-])=[O;D1;H0:6]):c:c:1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[C:3]-[C:2](-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[c:9])-[C:4] | 27.1 | [{"value": 27.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.9 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in acetonitrile (50 mL). After stirring for 20 min, 4-nitrophenyl-N-cyclopentylcarbamate (0.44 g, 1.85 mmol) was added. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Nitro group.Primary amine | Urea | c1ccccc1 | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | C(C)#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CCCC1>C(C)#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14435ce5619b43098a6af1585e7826cd | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Nc1cccnc1)ON1C(=O)CCC1=O>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.O=C1N(C(CC1)=O)OC(=O)NC=1C=NC=CC1>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC=1C=NC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:25]3[C:26]2=[O:27])[C:28](=[O:29])[NH:30]1.O=C1CCC(=O)N1O[C:16](=[O:17])[NH:18][c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Nc1cccnc1)ON1C(=O)CCC1=O | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | null | null | C(C)#N | Acylation | OtherReaction | b72231f0ce68d14b82c0b5dc8e77bb0358ffec1497faa29a27840d8959aefbc2 | 943dda93229373d8af3aaa08ae8db106d934de8921eb40cdbdad7b33a1554bea | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4]:[c:5]:[#7;a:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[#7;a:6]:[c:5]:[c:4]-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:8]-[c:9] | 30.5 | [{"value": 30.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC=1C=NC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.5, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC=1C=NC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.9 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in acetonitrile (50 mL). After stirring for 20 min, (2,5-dioxopyrrolidinyloxy)-N-(3-pyridyl)carboxamide (0.44 g, 1.85 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Tertiary amide.Tertiary amide.Primary amine | Urea | C1CCNC1 | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HO- | C(C)#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Nc1cccnc1)ON1C(=O)CCC1=O>C(C)#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dfb46c1d0d3403ba8b916c2274dc7e4 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | Cl.CCOCC.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC=1C=NC=CC1)=O)=O>>Cl.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC=1C=NC=CC1)=O)=O | [O:2]=[C:3]1[CH2:4][CH2:5][CH:6]([N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[NH:19][c:20]4[cH:21][cH:22][cH:23][n:24][cH:25]4)[c:26]3[C:27]2=[O:28])[C:29](=[O:30])[NH:31]1>>[O:2]=[C:3]1[CH2:4][CH2:5][CH:6]([N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([CH2:15][NH:16][C:1... | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | null | null | CO.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 | null | null | [] | null | null | 2 | HOUR | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.9 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in acetonitrile (50 mL). After stirring for 20 min, (2,5-dioxopyrrolidinyloxy)-N-(3-pyridyl)carboxamide (0.44 g, 1.85 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | CO.C(C)(=O)OCC | null | 2 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1>CO.C(C)(=O)OCC>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4cccnc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b92f50d6bca4235a268ecf58899edd0 | C1CCNCC1.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)N4CCCCC4)c3C2=O)C(=O)N1 | C(C)(C)N(CC)C(C)C.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.N1CCCCC1.C(C)(C)N(CC)C(C)C.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N1CCCCC1)=O)=O | [NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1.[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.ClC(Cl)(Cl)O[C:16](OC(Cl)(Cl)Cl)=[O:17]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][... | C1CCNCC1.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=C1CCC(N2C(=O)c3cccc(CNC(=O)N4CCCCC4)c3C2=O)C(=O)N1 | null | null | C(C)#N | Acylation | OtherReaction | 075e010aa242d893511507e9999273f6e4aaf78621d38d5b583bb121b24aa032 | a171696b7de78dbbbc9cc830c802d29643daeae80133889bf27fba2e22ed8263 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)N4CCCCC4)c3C2=O)C(=O)N1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[c:10])-[C:6]-[C:7] | 145.3 | [{"value": 53.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N1CCCCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 145.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N1CCCCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Diisopropylethylamine (0.88 g, 6.79 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (1.0 g, 3.09 mmol) in acetonitrile (50 mL). After stirring for 20 min, the mixture was slowly added to a stirred solution of triphosgene (0.34 g, 1.14 mmol) in ace... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine.Secondary amine | Urea | C1CCNCC1 | C1CC[NH]CC1 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1 | HCl | C(C)#N | null | 0.333333 | C1CCNCC1.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C(C)#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)N4CCCCC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-515a075d965b456ab2907b2f8edaf345 | CI.Cc1c(Br)cccc1C(=O)O>>COC(=O)c1cccc(Br)c1C | BrC=1C(=C(C(=O)O)C=CC1)C.C([O-])(O)=O.[Na+].IC>>BrC=1C(=C(C(=O)OC)C=CC1)C | I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[CH3:12] | CI.Cc1c(Br)cccc1C(=O)O | COC(=O)c1cccc(Br)c1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 103.3 | [{"value": 100.0, "product": "BrC=1C(=C(C(=O)OC)C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.3, "product": "BrC=1C(=C(C(=O)OC)C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 3-bromo-2-methylbenzoic acid (16 g, 74.4 mmol), sodium bicarbonate (12.5 g, 148.8 mmol) and iodomethane (21.2 g, 148.8 mmol) in DMF (160 mL) was heated at 60° C. for 2 hours. The mixture was cooled to room temperature and poured into ice water (400 mL). The mixture was extracted with ethyl acetate (4×100 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | CN(C)C=O | 60 | null | CI.Cc1c(Br)cccc1C(=O)O>CN(C)C=O>COC(=O)c1cccc(Br)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b650c99db20d4ba6b8fdcb17dc1d1211 | COC(=O)c1cccc(Br)c1C.O=C1CCC(=O)N1Br>>COC(=O)c1cccc(Br)c1CBr | BrC=1C(=C(C(=O)OC)C=CC1)C.BrN1C(CCC1=O)=O>>BrC=1C(=C(C(=O)OC)C=CC1)CBr | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[CH3:12].O=C1CCC(=O)N1[Br:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[CH2:12][Br:13] | COC(=O)c1cccc(Br)c1C.O=C1CCC(=O)N1Br | COC(=O)c1cccc(Br)c1CBr | null | null | C(C)#N | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 107.2 | [{"value": 97.0, "product": "BrC=1C(=C(C(=O)OC)C=CC1)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.2, "product": "BrC=1C(=C(C(=O)OC)C=CC1)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of methyl 3-bromo-2-methylbenzoate (17.0 g, 74.22 mmol) and N-bromosuccinimide (15.85 g, 89.06 mmol) in acetonitrile (200 mL) was heated under gently refluxing for 17 hours while a 200 W bulb situated 2 cm away was shining on the reaction flask. The mixture was cooled to room temperature and solvent was remov... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C)#N | null | null | COC(=O)c1cccc(Br)c1C.O=C1CCC(=O)N1Br>C(C)#N>COC(=O)c1cccc(Br)c1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c41d82aef6e44542b9d45c4257b7c152 | CC(C)(C)OC(=O)[C@@H](N)CCC(N)=O.COC(=O)c1cccc(Br)c1CBr>>CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O | C(C)N(CC)CC.BrC=1C(=C(C(=O)OC)C=CC1)CBr.Cl.C(C)(C)(C)OC([C@@H](N)CCC(N)=O)=O>>BrC1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[NH2:14].CO[C:23]([c:22]1[c:16]([CH2:15]Br)[c:17]([Br:18])[cH:19][cH:20][cH:21]1)=[O:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[N:14]1[CH2:15][c:16]2[c:17]([Br:18])[cH:... | CC(C)(C)OC(=O)[C@@H](N)CCC(N)=O.COC(=O)c1cccc(Br)c1CBr | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O | null | null | C1CCOC1 | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1NCc2ccccc21 | 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;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[C@@H;D3;+0:15](-[NH2;D1;+0:16])-[C:17]-[C:18]-[C:19](-[N;D1;H2:20])=[O;D1;H0:21]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[CH... | 48 | [{"value": 48.0, "product": "BrC1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "BrC1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triethylamine (4.66 g, 46.09 mmol) was added to a stirred suspension of methyl 3-bromo-2-bromomethylbenzoate (6.45 g, 20.95 mmol) and L-glutamine t-butyl ester hydrochloride (5.0 g, 20.95 mmol) in THF (100 mL). The mixture was heated to reflux for 18 hours. The mixture was cooled to room temperature and solvent was rem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HBr | C1CCOC1 | null | null | CC(C)(C)OC(=O)[C@@H](N)CCC(N)=O.COC(=O)c1cccc(Br)c1CBr>C1CCOC1>CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb213946227849cba6cbc5d842b1724b | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O>>CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O | CCOC(=O)C.C(=O)(O)[O-].[Na+].BrC1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O.CN(C)C=O>>C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O | Br[c:17]1[c:16]2[c:23]([cH:22][cH:21][cH:20]1)[C:24](=[O:25])[N:14]([CH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[CH2:15]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[N:14]1[CH2:15][c:16]2[c:17]([C:18]#[N:19])[cH:20][c... | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O | null | [Zn].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].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | null | Miscellaneous | OtherReaction | ff84fc4da928bc1dae741694660e3ab081edc2d6809ac065b8295fbc7c4a2cdf | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=C1NCc2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-1>>[N;D1;H0:10]#[C:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-1 | 74 | [{"value": 74.0, "product": "C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of tert-butyl 2-(4-bromo-1-oxoisoindolin-2-yl)-4-carbamoylbutanoate (1.2 g, 3.02 mmol), zinc cyamide (0.21 g, 1.81 mmol), tris(dibenzylideneacetone)dipalladium (0.06 g, 0.06 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.067 g, 0.12 mmol) in deoxygenated DMF (15 mL) was heated to 120° C. under N2 for 6 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | Br- | [Zn].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].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | 120 | null | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(Br)cccc2C1=O>[Zn].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].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2]>CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04120459d0214e5091aa46bf4c7477b0 | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O>>N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O | C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)OC(C)(C)C)CCC(N)=O.FC(C(=O)O)(F)F>>C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)O)CCC(N)=O | CC(C)(C)[O:19][C:17]([CH:11]([N:10]1[CH2:9][c:8]2[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][c:7]2[C:20]1=[O:21])[CH2:12][CH2:13][C:14]([NH2:15])=[O:16])=[O:18]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][N:10]([CH:11]([CH2:12][CH2:13][C:14]([NH2:15])=[O:16])[C:17](=[O:18])[OH:19])[C:20]2=[O:21] | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O | N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NCc2ccccc21 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)O)CCC(N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)O)CCC(N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of tert-butyl 2-(4-cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoate (1.0 g, 2.91 mmol) and trifluoroacetic acid (5 mL) was stirred for 2 hours. The mixture was concentrated and the residue was crystallized from ether (15 mL) to give 2-(4-cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acid (0.74 g, 89%) as a ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2c(c1)C[NH]C2 | Other | null | null | 2 | CC(C)(C)OC(=O)C(CCC(N)=O)N1Cc2c(C#N)cccc2C1=O>>N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a02a6eb08b5a43b8897cae94a49cff54 | N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O>>N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | C(#N)C1=C2CN(C(C2=CC=C1)=O)C(C(=O)O)CCC(N)=O>>O=C1NC(CCC1N1C(C=2C=CC=C(C2C1)C#N)=O)=O | O[C:17]([CH:11]([N:10]1[CH2:9][c:8]2[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][c:7]2[C:19]1=[O:20])[CH2:12][CH2:13][C:14](=[O:15])[NH2:16])=[O:18]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][N:10]([CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[NH:16][C:17]1=[O:18])[C:19]2=[O:20] | N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O | N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | null | null | C(C)#N | Miscellaneous | OtherReaction | 52c2be58e438dca32d8dfc2407dae12033d4d53c2248553cbdbd9b07dc6fc54c | ba17a8a91d881b019f9339558c9ed531b2e73dd4a7c4d7050727d51dac58dc25 | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7]-[C:8]-[C:9](-[NH2;D1;+0:10])=[O;D1;H0:11]>>[O;D1;H0:11]=[C:9]1-[C:8]-[C:7]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-1 | 83 | [{"value": 83.0, "product": "O=C1NC(CCC1N1C(C=2C=CC=C(C2C1)C#N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "O=C1NC(CCC1N1C(C=2C=CC=C(C2C1)C#N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-cyano-1-oxoisoindolin-2-yl)-4carbamoylbutanoic acid (0.6 g, 2.09 mmol) and 1,1-carbonyldiimidazole (0.44 g, 2.72 mmol) in acetonitrile (20 mL) was heated to reflux for 2 hours. The mixture was cooled to room temperature and filtered to give 2-(2,6-dioxo(3-piperidyl))-1-oxoisoindoline-4-carbonitrile (0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide | Unsubstituted dicarboximide | null | C1CCNCC1 | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | C(C)#N | null | null | N#Cc1cccc2c1CN(C(CCC(N)=O)C(=O)O)C2=O>C(C)#N>N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6604bbee49d413db01a10987e483767 | N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>>NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | O=C1NC(CCC1N1C(C=2C=CC=C(C2C1)C#N)=O)=O.Cl>>Cl.NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O | [N:2]#[C:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][N:11]([CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17][C:18]1=[O:19])[C:20]2=[O:21]>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][N:11]([CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17][C:18]1=[O:19])[C:20]2=[O:21] | N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | null | [Pd] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 99 | [{"value": 99.0, "product": "Cl.NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of 2-(2,6-dioxo(3-piperidyl))-1-oxoisoindoline-4-carbonitrile (1.0 g, 3.71 mmol) and 10% Pd/C (0.2 g) in 4N HCl (20 mL) and methanol (600 mL) was hydrogenated at 50 psi for 17 hours. The mixture was filtered through celite and the filtrate was concentrated. The residue was stirred with ether (30 mL) to give 3... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | [Pd].CO | null | 17 | N#Cc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>[Pd].CO>NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e0049b47acb409b9843b0b579786509 | NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1>>O=C1CCC(N2Cc3c(CNC(=O)C4CC4)cccc3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.C1(CC1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)C1CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([CH2:10][NH2:11])[cH:17][cH:18][cH:19][c:20]3[C:21]2=[O:22])[C:23](=[O:24])[NH:25]1.Cl[C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([CH2:10][NH:11][C:12](=[O:13])[CH:14]4[CH2:15][CH2:16]4)[cH:17][cH:18][cH:19... | NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1 | O=C1CCC(N2Cc3c(CNC(=O)C4CC4)cccc3C2=O)C(=O)N1 | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2Cc3c(CNC(=O)C4CC4)cccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[C:3]1-[C:4]-[C:5]-1 | 50.2 | [{"value": 50.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)C1CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.7 g, 4.62 mmol) was added to a stirred suspension of 3-[4-(aminomethyl)-1-oxoisoindolin-2-yl]piperidine-2,6-dione hydrochloride (0.65 g, 2.10 mmol) in acetonitrile (50 mL). After stirring for 30 min, cyclopropanecarbonyl chloride (0.24 g, 2.31 mmol) was added. The mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.C1CC1.c1ccc2c(c1)C[NH]C2 | HCl | C(C)#N | null | 0.5 | NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1>C(C)#N>O=C1CCC(N2Cc3c(CNC(=O)C4CC4)cccc3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-265838542203460ba52244619f8d3caf | CCN=C=O.NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>>CCNC(=O)NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.C(C)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)NCC)=O)=O | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[N... | CCN=C=O.NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | CCNC(=O)NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 42 | [{"value": 42.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)NCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(=O)NCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.44 g, 2.91 mmol) was added to a stirred suspension of 3-[4-(aminomethyl)-1-oxoisoindolin-2-yl]piperidine-2,6-dione hydrochloride (0.6 g, 1.94 mmol) in acetonitrile (50 mL). After stirring for 30 min, ethyl isocyanate (0.21 g, 2.91 mmol) was added. The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | C(C)#N | null | 0.5 | CCN=C=O.NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>C(C)#N>CCNC(=O)NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64b4a14edf7a46439a5c7511642b0ba2 | COC(=O)c1c(F)cccc1I.C[C@@H](NC(=O)OC(C)(C)C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1>>COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)OC(C)(C)C)cc1 | CC1(OB(OC1(C)C)C1=CC=C(C=C1)[C@@H](C)NC(OC(C)(C)C)=O)C.FC1=C(C(=O)OC)C(=CC=C1)I.C([O-])([O-])=O.[K+].[K+].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C>>C(C)(C)(C)OC(=O)N[C@H](C)C1=CC=C(C=C1)C=1C(=C(C=CC1)F)C(=O)OC | I[c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([F:7])[cH:8][cH:9][cH:10]1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15]([C@@H:16]([CH3:17])[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]2)OC1(C)C>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][c:15]([C@@H... | COC(=O)c1c(F)cccc1I.C[C@@H](NC(=O)OC(C)(C)C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)OC(C)(C)C)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1CCOC1.CCOC(=O)C.O | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccccc2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]):[c:14]>>[C;D1;H3:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 18.9 | [{"value": 18.9, "product": "C(C)(C)(C)OC(=O)N[C@H](C)C1=CC=C(C=C1)C=1C(=C(C=CC1)F)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of tert-butyl (1R)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (1.0 g, 2.9 mmol) and methyl 2-fluoro-6-iodobenzoate (1.2 g, 4.32 mmol) in 25 mL of a 5:1 THF:water mixture was added potassium carbonate (1.2 g, 8.64 mmol), tri-o-tolylphosphine (350 mg, 1.15 mmol) and last... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccccc1.B1OCCO1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.CCOC(=O)C.O | null | null | COC(=O)c1c(F)cccc1I.C[C@@H](NC(=O)OC(C)(C)C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.CCOC(=O)C.O>COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62a465eb4b2d4de2a03a1d9082e584b5 | COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1>>C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 | C(C)(C)(C)OC(=O)NC1(CC1)C(=O)N[C@H](C)C1=CC=C(C=C1)C=1C(=C(C=CC1)F)C(=O)OC>>NC1(CC1)C(=O)N[C@H](C)C1=CC=C(C=C1)C=1C(=C(C=CC1)F)C(=O)O | CC(C)(C)OC(=O)[NH:7][C:6]1([C:4]([NH:3][C@H:2]([CH3:1])[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([F:19])[c:20]3[C:21](=[O:22])[O:23]C)[cH:24][cH:25]2)=[O:5])[CH2:8][CH2:9]1>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[C:6]1([NH2:7])[CH2:8][CH2:9]1)[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][... | COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1 | C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Reduction | OtherReaction | 45ba1145533a4eb33085691a140a7d6c44cd27a48c5f512bc6db74fad0776eee | 227a9aafd021a1d701cc8df6de581eabea9da00b568a3611c608252ac09b2fe2 | O=C(NCc1ccc(-c2ccccc2)cc1)C1CC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1(-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6])-[C:7]-[C:8]-1.C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]1(-[NH2;D1;+0:1])-[C:7]-[C:8]-1.[O;D1;H0:11]=[C:10](-[OH;D1;+0:9])-[c:12] | null | [] | null | null | null | null | A solution of methyl 4′-{(1R)-1-[({1-[(tert-butoxycarbonyl)amino]-cyclopropyl}carbonyl)amino]ethyl}-3-fluoro-1,1′-biphenyl-2-carboxylate (466 mg, 1.0 mmol) in DCM (15 mL) and TFA (15 mL) was stirred under N2 for 20 minutes at ambient temperature, then the organic solvent was removed under vacuum. The residue was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Carboxylic acid.Primary amine | null | null | C1CC1.c1ccccc1.c1ccccc1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | null | COC(=O)c1c(F)cccc1-c1ccc([C@@H](C)NC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1>C(=O)(C(F)(F)F)O.C(Cl)Cl>C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd2ed1d732e747bca66ca981bc217465 | C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1.O=C(O)CC(F)(F)F>>C[C@@H](NC(=O)C1(NC(=O)CC(F)(F)F)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 | FC(CC(=O)O)(F)F.Cl.C(C)N=C=NCCCN(C)C.ON1N=NC2=C1N=CC=C2.NC1(CC1)C(=O)N[C@H](C)C1=CC=C(C=C1)C=1C(=C(C=CC1)F)C(=O)O.C(C)(C)N(C(C)C)CC>>FC1=C(C(=CC=C1)C1=CC=C(C=C1)[C@@H](C)NC(=O)C1(CC1)NC(CC(F)(F)F)=O)C(=O)O | [CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[C:6]1([NH2:7])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][c:25]([F:26])[c:27]2[C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O[C:8](=[O:9])[CH2:10][C:11]([F:12])([F:13])[F:14]>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[C:6]1([NH:7][C:8](=[O:9])[CH2:10][C:11]([F:12])... | C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1.O=C(O)CC(F)(F)F | C[C@@H](NC(=O)C1(NC(=O)CC(F)(F)F)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccc(-c2ccccc2)cc1)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]1(-[NH2;D1;+0:13])-[C:14]-[C:15]-1>>[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]1(-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])-[C:14]-[C:15]-1 | null | [] | null | null | 20 | MINUTE | To a solution of trifluoropropionic acid (128 mg, 1.0 mmol) in DCM (1 mL), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (229 mg, 1.2 mmol) and 1-hydroxy-7-azabenzotriazole (136 mg, 1.0 mmol) were added. The resulting solution was stirred at room temperature for 20 minutes, then 4′-((1R)-1-{[(1-aminocyclopr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.333333 | C[C@@H](NC(=O)C1(N)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1.O=C(O)CC(F)(F)F>C(Cl)Cl>C[C@@H](NC(=O)C1(NC(=O)CC(F)(F)F)CC1)c1ccc(-c2cccc(F)c2C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ae0c0d393cb48bfbc9062688fae2658 | COC(=O)c1ccccc1I.N#Cc1ccc(B(O)O)cc1>>COC(=O)c1ccccc1-c1ccc(C#N)cc1 | O.C([O-])([O-])=O.[K+].[K+].IC1=C(C(=O)OC)C=CC=C1.C(#N)C1=CC=C(C=C1)B(O)O>>C(#N)C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC | I[c:10]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1 | COC(=O)c1ccccc1I.N#Cc1ccc(B(O)O)cc1 | COC(=O)c1ccccc1-c1ccc(C#N)cc1 | null | [Pd](Cl)Cl.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:[c:3] | 86 | [{"value": 86.0, "product": "C(#N)C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To 500 mL of THF was added water (18.4 mL, 1.02 mol), potassium carbonate (70.5 g, 0.510 mol), methyl 2-iodobenzoate (53.5 g, 0.204 mol), 4-cyano-phenylboronic acid (30.0 g, 0.204 mol) and bis-(tri-o-tolylphosphine) palladium (II) chloride (1.65 g, 2.04 mmol). This mixture was heated to reflux for 3.5 hours and then co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HI.B | [Pd](Cl)Cl.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1CCOC1 | null | 8 | COC(=O)c1ccccc1I.N#Cc1ccc(B(O)O)cc1>[Pd](Cl)Cl.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1CCOC1>COC(=O)c1ccccc1-c1ccc(C#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-efb62edd7ac24fc0b072a8bc9da1cb21 | COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1>>COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1 | C(C)(C)(C)OC(=O)NC1(CC1)C(=O)NCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC.Cl>>NC1(CC1)C(=O)NCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC | CC(C)(C)OC(=O)[NH:20][C:19]1([C:17]([NH:16][CH2:15][c:14]2[cH:13][cH:12][c:11](-[c:10]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]3)[cH:24][cH:23]2)=[O:18])[CH2:21][CH2:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[C:19]2([NH... | COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1 | COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1 | null | null | CO.C(Cl)(Cl)Cl.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(NCc1ccc(-c2ccccc2)cc1)C1CC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1(-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6])-[C:7]-[C:8]-1>>[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]1(-[NH2;D1;+0:1])-[C:7]-[C:8]-1 | null | [] | 0 | CELSIUS | 30 | MINUTE | Methyl 4′-{[({1-[(tert-butoxycarbonyl)amino]cyclopropyl}carbonyl)-amino]methyl}-1,1′-biphenyl-2-carboxylate (0.84 g, 2.0 mmol) dissolved in a mixture of DCM (3 mL) and MeOH (45 mL) was cooled to 0° C. This homogenous solution was saturated with anhydrous hydrogen chloride and allowed to sit for 30 minutes. Dry nitrogen... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.C1CC1 | HO- | CO.C(Cl)(Cl)Cl.C(Cl)Cl | 0 | 0.5 | COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(NC(=O)OC(C)(C)C)CC2)cc1>CO.C(Cl)(Cl)Cl.C(Cl)Cl>COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea24b883e61146ae966eb07d2c1926f9 | CI.COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1>>CNC1(C(=O)NCc2ccc(-c3ccccc3C(=O)OC)cc2)CC1 | IC.IC.C(C)N(CC)CC.NC1(CC1)C(=O)NCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC>>CNC1(CC1)C(=O)NCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC | I[CH3:1].[NH2:2][C:3]1([C:4](=[O:5])[NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18](=[O:19])[O:20][CH3:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][NH:2][C:3]1([C:4](=[O:5])[NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18](=[O:19])[O:20][... | CI.COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1 | CNC1(C(=O)NCc2ccc(-c3ccccc3C(=O)OC)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 3c2788b3f372b76c1d2ee0d77963cb247b210aa8a28e76637b4e731826c4252a | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | O=C(NCc1ccc(-c2ccccc2)cc1)C1CC1 | I-[CH3;D1;+0:1].[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1(-[NH2;D1;+0:7])-[C:8]-[C:9]-1>>[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1(-[NH;D2;+0:7]-[CH3;D1;+0:1])-[C:8]-[C:9]-1 | 34.8 | [{"value": 34.8, "product": "CNC1(CC1)C(=O)NCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 4′-({[(1-aminocyclopropyl)carbonyl]amino}methyl)-1,1′-biphenyl-2-carboxylate (200 mg, 0.62 mmol), prepared according to Example 1, was dissolved in 5 mL of DCM along with iodomethane (130 mg, 0.93 mmol) and triethylamine (75 mg, 0.74 mmol). After no reaction was observed at ambient temperature, the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CC1 | HI | C(Cl)Cl | null | null | CI.COC(=O)c1ccccc1-c1ccc(CNC(=O)C2(N)CC2)cc1>C(Cl)Cl>CNC1(C(=O)NCc2ccc(-c3ccccc3C(=O)OC)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-896f0cb194bc4ec183ff7cc5a01dfa5a | O=C(CC(F)(F)F)NC1(C(=O)[O-])CC1>>O=C(CC(F)(F)F)NC1(C(=O)O)CC1 | FC(CC(=O)NC1(CC1)C(=O)[O-])(F)F>>FC(CC(=O)NC1(CC1)C(=O)O)(F)F | [O:1]=[C:2]([CH2:3][C:4]([F:5])([F:6])[F:7])[NH:8][C:9]1([C:10](=[O:11])[O-:12])[CH2:13][CH2:14]1>>[O:1]=[C:2]([CH2:3][C:4]([F:5])([F:6])[F:7])[NH:8][C:9]1([C:10](=[O:11])[OH:12])[CH2:13][CH2:14]1 | O=C(CC(F)(F)F)NC1(C(=O)[O-])CC1 | O=C(CC(F)(F)F)NC1(C(=O)O)CC1 | null | null | FC(C(=O)O)(F)F.C(Cl)Cl | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | C1CC1 | [C:1]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4]>>[C:1]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:3] | null | [] | null | null | 3.5 | HOUR | tert-Butyl (±)-cis-(acetyloxy)methyl]-1-[(3,3,3-trifluoropropanoyl)-amino]cyclopropane carboxylate (489 mg, 1.44 mmol) was dissolved in a mixture of 4 mL of methylene chloride and 1.22 mL of trifluoroacetic acid. The reaction mixture was allowed to stir at ambient temperature for 3.5 hours. The solvents were removed in... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | C1CC1 | null | FC(C(=O)O)(F)F.C(Cl)Cl | null | 3.5 | O=C(CC(F)(F)F)NC1(C(=O)[O-])CC1>FC(C(=O)O)(F)F.C(Cl)Cl>O=C(CC(F)(F)F)NC1(C(=O)O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0300c97a88a5417abebd157852f56576 | N[C@@]12C[C@H]1COC2=O.O=C(O)CC(F)(F)F>>O=C(CC(F)(F)F)N[C@@]12C[C@H]1COC2=O | C(C)N=C=NCCCN(C)C.N[C@@]12C(OC[C@@H]2C1)=O.FC(CC(=O)O)(F)F.OC1=CC=CC=2NN=NC21>>FC(CC(=O)N[C@@]12C(OC[C@@H]2C1)=O)(F)F | [NH2:8][C@@:9]12[CH2:10][C@H:11]1[CH2:12][O:13][C:14]2=[O:15].O[C:2](=[O:1])[CH2:3][C:4]([F:5])([F:6])[F:7]>>[O:1]=[C:2]([CH2:3][C:4]([F:5])([F:6])[F:7])[NH:8][C@@:9]12[CH2:10][C@H:11]1[CH2:12][O:13][C:14]2=[O:15] | N[C@@]12C[C@H]1COC2=O.O=C(O)CC(F)(F)F | O=C(CC(F)(F)F)N[C@@]12C[C@H]1COC2=O | null | null | O.CN(C=O)C.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1OC[C@@H]2CC12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[NH2;D1;+0:8]-[C:9]12-[C:10]-[C:11]-1-[C:12]-[#8:13]-[C:14]-2=[O;D1;H0:15]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]12-[C:10]-[C:11]-1-[C:12]-[#8:13]-[C:14]-2=[O;D1;H0:15] | 45 | [{"value": 45.0, "product": "FC(CC(=O)N[C@@]12C(OC[C@@H]2C1)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one (128 mg, 1.13 mmol) was mixed with 3,3,3-trifluoropropionic acid in 2.3 mL of N,N-dimethylformamide. Hydroxybenzotriazole (17.4 mg, 0.11 mmol) was added followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol). The pH of the reaction mixture was adju... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1OC[C@H]2C[C@@H]12 | HO- | O.CN(C=O)C.C(C)N(CC)CC | null | 2 | N[C@@]12C[C@H]1COC2=O.O=C(O)CC(F)(F)F>O.CN(C=O)C.C(C)N(CC)CC>O=C(CC(F)(F)F)N[C@@]12C[C@H]1COC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-816f4cc57baa49938806dfe8822092c7 | COC(=O)C(=O)NC1(C(=O)NCc2ccc(-c3cccc(F)c3C(=O)OC)cc2F)CC1.N>>COC(=O)c1c(F)cccc1-c1ccc(CNC(=O)C2(NC(=O)C(N)=O)CC2)c(F)c1 | FC1=C(C(=CC=C1)C1=CC(=C(C=C1)CNC(=O)C1(CC1)NC(C(=O)OC)=O)F)C(=O)OC.N>>NC(C(=O)NC1(CC1)C(=O)NCC1=C(C=C(C=C1)C=1C(=C(C=CC1)F)C(=O)OC)F)=O | CO[C:24]([C:22]([NH:21][C:20]1([C:18]([NH:17][CH2:16][c:15]2[cH:14][cH:13][c:12](-[c:11]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([F:7])[cH:8][cH:9][cH:10]3)[cH:31][c:29]2[F:30])=[O:19])[CH2:27][CH2:28]1)=[O:23])=[O:26].[NH3:25]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][c... | COC(=O)C(=O)NC1(C(=O)NCc2ccc(-c3cccc(F)c3C(=O)OC)cc2F)CC1.N | COC(=O)c1c(F)cccc1-c1ccc(CNC(=O)C2(NC(=O)C(N)=O)CC2)c(F)c1 | null | null | CO.C(Cl)Cl | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(NCc1ccc(-c2ccccc2)cc1)C1CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9].[NH3;D0;+0:10]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](-[NH2;D1;+0:10])=[O;D1;H0:2] | null | [] | null | null | 4 | HOUR | To a solution of methyl 3,3′-difluoro-4′-({[(1-{[methoxy(oxo)acetyl]-amino}cyclopropyl)carbonyl]amino}methyl)-1,1′-biphenyl-2-carboxylate (0.02 g, 0.045 mmol, Example 5) in methylene chloride (2 mL) at room temperature was added ammonia (0.224 mL of a 2M solution in methanol, 0.45 mmol). The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1.c1ccccc1.C1CC1 | HO- | CO.C(Cl)Cl | null | 4 | COC(=O)C(=O)NC1(C(=O)NCc2ccc(-c3cccc(F)c3C(=O)OC)cc2F)CC1.N>CO.C(Cl)Cl>COC(=O)c1c(F)cccc1-c1ccc(CNC(=O)C2(NC(=O)C(N)=O)CC2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca7acc999d4a4b90bdd5cd77f7621709 | COC(=O)c1ccc(CN(C)c2ccc(CO)cc2)cc1>>c1ccc2c(c1)Cc1ccccc1C2 | COC(C1=CC=C(C=C1)CN(C)C1=CC=C(C=C1)CO)=O.CNC.B(Cl)(Cl)Cl.S(O)(O)(=O)=O.[Na+].[Cl-].O>>C1=CC=CC=2CC3=CC=CC=C3CC12 | COC(=O)[c:11]1[cH:10][cH:9][c:8]([CH2:7]N(C)[c:4]2[cH:3][cH:2][c:1]([CH2:14]O)[cH:6][cH:5]2)[cH:13][cH:12]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14]2 | COC(=O)c1ccc(CN(C)c2ccc(CO)cc2)cc1 | c1ccc2c(c1)Cc1ccccc1C2 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 24875f989a02a0e8ed47062214ddf8d1effa61ce7a9813c0d049c846185ed9fd | e277919e1aafa02f374213d4ce654b318607078b6d21fa2b9646a7f1a106a457 | c1ccc2c(c1)Cc1ccccc1C2 | C-O-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-N(-C)-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c;H0;D3;+0:9](-[CH2;D2;+0:10]-O):[c:11]:[cH;D2;+0:12]:2):[cH;D2;+0:13]:[c:14]:1>>[CH2;D2;+0:10]1-[c;H0;D3;+0:13]2:[c:14]:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:2-[CH2;D2;+0:5]-[c;H0;D3;+0:12]2:[c:11]:[cH;D2;+0:9]:[c:8]:[c:7]:[c;H0;D3;... | null | [] | null | null | 8 | HOUR | To an ice cold solution of 4-{[(4-hydroxymethyl-phenyl)-methyl-amino]-methyl}-benzoic acid methyl ester (0.5 g, 1.8 mmol) and 3-isopropenyl-phenyl)-dimethyl-amine (0.31 g, 1.9 mmol) in methylene chloride (CH2Cl2, 25 mL)) is added dropwise a solution of boron trichloride (1 M BCl3 in CH2Cl2, 2 mL). The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Tertiary amine | null | c1ccccc1.c1ccccc1 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | HO- | C(Cl)Cl | null | 8 | COC(=O)c1ccc(CN(C)c2ccc(CO)cc2)cc1>C(Cl)Cl>c1ccc2c(c1)Cc1ccccc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d406d35cc3c140e4a123a0c440055f56 | CCNc1cc(O)ccc1C.O=C1OC(=O)c2cccc3cccc1c23>>CCN=c1cc2oc3cc(NCC)c(C)cc3c(-c3cccc4cccc(C(=O)O)c34)c-2cc1C | C(C)NC=1C=C(C=CC1C)O.C1(OC(C2=C3C(C=CC=C13)=CC=C2)=O)=O>>C(C)NC=1C=C2OC3=CC(C(=CC3=C(C2=CC1C)C=1C=CC=C2C=CC=C(C12)C(=O)O)C)=NCC | [CH3:1][CH2:2][NH:3][c:10]1[cH:9][c:8]([OH:7])[cH:17][cH:16][c:14]1[CH3:15].O=[C:13]1[c:19]2[cH:20][cH:21][cH:5][c:23]3[cH:4][cH:25][cH:26][c:27]([c:31]23)[C:28](=[O:29])[O:30]1>>[CH3:1][CH2:2][N:3]=[c:4]1[cH:5][c:6]2[o:7][c:8]3[cH:9][c:10]([NH:11][CH2:12][CH3:13])[c:14]([CH3:15])[cH:16][c:17]3[c:18](-[c:19]3[cH:20][cH... | CCNc1cc(O)ccc1C.O=C1OC(=O)c2cccc3cccc1c23 | CCN=c1cc2oc3cc(NCC)c(C)cc3c(-c3cccc4cccc(C(=O)O)c34)c-2cc1C | null | null | S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | eaf25e694d975ade044b44f23f6f6c65eba320d6471b6318df8b5e33ed6c7026 | f268f7a9729df6beedb2bc7244fb0bb1587af36ab26414ff5f6af869c9b6e262 | N=c1ccc2c(-c3cccc4ccccc34)c3ccccc3oc-2c1 | O=[C;H0;D3;+0:1]1-[O;H0;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]2:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]3:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c;H0;D3;+0:13]-1:[c:14]:2:3.[C;D1;H3:15]-[c:16]1:[c:17]:[cH;D2;+0:18]:[c:19](-[OH;D1;+0:20]):[c:21]:[c;H0;D3;+0:22]:1-[NH;D2;+0:23]-[C:24]-[C;D1;H3:25]>>[C;D1;H3:15]-[c:16]1:[c... | 10.8 | [{"value": 10.8, "product": "C(C)NC=1C=C2OC3=CC(C(=CC3=C(C2=CC1C)C=1C=CC=C2C=CC=C(C12)C(=O)O)C)=NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-Ethylamino-4-methyl-phenol (0.3 g, 2 mmol) and benzo[de]isochromene-1,3-dione (0.2 g, 1 mmol) in sulfuric acid (3 ml) was heated to 150° C. over a period of 6 h. The reaction mixture was pouring into crushed ice, allowed to stand over a period of 1 h and the precipitate was filtered. The filtrate was neutralized with... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Aromatic alcohol.Secondary amine | Carboxylic acid.Secondary amine | c1ccccc1.c1cc2c3c(cccc3c1)COC2 | c1ccc2oc3ccccc3cc2c1.c1ccc2ccccc2c1 | c1ccc2oc3ccccc3cc2c1.c1ccc2ccccc2c1 | null | S(O)(O)(=O)=O | null | 1 | CCNc1cc(O)ccc1C.O=C1OC(=O)c2cccc3cccc1c23>S(O)(O)(=O)=O>CCN=c1cc2oc3cc(NCC)c(C)cc3c(-c3cccc4cccc(C(=O)O)c34)c-2cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be133789f7474c46b372ca0c93b11f4e | COC=CC(=O)OC.N#CCc1ccc(C(F)(F)F)cc1Cl>>COC(=O)CC=C(C#N)c1ccc(C(F)(F)F)cc1Cl | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CC(C)([O-])C.[Na+].COC=CC(=O)OC.ClC1=C(C=CC(=C1)C(F)(F)F)CC#N>>COC(CC=C(C#N)C1=C(C=C(C=C1)C(F)(F)F)Cl)=O | CO[CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4].[CH2:7]([C:8]#[N:9])[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]=[C:7]([C:8]#[N:9])[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20] | COC=CC(=O)OC.N#CCc1ccc(C(F)(F)F)cc1Cl | COC(=O)CC=C(C#N)c1ccc(C(F)(F)F)cc1Cl | null | null | O1CCCC1 | C-C Coupling | OtherReaction | fdddd73459c44dd061e5b0d164cb9263de91417572ff4635a7371dcacf4bf859 | 26edb75ca4fecc789f6954d66c05aca32f0909f151ad47629af47ca81bad4cf7 | c1ccccc1 | C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:2]-[CH;D2;+0:1]=[C;H0;D3;+0:9](-[C:8]#[N;D1;H0:7])-[c:10](:[c:11]):[c:12] | 97.3 | [{"value": 97.0, "product": "COC(CC=C(C#N)C1=C(C=C(C=C1)C(F)(F)F)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "COC(CC=C(C#N)C1=C(C=C(C=C1)C(F)(F)F)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | To a solution of sodium tert-butoxide (3.28 g, 34.2 mmol) in tetrahydrofuran (20 mL) at 0° C. was added a solution of methyl 3-methoxyacrylate (2.65 g, 22.8 mmol) and (2-chloro-4-trifluoromethyl-phenyl)-acetonitrile (5.00 g, 22.8 mmol) in tetrahydrofuran (20 mL) dropwise over 45 minutes. The red solution was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester | null | null | c1ccccc1 | HO- | O1CCCC1 | 0 | 3 | COC=CC(=O)OC.N#CCc1ccc(C(F)(F)F)cc1Cl>O1CCCC1>COC(=O)CC=C(C#N)c1ccc(C(F)(F)F)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68c186e6a50c440999f7304d9c1dd3e5 | COC=CC(=O)OC.N#CCc1ccccc1Br>>COC(=O)CC=C(C#N)c1ccccc1Br | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.BrC1=C(C=CC=C1)CC#N.COC(C=COC)=O.CC(C)([O-])C.[Na+]>>COC(CC=C(C#N)C1=C(C=CC=C1)Br)=O | CO[CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4].[CH2:7]([C:8]#[N:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Br:16]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]=[C:7]([C:8]#[N:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Br:16] | COC=CC(=O)OC.N#CCc1ccccc1Br | COC(=O)CC=C(C#N)c1ccccc1Br | null | null | C(C)(C)(C)OC.O1CCCC1 | C-C Coupling | OtherReaction | fdddd73459c44dd061e5b0d164cb9263de91417572ff4635a7371dcacf4bf859 | 26edb75ca4fecc789f6954d66c05aca32f0909f151ad47629af47ca81bad4cf7 | c1ccccc1 | C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:2]-[CH;D2;+0:1]=[C;H0;D3;+0:9](-[C:8]#[N;D1;H0:7])-[c:10](:[c:11]):[c:12] | 99.5 | [{"value": 96.0, "product": "COC(CC=C(C#N)C1=C(C=CC=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "COC(CC=C(C#N)C1=C(C=CC=C1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-bromo-phenylacetonitrile (6.62 mL, 51.0 mmol) and methyl-3-methoxyacrylate (5.32 mL, 49.5 mmol) in tetrahydrofuran (10 ml) was added to a suspension of sodium tert-butoxide (5.05 g, 51.0 mmol) in tetrahydrofuran (70 mL) at 0° C. over 10 minutes under a stream of nitrogen. The reaction mixture was warmed... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester | null | null | c1ccccc1 | HO- | C(C)(C)(C)OC.O1CCCC1 | null | null | COC=CC(=O)OC.N#CCc1ccccc1Br>C(C)(C)(C)OC.O1CCCC1>COC(=O)CC=C(C#N)c1ccccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-764b14b9941241a4aa26e7910f5f2e10 | CCOC=CC(=O)OCC.N#CCc1ccccc1Br>>N#CC1=CC(=C2OCCO2)c2ccccc21 | S(O)(O)(=O)=O.CC(C)([O-])C.[Na+].BrC1=C(C=CC=C1)CC#N.C(C)OC(C=COCC)=O>>O1C(OCC1)=C1C=C(C2=CC=CC=C12)C#N | CC[O:10][C:6]([CH:5]=[CH:4]O[CH2:9][CH3:8])=[O:7].Br[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[CH2:3][C:2]#[N:1]>>[N:1]#[C:2][C:3]1=[CH:4][C:5](=[C:6]2[O:7][CH2:8][CH2:9][O:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | CCOC=CC(=O)OCC.N#CCc1ccccc1Br | N#CC1=CC(=C2OCCO2)c2ccccc21 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 | C(CO)O.O.O1CCCC1 | Acylation | OtherReaction | 67570292e87e0eca0e7502939e252013a45cf960781d5d135697411d46b48998 | 95372d00294ac9b4c53a7bcb2b904a19ae3d5134f044b14db9fbb02225bf88fd | C1=Cc2ccccc2C1=C1OCCO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[CH2;D2;+0:5]-[C:6]#[N;D1;H0:7]):[c:8].C-C-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-O-[CH2;D2;+0:14]-[CH3;D1;+0:15]>>[N;D1;H0:7]#[C:6]-[C;H0;D3;+0:5]1=[CH;D2;+0:13]-[C;H0;D3;+0:12](=[C;H0;D3;+0:10]2-[O;H0;D2;+0:9]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-[... | 80 | [{"value": 80.0, "product": "O1C(OCC1)=C1C=C(C2=CC=CC=C12)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "O1C(OCC1)=C1C=C(C2=CC=CC=C12)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of tricyclohexylphosphine (536 mg, 1.91 mmol) in tetrahydrofuran (25 mL) was charged with palladium (II) acetate (287 mg, 1.27 mmol) under nitrogen. After 1 hour the reaction mixture was cooled to 0° C. and charged with sodium tert-butoxide (31.6 g, 319 mmol). After 5 minutes a solution of 2-bromo-phenylacet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether | Ether.Ether | c1ccccc1 | C1COCO1.C1=Cc2ccccc2C1 | C1COCO1.C1=Cc2ccccc2C1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C(CO)O.O.O1CCCC1 | 0 | null | CCOC=CC(=O)OCC.N#CCc1ccccc1Br>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C(CO)O.O.O1CCCC1>N#CC1=CC(=C2OCCO2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9aeb12b8ac724711b637d517d0227baf | CCOC=CC(=O)OCC.O=S(=O)(Cc1ccccc1Br)c1ccccc1>>CCOC(=O)C1=CC(S(=O)(=O)c2ccccc2)c2ccccc21 | C(C)OC(C=COCC)=O.C1(=CC=CC=C1)S(=O)(=O)CC1=C(C=CC=C1)Br.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.CC(C)([O-])C.[Na+].P(=O)(O)(O)[O-].[K+]>>C(C)OC(=O)C1=CC(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1 | CCO[CH:7]=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].Br[c:23]1[c:18]([CH2:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH... | CCOC=CC(=O)OCC.O=S(=O)(Cc1ccccc1Br)c1ccccc1 | CCOC(=O)C1=CC(S(=O)(=O)c2ccccc2)c2ccccc21 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(C)(C)OC.O1CCCC1 | C-C Coupling | OtherReaction | a366f6e85c32623adad474d409e42376af4feda66c2ff117da5b9f19944e3357 | c6b9a8d2a5811acd67b90380dc39a63bb1e5eb1730f16ff91844bfb85d364339 | O=S(=O)(c1ccccc1)C1C=Cc2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[CH2;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9]):[c:10].C-C-O-[CH;D2;+0:11]=[CH;D2;+0:12]-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:16]-[#8:15]-[C:13](=[O;D1;H0:14])-[C;H0;D3;+0:12]1=[CH;D2;+0:11]-[CH;D3;+0:5](-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9])-[c:4](:[c:10]):[c;H0... | 85 | [{"value": 85.0, "product": "C(C)OC(=O)C1=CC(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "C(C)OC(=O)C1=CC(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | A solution of tricyclohexylphophine (46 mg, 0.164 mmol) in tetrahydrofuran (2.5 mL) under nitrogen was charged with palladium (II) acetate (24.5mg, 0.109 mmol). The reaction mixture was stirred for 45 minutes, then cooled to 0° C. and charged with sodium tert-butoxide (270 mg, 2.73 mmol). After 5 minutes a solution of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether | Ester | c1ccccc1 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)OC.O1CCCC1 | 0 | 0.75 | CCOC=CC(=O)OCC.O=S(=O)(Cc1ccccc1Br)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)OC.O1CCCC1>CCOC(=O)C1=CC(S(=O)(=O)c2ccccc2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ee70e79efcc4788a568601f44073199 | CCOC(O)=C1C=C(C#N)c2ccccc21>>CCOC(=O)C1CC(C#N)c2ccccc21 | C(=O)O.C(C)OC(=C1C=C(C2=CC=CC=C12)C#N)O.[Na]>>C(C)OC(=O)C1CC(C2=CC=CC=C12)C#N | [CH3:1][CH2:2][O:3][C:4]([OH:5])=[C:6]1[CH:7]=[C:8]([C:9]#[N:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH:8]([C:9]#[N:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | CCOC(O)=C1C=C(C#N)c2ccccc21 | CCOC(=O)C1CC(C#N)c2ccccc21 | null | [Pd] | C(C)O | Miscellaneous | OtherReaction | 06148c76d878034eced412b89c53922e6d73d88da9bad45275ca05942c78ecef | 41c21da9fd255f18f2773e8546ef0fb243c5e66ce0c62d14e68cd75fefb1b9e0 | c1ccc2c(c1)CCC2 | [C:1]-[#8:2]-[C;H0;D3;+0:3](-[OH;D1;+0:4])=[C;H0;D3;+0:5]1-[CH;D2;+0:6]=[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])-[c:10](:[c:11]):[c:12]-1:[c:13]>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH;D3;+0:7](-[C:8]#[N;D1;H0:9])-[c:10](:[c:11]):[c:12]-1:[c:13] | 87 | [{"value": 87.0, "product": "C(C)OC(=O)C1CC(C2=CC=CC=C12)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(ethoxy-hydroxy-methylene)-3H-indene-1-carbonitrile, sodium salt, (1.00 g, 4.70 mmol) in ethanol (40 mL) in a pressure reactor was purged with nitrogen for 5 minutes and charged with 5% palladium on carbon (1.00 g, 0.230 mmol) and formic acid (0.180 mL, 4.70 mmol), pH=5 at reaction initiation. The press... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Enol | Ester | C1=Cc2ccccc2C1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | [Pd].C(C)O | null | null | CCOC(O)=C1C=C(C#N)c2ccccc21>[Pd].C(C)O>CCOC(=O)C1CC(C#N)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe9d2c6d13af48da90b699d1f3a1186e | COC(=O)C1CC(CN)c2ccccc21>>O=C1NCC2CC1c1ccccc12 | COC(=O)C1CC(C2=CC=CC=C12)CN.CC(C)([O-])C.[Na+]>>O=C1C2C=3C=CC=CC3C(CN1)C2 | CO[C:2](=[O:1])[CH:7]1[CH2:6][CH:5]([CH2:4][NH2:3])[c:13]2[c:8]1[cH:9][cH:10][cH:11][cH:12]2>>[O:1]=[C:2]1[NH:3][CH2:4][CH:5]2[CH2:6][CH:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]12 | COC(=O)C1CC(CN)c2ccccc21 | O=C1NCC2CC1c1ccccc12 | null | null | CO | Miscellaneous | OtherReaction | 574f43f635fc178a747fb62afc76e026e89eb4f966e3ed4a9bd4e8431f774fc2 | 92bd4402d90a419a2f8338f9414db9222f74d64e606e4b1a47fea24edc8b3ea6 | O=C1NCC2CC1c1ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[C:6]-[C:7]-[NH2;D1;+0:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:8]-[C:7]-[C:6]-[C:5]-[C:3]-1-[c:4] | null | [] | null | null | null | null | To a solution of 3-aminomethyl-indan-1-carboxylic acid methyl ester (assume 20.0 mmol, 1 equivalent) in 50 mL of methanol was added 3.84 g of sodium tert-butoxide (40.0 mmol, 2.0 equivalent). The reaction mixture was heated to a reflux for 2 hours. The reaction was cooled to room temperature and concentrated in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | HO- | CO | null | null | COC(=O)C1CC(CN)c2ccccc21>CO>O=C1NCC2CC1c1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ea434e6c09642dfb5cbdfda72b919e8 | O=C1NCC2CC1c1ccccc12>>c1ccc2c(c1)C1CNCC2C1 | Cl.O=C1C2C=3C=CC=CC3C(CN1)C2.[BH4-].[Na+].O.C1(=CC=C(C=C1)S(=O)(=O)O)C.B(F)(F)F.CCOCC>>S(=O)(=O)(O)C1=CC=C(C)C=C1.C12C=3C=CC=CC3C(CNC1)C2 | O=[C:19]1[CH:18]2[c:16]3[c:15]([cH:14][cH:13][cH:12][cH:17]3)[CH:22]([CH2:21][NH:20]1)[CH2:23]2>>[cH:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[CH:18]1[CH2:19][NH:20][CH2:21][CH:22]2[CH2:23]1 | O=C1NCC2CC1c1ccccc12 | c1ccc2c(c1)C1CNCC2C1 | null | null | CO.O1CCCC1.C(C)(C)O | Reduction | Reduction of secondary amides to amines | ad879f3a74bcad0b9dd5e8fd73398142036862409bd8d4a0c7108821173206e8 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)C1CNCC2C1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[C:5])-[c:6]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4](-[C:5])-[c:6] | null | [] | 50 | CELSIUS | 30 | MINUTE | To a solution of 1.38 g of 9-oxo-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene (8.00 mmol, 1 equivalent) in 8 mL of tetrahydrofuran was added 603 mg of sodium borohydride (16.0 mmol, 2.0 equivalent) followed by slow addition of 2.77 mL of boron trifluoride diethyl etherate (21.6 mmol, 2.7 equivalent). Once the effe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | Other | CO.O1CCCC1.C(C)(C)O | 50 | 0.5 | O=C1NCC2CC1c1ccccc12>CO.O1CCCC1.C(C)(C)O>c1ccc2c(c1)C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f50af6e907c34b0d9fd2e41cc802c21a | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=[N+]([O-])O>>O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F | [N+](=O)(O)[O-].FC(S(=O)(=O)O)(F)F.C12C=3C=CC=CC3C(CN(C1)C(C(F)(F)F)=O)C2>>[N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O | [O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][cH:11][cH:15][cH:16][c:17]12)[C:18]([F:19])([F:20])[F:21].O[N+:12](=[O:13])[O-:14]>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][c:17]12)[C:18]([F:19])([F:20])[F:21] | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=[N+]([O-])O | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F | null | null | C(Cl)Cl | Functional Group Addition | Aromatic nitration with HNO3 | fbc183fc1c4671a7888d30681094affb85dfa1112d21be8a1cb6254bb6af1b07 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)C1CNCC2C1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | 78 | [{"value": 78.0, "product": "[N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "[N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | (Based on the method described by Coon, C. L.; Blucher, W. G.; Hill, M. E. J. Org. Chem. 1973, 25, 4243.) To a solution of trifluoromethanesulfonic acid (2.4 ml, 13.7 mmol) in CH2Cl2 (10 ml) stirred at 0° C. was slowly added nitric acid (0.58 ml, 27.4 mmol) generating a white precipitate. After 10 minutes the resulting... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | HO- | C(Cl)Cl | -78 | 0.5 | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=[N+]([O-])O>C(Cl)Cl>O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dc5260fbcaf4265958a4eac66912ab7 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F>>Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | [N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O>>NC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH:8]1[CH2:9][CH:10]2[CH2:11][N:12]([C:13](=[O:14])[C:15]([F:16])([F:17])[F:18])[CH2:19]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH:8]1[CH2:9][CH:10]2[CH2:11][N:12]([C:13](=[O:14])[C:15]([F:16])([F:17])[F:18])[CH2:19]1 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F | Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)C1CNCC2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 94.5 | [{"value": 94.5, "product": "NC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrogenation of 1-(4-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (2.0 g, 6.66 mmol) under a hydrogen atmosphere (40 psi, or approximately 2.7 atmospheres) and 10% Pd/C (200 mg) in methanol over 1.5 hours, filtration through Celite and concentration affords a yellow oil (1.7 g... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | Other | [Pd].CO | null | null | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])ccc12)C(F)(F)F>[Pd].CO>Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bcb560618ed647df924c3601e43a5253 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>>O=[N+]([O-])c1cc2c(cc1[N+](=O)[O-])C1CNCC2C1 | CO.C(Cl)Cl.[N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1[N+](=O)[O-])C3)C(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+].O>>[N+](=O)([O-])C1=CC=2C3CNCC(C2C=C1[N+](=O)[O-])C3 | O=C(C(F)(F)F)[N:15]1[CH2:14][CH:13]2[c:7]3[c:6]([cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:9]([N+:10](=[O:11])[O-:12])[cH:8]3)[CH:17]([CH2:16]1)[CH2:18]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[N+:10](=[O:11])[O-:12])[CH:13]1[CH2:14][NH:15][CH2:16][CH:17]2[CH2:18]1 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F | O=[N+]([O-])c1cc2c(cc1[N+](=O)[O-])C1CNCC2C1 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | f46cbee729057ebd415120d06c8d35552e9f6cc6e71a027737f358de057e1ec8 | 9d0759623d33e2d41aafe1af3bb1025d4d7a88f20060c872279b889c110cab65 | c1ccc2c(c1)C1CNCC2C1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | 1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in methanol (50 mL) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 m... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Tertiary amide | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | Other | CO | null | null | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>CO>O=[N+]([O-])c1cc2c(cc1[N+](=O)[O-])C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c19ea09f0b842fa85fbf56d92b2f314 | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12>>CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(N)c(N)cc12 | C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)[N+](=O)[O-])[N+](=O)[O-]>>C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)N)N | O=[N+:17]([O-])[c:16]1[cH:15][c:14]2[c:21]([cH:20][c:18]1[N+:19](=O)[O-])[CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH:12]2[CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][CH:12]([CH2:13]1)[c:14]1[cH:15][c:16]([NH2:17])[c:18]([NH2:19])[cH:20][c... | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12 | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(N)c(N)cc12 | null | [Pd] | CO | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc2c(c1)C1CNCC2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (1.9 g, 5.44 mmol) was hydrogenated in methanol under a H2 atmosphere (45 psi, or approximately 3 atmospheres) over 10% Pd/C (100 mg) for 1.5 hours then filtered through a Celite pad and concentrated to white solids (1.57 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12>[Pd].CO>CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(N)c(N)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c87a28432656476ca44431e7feb16a78 | CCCI.Cc1nc2cc3c(cc2[nH]1)C1CC3CN(C(=O)OC(C)(C)C)C1>>CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 | O.CS(=O)C.ICCC.C(C)(C)(C)OC(=O)N1CC2C=3C=C4NC(=NC4=CC3C(C1)C2)C>>C(C)(C)(C)OC(=O)N1CC2C=3C=C4N(C(=NC4=CC3C(C1)C2)C)CCC | I[CH2:3][CH2:2][CH3:1].[nH:4]1[c:5]([CH3:6])[n:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]12)[CH:14]1[CH2:15][CH:16]3[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5]([CH3:6])[n:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]12)[CH:14]1[CH2:15][CH:16]3[CH2:17][N:... | CCCI.Cc1nc2cc3c(cc2[nH]1)C1CC3CN(C(=O)OC(C)(C)C)C1 | CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 | null | null | CO.C(Cl)Cl.[OH-].[Na+] | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aad23a87a709faa184cade5ee8ef98668cac9bd08b2cae918b7a2312b85c430e | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:9](:[c:10]):[c:7](:[c:8]):[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | 40 | CELSIUS | null | null | (For conditions, see; Pilarski, B. Liebigs Ann. Chem. 1983, 1078.) 6-Methyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester (80 mg, 0.267 mmol) was stirred in 50% aqueous NaOH solution (3 mL) and DMSO (1 mL) then treated with 1-iodopropane (0.03 mL, 0.321 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nc2cc3c(cc2[nH]1)C1C[NH]CC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | HI | CO.C(Cl)Cl.[OH-].[Na+] | 40 | null | CCCI.Cc1nc2cc3c(cc2[nH]1)C1CC3CN(C(=O)OC(C)(C)C)C1>CO.C(Cl)Cl.[OH-].[Na+]>CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f83b060476964130952cd72d63482d88 | CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1>>CCCn1c(C)nc2cc3c(cc21)C1CNCC3C1 | C(C)(C)(C)OC(=O)N1CC2C=3C=C4N(C(=NC4=CC3C(C1)C2)C)CCC.C(C)(=O)OCC.Cl>>Cl.CC1=NC2=CC=3C4CNCC(C3C=C2N1CCC)C4 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH:14]2[c:11]3[c:10]([cH:9][c:8]4[n:7][c:5]([CH3:6])[n:4]([CH2:3][CH2:2][CH3:1])[c:13]4[cH:12]3)[CH:18]([CH2:17]1)[CH2:19]2>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5]([CH3:6])[n:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]12)[CH:14]1[CH2:15][NH:16][CH2:17][CH:18]3[CH2:19]1 | CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 | CCCn1c(C)nc2cc3c(cc21)C1CNCC3C1 | null | null | null | Reduction | Boc amine deprotection | dcd46ab88030f5ae0f98a0a8c5055b6f1f961ba3f911435fc414afcbf6254310 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 34 | [{"value": 34.0, "product": "Cl.CC1=NC2=CC=3C4CNCC(C3C=C2N1CCC)C4", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 6-Methyl-7-propyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester (90 mg, 0.253 mmol) was dissolved in 3N HCl ethyl acetate (5 mL) and warmed to 100° C. for ½ hour. The mixture was cooled, concentrated, slurried in ethyl acetate, and filtered to provide a whit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1nc2cc3c(cc2n1)C1CNCC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | HO- | null | 100 | null | CCCn1c(C)nc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1>>CCCn1c(C)nc2cc3c(cc21)C1CNCC3C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-931bc6064bc349a4bd207d7c42a61231 | CCCCNc1cc2c(cc1[N+](=O)[O-])C1CC2CN(C(=O)OC(C)(C)C)C1>>CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1 | C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)NCCCC)[N+](=O)[O-].C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)NCCCC)N | O=[N+:12]([O-])[c:11]1[c:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:7][c:8]2[c:9]([cH:10]1)[CH:13]1[CH2:14][CH:15]2[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][c:8]2[c:9]([cH:10][c:11]1[NH2:12])[CH:13]1[CH2:14][CH:15]2[CH2:16][N:17]([C:1... | CCCCNc1cc2c(cc1[N+](=O)[O-])C1CC2CN(C(=O)OC(C)(C)C)C1 | CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1 | null | [OH-].[OH-].[Pd+2] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)C1CNCC2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.3 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)NCCCC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)NCCCC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Butylamino-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxlic acid tert-butyl ester (460 mg, 1.27 mmol) was treated with ammonium formate (850 mg, 12.7 mmol) and 10%Pd(OH)2/C (50 mg) in methanol (20 mL) and brought to reflux for 1 hour then filtered through a Celite pad and concentrated. The solid... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | CCCCNc1cc2c(cc1[N+](=O)[O-])C1CC2CN(C(=O)OC(C)(C)C)C1>[OH-].[OH-].[Pd+2].CO>CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fd698ef781248f897af3e0a916d0162 | CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1>>CCCCn1cnc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 | CO.C(Cl)Cl.CC(=O)O.C(C)OC=C(C#N)C#N.C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)NCCCC)N>>C(C)(C)(C)OC(=O)N1CC2C=3C=C4N(C=NC4=CC3C(C1)C2)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:13]1[c:8]([NH2:7])[cH:9][c:11]2[c:10]([cH:12]1)[CH:16]1[CH2:15][CH:14]2[CH2:26][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]12)[CH:14]1[CH2:15][CH:16]3[CH2:17][N:18]([C:1... | CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1 | CCCCn1cnc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 58e4d4c9d07ce70a4dd58e6fc4c563bacf7e98649eca2489fa926dfb4a14e612 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6]2:[c;H0;D3;+0:7](:[cH;D2;+0:8]:[c:9]:1-[NH2;D1;+0:10])-[C:11]1-[C:12]-[C:13]-2-[C:14]-[#7:15]-[C:16]-1>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:17]:[n;H0;D2;+0:10]:[c:9]2:[cH;D2;+0:8]:[c;H0;D3;+0:6]3:[c;H0;D3;+0:7](:[cH;D2;+0:5]:[c:4]:2:1)-[C:11]1-[C:12]-[C:13]-3-[C:14]... | null | [] | 60 | CELSIUS | 18 | HOUR | 4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (440 mg, 1.27 mmol) was dissolved in ethanol (20 mL) and HOAc (2 mL) and treated with ethoxymethylenemalononitrile (186 mg, 1.52 mmol). The resulting mixture was warmed to 60° C. and stirred 18 hours. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccc2c(c1)C1C[NH]CC2C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | Other | C(C)O | 60 | 18 | CCCCNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1>C(C)O>CCCCn1cnc2cc3c(cc21)C1CC3CN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69507ca7e21845ed9a875238fec81819 | CC(=O)O.CC(C)CNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1>>Cc1nc2cc3c(cc2n1CC(C)C)C1CC3CN(C(=O)OC(C)(C)C)C1 | CO.C(Cl)Cl.CC(=O)O.C(C)(C)(C)OC(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)N)NCC(C)C>>C(C)(C)(C)OC(=O)N1CC2C=3C=C4N(C(=NC4=CC3C(C1)C2)C)CC(C)C | O=[C:2](O)[CH3:1].[NH2:3][c:4]1[cH:5][c:7]2[c:6]([cH:8][c:9]1[NH:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH:17]1[CH2:16][CH:15]2[CH2:27][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:18]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][c:9]2[n:10]1[CH2:11][CH:12]([CH3:13])[CH3:14])[CH:15]1[CH2:16][... | CC(=O)O.CC(C)CNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1 | Cc1nc2cc3c(cc2n1CC(C)C)C1CC3CN(C(=O)OC(C)(C)C)C1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 147bd722a7163a98731b13d4d837c181454bc91a562ab6f1acf8f083a0edef14 | 2c7e28df6187a1559bf3bdf429be12550f69083c743a14154a096b0d7c5276e7 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[c:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:8]2:[c;H0;D3;+0:9](:[cH;D2;+0:10]:[c:11]:1-[NH2;D1;+0:12])-[C:13]1-[C:14]-[C:15]-2-[C:16]-[#7:17]-[C:18]-1>>[C:3]-[C:4]-[n;H0;D3;+0:5]1:[c:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:9]3:[c;H0;D3;+0:8](:[cH;D2;+0:10]:[c:11]:2:[n;H0;D2;+0:12]:[c;... | null | [] | null | null | null | null | 4-Amino-5-isobutylamino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (250 mg, 0.74 mmol) from Example 29B was dissolved in ethanol (10 mL) and HOAc (2 mL) and treated with 1-ethoxyethylenemalononitrile (118 mg, 0.87 mmol). The reaction proceeded as in Example 28C (18 h) and was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | null | c1ccc2c(c1)C1C[NH]CC2C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | c1nc2cc3c(cc2[nH]1)C1CNCC3C1 | HO- | C(C)O | null | null | CC(=O)O.CC(C)CNc1cc2c(cc1N)C1CC2CN(C(=O)OC(C)(C)C)C1>C(C)O>Cc1nc2cc3c(cc2n1CC(C)C)C1CC3CN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1e478105e0c4ecf87f53b24e0cc7cb9 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>>Nc1cc2c(cc1N)C1CC2CN(C(=O)C(F)(F)F)C1 | [N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1[N+](=O)[O-])C3)C(C(F)(F)F)=O>>NC1=CC=2C3CN(CC(C2C=C1N)C3)C(C(F)(F)F)=O | O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[N+:8](=O)[O-])[CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]([C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[CH2:20]1>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[NH2:8])[CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]([C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[CH2:20]1 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F | Nc1cc2c(cc1N)C1CC2CN(C(=O)C(F)(F)F)C1 | null | [OH-].[OH-].[Pd+2] | CO | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc2c(c1)C1CNCC2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.0 g, 8.70 mmol) was hydrogenated in methanol (30 ml) under a hydrogen atmosphere (45 psi, or approximately 3 atmospheres) over Pd(OH)2 (300 mg of 20 wt %/C, 10% wt). After 2.5 hours the reaction was filtered through a Cel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>[OH-].[OH-].[Pd+2].CO>Nc1cc2c(cc1N)C1CC2CN(C(=O)C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c332f48e15544b4e8f7002466853992f | CC(=O)[O-].O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>>O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F | [N+](=O)([O-])C1=CC=2C3CN(CC(C2C=C1[N+](=O)[O-])C3)C(C(F)(F)F)=O.C(C)(=O)[O-].[K+]>>FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)[N+](=O)[O-])(F)F | CC(=O)[O-:16].O=[N+]([O-])[c:15]1[c:11]([N+:12](=[O:13])[O-:14])[cH:10][c:9]2[c:18]([cH:17]1)[CH:5]1[CH2:4][N:3]([C:2](=[O:1])[C:19]([F:20])([F:21])[F:22])[CH2:8][CH:7]2[CH2:6]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([OH:16])[cH:17][c:18]12)[C:19]([F:2... | CC(=O)[O-].O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 006287576b799c453e649b85a24fa56aa8126d7384c5d3e4e61e59299fcb8c72 | 86a548d176249a485272aef686188652b058190b5b30134e7b55d29d9f8bbe51 | c1ccc2c(c1)C1CNCC2C1 | C-C(=O)-[O-;H0;D1:1].O=[N+](-[O-])-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#7;+:6]):[c:7]>>[#7;+:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[OH;D1;+0:1]):[c:3]:[c:4] | 70 | [{"value": 70.0, "product": "FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)[N+](=O)[O-])(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)[N+](=O)[O-])(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 16 | HOUR | 1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (900 mg, 2.61 mmol) and potassium acetate (KOAc) (2.6 g, 26.1 mmol) were dissolved in DMSO (10 mL) and warmed with stirring to 100° C. for 16 hours. The mixture was cooled and diluted with H2O (50 mL) then extracted with 80%... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic alcohol | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | HO- | CS(=O)C.O | 100 | 16 | CC(=O)[O-].O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c([N+](=O)[O-])cc12)C(F)(F)F>CS(=O)C.O>O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64bd259c84b24a4d881ac13f3981aa61 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F>>Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)[N+](=O)[O-])(F)F>>FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)N)(F)F | O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[OH:8])[CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]([C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[CH2:20]1>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[OH:8])[CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]([C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[CH2:20]1 | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F | Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)C1CNCC2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 2,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone (575 mg, 1.82 mmol) was hydrogenated in methanol under a H2 atmosphere at (45 psi, or approximately 3 atmospheres) over 10% Pd/C (80 mg) for 1.5 hours then filtered through a Celite pad and concentrated to white solids... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | Other | [Pd].CO | null | null | O=C(N1CC2CC(C1)c1cc([N+](=O)[O-])c(O)cc12)C(F)(F)F>[Pd].CO>Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0e1cb1ebb244b41a71131589d967acf | Cl.Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1>>O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F | Cl.Cl.NC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O.N(=O)[O-].[Na+]>>ClC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O | [ClH:12].N[c:11]1[cH:10][c:9]2[c:15]([cH:14][cH:13]1)[CH:5]1[CH2:4][N:3]([C:2](=[O:1])[C:16]([F:17])([F:18])[F:19])[CH2:8][CH:7]2[CH2:6]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]12)[C:16]([F:17])([F:18])[F:19] | Cl.Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F | null | Cl[Cu] | O | Miscellaneous | OtherReaction | 2b7041887f1eceb6f9d882edcffad975e8ab2f416f1382973bb9f8b07f7ae752 | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2c(c1)C1CNCC2C1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 95 | [{"value": 95.0, "product": "ClC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (460 mg, 1.7 mmol) was dissolved in H2O (2 mL) and concentrated HCl solution(1 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (275 mg) in H2O (1 mL) dropwise. To the resulting solution was added a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | Other | Cl[Cu].O | 60 | null | Cl.Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1>Cl[Cu].O>O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-838100bfc1eb4170bffb41fdeff481cd | O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F>>Cl.Clc1ccc2c(c1)C1CNCC2C1 | ClC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>>Cl.ClC1=CC=2C3CNCC(C2C=C1)C3 | O=C(C(F)(F)F)[N:11]1[CH2:10][CH:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([Cl:1])[cH:8]3)[CH:13]([CH2:12]1)[CH2:14]2>>[ClH:1].[Cl:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]1[CH2:10][NH:11][CH2:12][CH:13]2[CH2:14]1 | O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F | Cl.Clc1ccc2c(c1)C1CNCC2C1 | null | null | CO.O | Miscellaneous | Hydrogenolysis of tertiary amines | a6137ef918539e263903a8a4ae0ea118fd5c2cd29e3061a4891158b906dcc255 | c917f007c6daf2ba5ac5faecc6c9acfa67f53d875fa50728fec5dcddec33c9e4 | c1ccc2c(c1)C1CNCC2C1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[c:4]:[c:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[c:8]:[c:9])-[C:10]-[C:11]>>[C:11]-[C:10]-[NH;D2;+0:1]-[C:2]-[C:3]-[c:4]:[c:5]:[c;H0;D3;+0:6](-[Cl;D1;H0:12]):[c:8]:[c:9].[ClH;D0;+0:7] | null | [] | null | null | 2 | HOUR | 1-(4-Chloro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (470 mg, 1.62 mmol) and Na2CO3 (344 mg, 3.24 mmol) in methanol (30 mL) and H2O (10 mL) were heated to reflux. After 2 hours, the reaction was cooled and diluted with water then extracted with ethyl acetate (4×40 mL), dried (Na2... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Tertiary amide | Aromatic halide.Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | Other | CO.O | null | 2 | O=C(N1CC2CC(C1)c1cc(Cl)ccc12)C(F)(F)F>CO.O>Cl.Clc1ccc2c(c1)C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61f22df1abf941a0bb796b93e209b430 | Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1.[I-]>>O=C(N1CC2CC(C1)c1cc(I)ccc12)C(F)(F)F | [I-].[K+].NC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O.N(=O)[O-].[Na+]>>IC1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O | N[c:11]1[cH:10][c:9]2[c:15]([cH:14][cH:13]1)[CH:5]1[CH2:4][N:3]([C:2](=[O:1])[C:16]([F:17])([F:18])[F:19])[CH2:8][CH:7]2[CH2:6]1.[I-:12]>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]12)[C:16]([F:17])([F:18])[F:19] | Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1.[I-] | O=C(N1CC2CC(C1)c1cc(I)ccc12)C(F)(F)F | null | null | O.OS(=O)(=O)O | Functional Group Interconversion | OtherReaction | d85248fa2dcf066a404d25d0a3dc9531961e235579e6a0103df5b0ec1c500653 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccc2c(c1)C1CNCC2C1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[I-;H0;D0:6]>>[I;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 18 | HOUR | 1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (500 mg, 1.85 mmol) was dissolved in H2O (5 mL) and concentrated H2SO4 solution (0.5 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (140 mg, 2.04 mmol) in H2O (2 mL) dropwise. Potassium iodide (46... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | Other | O.OS(=O)(=O)O | null | 18 | Nc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1.[I-]>O.OS(=O)(=O)O>O=C(N1CC2CC(C1)c1cc(I)ccc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a5a32196acf4e768cde31de4aed7d60 | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(C#N)ccc12>>N#Cc1ccc2c(c1)C1CNCC2C1 | C(C)(C)(C)OC(=O)N1CC2C=3C=CC(=CC3C(C1)C2)C#N.C(C)(=O)OCC.Cl>>Cl.C12C=3C=C(C=CC3C(CNC1)C2)C#N | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH:10]2[c:8]3[c:7]([cH:6][cH:5][c:4]([C:3]#[N:2])[cH:9]3)[CH:14]([CH2:13]1)[CH2:15]2>>[N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]1[CH2:11][NH:12][CH2:13][CH:14]2[CH2:15]1 | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(C#N)ccc12 | N#Cc1ccc2c(c1)C1CNCC2C1 | null | null | null | Reduction | Boc amine deprotection | 16a87a91f73ba41dd2fbaeff5b0b018f397c5ad5c549cbd7af59e94acd9700c1 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c(c1)C1CNCC2C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | 18 | HOUR | 4-Cyano-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester was treated with 3N HCl ethyl acetate (6 mL) and warmed to reflux for 2 hours, then concentrated, dissolved in a minimum of methanol which was saturated with Et2O and stirred 18 hours. The product was collected by filtration (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | HO- | null | null | 18 | CC(C)(C)OC(=O)N1CC2CC(C1)c1cc(C#N)ccc12>>N#Cc1ccc2c(c1)C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99b5561f14694dee9f68132e67b69d9b | CC(=O)Cl.O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F>>CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | C(=O)(O)[O-].[Na+].C12C=3C=CC=CC3C(CN(C1)C(C(F)(F)F)=O)C2.C(=O)(C)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(=O)C1=CC=2C3CN(CC(C2C=C1)C3)C(C(F)(F)F)=O | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]1[CH2:11][CH:12]2[CH2:13][N:14]([C:15](=[O:16])[C:17]([F:18])([F:19])[F:20])[CH2:21]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]1[CH2:11][CH:12]2[CH2:13][N:14]([C:15](=[O:16])[C:17]([F:18])([F:19])[F:20])[CH2:21]1 | CC(=O)Cl.O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F | CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 440542c1d377bda35f0172763cc622606266c84265c45cd45a3812b0fb5cd1dc | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)C1CNCC2C1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 30 | MINUTE | 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (253 mg, 1.0 mmol) and AcCl (0.68 mL, 10 mmol) were dissolved in DCE (3 mL) and treated with aluminum chloride (AlCl3) (667 mg, 5.0 mmol). The resulting yellow mixture was stirred for 30 minutes then poured over ice and saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | HCl | ClCCCl | null | 0.5 | CC(=O)Cl.O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F>ClCCCl>CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b60e3c5ebb754101980b3f930fd4d1c7 | CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)OC(C)(C)C)C1>>CC(=O)c1ccc2c(c1)C1CNCC2C1 | C(C)(C)(C)OC(=O)N1CC2C=3C=CC(=CC3C(C1)C2)C(C)=O.C(C)(=O)OCC.Cl>>Cl.C12C=3C=C(C=CC3C(CNC1)C2)C(C)=O | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH:10]2[c:8]3[c:7]([cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:9]3)[CH:14]([CH2:13]1)[CH2:15]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]1[CH2:11][NH:12][CH2:13][CH:14]2[CH2:15]1 | CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)OC(C)(C)C)C1 | CC(=O)c1ccc2c(c1)C1CNCC2C1 | null | null | null | Reduction | Boc amine deprotection | 16a87a91f73ba41dd2fbaeff5b0b018f397c5ad5c549cbd7af59e94acd9700c1 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c(c1)C1CNCC2C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | 70 | CELSIUS | null | null | 4-Acetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (190 mg, 0.63 mmol) was treated with excess 3N HCl ethyl acetate and warmed to 70° C. for 1 hour then concentrated and dissolved in a minimum of methanol. The resulting solution was saturated with Et2O and stirred. After 18 h... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | HO- | null | 70 | null | CC(=O)c1ccc2c(c1)C1CC2CN(C(=O)OC(C)(C)C)C1>>CC(=O)c1ccc2c(c1)C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1f2c8cc27034c179f1b4822f27ad1dc | CC(=O)Oc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1>>O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F | FC(C(=O)N1CC2C=3C=CC(=CC3C(C1)C2)OC(C)=O)(F)F.C(=O)(O)[O-].[Na+]>>FC(C(=O)N1CC2C=3C=CC(=CC3C(C1)C2)O)(F)F | CC(=O)[O:12][c:11]1[cH:10][c:9]2[c:15]([cH:14][cH:13]1)[CH:5]1[CH2:4][N:3]([C:2](=[O:1])[C:16]([F:17])([F:18])[F:19])[CH2:8][CH:7]2[CH2:6]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]12)[C:16]([F:17])([F:18])[F:19] | CC(=O)Oc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1 | O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccc2c(c1)C1CNCC2C1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Acetic acid 10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl ester (900 mg, 2.87 mmol) was stirred in methanol (20 mL) and saturated aqueous NaHCO3 solution (15 mL) for 48 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) then dried through a cotton plug. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | HO- | CO | null | null | CC(=O)Oc1ccc2c(c1)C1CC2CN(C(=O)C(F)(F)F)C1>CO>O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bca363c09c8445f68bf4196a6fca5bb7 | O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F>>Oc1ccc2c(c1)C1CNCC2C1 | FC(C(=O)N1CC2C=3C=CC(=CC3C(C1)C2)O)(F)F.C(=O)([O-])[O-].[Na+].[Na+].C(C)(=O)OCC.Cl>>Cl.C12C=3C=C(C=CC3C(CNC1)C2)O | O=C(C(F)(F)F)[N:11]1[CH2:10][CH:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([OH:2])[cH:8]3)[CH:13]([CH2:12]1)[CH2:14]2>>[OH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]1[CH2:10][NH:11][CH2:12][CH:13]2[CH2:14]1 | O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F | Oc1ccc2c(c1)C1CNCC2C1 | null | null | CO.O | Reduction | Hydrogenolysis of tertiary amines | f46cbee729057ebd415120d06c8d35552e9f6cc6e71a027737f358de057e1ec8 | 9d0759623d33e2d41aafe1af3bb1025d4d7a88f20060c872279b889c110cab65 | c1ccc2c(c1)C1CNCC2C1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | 65 | CELSIUS | null | null | 2,2,2-Trifluoro-1-(4-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone (50 mg, 0.184 mmol) was dissolved in methanol/H2O (3/1, 5 mL), treated with Na2CO3(s) (40 mg, 0.369 mmol) and warmed to 65° C. for 2 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) the... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Tertiary amide | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1CNCC2C1 | c1ccc2c(c1)C1CNCC2C1 | Other | CO.O | 65 | null | O=C(N1CC2CC(C1)c1cc(O)ccc12)C(F)(F)F>CO.O>Oc1ccc2c(c1)C1CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35ab5842722f47c4979b47f623f112e4 | CC(=O)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.NO>>CC(=NO)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | C(C)(=O)C1=CC=2C3CN(CC(C2C=C1O)C3)C(C(F)(F)F)=O.Cl.NO.C(C)(=O)[O-].[Na+]>>FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)C(C)=NO)(F)F | O=[C:2]([CH3:1])[c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1[OH:11])[CH:12]1[CH2:13][CH:14]2[CH2:15][N:16]([C:17](=[O:18])[C:19]([F:20])([F:21])[F:22])[CH2:23]1.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1[OH:11])[CH:12]1[CH2:13][CH:14]2[CH2:15][N:16]([C:17](=[O:18])[C:19]([F:20])([F:21])[F:2... | CC(=O)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.NO | CC(=NO)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | null | null | CO.O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc2c(c1)C1CNCC2C1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 93 | [{"value": 93.0, "product": "FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)C(C)=NO)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.1, "product": "FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)C(C)=NO)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(4-Acetyl-5-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (190 mg, 0.605 mmol), hydroxylamine HCl (99 mg, 1.21 mmol) and sodium acetate (118 mg, 1.21 mmol) were combined in methanol (4 mL) and H2O (1 mL) and warmed to 65° C. for 18 hours. The mixture was cooled, diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccc2c(c1)C1C[NH]CC2C1 | HO- | CO.O | null | null | CC(=O)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.NO>CO.O>CC(=NO)c1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-032980fbd7fc499094c1d87313b64b51 | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=S(=O)(O)Cl>>O=C(N1CC2CC(C1)c1cc(S(=O)(=O)Cl)ccc12)C(F)(F)F | C12C=3C=CC=CC3C(CN(C1)C(C(F)(F)F)=O)C2.ClS(=O)(=O)O>>FC(C(=O)N1CC2C=3C=CC(=CC3C(C1)C2)S(=O)(=O)Cl)(F)F | [O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][cH:11][cH:16][cH:17][c:18]12)[C:19]([F:20])([F:21])[F:22].O=[S:12]([OH:13])(=[O:14])[Cl:15]>>[O:1]=[C:2]([N:3]1[CH2:4][CH:5]2[CH2:6][CH:7]([CH2:8]1)[c:9]1[cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][cH:17][c:18]12)[C:19]([F:20])([F:21])[F:22] | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=S(=O)(O)Cl | O=C(N1CC2CC(C1)c1cc(S(=O)(=O)Cl)ccc12)C(F)(F)F | null | null | null | Protection | Aromatic sulfonyl chlorination | e5a1262dd987e1cbc7fec85c9059213cf3049113a4cf5e7238533ed51231b9db | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2c(c1)C1CNCC2C1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | 87 | [{"value": 87.0, "product": "FC(C(=O)N1CC2C=3C=CC(=CC3C(C1)C2)S(=O)(=O)Cl)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone mg, 2.1 mmol) was added to chlorosulfonic acid (2 mL, 30 mmol) and stirred for 5 minutes. The mixture was quenched with ice, extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated to provide an oil (640 mg, 87%). (TLC 3... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | c1ccc2c(c1)C1C[NH]CC2C1 | HO- | null | null | 0.083333 | O=C(N1CC2CC(C1)c1ccccc12)C(F)(F)F.O=S(=O)(O)Cl>>O=C(N1CC2CC(C1)c1cc(S(=O)(=O)Cl)ccc12)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88a46a881e0040319b6f874fdc35cd86 | Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.O=C(Cl)Cc1ccccc1>>Cl.c1ccc(Cc2nc3cc4c(cc3o2)C2CNCC4C2)cc1 | FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)N)(F)F.C1(=CC=CC=C1)CC(=O)Cl>>Cl.C(C1=CC=CC=C1)C=1OC2=CC=3C4CNCC(C3C=C2N1)C4 | O=C(C(F)(F)F)[N:18]1[CH2:17][CH:16]2[c:12]3[c:11]([cH:10][c:9]([NH2:8])[c:14]([OH:15])[cH:13]3)[CH:20]([CH2:19]1)[CH2:21]2.O=[C:7]([Cl:1])[CH2:6][c:5]1[cH:4][cH:3][cH:2][cH:23][cH:22]1>>[ClH:1].[cH:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[n:8][c:9]3[cH:10][c:11]4[c:12]([cH:13][c:14]3[o:15]2)[CH:16]2[CH2:17][NH:18][CH2:19][CH... | Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.O=C(Cl)Cc1ccccc1 | Cl.c1ccc(Cc2nc3cc4c(cc3o2)C2CNCC4C2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 195dcfd9849a6bacc638b00f2ff33e90dc043dfa52207d61d6fb173e8f01110b | 17d0c0b2e2a3248b62a86941fc178c06b92c2384911e7d108e6679cac538949f | c1ccc(Cc2nc3cc4c(cc3o2)C2CNCC4C2)cc1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11].O=[C;H0;D3;+0:12](-[Cl;H0;D1;+0:13])-[C:14]-[c:15]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[c:8]:[c:7]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:12](-[C:14]-[c:15]):[o;H0;D2;+0:10]:[c:9]:1:[c:11].[ClH;D0;+0:13] | null | [] | null | null | null | null | 2,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone and phenyl-acetyl chloride were converted to the title compound following the procedures described in Example 54. 1H NMR (400 MHz, CD3OD) δ 7.63 (s, 1H), 7.58 (s, 1H), 7.36–7.24 (5H), 4.29 (s, 2H), 3.46 (d, J=2.5 Hz, 2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Tertiary amide.Aromatic alcohol.Primary amine | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1nc2cc3c(cc2o1)C1CNCC3C1 | c1ccccc1.c1nc2cc3c(cc2o1)C1CNCC3C1 | HF | null | null | null | Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1.O=C(Cl)Cc1ccccc1>>Cl.c1ccc(Cc2nc3cc4c(cc3o2)C2CNCC4C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-128b4aeccb114b75ba2665b33ee49ad6 | CCC(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1>>CCc1nc2cc3c(cc2o1)C1CNCC3C1.Cl | FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)N)(F)F.C(CC)(=O)Cl>>Cl.C(C)C=1OC2=CC=3C4CNCC(C3C=C2N1)C4 | O=[C:3]([CH2:2][CH3:1])[Cl:18].O=C(C(F)(F)F)[N:14]1[CH2:13][CH:12]2[c:8]3[c:7]([cH:6][c:5]([NH2:4])[c:10]([OH:11])[cH:9]3)[CH:16]([CH2:15]1)[CH2:17]2>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][c:10]2[o:11]1)[CH:12]1[CH2:13][NH:14][CH2:15][CH:16]3[CH2:17]1.[ClH:18] | CCC(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | CCc1nc2cc3c(cc2o1)C1CNCC3C1.Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 195dcfd9849a6bacc638b00f2ff33e90dc043dfa52207d61d6fb173e8f01110b | 17d0c0b2e2a3248b62a86941fc178c06b92c2384911e7d108e6679cac538949f | c1nc2cc3c(cc2o1)C1CNCC3C1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11].O=[C;H0;D3;+0:12](-[Cl;H0;D1;+0:13])-[C:14]-[C;D1;H3:15]>>[C;D1;H3:15]-[C:14]-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1.[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[ClH;D0;+0... | null | [] | null | null | null | null | 2,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone and propionyl chloride were converted to the title compound following the procedures described in Example 40 and Goldstein, S. W.; Dambek, P. J. J. Het. Chem. 1990, 27, 335. 1H NMR (400 MHz, CD3OD) δ 7.64 (s, 1H), 7.62... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Tertiary amide.Aromatic alcohol.Primary amine | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1nc2cc3c(cc2o1)C1CNCC3C1 | c1nc2cc3c(cc2o1)C1CNCC3C1 | HF | null | null | null | CCC(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1>>CCc1nc2cc3c(cc2o1)C1CNCC3C1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddf33257574b40a69f6d86c33b8b371a | CC(C)C(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1>>CC(C)c1nc2cc3c(cc2o1)C1CNCC3C1.Cl | FC(C(=O)N1CC2C=3C=C(C(=CC3C(C1)C2)O)N)(F)F.C(C(C)C)(=O)Cl>>Cl.C(C)(C)C=1OC2=CC=3C4CNCC(C3C=C2N1)C4 | O=[C:4]([CH:2]([CH3:1])[CH3:3])[Cl:19].O=C(C(F)(F)F)[N:15]1[CH2:14][CH:13]2[c:9]3[c:8]([cH:7][c:6]([NH2:5])[c:11]([OH:12])[cH:10]3)[CH:17]([CH2:16]1)[CH2:18]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]2[cH:7][c:8]3[c:9]([cH:10][c:11]2[o:12]1)[CH:13]1[CH2:14][NH:15][CH2:16][CH:17]3[CH2:18]1.[ClH:19] | CC(C)C(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1 | CC(C)c1nc2cc3c(cc2o1)C1CNCC3C1.Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 195dcfd9849a6bacc638b00f2ff33e90dc043dfa52207d61d6fb173e8f01110b | 17d0c0b2e2a3248b62a86941fc178c06b92c2384911e7d108e6679cac538949f | c1nc2cc3c(cc2o1)C1CNCC3C1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11].O=[C;H0;D3;+0:12](-[Cl;H0;D1;+0:13])-[C:14](-[C;D1;H3:15])-[C;D1;H3:16]>>[C;D1;H3:15]-[C:14](-[C;D1;H3:16])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1.[C:3]-[C:2]-[NH;D... | null | [] | null | null | null | null | 2,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone and isobutyryl chloride were converted to the title compound following the procedures described in Example 54. (TLC 25% ethyl acetate/hexanes Rf 0.14). 1H NMR (400 MHz, CD3OD) δ 7.65 (2H), 3.49 (br s, 2H), 3.41 (d, J=1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Tertiary amide.Aromatic alcohol.Primary amine | Secondary amine | c1ccc2c(c1)C1C[NH]CC2C1 | c1nc2cc3c(cc2o1)C1CNCC3C1 | c1nc2cc3c(cc2o1)C1CNCC3C1 | HF | null | null | null | CC(C)C(=O)Cl.Nc1cc2c(cc1O)C1CC2CN(C(=O)C(F)(F)F)C1>>CC(C)c1nc2cc3c(cc2o1)C1CNCC3C1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1760007316da4df791d25f5e9c52543d | COC(=O)CC(OC)OC>>COC(CC(=O)[O-])OC.[Li+] | COC(CC(OC)OC)=O.O[Li].O.O>>[Li+].COC(CC(=O)[O-])OC | C[O:7][C:5]([CH2:4][CH:3]([O:2][CH3:1])[O:8][CH3:9])=[O:6]>>[CH3:1][O:2][CH:3]([CH2:4][C:5](=[O:6])[O-:7])[O:8][CH3:9].[Li+:10] | COC(=O)CC(OC)OC | COC(CC(=O)[O-])OC.[Li+] | null | null | C1CCOC1 | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4] | 98.7 | [{"value": 98.7, "product": "[Li+].COC(CC(=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (Related to methods described in Alabaster, C. T. et. al., J. Med. Chem. 1988, 31, 2048–2056.) 3,3-Dimethoxypropanoic acid methyl ester (14.25 g, 96.2 mmol) in THF (100 mL) was treated with LiOH.H2O (2.5 g, 106 mmol) and H2O (2 mL). The mixture was brought to reflux for 4 hours, cooled to room temperature and azeotropi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | null | C1CCOC1 | null | null | COC(=O)CC(OC)OC>C1CCOC1>COC(CC(=O)[O-])OC.[Li+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b4d6b3277093439c8ceae4c543cc0e02 | O=C(c1c2c(cc3[nH]c(=O)ccc13)C1CNCC2C1)C(F)(F)F.O=P(Cl)(Cl)Cl>>O=C(c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1)C(F)(F)F | C12C=3C=C4NC(C=CC4=C(C3C(CNC1)C2)C(C(F)(F)F)=O)=O.O=P(Cl)(Cl)Cl>>ClC1=NC2=CC=3C4CNCC(C3C(=C2C=C1)C(C(F)(F)F)=O)C4 | O=[c:9]1[nH:8][c:7]2[cH:6][c:5]3[c:4]([c:3]([C:2](=[O:1])[C:20]([F:21])([F:22])[F:23])[c:13]2[cH:12][cH:11]1)[CH:18]1[CH2:17][NH:16][CH2:15][CH:14]3[CH2:19]1.O=P(Cl)(Cl)[Cl:10]>>[O:1]=[C:2]([c:3]1[c:4]2[c:5]([cH:6][c:7]3[n:8][c:9]([Cl:10])[cH:11][cH:12][c:13]13)[CH:14]1[CH2:15][NH:16][CH2:17][CH:18]2[CH2:19]1)[C:20]([F... | O=C(c1c2c(cc3[nH]c(=O)ccc13)C1CNCC2C1)C(F)(F)F.O=P(Cl)(Cl)Cl | O=C(c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1)C(F)(F)F | null | null | null | Functional Group Interconversion | OtherReaction | 026eb9dc25a7ccadb3fb0299071f6390008431a26aec6a612d9eb4f53467cc3c | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6](:[c:7]):[nH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6](:[c:7]):[n;H0;D2;+0:8]:1 | null | [] | 100 | CELSIUS | 3 | HOUR | 1-(5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,7,9-tetraen-6-one-10-yl)-2,2,2-trifluoro-ethanone (156 mg, 0.49 mmol) was treated with POCl3 (5 mL) and warmed to 100° C. with stirring for 3 hours. After concentration in vacuo, the residue was diluted with CH2Cl2 (15 mL) and carefully treated with saturated N... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cc3c(cc2n1)C1CNCC3C1 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | HCl | null | 100 | 3 | O=C(c1c2c(cc3[nH]c(=O)ccc13)C1CNCC2C1)C(F)(F)F.O=P(Cl)(Cl)Cl>>O=C(c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05d8266adde34236ba2855ba742981b5 | CC(C)(C)OC(=O)c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1.CO>>COc1ccc2c(C(=O)OC(C)(C)C)c3c(cc2n1)C1CNCC3C1 | [Na].CO.C(C)(C)(C)OC(=O)C1=C2C=CC(=NC2=CC=2C3CNCC(C12)C3)Cl.CO>>C(C)(C)(C)OC(=O)C1=C2C=CC(=NC2=CC=2C3CNCC(C12)C3)OC | Cl[c:3]1[cH:4][cH:5][c:6]2[c:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]3[c:16]([cH:17][c:18]2[n:19]1)[CH:20]1[CH2:21][NH:22][CH2:23][CH:24]3[CH2:25]1.[CH3:1][OH:2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]3[c:16]([cH:17][c:18]2[n:19]1)[C... | CC(C)(C)OC(=O)c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1.CO | COc1ccc2c(C(=O)OC(C)(C)C)c3c(cc2n1)C1CNCC3C1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8c774238786d4a1a5fbc42657602149adc59fb3eba0ee102e7029b95f561c796 | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | Sodium metal (˜12 mg) was dissolved in methanol (1 mL) under nitrogen with stirring and treated with a solution of 6-chloro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester (118 mg, 0.33 mmol) in methanol (3 mL) and brought to reflux for 18 hours. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1cnc2cc3c(cc2c1)C1CNCC3C1 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | c1cnc2cc3c(cc2c1)C1CNCC3C1 | HCl | null | null | null | CC(C)(C)OC(=O)c1c2c(cc3nc(Cl)ccc13)C1CNCC2C1.CO>>COc1ccc2c(C(=O)OC(C)(C)C)c3c(cc2n1)C1CNCC3C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-439e7a687fe84598b3e1c881ce019501 | CC(=O)c1ccc(Br)cc1.Cc1cc(Br)ccc1C(=O)O>>O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1 | CO.CC(=O)C1=CC=C(C=C1)Br.CC1=C(C(=O)O)C=CC(=C1)Br.[H-].[Na+]>>BrC1=CC=C(C=C1)C(CC(C1=CC=C(C=C1)Br)=O)=O | [CH3:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1.C[c:19]1[c:13]([C:2](O)=[O:1])[cH:14][cH:15][c:16]([Br:17])[cH:18]1>>[O:1]=[C:2]([CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1 | CC(=O)c1ccc(Br)cc1.Cc1cc(Br)ccc1C(=O)O | O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1 | null | null | C1=CC=CC=C1 | C-C Coupling | OtherReaction | 8d7e298e82e4bbd5de481dd29095f1032a2d8e2f2274cb4a92b2e336e5e965b1 | 49910546f6df8ca015ce53553723035869f216f30f58ae8019dcd4622353d7b5 | O=C(CC(=O)c1ccccc1)c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](-O)=[O;D1;H0:6]):[c:7].[CH3;D1;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:5](-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11])-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | 60 | CELSIUS | null | null | In a 1-liter three neck round bottom flask, 43 g (0.2 mol) methyl 4-bromobenzoic acid and 17.6 g (0.4 mol) sodium hydride were dissolved in 200 ml dried benzene and heated to 60° C. Next, 39.8 g (0.2 mol) 4-bromoacetophenone in 100 ml dry benzene was slowly added through a dropping funnel, and 1 ml methanol was added t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C1=CC=CC=C1 | 60 | null | CC(=O)c1ccc(Br)cc1.Cc1cc(Br)ccc1C(=O)O>C1=CC=CC=C1>O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0adf17f674044210915e55a9d072a99b | NO.O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1>>Brc1ccc(-c2cc(-c3ccc(Br)cc3)on2)cc1 | BrC1=CC=C(C=C1)C(CC(C1=CC=C(C=C1)Br)=O)=O.Cl.NO.[OH-].[Na+]>>BrC1=CC=C(C=C1)C1=NOC(=C1)C1=CC=C(C=C1)Br | [OH:16][NH2:17].O=[C:6]([c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:19][cH:18]1)[CH2:7][C:8](=O)[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]3)[o:16][n:17]2)[cH:18][cH:19]1 | NO.O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1 | Brc1ccc(-c2cc(-c3ccc(Br)cc3)on2)cc1 | null | null | O.O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 35a6a92be0c7e0e68e03ff68db08d05a69eb1b9c87e7a94f0e9524b2861379a6 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13].[NH2;D1;+0:14]-[OH;D1;+0:15]>>[c:6]:[c:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[n;H0;D2;+0:14]:[o;H0;D2;+0:15]:1... | null | [] | null | null | 12 | HOUR | In a 250 ml round bottom flask, 4 g (10.4 mmol) of [2] was dissolved in 100 ml dry dioxane and heated to reflux, then 3.0 g (43.2 mmol) hydroxylamine hydrogen chloride in 10 ml water and 5 ml (25 mmol) 5 N NaOH was then dropped into the refluxing mixture. After 12 hours, the reaction mixture was cooled down to room tem... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | HO- | O.O1CCOCC1 | null | 12 | NO.O=C(CC(=O)c1ccc(Br)cc1)c1ccc(Br)cc1>O.O1CCOCC1>Brc1ccc(-c2cc(-c3ccc(Br)cc3)on2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c817a0ea0ac64877a846f4b006c3f5c4 | O=C([O-])C(=O)[O-].[Ce+3].[O-2].[O-2].[O-2]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] | C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+].[Cl-].[Ce+3].[Cl-].[Cl-].[O-2].[Ce+3].[O-2].[O-2].[Ce+3]>>C(C(=O)[O-])(=O)[O-].[Ce+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Ce+3] | [O:1]=[C:2]([O-:3])[C:10](=[O:11])[O-:12].[Ce+3:19].[O-2:6].[O-2:18].[O-2:5]>>[O:1]=[C:2]([O-:3])[C:4](=[O:5])[O-:6].[O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[O:13]=[C:14]([O-:15])[C:16](=[O:17])[O-:18].[Ce+3:19] | O=C([O-])C(=O)[O-].[Ce+3].[O-2].[O-2].[O-2] | O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] | null | null | null | Acylation | OtherReaction | 03df169542e61bc25f850d05576488c0b54839b94e3082a72ebb3e4f24252841 | 46615a373e6434dd65776b88d9fcc22218d37124c5265a98f610d7564f54362b | null | [O-2;H0;D0:1].[O-2;H0;D0:2].[O-2;H0;D0:3].[O;-;D1;H0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[C:10]-[C:11](-[O-;H0;D1:2])=[O;D1;H0:12].[O-;H0;D1:1]-[C:13](=[O;H0;D1;+0:3])-[C;H0;D3;+0:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:14](-[O;-;D1;H0:15])=[O... | null | [] | 1,500 | CELSIUS | null | null | A cerium oxalate powder was prepared by adding an aqueous solution of ammonium oxalate to an aqueous solution of cerium chloride under stirring, causing the precipitation of cerium oxalate, filtering, and drying. The powder was ground with a jet-mill to obtain a starting material powder with a mean particle diameter of... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | 1,500 | null | O=C([O-])C(=O)[O-].[Ce+3].[O-2].[O-2].[O-2]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37e898ff656e4c9e94b943275265965e | COc1ccc(C(=O)Cl)cc1.COc1cccc(OC)c1>>COc1ccc(C(=O)c2ccc(OC)cc2OC)cc1 | Cl.COC1=CC(=CC=C1)OC.C(C1=CC=C(C=C1)OC)(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>COC1=C(C=CC(=C1)OC)C(=O)C1=CC=C(C=C1)OC | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1)=[O:8].[cH:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]1[O:17][CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1 | COc1ccc(C(=O)Cl)cc1.COc1cccc(OC)c1 | COc1ccc(C(=O)c2ccc(OC)cc2OC)cc1 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:10]:[c:11] | null | [] | null | null | null | null | 1,3-Dimethoxybenzene (13.8 g) and p-anisoyl chloride (17 g) were dissolved in a reaction flask containing 200 mL of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 g) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | COc1ccc(C(=O)Cl)cc1.COc1cccc(OC)c1>C(Cl)Cl>COc1ccc(C(=O)c2ccc(OC)cc2OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b20b70246a44d1e8b70b50336b7441c | COc1ccc(C(=O)Cl)cc1.O=C(Cl)c1ccccc1F>>COc1ccc(C(=O)c2ccccc2F)cc1 | C(C1=CC=C(C=C1)OC)(=O)Cl.NC1=CC=CC2=CC=CC=C12.FC1=C(C(=O)Cl)C=CC=C1.C1(=CC=CC=C1)OC>>FC1=C(C=CC=C1)C(=O)C1=CC=C(C=C1)OC | O=C(Cl)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][cH:16]1.Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[cH:16][cH:17]1 | COc1ccc(C(=O)Cl)cc1.O=C(Cl)c1ccccc1F | COc1ccc(C(=O)c2ccccc2F)cc1 | null | null | null | C-C Coupling | OtherReaction | 2141d805cb200c555dd0a65a475dafdab76558b89bb294884d98559bfa317f3e | 75a41004d03d2a6fb764d4720e5d90b58a710658470b24716bc9c18b018af260 | O=C(c1ccccc1)c1ccccc1 | Cl-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The procedure of Example 10 was followed except as follows. In Part A, 1-amino napthalene (47 g) was used in place of 4-methoxy aniline. In Step 1 of Part B, 2-fluorobenzoyl chloride (15.8 g) and anisole (10.8 g) were used in place of 1,3-dimethoxybenezene and p-anisoyl chloride respectively to produce (2-fluoro-phenyl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | COc1ccc(C(=O)Cl)cc1.O=C(Cl)c1ccccc1F>>COc1ccc(C(=O)c2ccccc2F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dfe4ced729254e01be55cc9bea0175d5 | O=C(O)c1ccc(O)cc1.OCCCCCCCl>>O=C(O)c1ccc(OCCCCCCO)cc1 | OC1=CC=C(C(=O)O)C=C1.ClCCCCCCO>>OCCCCCCOC1=CC=C(C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:16][cH:17]1.Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[cH:16][cH:17]1 | O=C(O)c1ccc(O)cc1.OCCCCCCCl | O=C(O)c1ccc(OCCCCCCO)cc1 | null | null | [OH-].[K+] | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 80 | [{"value": 80.0, "product": "OCCCCCCOC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Monomers in which the bulky organic group was a t-butyl group and the alkyl groups were hexyl groups were made as follows. 4-hydroxybenzoic acid was dissolved in 30% ethanolic KOH. About 1% of KI was added as a catalyst. The mixture was heated to about 60° C. and a stoichiometric amount of 6-chloro-1-hexanol was slowly... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | [OH-].[K+] | 60 | null | O=C(O)c1ccc(O)cc1.OCCCCCCCl>[OH-].[K+]>O=C(O)c1ccc(OCCCCCCO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6961669486c8494bb2c3a3bdd60048e7 | NC(=O)c1ccncc1>>NC(=O)c1ccncc1 | C1=C(N=C(S1)NC(=N)N)CSCCC(=N)NS(=O)(=O)N.C1=C(N=C(S1)NC(=N)N)CSCCC(=N)NS(=O)(=O)N.C(C1=CC=NC=C1)(=O)N.C(C(O)C)(=O)O>>C(C1=CC=NC=C1)(=O)N.C(C(O)C)(=O)O | [NH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1>>[NH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1 | NC(=O)c1ccncc1 | NC(=O)c1ccncc1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccncc1 | null | null | [] | null | null | null | null | To 1 g of famotidine and 5 g of isonicotinic acid amide were added about 80 ml of water for injection and 2.20 ml of a 100 mg/ml aqueous lactic acid solution, followed by stirring to dissolve them. After complete dissolution of famotidine, water for injection was added to make the total volume 100 ml, whereby an inject... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1 | null | O | null | null | NC(=O)c1ccncc1>O>NC(=O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f7b41588ad642d29308ad28a09d5a18 | Cc1ccc2sc3cc(C(=O)O)ccc3c(=O)c2c1.O=S(Cl)Cl>>Cc1ccc2sc3cc(C(=O)Cl)ccc3c(=O)c2c1 | CC1=CC=C2SC=3C=C(C=CC3C(C2=C1)=O)C(=O)O.S(=O)(Cl)Cl.CN(C=O)C>>CC1=CC=C2SC=3C=C(C=CC3C(C2=C1)=O)C(=O)Cl | O[C:10]([c:9]1[cH:8][c:7]2[s:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:19][c:18]3[c:16](=[O:17])[c:15]2[cH:14][cH:13]1)=[O:11].O=S(Cl)[Cl:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[s:6][c:7]3[cH:8][c:9]([C:10](=[O:11])[Cl:12])[cH:13][cH:14][c:15]3[c:16](=[O:17])[c:18]2[cH:19]1 | Cc1ccc2sc3cc(C(=O)O)ccc3c(=O)c2c1.O=S(Cl)Cl | Cc1ccc2sc3cc(C(=O)Cl)ccc3c(=O)c2c1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=c1c2ccccc2sc2ccccc12 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[c:7]:[#16;a:8]>>[#16;a:8]:[c:7]:[c:6]:[c:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3]):[c:5] | 85 | [{"value": 85.0, "product": "CC1=CC=C2SC=3C=C(C=CC3C(C2=C1)=O)C(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The 7-methyl-9-oxothioxanthene-3-carboxylic acid (MTA), 50.0 g (0.185 mol), was dissolved in 350 ml of toluene and 415 ml (5.69 mol) of thionyl chloride using an overhead stirrer in a 2 liter 3-neck round bottom flask. N,N-Dimethylformamide (DMF), 2 ml, was added and the reaction was brought to reflux for 2 hours. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2sc3ccccc3cc2c1 | HCl | C1(=CC=CC=C1)C | null | 16 | Cc1ccc2sc3cc(C(=O)O)ccc3c(=O)c2c1.O=S(Cl)Cl>C1(=CC=CC=C1)C>Cc1ccc2sc3cc(C(=O)Cl)ccc3c(=O)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-21dd6ba93a02489eb74c79b936dfe3ac | CC(=O)OC(C)=O.O=C(O)/C=C\C(=O)NCCCCCC(=O)O.c1ccc2c(c1)Nc1ccccc1S2>>O=C(CCCCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O | O=C(\C=C/C(=O)O)NCCCCCC(=O)O.C(C)(=O)OC(C)=O.C1=CC=CC=2SC3=CC=CC=C3NC12.Cl.O>>C1CC(=O)N(C1=O)OC(=O)CCCCCN2C(=O)C=CC2=O | CC(=O)OC(C)=[O:18].[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:13](/[CH:12]=[CH:11]\[C:9](=[O:10])[OH:22])=[O:14])[OH:15].c1cc[c:21]2c(c1)Sc1cc[cH:20][cH:19][c:17]1[NH:16]2>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[CH:11]=[CH:12][C:13]1=[O:14])[O:15][N:16]1[C:17](=[O:18])[CH2:19][... | CC(=O)OC(C)=O.O=C(O)/C=C\C(=O)NCCCCCC(=O)O.c1ccc2c(c1)Nc1ccccc1S2 | O=C(CCCCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O | null | null | C1CCOC1.C(C)N(CC)CC | C-C Coupling | OtherReaction | 6db43b436ba612c61d3a5f5367e148113f0fee4b92812126b59adc2e26919ec0 | 669dea8e1aa93881007fcd6c4da5254692628cb2aef0cdc3dbd59cf58249f8d6 | O=C(CCCCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O | C-C(=O)-O-C(-C)=[O;H0;D1;+0:1].S1-c2:c:c:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4]:2-[NH;D2;+0:5]-[c;H0;D3;+0:6]2:c:c:c:c:c:2-1.[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])/[C:16]=[C:17]\[C;H0;D3;+0:18](=[O;D1;H0:19])-[OH;D1;+0:20]>>[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[... | null | [] | null | null | null | null | (Z)-4-Oxo-5-aza-2-undecendioic acid, 150.0 g (0.654 moles), acetic anhydride, 68 ml (73.5 g, 0.721 moles), and phenothiazine, 500 mg, were added to a 2 liter three-neck round bottom flask equipped with an overhead stirrer. Triethylamine, 91 ml (0.653 moles), and 600 ml of THF were added and the mixture was heated to re... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amine.Monosulfide | Substituted dicarboximide.Tertiary amide.Tertiary amide | c1ccc2c(c1)Nc1ccccc1S2 | C1=CC[NH]C1.C1CC[NH]C1 | C1=CC[NH]C1.C1CC[NH]C1 | Other | C1CCOC1.C(C)N(CC)CC | null | null | CC(=O)OC(C)=O.O=C(O)/C=C\C(=O)NCCCCCC(=O)O.c1ccc2c(c1)Nc1ccccc1S2>C1CCOC1.C(C)N(CC)CC>O=C(CCCCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8515cfed68d2474e998cef70299e4581 | COc1ccc(C(C)=O)cc1.O=C/C=C/c1ccccc1>>COc1ccc(C(=O)C=CC=Cc2ccccc2)cc1 | C(\C=C\C1=CC=CC=C1)=O.CC(=O)C1=CC=C(C=C1)OC.[OH-].[Na+]>>COC1=CC=C(C=C1)C(C=CC=CC1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH3:9])[cH:19][cH:20]1.O=[CH:10]/[CH:11]=[CH:12]/[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]=[CH:10][CH:11]=[CH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | COc1ccc(C(C)=O)cc1.O=C/C=C/c1ccccc1 | COc1ccc(C(=O)C=CC=Cc2ccccc2)cc1 | null | null | C(C)O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | f500c100f5cd3378729ee1542c3d95141e4f1833211cc2ce0c35099b4e896130 | 101c8d17ab7e80420efd3d968b7962dd5450cc718389428be42f0baaa6391f61 | O=C(C=CC=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]/[C:2]=[C:3]/[c:4](:[c:5]):[c:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[O;D1;H0:9]=[C:8](-[c:10])-[CH;D2;+0:7]=[CH;D2;+0:1]-[C:2]=[C:3]-[c:4](:[c:5]):[c:6] | 72 | [{"value": 72.0, "product": "COC1=CC=C(C=C1)C(C=CC=CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 2 ml of trans-cinnamaldehyde and 2.5 g of 4-methoxy acetophenone were dissolved in 50 ml of ethanol at room temperature. 10 ml of sodium hydroxide solution was then added and stirred for 12 h to form yellow solid precipitation. Filtering the precipitation to obtain the compound 1, with yield of 72% and purity of 96.3%.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Conjugated diene | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | 12 | COc1ccc(C(C)=O)cc1.O=C/C=C/c1ccccc1>C(C)O>COc1ccc(C(=O)C=CC=Cc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbc38cb4d21e4dbba0e6138c6543b664 | O=C(O)c1ccccc1-c1ccccc1C(=O)O>>O=C(O)c1cccc2c1-c1ccccc1C2=O | C=1(C(C(=O)O)=CC=CC1)C=1C(C(=O)O)=CC=CC1>>C1=CC=C2C(=C1)C3=C(C2=O)C=CC=C3C(=O)O | O=[C:16]([c:15]1[c:10](-[c:9]2[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][cH:7][cH:8]2)[cH:11][cH:12][cH:13][cH:14]1)[OH:17]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]2=[O:17] | O=C(O)c1ccccc1-c1ccccc1C(=O)O | O=C(O)c1cccc2c1-c1ccccc1C2=O | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 7ef164e95534b750b8f447337d5960d1ddb5d629daec09f6c5afef2d8b94fe7a | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1c2ccccc2-c2ccccc21 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[c:3](:[c:4]):[c:5]-[c:6](:[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[c:7]:[c:6]1:[c;H0;D3;+0:11](:[c:12]:[c:13])-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]-1 | null | [] | 70 | CELSIUS | null | null | The following steps are suitable for synthesizing some charge transport materials of this invention involving a linking reaction as described in the following. In the first step, diphenic acid or its derivative is dissolved in large access of concentrated sulfuric acid and the solution is heated at approximately 70° C.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HO- | S(O)(O)(=O)=O | 70 | null | O=C(O)c1ccccc1-c1ccccc1C(=O)O>S(O)(O)(=O)=O>O=C(O)c1cccc2c1-c1ccccc1C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b44b058630ea4732a4877a0e475a05d2 | O=C(O)c1cccc2c1-c1ccccc1C2=O.O=S(Cl)Cl>>O=C(Cl)c1cccc2c1-c1ccccc1C2=O | C1=CC=C2C(=C1)C3=C(C2=O)C=CC=C3C(=O)O.S(=O)(Cl)Cl>>C1=CC=C(C=2C3=CC=CC=C3C(C12)=O)C(=O)Cl | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]2=[O:17].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]2=[O:17] | O=C(O)c1cccc2c1-c1ccccc1C2=O.O=S(Cl)Cl | O=C(Cl)c1cccc2c1-c1ccccc1C2=O | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1c2ccccc2-c2ccccc21 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | The following steps are suitable for synthesizing some charge transport materials of this invention involving a linking reaction as described in the following. In the first step, diphenic acid or its derivative is dissolved in large access of concentrated sulfuric acid and the solution is heated at approximately 70° C.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | HCl | null | null | null | O=C(O)c1cccc2c1-c1ccccc1C2=O.O=S(Cl)Cl>>O=C(Cl)c1cccc2c1-c1ccccc1C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5934e900187f46f2962c30933ab22f3e | NC(CO)(CO)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=P([O-])(O)O>>N[C@H]1C(O)O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O | OP(=O)(O)[O-].[K+].[Na+].[Cl-].C(CC(O)(C(=O)O)CC(=O)O)(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(C(CO)(CO)N)O.[NH4+].[OH-]>>P(=O)(O)(O)OC[C@@H]1[C@H]([C@@H]([C@H](C(O)O1)N)O)O | OC[C:2](CO)([NH2:1])[CH2:3][OH:4].OC[C@@H](O)[C@H:15]([C@@H:13]([C@@H:6]([OH:5])[CH:7]=[O:8])[OH:14])[OH:16].[O-][P:9](=[O:10])([OH:11])[OH:12]>>[NH2:1][C@H:2]1[CH:3]([OH:4])[O:5][C@H:6]([CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12])[C@@H:13]([OH:14])[C@@H:15]1[OH:16] | NC(CO)(CO)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=P([O-])(O)O | N[C@H]1C(O)O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O | null | [O-]S(=O)(=O)[O-].[Mn+2].O | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b9daa8571298221fc3f0f80f38b01eb9c8fd4973f6f786c32e86dbcb530321d | f450bbdca41fe80f7e780f687ed680a7c86943e5b833f2419f80307e98e9aa07 | C1CCOCC1 | O-C-[C;H0;D4;+0:1](-[N;D1;H2:2])(-C-O)-[CH2;D2;+0:3]-[O;D1;H1:4].O-C-[C@@H](-O)-[C@@H;D3;+0:5](-[O;D1;H1:6])-[C:7](-[O;D1;H1:8])-[C:9](-[OH;D1;+0:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12].[O-]-[P;H0;D4;+0:13](=[O;D1;H0:14])(-[O;D1;H1:15])-[O;D1;H1:16]>>[N;D1;H2:2]-[C@@H;D3;+0:1]1-[C@@H;D3;+0:5](-[O;D1;H1:6])-[C:7](-[O;D1;H1:8... | null | [] | null | null | 24 | HOUR | coli cells from frozen vials were inoculated into a flask culture containing 12 L fermentation seed medium. The medium contained the following chemicals (g/L): corn steep liquor, 10; KH2PO4, 2.5; MgSO4.7H2O, 2.0; (NH4)2SO4, 0.5; citric acid, 0.192; FeSO4.7H2O, 0.03; MnSO4.H2O, 0.021; antifoam 6000K, 0.5; dextrose, 84. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Ether.Secondary alcohol.Secondary alcohol.Phosphate ester | null | C1CCOCC1 | C1CCOCC1 | HO- | [O-]S(=O)(=O)[O-].[Mn+2].O | null | 24 | NC(CO)(CO)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=P([O-])(O)O>[O-]S(=O)(=O)[O-].[Mn+2].O>N[C@H]1C(O)O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbe48744c0294939ba6d1cf3cf9c9148 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3C[C@@H]12>>C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O | C[C@]1(C=2C=CC=C(C2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C>>O=C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H:8]1[C:10](=O)[OH:11].CN(C)[C@@H]1C([OH:5])=C(C(N)=O)C(=O)[C@@:6]2([OH:7])C([OH:9])=C3C(=O)c4c(O)cccc4[C@@:2]([CH3:1])([OH:3])[C@H:4]3C[C@@H]12>>[CH3:1][C@H:2]([OH:3])[C@H:4]([OH:5])[C@@H:6]([OH:7])[C@@H:8]([OH:9])[CH:10]=[O:11] | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3C[C@@H]12 | C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O | null | null | null | Acylation | OtherReaction | 684f06e05d012b9e101b6ece1a91fbd4be217656196f53791cc06681757be199 | 79340e30ff356cc2f5a500bf7fcf29daef145103f8b1fd59f21154fcea797f4a | null | null | null | [] | null | null | null | null | The plasmid pBRsacH3 (Example 1) was used for cloning the rMET1 antibody (Example 9). In this case, the kappa and heavy chains were engineered with human ceruloplasmin and human neutrophil defensin signal sequences, respectively (Example 9). This plasmid was electroporated into E. coli strain DH10B rha+ to generate clo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Primary amide.Secondary amide.Tertiary amide.Tertiary alcohol.Tertiary alcohol.Aromatic alcohol.Enol.Enol.Primary amine.Tertiary amine.Monosulfide | Aldehyde.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.C1CN2CC[C@H]2S1.C1=CC[C@H]2C=C3Cc4ccccc4C[C@H]3C[C@H]2C1 | null | null | Other | null | null | null | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3C[C@@H]12>>C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-afeca0c943ca41f0aa079e3950bd9291 | CC(=O)OC(C)(C)C.O=C1C[C@H](O)CO1>>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO | C(C)(C)[N-]C(C)C.[Li+].C(C)(C)[N-]C(C)C.[Li+].C(CCC)[Li].C(C)(C)NC(C)C.Cl.O[C@H]1CC(=O)OC1.C(C)(=O)OC(C)(C)C>>C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].[C:9]1(=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][OH:15] | CC(=O)OC(C)(C)C.O=C1C[C@H](O)CO1 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO | null | null | C(C)(=O)OCC.O1CCCC1.CCCCCC | C-C Coupling | OtherReaction | 6101cad8e2935c8b5c0ac7b0e1858cf3a3d323219bb17c58420a61905745e852 | 1002d3291f2ad18779eb4fab129659f5bfd76d885e10bba8befbd85b6c532bbb | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8].[O;D1;H0:9]=[C;H0;D3;+0:10]1-[C:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:8])-[CH2;D2;+0:7]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[C:11]-[C:12]-[C:13]-[OH;D1;+0:14] | 6 | [{"value": 6.0, "product": "C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.7, "product": "C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | To 30 mL (45 mmol) of a solution of n-butyllithium in hexane (1.5 mol/L) was added a solution of diisopropylamine (5.01 g, 49.5 mmol)-tetrahydrofuran (5 mL) dropwise under stirring at 5° C., and the mixture was stirred under argon for 1 hour to prepare a lithium diisopropylamide solution. In a separate vessel, 1.02 g (... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone.Ester.Primary alcohol | C1CCOC1 | null | null | null | C(C)(=O)OCC.O1CCCC1.CCCCCC | 5 | null | CC(=O)OC(C)(C)C.O=C1C[C@H](O)CO1>C(C)(=O)OCC.O1CCCC1.CCCCCC>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fa056755395410a8769840af876295d | CC(C)(C)OC(=O)CBr.O=C1C[C@H](O)CO1>>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO | BrCC(=O)OC(C)(C)C.C[Si](C)(C)Cl.BrCC(=O)OC(C)(C)C.O[C@H]1CC(=O)OC1.[OH-].[Na+]>>C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[C:9]1(=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][OH:15] | CC(C)(C)OC(=O)CBr.O=C1C[C@H](O)CO1 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO | null | [Zn] | O.O1CCCC1 | C-C Coupling | OtherReaction | c6f8192bbe03a14b72dd6a446dcadca28ed9a702b97f7f2c9f67505ce87241e7 | 927029737ca4800f17176897b097086b9e9024d361c17b2cd676dad17a2af962 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[O;D1;H0:9]=[C;H0;D3;+0:10]1-[C:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-1>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[C:11]-[C:12]-[C:13]-[OH;D1;+0:14] | 116.1 | [{"value": 29.0, "product": "C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 116.1, "product": "C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 30 | MINUTE | To a suspension of 9.82 g (150 mmol) of zinc dust in 40 mL of tetrahydrofuran was added 1.9 mL (15 mmol) of trimethylsilyl chloride at room temperature, and the mixture was stirred for 30 minutes. To this mixture were added 2.4 mL (10.5 mmol) of tert-butyl α-bromoacetate and 4.27 g (42 mmol) of (S)-β-hydroxy-γ-butyrola... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ketone.Ester.Primary alcohol | C1CCOC1 | null | null | Br- | [Zn].O.O1CCCC1 | 65 | 0.5 | CC(C)(C)OC(=O)CBr.O=C1C[C@H](O)CO1>[Zn].O.O1CCCC1>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29050331286246aa9b5102f1f43d720f | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO.O=C(Cl)c1ccccc1>>CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1 | [OH-].[Na+].C(C)(C)(C)OC(CC(C[C@@H](CO)O)=O)=O.N1=CC=CC=C1.C(C1=CC=CC=C1)(=O)Cl>>C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][OH:15].Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:... | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO.O=C(Cl)c1ccccc1 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1 | null | null | O.C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78 | [{"value": 78.0, "product": "C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of 16.8 g (77 mmol) of the (5S)-5,6-dihydroxy-3-oxohexanoic tert-butyl ester produced in Example 1 in 120 mL of methylene chloride were added 11.2 mL of pyridine and 10.2 mL of benzoyl chloride at 0° C., and the mixture was stirred at 0° C. for 2 hours. After completion of the reaction, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | O.C(Cl)Cl | 0 | 2 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CO.O=C(Cl)c1ccccc1>O.C(Cl)Cl>CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26bcb764111141deba45aba2d82d8f7e | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1>>CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)=O)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(C)(=O)OCC>>C(C)(C)(C)OC(C[C@@H](C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21... | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1 | CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 | null | null | P(=O)([O-])([O-])[O-] | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | null | [] | 27 | CELSIUS | 2.5 | DAY | A large test tube was charged with 5 ml of Medium A described hereinbefore and, after sterilization, inoculated with one of the microorganisms indicated in Table 1 and Table 2. Aerobic shake culture was carried out at 27° C. for 2 to 3 days. From a 1.5 ml portion of the resulting culture, the cells were harvested by ce... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | P(=O)([O-])([O-])[O-] | 27 | 60 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1>P(=O)([O-])([O-])[O-]>CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf0fdec98e874af7be6a18c9a6110a97 | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1>>CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)=O)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>C(C)(C)(C)OC(C[C@@H](C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]([OH:13])[CH2:14][O:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21... | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1 | CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 | null | null | P(=O)([O-])([O-])[O-] | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | null | [] | null | null | null | null | Using 5 ml of Medium C described hereinbefore, the microorganisms indicated in Table 4 were cultured in the same manner as in Example 11. From 5 ml of each culture, the cells were centrifugally harvested, suspended in 0.5 ml of 100 mM phosphate buffer (pH 6.5) containing 0.05% of (5S)-6-benzoyloxy-5-hydroxy-3-oxohexano... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | P(=O)([O-])([O-])[O-] | null | null | CC(C)(C)OC(=O)CC(=O)C[C@H](O)COC(=O)c1ccccc1>P(=O)([O-])([O-])[O-]>CC(C)(C)OC(=O)C[C@H](O)C[C@H](O)COC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-980177fca8a041c8ab1d3755eefdece6 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(O)([O-])=O.[Na+].C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | 72 | [{"value": 72.0, "product": "C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | To a solution composed of 8.94 g (27.6 mmol) of (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 35.8 mL of 2,2-dimethoxypropane, and 2.5 mL of methylene chloride was added 269 mg (1.4 mmol) of p-toluenesulfonic acid-1H2O, and the mixture was stirred at 20° C. for 4 hours, after which 50... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | C(Cl)Cl | 20 | 4 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a04649c10df4184a5d8aa78ef30e2a3 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.CC(=O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | 40 | CELSIUS | 16 | HOUR | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone was added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O, and the mixture was stirred at 40° C. for 16 hou... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | O.C(C)#N | 40 | 16 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0993d93248bf475d918c0a23581a47a7 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 78.8%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 7.5%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 5.9%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 3.0%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6dcf5cdee5f4580990d89ae67e88dda | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | N1=CC=CC=C1.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | null | null | null | null | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O and 11.9 mg (0.15 mmol) of pyridine, and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8e538f0579c41db942698431874f3f6 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 93.1%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 3.4%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24353d021c514b1880414b4e363889fe | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)N(CC)CC.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | null | null | null | null | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O and 15.2 mg (0.15 mmol) of triethylamine, and th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdf8bb4b2ddc49f28298a435bb43b722 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 93.3%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 3.0%; (2S, 4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1166148f5b4d48509429004f74eb2ee2 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | N1C=NC=C1.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | null | null | null | null | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O and 10.2 mg (0.15 mmol) of imidazole, and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bd7853f654c47c781dcb1430a6b6a20 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 93.9%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 3.0%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d475ed245f9540058b93905df4149af0 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC=1C=NC=CC1.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | null | null | null | null | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O and 14.0 mg (0.15 mmol) of 3-methylpyridine, and... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76b1b6cdfdab46429b9b29b828b67971 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 93.8%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 2.8%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
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