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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b37387234d9b48f3aa711f14904bb138 | CCCCS(=O)(=O)Cl.COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N>>CCCCS(=O)(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1OC | C(CCC)S(=O)(=O)Cl.NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC.C(C)N(CC)CC>>COC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1NS(=O)(=O)CCCC | Cl[S:5]([CH2:4][CH2:3][CH2:2][CH3:1])(=[O:6])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21]3[CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]32)[cH:29][c:30]1[O:31][CH3:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([C:13... | CCCCS(=O)(=O)Cl.COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N | CCCCS(=O)(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1OC | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 102.9 | [{"value": 102.9, "product": "COC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1NS(=O)(=O)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of 0.10 g of 10,11-dihydro-10-(4-amino-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 60 mg of triethylamine followed by a solution of 56 mg of n-butylsulfonyl chloride in 0.5 ml of methylene chloride. After stirring at room temperature for 2 hours, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 2 | CCCCS(=O)(=O)Cl.COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N>C(Cl)Cl>CCCCS(=O)(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-170e488e116e4e0492b95134d1d42168 | CC(C)(CO)CO.O=C1CCCC(=O)C1>>CC1(C)COC2(CCCC(=O)C2)OC1 | C1(CC(CCC1)=O)=O.CC(CO)(CO)C>>CC1(COC2(OC1)CC(CCC2)=O)C | O[CH2:14][C:2]([CH3:1])([CH3:3])[CH2:4][OH:5].[C:6]1(=[O:13])[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[CH2:12]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][C:6]2([CH2:7][CH2:8][CH2:9][C:10](=[O:11])[CH2:12]2)[O:13][CH2:14]1 | CC(C)(CO)CO.O=C1CCCC(=O)C1 | CC1(C)COC2(CCCC(=O)C2)OC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | a715eea77bc86a3813dadf8adc372e0b7b940f7e64de03921d37f88c29409800 | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | O=C1CCCC2(C1)OCCCO2 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[OH;D1;+0:6].[O;D1;H0:7]=[C:8]1-[C:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]-[C:13]-[C:14]-1>>[C;D1;H3:3]-[C:2]1(-[C;D1;H3:4])-[C:5]-[O;H0;D2;+0:6]-[C;H0;D4;+0:10]2(-[C:9]-[C:8](=[O;D1;H0:7])-[C:14]-[C:13]-[C:12]-2)-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | 125 g (630 mmole) 3,3-dimethyl-1,5-dioxa-spiro[5,5]undecan-8-one, which was obtained by the azeotropic acetylation of cyclohexane-1,3-dione with 2,2-dimethylpropane-1,3-diol in toluene as a solvent using p-toluenesulphonic acid as a catalyst, and 59 g (630 mmole) dimethylammonium methylene chloride were stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | C1CCCCC1 | C1CCC2(CC1)OCCCO2 | C1CCC2(CC1)OCCCO2 | HO- | C1(=CC=CC=C1)C | null | null | CC(C)(CO)CO.O=C1CCCC(=O)C1>C1(=CC=CC=C1)C>CC1(C)COC2(CCCC(=O)C2)OC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ddb642f02864792bfbacd5b7be3fb31 | Brc1cccc(OCc2ccccc2)c1.CN(C)CC1CCC(C(F)(F)F)CC1=O>>CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(OCc2ccccc2)c1 | [Mg].CN(C)CC1C(CC(CC1)C(F)(F)F)=O.FC(C1CC(CCC1)=O)(F)F.CN(C)C(Cl)Cl.C(C1=CC=CC=C1)OC=1C=C(C=CC1)Br.[Cl-].[NH4+].C(C1=CC=CC=C1)OC=1C=C(C=CC1)Br>>C(C1=CC=CC=C1)OC=1C=C(C=CC1)C1(C(CCC(C1)C(F)(F)F)CN(C)C)O | Br[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:9]([F:10])([F:11])[F:12])[CH2:13][C:14]1=[O:15]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:9]([F:10])([F:11])[F:12])[CH2:13][C:14]1([OH:15])... | Brc1cccc(OCc2ccccc2)c1.CN(C)CC1CCC(C(F)(F)F)CC1=O | CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(OCc2ccccc2)c1 | null | null | C(C)#N.CCOCC.O1CCCC1 | C-C Coupling | Grignard_alcohol | a931995fda9e1945c54e5e8576d835233f84350823d88bf0c76b4c2a9041417b | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(COc2cccc(C3CCCCC3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[C:8])-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]-[C:12]>>[C:6]-[C:7](-[C:8])-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:11]-[C:12] | null | [] | null | null | 8 | HOUR | 43.9 g (167 mmole) 3-benzyloxy-1-bromobenzene, dissolved in 200 ml of dry tetrahydrofuran, were added drop-wise to 4.06 g (167 mmole) magnesium turnings in 40 ml of dry tetrahydrofuran so that the reaction mixture boiled gently. After the addition of 3-benzyloxy-1-bromobenzene was complete, the mixture was heated for o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.C1CCCCC1 | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | Br- | C(C)#N.CCOCC.O1CCCC1 | null | 8 | Brc1cccc(OCc2ccccc2)c1.CN(C)CC1CCC(C(F)(F)F)CC1=O>C(C)#N.CCOCC.O1CCCC1>CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(OCc2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25abf8f48bd44a67ad9fc5f31b8887db | CN(C)C(Cl)Cl.CN(C)CC1CCC(C(F)(F)F)CC1=O.O=C1CCCC(C(F)(F)F)C1>>CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(O)c1.Cl | CN(C)CC1C(CC(CC1)C(F)(F)F)=O.FC(C1CC(CCC1)=O)(F)F.CN(C)C(Cl)Cl>>Cl.CN(C)CC1C(CC(CC1)C(F)(F)F)(O)C=1C=C(C=CC1)O | CN(C)C(Cl)[Cl:23].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:9]([F:10])([F:11])[F:12])[CH2:13][C:14]1=[O:15].FC(F)(F)[CH:16]1[CH2:17][CH2:18][CH2:19][C:20](=[O:21])[CH2:22]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:9]([F:10])([F:11])[F:12])[CH2:13][C:14]1([OH:15])[c:16]1[cH:17][cH:18]... | CN(C)C(Cl)Cl.CN(C)CC1CCC(C(F)(F)F)CC1=O.O=C1CCCC(C(F)(F)F)C1 | CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(O)c1.Cl | null | null | C(C)#N | C-C Coupling | OtherReaction | 82cfc8f1457ad049b251d09c6f9bcc4aa9572756002ac75bf1c96e05de003fbb | 0ae6cdd34731ce2234e741f143fe6a852addfd96c99ae9080da4c65a3542e246 | c1ccc(C2CCCCC2)cc1 | C-N(-C)-C(-Cl)-[Cl;H0;D1;+0:1].F-C(-F)(-F)-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[CH2;D2;+0:8]-1.[C:9]-[C:10](-[C:11])-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14]-[C:15]>>[C:9]-[C:10](-[C:11])-[C;H0;D4;+0:12](-[OH;D1;+0:13])(-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D... | null | [] | null | null | null | null | The 5-epimer (27) of compound (25) was prepared, under the conditions given in Example 27, from (2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone, prepared from 3-trifluoromethyl-cyclohexanone and dimethylaminomethylene chloride in acetonitrile. (27) was obtained in a yield of 27% theoretical and had a me... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary halide.Secondary halide.Ketone.Ketone.Tertiary amine | Tertiary alcohol.Aromatic alcohol | C1CCCCC1.C1CCCCC1 | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | HF | C(C)#N | null | null | CN(C)C(Cl)Cl.CN(C)CC1CCC(C(F)(F)F)CC1=O.O=C1CCCC(C(F)(F)F)C1>C(C)#N>CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(O)c1.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b4ebe9966634e10a9ec36b7cb413dc4 | C1=CCC=C1.CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)Cl>>CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)C1C=CC=C1 | C(CCC)[Li].C1=CC=CC1.C[Si](Cl)(C1=C(C=CC=2C3=CC=C(C=C3CC12)C(C)(C)C)C(C)(C)C)C>>C[Si](C1C=CC=C1)(C1=C(C=CC=2C3=CC=C(C=C3CC12)C(C)(C)C)C(C)(C)C)C | [CH2:25]1[CH:26]=[CH:27][CH:28]=[CH:29]1.Cl[Si:22]([c:21]1[c:12]2[c:13]([cH:14][cH:15][c:16]1[C:17]([CH3:18])([CH3:19])[CH3:20])-[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:10][c:9]1[CH2:11]2)([CH3:23])[CH3:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][c:12]1[c:13]-2[... | C1=CCC=C1.CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)Cl | CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)C1C=CC=C1 | null | null | O=O.CCCCCC.O | Functional Group Interconversion | OtherReaction | f09801366e2c82549f138d35b538c6a049e546453060a00297c4b0e8d39dd8d8 | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | C1=CC([SiH2]c2cccc3c2Cc2ccccc2-3)C=C1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[c:4](:[c:5]):[c:6].[C:7]1=[C:8]-[C:9]=[C:10]-[CH2;D2;+0:11]-1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[CH;D3;+0:11]1-[C:7]=[C:8]-[C:9]=[C:10]-1)-[c:4](:[c:5]):[c:6] | 52.3 | [{"value": 51.0, "product": "C[Si](C1C=CC=C1)(C1=C(C=CC=2C3=CC=C(C=C3CC12)C(C)(C)C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.3, "product": "C[Si](C1C=CC=C1)(C1=C(C=CC=2C3=CC=C(C=C3CC12)C(C)(C)C)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 8.5 ml (21 mmol) of a 2.5M solution of butyllithium in hexane were added dropwise to 1.4 g (21 mmol) of cyclopentadiene in 45 ml of O2 -free and H2O-free THF at 0° C. under argon and the mixture was stirred for a further 2 hours at room temperature. This solution was subsequently added at room temperature to a solution... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | C1=CCC=C1 | C1=CCC=C1 | c1ccc2c(c1)Cc1ccccc12.C1=CCC=C1 | HCl | O=O.CCCCCC.O | null | 2 | C1=CCC=C1.CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)Cl>O=O.CCCCCC.O>CC(C)(C)c1ccc2c(c1)Cc1c-2ccc(C(C)(C)C)c1[Si](C)(C)C1C=CC=C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88c4d02c8563491e94268fb63352bd18 | C#CCBr.CC(C)(C)n1nc(-c2cc(Cl)nc(Cl)c2)[nH]c1=O>>C#CCn1c(-c2cc(Cl)nc(Cl)c2)nn(C(C)(C)C)c1=O | C(C#C)Br.C(C)(C)(C)N1N=C(NC1=O)C1=CC(=NC(=C1)Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)(C)N1N=C(N(C1=O)CC#C)C1=CC(=NC(=C1)Cl)Cl | Br[CH2:3][C:2]#[CH:1].[nH:4]1[c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10][c:11]([Cl:12])[cH:13]2)[n:14][n:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]1=[O:21]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10][c:11]([Cl:12])[cH:13]2)[n:14][n:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]1=[O:21] | C#CCBr.CC(C)(C)n1nc(-c2cc(Cl)nc(Cl)c2)[nH]c1=O | C#CCn1c(-c2cc(Cl)nc(Cl)c2)nn(C(C)(C)C)c1=O | null | O | C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8bef00eaa42d3c717b13b9e6e5eb0aaa548aa02b0e5b8a7323f70bc5d1c7c865 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]nc(-c2ccncc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C:4]-[#7;a:5]1:[#7;a:6]:[c:7](-[c:8]):[nH;D2;+0:9]:[c:10]:1=[O;D1;H0:11]>>[C:4]-[#7;a:5]1:[#7;a:6]:[c:7](-[c:8]):[n;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3]):[c:10]:1=[O;D1;H0:11] | null | [] | null | null | 2.5 | HOUR | To 2.06 g (7.2 mmol) of crude 2-(t-butyl)-5-(2,6-dichloro-4-pyridyl)-1,2,4-triazolin-3-one were added 30 mL of ethyl acetate, 1 drop of water, and 1.00 g (7.30 mmol) of powdered K2CO3. The mixture was heated to reflux and after 15 min 1.10 g (7.4 mmol) of an 80% by weight solution of propargyl bromide in toluene was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccncc1 | HBr | O.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | 2.5 | C#CCBr.CC(C)(C)n1nc(-c2cc(Cl)nc(Cl)c2)[nH]c1=O>O.C1(=CC=CC=C1)C.C(C)(=O)OCC>C#CCn1c(-c2cc(Cl)nc(Cl)c2)nn(C(C)(C)C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-039f04557c6449468449a7e6c9502c8d | CCNc1nc(Cl)nc(NC(C)C)n1>>CCNc1nc(Cl)nc(NCC)n1 | NN1C(=NN=C(C1=O)C(C)(C)C)SC.ClC1=NC(=NC(=N1)NCC)NC(C)C.CSC1=NC(=NC(=N1)NCCOC)NC(C)C.CSC1=NC(=NC(=N1)NC(C)C)NC(C)C.COC1=NC(=NC(=N1)NC(C)C)NC(C)C.ClC1=NC(=NC(=N1)NCC)NCCCOC.CSC1=NC(=NC(=N1)NCC)NC(C)C.COC1=NC(=NC(=N1)NCC)NC(C)C.ClC1=NC(=NC(=N1)NCCCOC)NCCCOC.ClC1=NC(=NC(=N1)NC(C)C)NC(C)C>>ClC1=NC(=NC(=N1)NCC)NCC | C[CH:2]([CH3:1])[NH:3][c:4]1[n:5][c:6]([Cl:7])[n:8][c:9]([NH:10][CH2:11][CH3:12])[n:13]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([Cl:7])[n:8][c:9]([NH:10][CH2:11][CH3:12])[n:13]1 | CCNc1nc(Cl)nc(NC(C)C)n1 | CCNc1nc(Cl)nc(NCC)n1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | C-[CH;D3;+0:1](-[C;D1;H3:2])-[#7:3]-[c:4](:[#7;a:5]):[#7;a:6]>>[#7;a:5]:[c:4](-[#7:3]-[CH2;D2;+0:1]-[C;D1;H3:2]):[#7;a:6] | null | [] | null | null | null | null | 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; 2-chloro-4,6-bis(3-methoxy-n-propylamino)-s-triazine; 2-methoxy-4,6-bis(isopropylamino)-s-triazine; 2-chloro-4-ethylamino-6-(3-methoxy-n-propylamino)-s-triazine; 2-methylmercapto-4,6-bis(isopropylamino)-s-triazine; 2-methylmercapto-4,6-bis(ethylamino)-2-triazine; 2-met... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | Other | null | null | null | CCNc1nc(Cl)nc(NC(C)C)n1>>CCNc1nc(Cl)nc(NCC)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bee7f21eecd8496aa01893e1f72c5f69 | O=[N+]([O-])c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1>>O=[N+]([O-])c1ccc(Oc2ccc(Cl)cc2Cl)cc1 | C1=CC(=CC=C1[N+](=O)[O-])OC2=C(C=C(C=C2Cl)Cl)Cl.ClC1=C(OC=2C=CC(=C(C(=O)NS(=O)(=O)C)C2)[N+](=O)[O-])C=CC(=C1)C(F)(F)F.C1=CC(=CC=C1[N+](=O)[O-])OC2=C(C=C(C=C2)C(F)(F)F)[N+](=O)[O-].ClC1=C(OC=2C=CC(=C(C(=O)[O-])C2)[N+](=O)[O-])C=CC(=C1)C(F)(F)F.[Na+].ClC1=C(OC=2C=CC(=C(C(=O)OC(C)C(=O)OCC)C2)[N+](=O)[O-])C=CC(=C1)C(F)(F)F... | Cl[c:10]1[c:9]([O:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][cH:17]2)[c:15]([Cl:16])[cH:14][c:12]([Cl:13])[cH:11]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[Cl:16])[cH:17][cH:18]1 | O=[N+]([O-])c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1 | O=[N+]([O-])c1ccc(Oc2ccc(Cl)cc2Cl)cc1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(Oc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6]>>[#8:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | 2,4,6-trichloro-4'-nitrodiphenyl ether; 2,4-dichloro-6-fluoro-4'-nitrodiphenyl ether; 3-methyl-4'-nitrodiphenyl ether; 3,5-dimethyl-5'-nitrodiphenyl ether; 2,4'-dinitro-4-(trifluoromethyl)diphenyl ether; 2,4-dichloro-3'-methoxy-4'-nitrodiphenyl ether; sodium 5-(2-chloro-4-(trifiuoromethyl)phenoxy)-2-nitrobenzoate; 2-ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | O=[N+]([O-])c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1>>O=[N+]([O-])c1ccc(Oc2ccc(Cl)cc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f427f83b55a247d196e561af4d7c4b2f | CC(C)N(C(=O)CCl)c1ccccc1.CCCC(C)C(=O)Nc1ccc(C)c(Cl)c1.CCCCOCN(C(=O)CCl)c1c(CC)cccc1CC.CCc1cccc(CC)c1N(COC)C(=O)CCl>>CCc1cccc(C)c1N(C(=O)CCl)C(C)COC | ClCC(=O)N(C1=C(C=CC=C1CC)CC)CCOCCC.ClC=1C=C(C=CC1Cl)NC(C(C)(C)C)=O.ClC=1C=C(C=CC1Cl)NC(C(=C)C)=O.ClC=1C=C(C=CC1C)NC(C(CCC)C)=O.ClC=1C=C(C=CC1Cl)NC(C(CCC)(C)C)=O.C(C)(C)N(C(CCl)=O)C1=CC=CC=C1.COCN(C(CCl)=O)C1=C(C=CC=C1CC)CC.ClC=1C=C(C=CC1Cl)NC(CC)=O.C(CCC)OCN(C(CCl)=O)C1=C(C=CC=C1CC)CC>>ClCC(=O)N(C(COC)C)C1=C(C=CC=C1C)C... | c1cc[c:9]([N:10]([C:11](=[O:12])[CH2:13][Cl:14])[CH:15]([CH3:16])[CH3:17])cc1.CCCC(C)C(=O)Nc1cc[c:7]([CH3:8])c(Cl)c1.CCCCOCN(C(=O)CCl)c1c(CC)[cH:6][cH:5][cH:4][c:3]1[CH2:2][CH3:1].CCc1cccc(CC)c1N(C[O:18][CH3:19])C(=O)CCl>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[N:10]([C:11](=[O:12])[CH2:13][Cl:14])[C... | CC(C)N(C(=O)CCl)c1ccccc1.CCCC(C)C(=O)Nc1ccc(C)c(Cl)c1.CCCCOCN(C(=O)CCl)c1c(CC)cccc1CC.CCc1cccc(CC)c1N(COC)C(=O)CCl | CCc1cccc(C)c1N(C(=O)CCl)C(C)COC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5f7ac81bc2e64d72729ac470005c3ee71e354627f26230944d3a12b34a5a3e5b | 09d1953db3e436502d4188470fcfff2224d0a4939ec94cd27d6e7225ad0863ec | c1ccccc1 | C-C-C-C(-C)-C(=O)-N-c1:c:c:[c;H0;D3;+0:1](-[C;D1;H3:2]):c(-Cl):c:1.C-C-C-C-O-C-N(-C(=O)-C-Cl)-c1:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]:[c:7]:[cH;D2;+0:8]:c:1-C-C.C-C-c1:c:c:c:c(-C-C):c:1-N(-C-[O;H0;D2;+0:9]-[C;D1;H3:10])-C(=O)-C-Cl.[C:11]-[C:12](=[O;D1;H0:13])-[#7:14](-[C:15](-[C;D1;H3:16])-[CH3;D1;+0:17])-[c;H0;D3;... | null | [] | null | null | null | null | 2-chloro-2',6'-diethyl-N-(2-propyloxyethyl)acetanilide; N-(3,4-dichlorophenyl)propionamide; N-(3,4-dichlorophenyl)methacrylamide; N-(3-chloro-4-methylphenyl)-2-methylpentanamide; N-(3,4-dichlorophenyl)trimethylacetamide; N-(3,4-dichlorophenyl)-alpha,alpha-dimethylvaleramide; N-isopropyl-N-phenylchloroacetamide; N-n-but... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Ether.Ether.Secondary amide.Tertiary amide.Tertiary amide | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | CC(C)N(C(=O)CCl)c1ccccc1.CCCC(C)C(=O)Nc1ccc(C)c(Cl)c1.CCCCOCN(C(=O)CCl)c1c(CC)cccc1CC.CCc1cccc(CC)c1N(COC)C(=O)CCl>>CCc1cccc(C)c1N(C(=O)CCl)C(C)COC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1f5da75e69d34567ab43993557d098c2 | Cc1[nH]c(=O)n(C(C)C)c(=O)c1Br.Cc1c(Br)c(=O)n(C2CCCCC2)c(=O)n1C>>CCC(C)n1c(=O)[nH]c(C)c(Br)c1=O | C(C)(C)(C)N1C(NC(=C(C1=O)Cl)C)=O.BrC=1C(N(C(N(C1C)C)=O)C1CCCCC1)=O.C1CCC(CC1)N2C(=O)C3=C(CCC3)NC2=O.BrC=1C(N(C(NC1C)=O)C(C)C)=O>>BrC=1C(N(C(NC1C)=O)C(C)CC)=O | [CH3:2][CH:3]([CH3:4])[n:5]1[c:6](=[O:7])[nH:8][c:9]([CH3:10])[c:11]([Br:12])[c:13]1=[O:14].Cc1c(Br)c(=O)n(C2CCCCC2)c(=O)n1[CH3:1]>>[CH3:1][CH2:2][CH:3]([CH3:4])[n:5]1[c:6](=[O:7])[nH:8][c:9]([CH3:10])[c:11]([Br:12])[c:13]1=[O:14] | Cc1[nH]c(=O)n(C(C)C)c(=O)c1Br.Cc1c(Br)c(=O)n(C2CCCCC2)c(=O)n1C | CCC(C)n1c(=O)[nH]c(C)c(Br)c1=O | null | null | null | C-C Coupling | C-methylation | 93f68dd3ba09c5c42e76f97691dbf10972c8e98a18739913be8ba0f45f175ecd | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=c1cc[nH]c(=O)[nH]1 | Br-c1:c(-C):n(-[CH3;D1;+0:1]):c(=O):n(-C2-C-C-C-C-C-2):c:1=O.[#7;a:2]-[C:3](-[C;D1;H3:4])-[CH3;D1;+0:5]>>[#7;a:2]-[C:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | null | null | 5-bromo-3-cyclohexyl-1,6-dimethyluracil; 3-cyclohexyl-5,6-trimethyleneuracil; 5-bromo-3-isopropyl-6-methyluracil; 3-tert-butyl-5-chloro-6-methyluracil;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1.C1CCCCC1 | null | c1cncnc1 | HBr | null | null | null | Cc1[nH]c(=O)n(C(C)C)c(=O)c1Br.Cc1c(Br)c(=O)n(C2CCCCC2)c(=O)n1C>>CCC(C)n1c(=O)[nH]c(C)c(Br)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ba4707e745246638c23f29d6c797bb8 | C#CC(C)(C)NC(=O)c1cc(Cl)cc(Cl)c1.CC1(C)CON(Cc2ccccc2Cl)C1=O.Nc1c(Cl)c(Cl)nc(C(=O)O)c1Cl>>C=CCN(CC=C)C(=O)CCl | CC(C#C)(C)NC(C1=CC(=CC(=C1)Cl)Cl)=O.C[N+]1=CC=C(C=C1)C1=CC=[N+](C=C1)C.FC(C1=CC(=CC=C1)N1N=CC=CC1=O)(F)F.C(CC)N(C1=C(C=C(C=C1[N+](=O)[O-])C)[N+](=O)[O-])CCC.C[As]([O-])(=O)[O-].[Na+].[Na+].C(\C=C/C(=O)O)(=O)NN.C[As](O)(=O)[O-].[Na+].COC(=S)SSC(=S)OC.C(CC)N(C1=C(C=C(C=C1[N+](=O)[O-])S(=O)(=O)C)[N+](=O)[O-])CCC.NC1=C(C(=... | C[C:5](C)([NH:4][C:8](c1cc(Cl)cc(Cl)c1)=[O:9])[C:6]#[CH:7].CC1(C)C(=O)N(Cc2c(Cl)cc[cH:2][cH:1]2)O[CH2:3]1.Nc1c(Cl)c(Cl)nc(C(=O)O)[c:10]1[Cl:11]>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[C:8](=[O:9])[CH2:10][Cl:11] | C#CC(C)(C)NC(=O)c1cc(Cl)cc(Cl)c1.CC1(C)CON(Cc2ccccc2Cl)C1=O.Nc1c(Cl)c(Cl)nc(C(=O)O)c1Cl | C=CCN(CC=C)C(=O)CCl | null | null | null | C-C Coupling | OtherReaction | 4208ff847a858a996cd6a35dc1cff7f13c9e9b878ad7515ae1f73b7ad7e10a7a | 6a6116a667a640bd98f07527987eca2e57ac79999f5e60052647f500e6aa83c6 | null | C-C1(-C)-[CH2;D2;+0:1]-O-N(-C-c2:[cH;D2;+0:2]:[cH;D2;+0:3]:c:c:c:2-Cl)-C-1=O.C-[C;H0;D4;+0:4](-C)(-[C;H0;D2;+0:5]#[CH;D1;+0:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-c1:c:c(-Cl):c:c(-Cl):c:1.Cl-c1:n:c(-C(-O)=O):[c;H0;D3;+0:10](-[Cl;D1;H0:11]):c(-N):c:1-Cl>>[CH2;D1;+0:2]=[CH;D2;+0:3]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C... | null | [] | null | null | null | null | N-(1,1-dimethyl-2-propynyl)-3,5-dichlorobenzamide; maleic hydrazide; 3-amino-1,2,4-triazole; monosodium methanearsonate; disodium methanearsonate; N,N-dimethyl-alpha,alpha-diphenylacetamide; N-N-di(n-propyl)-2,6-dinitro-4-(trifiuoromethyl)aniline; N,N-di(n-propyl)-2,6-dinitro-4-methylaniline; N,N-di(n-propyl)-2,6-dinit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Secondary amide.Tertiary amide.Primary amine.Alkyne | Primary halide.Tertiary amide.Allyl.Allyl | c1ccccc1.C1CNOC1.c1ccccc1.c1ccncc1 | null | null | HCl | null | null | null | C#CC(C)(C)NC(=O)c1cc(Cl)cc(Cl)c1.CC1(C)CON(Cc2ccccc2Cl)C1=O.Nc1c(Cl)c(Cl)nc(C(=O)O)c1Cl>>C=CCN(CC=C)C(=O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa33d2dcc235487b9f952619afa7f8ab | O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21>>O=C([O-])[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21 | C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O.C(C)C(C(=O)[O-])CCCC.[K+].C(C)(=O)OCC.S(O)(O)(=O)=O>>C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)[O-].[K+] | [O:1]=[C:2]([OH:3])[C@H:4]1/[C:5](=[CH:6]/[CH2:7][OH:8])[O:9][C@@H:10]2[CH2:11][C:12](=[O:13])[N:14]12>>[O:1]=[C:2]([O-:3])[C@H:4]1/[C:5](=[CH:6]/[CH2:7][OH:8])[O:9][C@@H:10]2[CH2:11][C:12](=[O:13])[N:14]12 | O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21 | O=C([O-])[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21 | null | null | C(C(C)C)C(=O)C | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | [CH]=C1CN2C(=O)C[C@H]2O1 | [#7:1]-[C:2](-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5])\[C:6]=[C:7]>>[#7:1]-[C:2](-[C:3](-[O-;H0;D1:5])=[O;D1;H0:4])\[C:6]=[C:7] | 73 | [{"value": 73.0, "product": "C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | 100 ml of the solvent mixture of ethyl acetate and methyl isobutyl ketone (4:1) already cooled to 5° C. was added to 100 ml of aqueous solution containing clavulanic acid (12 mg/ml). While agitating the mixture, 50% sulfuric acid was slowly added in order to control pH at 1.5. After extracting the said mixture, the ext... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CN2CC[C@H]2O1 | null | C(C(C)C)C(=O)C | 5 | 0.5 | O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21>C(C(C)C)C(=O)C>O=C([O-])[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f7b8b5a24c1b45c195681022ace26b53 | Nc1nc2c(ncn2COCCCO)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(=S)nc[nH]c32)[C@H](O)[C@@H]1O>>Nc1nc(O)c2ncn(COC(CO)CO)c2n1 | N(=[N+]=[N-])[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1.FC=1C(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C1)=O)=O.C1=NC(=S)C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O.OCCCOCN1C=2N=C(NC(C2N=C1)=O)N.C(C)OCN1C=2N=C(NC(C2N=C1)=O)N.F[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1>>C1=NC2=C(N1COC(CO)CO)N=C(N=C2O)N | C([CH2:12][O:11][CH2:10][n:9]1[cH:8][n:7][c:6]2[c:4](=[O:5])[nH:3][c:2]([NH2:1])[n:18][c:17]21)[CH2:15][OH:16].O[C@@H]1[C@H](O)[C@@H]([CH2:13][OH:14])O[C@H]1n1cnc2c(=S)nc[nH]c21>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[n:7][cH:8][n:9]([CH2:10][O:11][CH:12]([CH2:13][OH:14])[CH2:15][OH:16])[c:17]2[n:18]1 | Nc1nc2c(ncn2COCCCO)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(=S)nc[nH]c32)[C@H](O)[C@@H]1O | Nc1nc(O)c2ncn(COC(CO)CO)c2n1 | null | null | null | C-C Coupling | OtherReaction | 0656e0fd7f53ea788af289f3a1873e99953fecad8265e358fdb715bba51c6c81 | aca30821eb88ead31922727daff3152f60c54d4c0c81931ee661c38abd61921c | c1ncc2nc[nH]c2n1 | O-[C@H]1-[C@@H](-[CH2;D2;+0:1]-[O;D1;H1:2])-O-[C@@H](-n2:c:n:c3:c(=S):n:c:[nH]:c:3:2)-[C@H]-1-O.[N;D1;H2:3]-[c:4]1:[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]-[#8:9]-[CH2;D2;+0:10]-C-[CH2;D2;+0:11]-[O;D1;H1:12]):[c:13]:[#7;a:14]:[c:15]:2:[c;H0;D3;+0:16](=[O;H0;D1;+0:17]):[nH;D2;+0:18]:1>>[N;D1;H2:3]-[c:4]1:[#7;a:5]:[c:6]2:[#7;a:7]... | null | [] | null | null | null | null | 3'-deoxy-3'-azidothymidine, 3'-deoxy-3'-fluorothymidine, 5-fluorouridine, 6-mercaptopurine-9-β-D-ribofuranoside, 6-methylmercaptopurine-9-β-D-ribofuranoside, 9-{[(1-hydroxymethyl)ethoxy]-methyl}guanine and 9- (ethoxymethyl)guanine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Thiocarbonyl | Ether.Primary alcohol.Primary alcohol.Aromatic alcohol | c1ncc2nc[nH]c2n1.C1CCOC1.c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | null | null | null | Nc1nc2c(ncn2COCCCO)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(=S)nc[nH]c32)[C@H](O)[C@@H]1O>>Nc1nc(O)c2ncn(COC(CO)CO)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cc12e5c031414063a4d8c42a97e5d896 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.O=[N+]([O-])O>>CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=CNC2C1=O)CCCC.[N+](=O)(O)[O-]>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][cH:10][n:14][c:15]2[n:16]([CH2:17][CH2:18][CH2:19][CH3:20])[c:21]1=[O:22].O[N+:11](=[O:12])[O-:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([N+:11](=[O:12])[O-:13])[n:14][c:15]2[n:16]([CH2:17][CH2:18][CH2:19][CH3:20])[c:21]1=[O:22] | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.O=[N+]([O-])O | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 45375bf4e9a170de6f024fab6537ab0a76337871805a02ef6d8fd224be309b01 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[#7;a:6]:[cH;D2;+0:7]:[#7;a:8]:[c:9]:1:[c:10]:[#7;a:11]>>[#7;a:4]:[c:5]1:[#7;a:6]:[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[#7;a:8]:[c:9]:1:[c:10]:[#7;a:11] | null | [] | 5 | CELSIUS | 1 | HOUR | 1,3-Di-n-butylxanthine (73 g, 0.28 mol) was dissolved in acetic acid (120 ml) and then treated with concentrated nitric acid (49 g) at 87° C. After 1 hour, the mixture was cooled to 5° C., the resulting yellow precipitate filtered off and washed with water (50 ml). The yellow crystals were dissolved in dichloromethane ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | C(C)(=O)O | 5 | 1 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.O=[N+]([O-])O>C(C)(=O)O>CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f3bd66fd965f4b3c8102b0b4627404bb | O=[N+]([O-])O.O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1 | C1(CC1)CN1C(=O)N(C=2N=CNC2C1=O)CC1CC1.[N+](=O)(O)[O-]>>C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CC1 | O[N+:6](=[O:7])[O-:8].[O:1]=[c:2]1[c:3]2[nH:4][cH:5][n:9][c:10]2[n:11]([CH2:12][CH:13]2[CH2:14][CH2:15]2)[c:16](=[O:17])[n:18]1[CH2:19][CH:20]1[CH2:21][CH2:22]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([N+:6](=[O:7])[O-:8])[n:9][c:10]2[n:11]([CH2:12][CH:13]2[CH2:14][CH2:15]2)[c:16](=[O:17])[n:18]1[CH2:19][CH:20]1[CH2:21][CH2:22]... | O=[N+]([O-])O.O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1 | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 45375bf4e9a170de6f024fab6537ab0a76337871805a02ef6d8fd224be309b01 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[#7;a:6]:[cH;D2;+0:7]:[#7;a:8]:[c:9]:1:[c:10]:[#7;a:11]>>[#7;a:4]:[c:5]1:[#7;a:6]:[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[#7;a:8]:[c:9]:1:[c:10]:[#7;a:11] | 56.5 | [{"value": 56.5, "product": "C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.1, "product": "C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | 1,3-Di-cyclopropylmethyl xanthine (20 g, 0,076 mol) was dissolved in acetic acid (33 ml) and then treated with concentrated nitric acid (13.2 g) at 87° C. After 1 hour, the mixture was cooled to 5° C. and the resulting yellow precipitate filtered off. The yellow crystals were dissolved in dichloromethane and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC1.C1CC1 | HO- | C(C)(=O)O | 5 | 1 | O=[N+]([O-])O.O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1>C(C)(=O)O>O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-534fa2ca7c244660957e8d53d52d0191 | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC.[Sn].Cl>>Cl.C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N)CCCC | O=[N+:11]([O-])[c:10]1[nH:9][c:8]2[c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:19](=[O:20])[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:13]2[n:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([NH2:11])[n:12][c:13]2[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:19]1=[O:20] | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O | CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[#7;a:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]:1):[c:8]:[#7;a:9]>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | 10 | MINUTE | 1,3-Di-n-butyl-8-nitro xanthine from Example 1 (8.5 g) was suspended in concentrated hydrochloric acid (85 ml) and then treated at room temperature with tin powder (14.5 g) in small portions. After stirring for 10 minutes the yellow colour of the suspension disappeared. Thereafter the precipitate was filtered off and r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncc2[nH]cnc2n1 | Other | null | null | 0.166667 | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6437b784cf604f0ba86ac0d067c33742 | O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CC2)c(=O)n1C1CC1>>Nc1nc2c([nH]1)c(=O)n(C1CC1)c(=O)n2C1CC1 | C1(CC1)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])C1CC1.S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>C1(CC1)N1C(=O)N(C=2N=C(NC2C1=O)N)C1CC1 | O=[N+:1]([O-])[c:2]1[n:3][c:4]2[c:5]([nH:6]1)[c:7](=[O:8])[n:9]([CH:10]1[CH2:11][CH2:12]1)[c:13](=[O:14])[n:15]2[CH:16]1[CH2:17][CH2:18]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([nH:6]1)[c:7](=[O:8])[n:9]([CH:10]1[CH2:11][CH2:12]1)[c:13](=[O:14])[n:15]2[CH:16]1[CH2:17][CH2:18]1 | O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CC2)c(=O)n1C1CC1 | Nc1nc2c([nH]1)c(=O)n(C1CC1)c(=O)n2C1CC1 | null | null | CO.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1c2[nH]cnc2n(C2CC2)c(=O)n1C1CC1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[#7;a:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]:1):[c:8]:[#7;a:9]>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 1,3-Di-cyclopropyl-8-nitro xanthine (0.4 g, 0.0014 mol) was dissolved in methanol (20 ml) and treated with a sodium dithionite solution in water (0.5 g in 5 ml) at room temperature with stirring. After stirring for three hours the solvent was removed in vacuo, the residue taken up with dichloromethane and extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncc2nc[nH]c2n1.C1CC1.C1CC1 | Other | CO.O | null | null | O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CC2)c(=O)n1C1CC1>CO.O>Nc1nc2c([nH]1)c(=O)n(C1CC1)c(=O)n2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-783aa34abc904c888725745becf88ea1 | CC(=O)OC(C)=O.CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(NC(C)=O)nc2n(CCCC)c1=O | C(C)(=O)OC(C)=O.C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N)CCCC.Cl.C(C)N(CC)CC>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)NC(C)=O)CCCC | CC(=O)O[C:12]([CH3:13])=[O:14].[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([NH2:11])[n:15][c:16]2[n:17]([CH2:18][CH2:19][CH2:20][CH3:21])[c:22]1=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([NH:11][C:12]([CH3:13])=[O:14])[n:15][c:16]2[n:17]([CH2:18][CH2:19][CH2:20][CH3... | CC(=O)OC(C)=O.CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O | CCCCn1c(=O)c2[nH]c(NC(C)=O)nc2n(CCCC)c1=O | null | null | C1(=CC=CC=C1)C | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[#7;a:6]:[c:7](-[NH2;D1;+0:8]):[#7;a:9]:[c:10]:1:[c:11]:[#7;a:12]>>[#7;a:4]:[c:5]1:[#7;a:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[#7;a:9]:[c:10]:1:[c:11]:[#7;a:12] | null | [] | null | null | null | null | 1.3-Di-n-butyl-8-amino xanthine (0.5 g), hydrochloride in toluene (30 ml) was stirred for 30 minutes with triethylamine (0.16 g). After addition of acetic anhydride (0.32 g), the mixture was refluxed for 6 hours. The reaction mixture was extracted with water (4×30 ml), the organic layer separated and dried over anhydro... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ncc2[nH]cnc2n1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)OC(C)=O.CCCCn1c(=O)c2[nH]c(N)nc2n(CCCC)c1=O>C1(=CC=CC=C1)C>CCCCn1c(=O)c2[nH]c(NC(C)=O)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-15f8af76545c4427afa00c3550df7223 | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O.Cl>>CCCCn1c(=O)c2[nH]c(Cl)nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC.Cl>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Cl)CCCC | O=[N+]([O-])[c:10]1[nH:9][c:8]2[c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:19](=[O:20])[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:13]2[n:12]1.[ClH:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([Cl:11])[n:12][c:13]2[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:19]1=[O:20] | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O.Cl | CCCCn1c(=O)c2[nH]c(Cl)nc2n(CCCC)c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 096579604b331b7f6d1b4e74c55863b1cd7b2077ff2331598668cfa6242a01ad | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[ClH;D0;+0:11]>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[#7;a:10]:[c;H0;D3;+0:1](-[Cl;H0;D1;+0:11]):[#7;a:2]:[c:3]:1:2 | null | [] | null | null | null | null | 1,3-Di-n-butyl-8-nitro xanthine (0.5 g, 0.0016 mol) was refluxed for 18 hours with concentrated hydrochloric acid (8 ml). The reaction mixture was extracted with dichloromethane (20 ml), the organic layer washed with water to neutrality and then dried over anhydrous sodium sulphate. The solvent was then removed by evap... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | null | null | null | CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O.Cl>>CCCCn1c(=O)c2[nH]c(Cl)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38d4d17186b6440b9a7304522d7693ad | Br.CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC.Br>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC | [BrH:11].O=[N+]([O-])[c:10]1[nH:9][c:8]2[c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:19](=[O:20])[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:13]2[n:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([Br:11])[n:12][c:13]2[n:14]([CH2:15][CH2:16][CH2:17][CH3:18])[c:19]1=[O:20] | Br.CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O | CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 096579604b331b7f6d1b4e74c55863b1cd7b2077ff2331598668cfa6242a01ad | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[BrH;D0;+0:11]>>[Br;H0;D1;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | 1,3-Di-n-butyl-8-bromo xanthine was prepared from 1,3-di-n-butyl-8-nitro xanthine (0.5 g, 0.0016 mol) and concentrated hydrobromic acid (8 ml) using the procedure as described in Example 15. The title product was obtained after recrystallisation from ethanol, yield 0.4 g (91%), m.pt. 178° C.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | null | null | null | Br.CCCCn1c(=O)c2[nH]c([N+](=O)[O-])nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a647d1ec9cd418397bbe1ea009898ce | ClOCl.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1 | C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CC1.O(Cl)Cl.O>>C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)Cl)CC1CC1 | ClO[Cl:6].O=[N+]([O-])[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:16]([CH2:17][CH:18]3[CH2:19][CH2:20]3)[c:14](=[O:15])[n:9]([CH2:10][CH:11]3[CH2:12][CH2:13]3)[c:8]2[n:7]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([Cl:6])[n:7][c:8]2[n:9]([CH2:10][CH:11]2[CH2:12][CH2:13]2)[c:14](=[O:15])[n:16]1[CH2:17][CH:18]1[CH2:19][CH2:20]1 | ClOCl.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1 | O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 096579604b331b7f6d1b4e74c55863b1cd7b2077ff2331598668cfa6242a01ad | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | Cl-O-[Cl;H0;D1;+0:1].O=[N+](-[O-])-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:[#7;a:11]:1>>[C:9]-[#7;a:8]1:[c:7]:[#7;a:6]:[c:5]:[c:4]2:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:11]:[c:10]:1:2 | null | [] | null | null | 1 | HOUR | 1,3-Di-cyclopropylmethyl-8-nitro xanthine (6 g, 0,023 mol) was dissolved in dimethylformamide (20 ml) and reacted with phosporous oxychloride (14 g) for 1 hour at 120° C. The mixture was then treated with water and stirred for 1 hour at room temperature. The precipitate was filtered off, dissolved in ethyl acetate, dri... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC1.C1CC1 | Other | CN(C=O)C | null | 1 | ClOCl.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CC2)c(=O)n1CC1CC1>CN(C=O)C>O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c0da7e20dd64167a0eceb9e22ecda3c | O=P(Cl)(Cl)Cl.O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CCCCC2)c(=O)n1C1CCCCC1>>O=c1c2[nH]c(Cl)nc2n(C2CCCCC2)c(=O)n1C1CCCCC1 | C1(CCCCC1)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])C1CCCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCCC1)N1C(=O)N(C=2N=C(NC2C1=O)Cl)C1CCCCC1 | O=P(Cl)(Cl)[Cl:6].O=[N+]([O-])[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[c:16](=[O:17])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:8]2[n:7]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([Cl:6])[n:7][c:8]2[n:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[c:16](=[O:17... | O=P(Cl)(Cl)Cl.O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CCCCC2)c(=O)n1C1CCCCC1 | O=c1c2[nH]c(Cl)nc2n(C2CCCCC2)c(=O)n1C1CCCCC1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 096579604b331b7f6d1b4e74c55863b1cd7b2077ff2331598668cfa6242a01ad | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | O=c1c2[nH]cnc2n(C2CCCCC2)c(=O)n1C1CCCCC1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[N+](-[O-])-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:[#7;a:11]:1>>[C:9]-[#7;a:8]1:[c:7]:[#7;a:6]:[c:5]:[c:4]2:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:11]:[c:10]:1:2 | null | [] | null | null | null | null | 1,3-Di-cyclohexyl-8-chloro xanthine was prepared from 1,3-di-cyclohexyl-8-nitro xanthine (2 g, 0.006 mol) and phosphorous oxychloride (3.9 g) in dimethylformamide (6 ml), using an analogous procedure to that described in Example 17. The product was obtained as a crystalline product after recrystallisation from ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCCCC1.C1CCCCC1 | Other | CN(C=O)C | null | null | O=P(Cl)(Cl)Cl.O=c1c2[nH]c([N+](=O)[O-])nc2n(C2CCCCC2)c(=O)n1C1CCCCC1>CN(C=O)C>O=c1c2[nH]c(Cl)nc2n(C2CCCCC2)c(=O)n1C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fe8f501adbbe4ac2972456200d435247 | C1CCNCC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(N3CCCCC3)nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC.N1CCCCC1>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N1CCCCC1)CCCC | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.Br[c:10]1[nH:9][c:8]2[c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:24](=[O:25])[n:19]([CH2:20][CH2:21][CH2:22][CH3:23])[c:18]2[n:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[n:17][c:18]2[n... | C1CCNCC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O | CCCCn1c(=O)c2[nH]c(N3CCCCC3)nc2n(CCCC)c1=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9ae396801b06219c8da3fee187411f8d55109225e738cc20dd46c717ad6babc9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCCCC3)nc2[nH]1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1)-[C:14]-[C:15] | null | [] | null | null | null | null | 1,3-Di-n-butyl-8-bromo xanthine (2 g, 0.0029 mol) was dissolved in toluene (50 ml). After addition of piperidine (5 g, 0.0058 mol) the mixture was refluxed for 9 hours. The reaction mixture was then extracted with water (4×30 ml), the organic layer dried over anhydrous sodium sulphate and the solvent removed in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC[NH]CC1 | c1ncc2[nH]cnc2n1.C1CC[NH]CC1 | HBr | C1(=CC=CC=C1)C | null | null | C1CCNCC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O>C1(=CC=CC=C1)C>CCCCn1c(=O)c2[nH]c(N3CCCCC3)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8724cdb4a4f141bd9d5804ebfdc64b3a | C1COCCN1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c(N3CCOCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)Cl)CC1CC1.N1CCOCC1>>C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCOCC1)CC1CC1 | [NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.Cl[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:21]([CH2:22][CH:23]3[CH2:24][CH2:25]3)[c:19](=[O:20])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[c:13]2[n:12]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[n:12][c:13]2[n:14]([CH2:15][CH:16]2[CH2:17][CH2:18]2)[c:... | C1COCCN1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1 | O=c1c2[nH]c(N3CCOCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 995572a62f8e8f3ae7fc8cad6db6c9d8d2615feb30fdf251cebb8ad719e9f80c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1c2[nH]c(N3CCOCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[#8:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[#7;a:10]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]3-[C:13]-[C:12]-[#8:11]-[C:16]-[C:15]-3):[#7;a:2]:[c:3]:1:2 | null | [] | null | null | null | null | 1,3-Di-cyclopropylmethyl-8-morpholino xanthine was prepared from 1,3-di-cyclopropylmethyl-8-chloroxanthine (0.3 g, 0.001 mol) and morpholine (0.2 g, 0.0022 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C., yield 0.09 g (26%).
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1COCC[NH]1 | c1ncc2[nH]cnc2n1.C1COCC[NH]1.C1CC1.C1CC1 | HCl | null | null | null | C1COCCN1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c(N3CCOCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4381712e0b94957ad0bd9bce274790d | C1CCNC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(N3CCCC3)nc2n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC.N1CCCC1>>C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N1CCCC1)CCCC | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1.Br[c:10]1[nH:9][c:8]2[c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:23](=[O:24])[n:18]([CH2:19][CH2:20][CH2:21][CH3:22])[c:17]2[n:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][c:10]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[n:16][c:17]2[n:18]([CH2:19][CH... | C1CCNC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O | CCCCn1c(=O)c2[nH]c(N3CCCC3)nc2n(CCCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b56d265e56e2c913e9899a4a408b778b8d78ae8a7634bb84bbe7bcf3fc0d81e4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCCC3)nc2[nH]1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[#7;a:10]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]3-[C:11]-[C:12]-[C:13]-[C:14]-3):[#7;a:2]:[c:3]:1:2 | null | [] | null | null | null | null | The title compound was prepared from 1,3-di-n-butyl-8-bromo xanthine (1 g, 0.0029 ml) and pyrrolidine (0.041 g, 0.0057 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC[NH]C1 | c1ncc2[nH]cnc2n1.C1CC[NH]C1 | HBr | null | null | null | C1CCNC1.CCCCn1c(=O)c2[nH]c(Br)nc2n(CCCC)c1=O>>CCCCn1c(=O)c2[nH]c(N3CCCC3)nc2n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aba789f7e6174c6e9200510395e30ecf | C1CCNC1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c(N3CCCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)Cl)CC1CC1.N1CCCC1>>C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCCC1)CC1CC1 | [NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.Cl[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:20]([CH2:21][CH:22]3[CH2:23][CH2:24]3)[c:18](=[O:19])[n:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[c:12]2[n:11]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([N:6]3[CH2:7][CH2:8][CH2:9][CH2:10]3)[n:11][c:12]2[n:13]([CH2:14][CH:15]2[CH2:16][CH2:17]2)[c:18](=[O:19])... | C1CCNC1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1 | O=c1c2[nH]c(N3CCCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b56d265e56e2c913e9899a4a408b778b8d78ae8a7634bb84bbe7bcf3fc0d81e4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1c2[nH]c(N3CCCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[#7;a:10]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]3-[C:11]-[C:12]-[C:13]-[C:14]-3):[#7;a:2]:[c:3]:1:2 | null | [] | null | null | null | null | The title compound was prepared from 1,3-di-cyclopropylmethyl-8-chloro xanthine (0.3 g, 0.0011 mol) and pyrrolidine (0.2 g, 0.0028 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC[NH]C1 | c1ncc2[nH]cnc2n1.C1CC[NH]C1.C1CC1.C1CC1 | HCl | null | null | null | C1CCNC1.O=c1c2[nH]c(Cl)nc2n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]c(N3CCCC3)nc2n(CC2CC2)c(=O)n1CC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc2d669ae91a4d3ca99ba757588a1739 | C1CCNCC1.O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1>>O=c1c2[nH]c(N3CCCCC3)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)Br)CC1CCCCC1.N1CCCCC1>>C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCCCC1)CC1CCCCC1 | [NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.Br[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:24]([CH2:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[c:22](=[O:23])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[c:13]2[n:12]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([N:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[n:12... | C1CCNCC1.O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | O=c1c2[nH]c(N3CCCCC3)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9ae396801b06219c8da3fee187411f8d55109225e738cc20dd46c717ad6babc9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1c2[nH]c(N3CCCCC3)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1)-[C:14]-[C:15] | null | [] | null | null | null | null | The title compound was prepared from 1,3-di-cyclohexylmethyl-8-bromo xanthine (0.7 g, 0.0017 mol) and piperidine (0.28 g, 0,003 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. 266° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC[NH]CC1 | c1ncc2[nH]cnc2n1.C1CC[NH]CC1.C1CCCCC1.C1CCCCC1 | HBr | null | null | null | C1CCNCC1.O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1>>O=c1c2[nH]c(N3CCCCC3)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-712a4c23c26a4619a1659f080875532d | Br.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1>>O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CCCCC1.Br>>C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)Br)CC1CCCCC1 | [BrH:6].O=[N+]([O-])[c:5]1[nH:4][c:3]2[c:2](=[O:1])[n:19]([CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[c:17](=[O:18])[n:9]([CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[c:8]2[n:7]1>>[O:1]=[c:2]1[c:3]2[nH:4][c:5]([Br:6])[n:7][c:8]2[n:9]([CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2... | Br.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 096579604b331b7f6d1b4e74c55863b1cd7b2077ff2331598668cfa6242a01ad | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | O=c1c2[nH]cnc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[BrH;D0;+0:11]>>[Br;H0;D1;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | The title compound was prepared from 1,3-di-cyclohexylmethyl-8-nitro xanthine (1 g, 0.0026 mol) and concentrated hydrobromic acid (40 ml, 48%) over 32 hours using an analogous procedure to that described in Example 15. The title product was obtained as a crystalline solid, m.pt. 247° C.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCCCC1.C1CCCCC1 | HO- | null | null | null | Br.O=c1c2[nH]c([N+](=O)[O-])nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1>>O=c1c2[nH]c(Br)nc2n(CC2CCCCC2)c(=O)n1CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f3ffc7a6ed242c8bda616b6d51cef03 | NC=O.Nc1cc(=O)n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | S(=O)([O-])S(=O)[O-].[Na+].[Na+].N(=O)[O-].[Na+].C1(CC1)CN1C(=O)N(C(=O)C=C1N)CC1CC1.C(=O)N.C(=O)O>>C1(CC1)CN1C(=O)N(C=2N=CNC2C1=O)CC1CC1 | O=[CH:5][NH2:4].[O:1]=[c:2]1[cH:3][c:7]([NH2:6])[n:8]([CH2:9][CH:10]2[CH2:11][CH2:12]2)[c:13](=[O:14])[n:15]1[CH2:16][CH:17]1[CH2:18][CH2:19]1>>[O:1]=[c:2]1[c:3]2[nH:4][cH:5][n:6][c:7]2[n:8]([CH2:9][CH:10]2[CH2:11][CH2:12]2)[c:13](=[O:14])[n:15]1[CH2:16][CH:17]1[CH2:18][CH2:19]1 | NC=O.Nc1cc(=O)n(CC2CC2)c(=O)n1CC1CC1 | O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 68e0c3163dc53970fbb3cb6c8ecbddb0473bb8009e82f24cb791f68f57492394 | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 | O=[CH;D2;+0:1]-[NH2;D1;+0:2].[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C:7]):[c:8](-[NH2;D1;+0:9]):[cH;D2;+0:10]:[c:11]:1=[O;D1;H0:12]>>[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C:7]):[c:8]2:[n;H0;D2;+0:9]:[cH;D2;+0:1]:[nH;D2;+0:2]:[c;H0;D3;+0:10]:2:[c:11]:1=[O;D1;H0:12] | null | [] | 100 | CELSIUS | null | null | 1,3-Di-cyclopropylmethyl xanthine was prepared using an analogous procedure to that described in Chem. Berichte 88, 1306-1312, 1955: 20.2 g (0.0855 mol) of 1,3-dicyclopropylmethyl-6-amino-uracil was dissolved in 100 ml of formamide, then 5.9 g sodium nitrite was added and at 60° C. 13.4 ml formic acid was added slowly ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1cncnc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC1.C1CC1 | HO- | null | 100 | null | NC=O.Nc1cc(=O)n(CC2CC2)c(=O)n1CC1CC1>>O=c1c2[nH]cnc2n(CC2CC2)c(=O)n1CC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-12e40ee7e23541c4b9a7cdf8dcd80cd1 | CCCN.N#CC(N)C(N)=O>>CCCn1cnc(C(N)=O)c1N | NC(C(=O)N)C#N.COC(OC)OC.C(CC)N>>NC1=C(N=CN1CCC)C(=O)N | [CH3:1][CH2:2][CH2:3][NH2:4].[NH2:6][CH:7]([C:8]([NH2:9])=[O:10])[C:11]#[N:12]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]([C:8]([NH2:9])=[O:10])[c:11]1[NH2:12] | CCCN.N#CC(N)C(N)=O | CCCn1cnc(C(N)=O)c1N | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | a3981cf56030daa644129790a219d1ae86886cbda4e11ddc0bdde6693ab8ec83 | 1aa7191beb21c0c960b18631a0bd52edc8e0a5e54fb7edd4fc42913ae18d9901 | c1c[nH]cn1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[NH2;D1;+0:8])-[C;H0;D2;+0:9]#[N;H0;D1;+0:10]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:11]:[n;H0;D2;+0:8]:[c;H0;D3;+0:7](-[C:5](-[N;D1;H2:4])=[O;D1;H0:6]):[c;H0;D3;+0:9]:1-[NH2;D1;+0:10] | 61.1 | [{"value": 61.0, "product": "NC1=C(N=CN1CCC)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "NC1=C(N=CN1CCC)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | A mixture of 2-amino-2-cyanoacetamide (2.8 g, 0.0282 mol), trimethylorthoformate (3.4 g, 0.0321 mol) and acetonitrile (55 ml) was heated under reflux for 0.75 hour, then allowed to cool. n-Propylamine (1.8 g, 0.0305 mol) was then added dropwise, and the resulting mixture stirred at ambient temperature for 36 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Primary amine | null | c1c[nH]cn1 | c1c[nH]cn1 | Other | C(C)#N | null | 36 | CCCN.N#CC(N)C(N)=O>C(C)#N>CCCn1cnc(C(N)=O)c1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a5e2995d24f4bac852bdb664f6ad601 | CCCn1cnc(C(N)=O)c1N.CCOc1ccccc1C(=O)O>>CCCn1cnc(C(N)=O)c1NC(=O)c1ccccc1OCC | C(C(=O)Cl)(=O)Cl.C(C)OC1=C(C(=O)O)C=CC=C1.CN(C=O)C.NC1=C(N=CN1CCC)C(=O)N>>C(C)OC1=C(C(=O)NC2=C(N=CN2CCC)C(=O)N)C=CC=C1 | [CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]([C:8]([NH2:9])=[O:10])[c:11]1[NH2:12].O[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]([C:8]([NH2:9])=[O:10])[c:11]1[NH:12][C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH2:22][CH3:... | CCCn1cnc(C(N)=O)c1N.CCOc1ccccc1C(=O)O | CCCn1cnc(C(N)=O)c1NC(=O)c1ccccc1OCC | null | null | ClCCl.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc[nH]1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10](-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]):[c:14]:1-[NH2;D1;+0:15]>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10](-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]):[c:14]:1-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 77 | [{"value": 77.0, "product": "C(C)OC1=C(C(=O)NC2=C(N=CN2CCC)C(=O)N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "C(C)OC1=C(C(=O)NC2=C(N=CN2CCC)C(=O)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Oxalyl chloride (1.74 g, 0.137 mol) was added dropwise to a stirred solution of 2-ethoxybenzoic acid (1.1 g, 0.00663 mol) and dimethylformamide (0.1 ml) in dichloromethane (20 ml) and the resulting mixture stirred at ambient temperature for 4 hours, then evaporated under vacuum. The residue was azeotroped with dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1c[nH]cn1.c1ccccc1 | HO- | ClCCl.N1=CC=CC=C1 | null | 4 | CCCn1cnc(C(N)=O)c1N.CCOc1ccccc1C(=O)O>ClCCl.N1=CC=CC=C1>CCCn1cnc(C(N)=O)c1NC(=O)c1ccccc1OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db920a7cf3b74cdbbcd3ab9ee72edff5 | C=C(C)C.N#Cc1nccnc1C#N.O=S(=O)(O)O>>CC(C)(C)NC(=O)c1cnccn1.CC(C)(C)NC(=O)c1nccnc1C#N | C(#N)C1=NC=CN=C1C#N.CC(C)=C.S(O)(O)(=O)=O>>C(C)(C)(C)NC(=O)C1=NC=CN=C1.C(#N)C=1C(=NC=CN1)C(=O)NC(C)(C)C | [CH3:1][C:15](=[CH2:9])[CH3:17].[n:5]1[cH:24][cH:23][n:22][c:21]([C:19]#[N:18])[c:26]1[C:27]#[N:28].O=S(=O)([OH:7])[OH:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][cH:12][n:13]1.[CH3:14][C:15]([CH3:16])([CH3:17])[NH:18][C:19](=[O:20])[c:21]1[n:22][cH:23][cH:24][n:25][c:26]1[C:27]#[N:2... | C=C(C)C.N#Cc1nccnc1C#N.O=S(=O)(O)O | CC(C)(C)NC(=O)c1cnccn1.CC(C)(C)NC(=O)c1nccnc1C#N | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | 7f180c339c52ce4d86dc16b90587226c2770b57da5e8ad895079e1d8b92ef0a7 | 9b55453c53e3e5249853d5cd7ff87a315e08b38fccb790622c7e13bc934e3bb4 | c1cnccn1.c1cnccn1 | O=S(=O)(-[OH;D1;+0:1])-[OH;D1;+0:2].[C;D1;H3:3]-[C;H0;D3;+0:4](=[CH2;D1;+0:5])-[CH3;D1;+0:6].[N;D1;H0:7]#[C:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:1-[C;H0;D2;+0:15]#[N;H0;D1;+0:16]>>[#7;a:17]:[c:18](-[C:19](=[O;H0;D1;+0:2])-[NH;D2;+0:10]-[C:20](-[C;D1;H3:21])(-[C;D1;H3:22])-[CH3;D1;+0:... | null | [] | null | null | null | null | A compound having the formula (4) can be obtained as follows. The corresponding 2, 3-dicyano-pyrazine is reacted with tert-butyl alcohol or isobutylene in the presence of sulfuric acid to obtain the corresponding N-tert-butyl-2-pyrazinecarboxamide and/or 3-cyano-N-tert-butyl-2-pyrazinecarboxamide. Then, thus obtained c... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Vinyl | Secondary amide.Secondary amide | c1cnccn1 | c1cnccn1.c1cnccn1 | c1cnccn1.c1cnccn1 | null | C(C)(C)(C)O | null | null | C=C(C)C.N#Cc1nccnc1C#N.O=S(=O)(O)O>C(C)(C)(C)O>CC(C)(C)NC(=O)c1cnccn1.CC(C)(C)NC(=O)c1nccnc1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a23e58160f8d42ea84086afccb55201f | CC(C)(C)O.N#Cc1cnccn1>>CC(C)(C)NC(=O)c1cnccn1 | C(C)(C)(C)O.S(O)(O)(=O)=O.C(#N)C1=NC=CN=C1.[OH-].[Na+]>>C(C)(C)(C)NC(=O)C1=NC=CN=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:7].[N:5]#[C:6][c:8]1[cH:9][n:10][cH:11][cH:12][n:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][cH:12][n:13]1 | CC(C)(C)O.N#Cc1cnccn1 | CC(C)(C)NC(=O)c1cnccn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 1d5b8ab7abc796c8fe1a4bbe88d643f3667784ffa1e5d5bdf2ecec75239c4174 | 351ef33c26e45ccdbae92f97c6925d748e3ebc471a863d8f431e8ded2d7e850d | c1cnccn1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[OH;D1;+0:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:5])-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1 | null | [] | null | null | 3 | HOUR | To 1030 g of an 80% aqueous solution of sulfuric acid (8.40 moles of sulfuric acid), 220.5 g (2.10 moles) of 2-cyanopyrazine was added dropwise keeping the internal temperature at 40° C. or less with stirring. In succession, 187 g (2.52 moles) of tert-butyl alcohol was added dropwise to the mixture, keeping the interna... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary alcohol | Secondary amide | null | null | c1cnccn1 | null | O | null | 3 | CC(C)(C)O.N#Cc1cnccn1>O>CC(C)(C)NC(=O)c1cnccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0a5f477af2d4178b1eacf13ac36441b | CC(C)(C)O.N#Cc1cnccn1>>CC(C)(C)NC(=O)c1cnccn1 | C(C)(C)(C)O.S(O)(O)(=O)=O.C(#N)C1=NC=CN=C1.[OH-].[Na+]>>C(C)(C)(C)NC(=O)C1=NC=CN=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:7].[N:5]#[C:6][c:8]1[cH:9][n:10][cH:11][cH:12][n:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][cH:12][n:13]1 | CC(C)(C)O.N#Cc1cnccn1 | CC(C)(C)NC(=O)c1cnccn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 1d5b8ab7abc796c8fe1a4bbe88d643f3667784ffa1e5d5bdf2ecec75239c4174 | 351ef33c26e45ccdbae92f97c6925d748e3ebc471a863d8f431e8ded2d7e850d | c1cnccn1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[OH;D1;+0:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:5])-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1 | null | [] | null | null | 3 | HOUR | To 1030 g of an 80% aqueous solution of sulfuric acid (8.40 moles of sulfuric acid), 220.5 g (2.10 moles) of 2-cyanopyrazine was added dropwise keeping the internal temperature at 40° C. or less with stirring. In succession, 187 g (2.52 moles) of tert-butyl alcohol was added dropwise to the mixture of which internal te... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary alcohol | Secondary amide | null | null | c1cnccn1 | null | O | null | 3 | CC(C)(C)O.N#Cc1cnccn1>O>CC(C)(C)NC(=O)c1cnccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18d0c7be8ef340e5b002ed0b9fb78e76 | CC(C)(C)[Si](C)(C)Cl.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]c1=O | [C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1.N1C=NC=C1.C(C)(C)(C)[Si](C)(C)Cl>>[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O | Cl[Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@H:9]([CH2:10][OH:11])[O:19]2)[c:20](=[O:21])[nH:22][c:23]1=[O:24]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@H:9]([CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17]... | CC(C)(C)[Si](C)(C)Cl.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]c1=O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 70.1 | [{"value": 70.0, "product": "[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2.42 g (10 mmol) thymidine in 15 ml DMF was added 1.7 g (25 mmol) imidazole and 1.6 g (10.6 mmol) tert-butyldimethyl silyl chloride. The solution was stirred at room temperature for 3 hours. DMF was then removed in vacuo and the residue was dissolved in 150 ml of ethyl acetate. The solution was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1cncnc1.C1CCOC1 | HCl | CN(C)C=O | null | 3 | CC(C)(C)[Si](C)(C)Cl.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>CN(C)C=O>Cc1cn([C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2aa6ee52497c47eaaa4a3b64a6066424 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1 | CO.C(C)N(CC)CC.[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1.COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1>>COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O)C=C1 | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][cH:39]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][c:34]([O:35][CH3:36])[cH:37][cH:38]1.[OH:8][CH2:9][C@H:10]1[O:11][C@@H:12]([n:13]2[cH:14][c:15]([CH3:16])[c:17](=[O:18])[nH:19][c:20]2=[O:21])[CH2:22][C@@H:23]1[OH:24]>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | O=c1ccn([C@H]2CC[C@@H](COC(c3ccccc3)(c3ccccc3)c3ccccc3)O2)c(=O)[nH]1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13]-[OH;D1;+0:14]>>[#8:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 85.3 | [{"value": 85.3, "product": "COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triethylamine (10 ml) in 200 ml THF was injected into a solid mixture of 6.8 g (28.0 mmol) thymidine and 10.2 g (28.6 mmol) 4,4'-dimethoxytrityl chloride under nitrogen with stirring. The solution was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml methanol was added to consume the exce... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | c1ccccc1.C1CCOC1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | null | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>C1CCOC1>COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9d36f011148549ad959252f600a05470 | CC(C)(C)[Si](C)(C)Cl.COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1>>COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O)C=C1.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O[Si](C)(C)C(C)(C)C)C=C1 | Cl[Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([O:8][CH2:9][C@H:10]2[O:11][C@@H:12]([n:13]3[cH:14][c:15]([CH3:16])[c:17](=[O:18])[nH:19][c:20]3=[O:21])[CH2:22][C@@H:23]2[OH:24])([c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[c:38]2[cH:39][cH:40][c:41]([O:42][CH3:... | CC(C)(C)[Si](C)(C)Cl.COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1 | COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | O=c1ccn([C@H]2CC[C@@H](COC(c3ccccc3)(c3ccccc3)c3ccccc3)O2)c(=O)[nH]1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#8:8]-[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[#8:8]-[C:9]-[C:10](-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:12] | null | [] | null | null | 3 | HOUR | To a solution of 13.0 g (23.9 mmol) 5'-O-(4,4'-dimethoxytrityl)thymidine 16 in 50 ml DMF was added 3.0 g (44 mmol) imidazole and 3.6 g (23.9 mmol) tert-butyl-dimethylsilyl chloride. The solution was stirred at room temperature for 3 hours. DMF was then removed in vacuo and the residue was dissolved in 300 ml of ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1.C1CCOC1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 3 | CC(C)(C)[Si](C)(C)Cl.COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1>CN(C)C=O>COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e89884540c3943e9884cf23c9919b30f | COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1>>Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)c(=O)[nH]c1=O | COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O[Si](C)(C)C(C)(C)C)C=C1.C(=O)([O-])[O-].[Na+].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1 | COc1ccc(C(c2ccccc2)(c2ccc(OC)cc2)[O:18][CH2:17][C@@H:16]2[C@@H:7]([O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:6][C@H:5]([n:4]3[cH:3][c:2]([CH3:1])[c:23](=[O:24])[nH:22][c:20]3=[O:21])[O:19]2)cc1>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([... | COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)c(=O)[nH]c1=O | null | null | C(C)(=O)O | Reduction | Ether cleavage to primary alcohol | 3c774c3a9fd2ef58fbe8dee191cc403dad4a91328640b5488b4df48c909fa0c2 | b2214ffe41910f7559d12600b09f53ad0061fceb1356758bbd9ba2fd28fd0a54 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-O-c1:c:c:c(-C(-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4])(-c2:c:c:c:c:c:2)-c2:c:c:c(-O-C):c:c:2):c:c:1>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 92.6 | [{"value": 92.6, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5 g (7.6 mmol) 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl) thymidine 17 in 100 ml 80% aq. acetic acid was stirred until the removal of dimethoxytrityl group was completed. Saturated Na2CO3 was then added to adjust the pH of the solution to 6-7. The solution was then extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Primary alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1 | HO- | C(C)(=O)O | null | null | COc1ccc(C(OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1>C(C)(=O)O>Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)c(=O)[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dcc14ee6b9974d65bb8d7fa919a98560 | Nc1ncnc2c1ncn2[C@]1(C2CCCCC2)O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)O.C1(CCCCC1)[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12.[Mg+2].[Cl-].[Cl-]>>[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 | C1CCC([C@@:11]2([n:10]3[c:6]4[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]4[n:8][cH:9]3)[O:12][C@H:13]([CH2:14][OH:15])[C@@H:16]([OH:17])[C@H:18]2[OH:19])CC1>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@@H:11]1[O:12][C@H:13]([CH2:14][OH:15])[C@@H:16]([OH:17])[C@H:18]1[OH:19] | Nc1ncnc2c1ncn2[C@]1(C2CCCCC2)O[C@H](CO)[C@@H](O)[C@H]1O | Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | null | null | C(CC)N1C(N(C=2NC(=NC2C1=O)C1CC2=CC=CC=C2CC1)CCC)=O | Miscellaneous | OtherReaction | b7f474113cff3858bd70576e08f14eeddb52bd257f13a755ace775979112f7c3 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | c1ncc2ncn([C@H]3CCCO3)c2n1 | [#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[C@;H0;D4;+0:7]1(-C2-C-C-C-C-C-2)-[#8:8]-[C:9]-[C:10]-[C:11]-1-[O;D1;H1:12]>>[#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[C@@H;D3;+0:7]1-[#8:8]-[C:9]-[C:10]-[C:11]-1-[O;D1;H1:12] | null | [] | null | null | 60 | MINUTE | Incubation tubes, in triplicate, receive 100 μl of [3H]NECA (94 nM in the assay), 100 μl of 1 μM cyclohexyl-adenosine (CHA), 100 μl of 100 mM MgCl2, 100 μl of 1 IU/ml adenosine deaminase, 100 μl of test compounds at various concentrations over the range of 10-10M to 10-4M diluted with assay buffer (50 mM Tris-HCl, pH 7... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | C1CCCCC1.C1CCOC1 | C1CCOC1 | c1ncnc2nc[nH]c12.C1CCOC1 | Other | C(CC)N1C(N(C=2NC(=NC2C1=O)C1CC2=CC=CC=C2CC1)CCC)=O | null | 1 | Nc1ncnc2c1ncn2[C@]1(C2CCCCC2)O[C@H](CO)[C@@H](O)[C@H]1O>C(CC)N1C(N(C=2NC(=NC2C1=O)C1CC2=CC=CC=C2CC1)CCC)=O>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c11192e28cf449f8f4481cc2630305b | CCCn1c(N)cc(=O)n(CCC)c1=O>>CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O | Cl.C(CC)N1C(=O)N(C(=O)C=C1N)CCC.C(C)(=O)O.N(=O)[O-].[Na+]>>C(CC)N1C(=O)N(C(=O)C(=C1N)N=O)CCC | [CH3:1][CH2:2][CH2:3][n:4]1[c:5]([NH2:6])[cH:7][c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH3:15])[c:16]1=[O:17]>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5]([NH2:6])[c:7]([N:8]=[O:9])[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH3:15])[c:16]1=[O:17] | CCCn1c(N)cc(=O)n(CCC)c1=O | CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O | null | null | O | Functional Group Addition | OtherReaction | 37b5dbf927322d4de54944b07579e1c735be607324387f2bb7b266fb591d966b | c852dfd7a307035d7b21dc79db1d13bba1cfffe7578c3caa265be3f4f0c038c5 | O=c1cc[nH]c(=O)[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C:5]):[c:6](-[N;D1;H2:7]):[cH;D2;+0:8]:[c:9]:1=[O;D1;H0:10]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C:5]):[c:6](-[N;D1;H2:7]):[c;H0;D3;+0:8](-[#7:11]=[O;D1;H0:12]):[c:9]:1=[O;D1;H0:10] | 146.3 | [{"value": 146.3, "product": "C(CC)N1C(=O)N(C(=O)C(=C1N)N=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 1,3-Di-n-propyl-6-aminouracil (30 g) was suspended in 1 L of water with 41 ml of 20% acetic acid and overhead stirring. Sodium nitrite (9.03 g) in 41 ml of water was added in portions, keeping the solution acidic with 12 ml of concentrated hydrochloric acid. A purple precipitate formed. Addition was complete in 10 minu... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitroso | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | O | null | 0.166667 | CCCn1c(N)cc(=O)n(CCC)c1=O>O>CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7844fca8b36648daa76fa1325c5434bd | CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O>>CCCn1c(N)c(N)c(=O)n(CCC)c1=O | C(CC)N1C(=O)N(C(=O)C(=C1N)N=O)CCC.[OH-].[NH4+].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC | O=[N:8][c:7]1[c:5]([NH2:6])[n:4]([CH2:3][CH2:2][CH3:1])[c:15](=[O:16])[n:11]([CH2:12][CH2:13][CH3:14])[c:9]1=[O:10]>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5]([NH2:6])[c:7]([NH2:8])[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH3:14])[c:15]1=[O:16] | CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O | CCCn1c(N)c(N)c(=O)n(CCC)c1=O | null | null | O | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | O=c1cc[nH]c(=O)[nH]1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](-[N;D1;H2:4]):[#7;a:5](-[C:6]):[c:7]:[#7;a:8](-[C:9]):[c:10]:1=[O;D1;H0:11]>>[C:9]-[#7;a:8]1:[c:7]:[#7;a:5](-[C:6]):[c:3](-[N;D1;H2:4]):[c:2](-[NH2;D1;+0:1]):[c:10]:1=[O;D1;H0:11] | 64.3 | [{"value": 64.3, "product": "C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 1,3-di-n-propyl-5-nitroso-6-aminouracil (61.6 g) was suspended in 1 L of water, and the suspension was made alkaline to pH 11 with 50% ammonium hydroxide and treated with 100 g of sodium dithionite, in portions, until the purple color faded. The aqueous mixture was extracted with chloroform (8×200 ml), dried over m... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1cncnc1 | Other | O | null | null | CCCn1c(N)c(N=O)c(=O)n(CCC)c1=O>O>CCCn1c(N)c(N)c(=O)n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a89a3e5e7d9441a2aad27464a69c6f6b | CC(C)COC(=O)Cl.CC(CC(=O)O)c1ccccc1.CCCn1c(N)c(N)c(=O)n(CCC)c1=O>>CCCC1C(=O)C(NC(=O)CC(C)c2ccccc2)=C(N)C(CCC)C1=O | C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC.CN1CCOCC1.C1(=CC=CC=C1)C(CC(=O)O)C.O1CCCC1.ClC(=O)OCC(C)C>>NC1=C(C(C(C(C1CCC)=O)CCC)=O)NC(CC(C)C1=CC=CC=C1)=O | CC([CH3:4])[CH2:22]OC(=O)Cl.O[C:9](=[O:10])[CH2:11][CH:12]([CH3:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.n1([CH2:3][CH2:2][CH3:1])[c:5](=[O:6])[c:7]([NH2:8])[c:20]([NH2:21])n([CH2:23][CH2:24][CH3:25])[c:26]1=[O:27]>>[CH3:1][CH2:2][CH2:3][CH:4]1[C:5](=[O:6])[C:7]([NH:8][C:9](=[O:10])[CH2:11][CH:12]([CH3:13])[c:14... | CC(C)COC(=O)Cl.CC(CC(=O)O)c1ccccc1.CCCn1c(N)c(N)c(=O)n(CCC)c1=O | CCCC1C(=O)C(NC(=O)CC(C)c2ccccc2)=C(N)C(CCC)C1=O | null | null | C(C)OCC | C-C Coupling | OtherReaction | 5c8a2d6646c71c2a83fdc3fdc59433d41ad0350271ad1fefbcb0092808138d1b | bc39b0e4c0620bce2a05ac4e5898b1c189da43135bbce9ca122e66c06fe4fa42 | O=C1CC=C(NC(=O)CCc2ccccc2)C(=O)C1 | C-C(-[CH3;D1;+0:1])-[CH2;D2;+0:2]-O-C(-Cl)=O.O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[C:6].[C;D1;H3:7]-[C:8]-[CH2;D2;+0:9]-n1:[c;H0;D3;+0:10](=[O;D1;H0:11]):n(-[CH2;D2;+0:12]-[C:13]-[C;D1;H3:14]):[c;H0;D3;+0:15](-[N;D1;H2:16]):[c;H0;D3;+0:17](-[NH2;D1;+0:18]):[c;H0;D3;+0:19]:1=[O;D1;H0:20]>>[C:6]-[C:5]-[C;H0;D3;+0:3](=[O;... | null | [] | -20 | CELSIUS | null | null | Dissolve 3-phenylbutyric acid (1.0 g, 6.1 mmol) in tetrahydrofuran (20 ml), treat with N-methylmorpholine (0.67 ml, 6.1 mmol) and cool to -20° C. Add isobutyl chloroformate (0.79 ml, 6.1 mmol) and stir for 20 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.4 g, 6.1 mmol, in 5 ml dimethylformamide) and stir the r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether.Primary amine | Enamine.Enamine.Ketone.Ketone.Secondary amide | c1cncnc1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HCl | C(C)OCC | -20 | null | CC(C)COC(=O)Cl.CC(CC(=O)O)c1ccccc1.CCCn1c(N)c(N)c(=O)n(CCC)c1=O>C(C)OCC>CCCC1C(=O)C(NC(=O)CC(C)c2ccccc2)=C(N)C(CCC)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d42d3e8acbb4e3db3bb6bef4ab7f44e | CC(C)COC(=O)Cl.CCCn1c(N)c(N)c(=O)n(CCC)c1=O.O=C(O)C1CCc2ccccc2C1>>CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O | C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC.CN1CCOCC1.C1C(CCC2=CC=CC=C12)C(=O)O.O1CCCC1.ClC(=O)OCC(C)C>>NC1=C(C(C(C(C1CCC)=O)CCC)=O)NC(=O)C1CC2=CC=CC=C2CC1 | CC([CH3:4])[CH2:23]OC(=O)Cl.n1([CH2:3][CH2:2][CH3:1])[c:5](=[O:6])[c:7]([NH2:8])[c:21]([NH2:22])n([CH2:24][CH2:25][CH3:26])[c:27]1=[O:28].O[C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[CH2:20]1>>[CH3:1][CH2:2][CH2:3][CH:4]1[C:5](=[O:6])[C:7]([NH:8][C:9](=[O:10])[CH:11]2[CH2:12][CH2:13... | CC(C)COC(=O)Cl.CCCn1c(N)c(N)c(=O)n(CCC)c1=O.O=C(O)C1CCc2ccccc2C1 | CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O | null | null | C(C)OCC | Acylation | OtherReaction | f555303b1e2b4f0253b2d226928de2f031d3ec8246add55f1668729a034dabdc | f81b4d81458997ec9b7ad1062ac59bfc97eed028c6444e74b2e032f9e7c50629 | O=C1CC=C(NC(=O)C2CCc3ccccc3C2)C(=O)C1 | C-C(-[CH3;D1;+0:1])-[CH2;D2;+0:2]-O-C(-Cl)=O.O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C:7].[C;D1;H3:8]-[C:9]-[CH2;D2;+0:10]-n1:[c;H0;D3;+0:11](=[O;D1;H0:12]):n(-[CH2;D2;+0:13]-[C:14]-[C;D1;H3:15]):[c;H0;D3;+0:16](-[N;D1;H2:17]):[c;H0;D3;+0:18](-[NH2;D1;+0:19]):[c;H0;D3;+0:20]:1=[O;D1;H0:21]>>[C:6]-[C:5](-[C;H0;D3;... | null | [] | null | null | null | null | Dissolve 1,2,3,4-tetrahydro-2-naphthoic acid (1.0 g, 5.67 mmol) in tetrahydrofuran (40 ml). Add N-methylmorpholine (0.62 ml, 5.67 mmol) and cool to -20° C. Add isobutyl chloroformate (0.73 ml, 5.67 mmol) and stir for 25 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.28 g, 5.67 mmol, in 5 ml dimethylformamide) a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether.Primary amine | Enamine.Enamine.Ketone.Ketone.Secondary amide | c1cncnc1 | C1=CCCCC1 | C1=CCCCC1.c1ccc2c(c1)CCCC2 | HCl | C(C)OCC | null | null | CC(C)COC(=O)Cl.CCCn1c(N)c(N)c(=O)n(CCC)c1=O.O=C(O)C1CCc2ccccc2C1>C(C)OCC>CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08dfdae2443b4d4698992a68f3846a73 | CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O>>CCCn1c(=O)c2nc(C3CCc4ccccc4C3)[nH]c2n(CCC)c1=O | NC1=C(C(C(C(C1CCC)=O)CCC)=O)NC(=O)C1CC2=CC=CC=C2CC1.C(C)O.[OH-].[K+].Cl>>C(CC)N1C(N(C=2NC(=NC2C1=O)C1CC2=CC=CC=C2CC1)CCC)=O | O=[C:9]([NH:8][C:7]1=[C:21]([NH2:4])C([CH2:23][CH2:24][CH3:25])[C:26](=[O:27])C([CH2:3][CH2:2][CH3:1])[C:5]1=[O:6])[CH:10]1[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH2:19]1>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[CH2:... | CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O | CCCn1c(=O)c2nc(C3CCc4ccccc4C3)[nH]c2n(CCC)c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6a3baf97395af5a58a0be53c81249ca5684d413ceea313991e2da03fb40d4c2c | 2061c33e1242727c187d28a122e44a8c814865d9283c90305f536a8e0cbd317f | O=c1[nH]c(=O)c2nc(C3CCc4ccccc4C3)[nH]c2[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[NH2;D1;+0:5])-C(-[CH2;D2;+0:6]-[C:7]-[C;D1;H3:8])-[C;H0;D3;+0:9](=[O;D1;H0:10])-C(-[CH2;D2;+0:11]-[C:12]-[C;D1;H3:13])-[C;H0;D3;+0:14]-1=[O;D1;H0:15])-[C:16](-[C:17])-[C:18]>>[C:17]-[C:16](-[c;H0;D3;+0:1]1:[#7;a:19]:[c;H0;D3;+0:4]2:[#7;a:20](-[CH2;D2;+0:6]... | null | [] | 70 | CELSIUS | null | null | Dissolve 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide (2.0 g, 5.2 mmol) in ethanol (50 ml), add 15% potassium hydroxide (50 ml) and heat to 70° C. for 4 hours. After cooling to 0° C., acidify the reaction with concentrated hydrochloric acid (13 ml). Add water (100... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ketone.Ketone.Secondary amide | null | C1=CCCCC1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccc2c(c1)CCCC2 | HO- | null | 70 | null | CCCC1C(=O)C(NC(=O)C2CCc3ccccc3C2)=C(N)C(CCC)C1=O>>CCCn1c(=O)c2nc(C3CCc4ccccc4C3)[nH]c2n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ea318ee0bf546738988ec43ff7e3d9c | C=CCn1c(N)cc(=O)n(CC=C)c1=O>>C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O | Cl.C(C=C)N1C(=O)N(C(=O)C=C1N)CC=C.C(C)(=O)O.N(=O)[O-].[Na+]>>C(C=C)N1C(=O)N(C(=O)C(=C1N)N=O)CC=C | [CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([NH2:6])[cH:7][c:10](=[O:11])[n:12]([CH2:13][CH:14]=[CH2:15])[c:16]1=[O:17]>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([NH2:6])[c:7]([N:8]=[O:9])[c:10](=[O:11])[n:12]([CH2:13][CH:14]=[CH2:15])[c:16]1=[O:17] | C=CCn1c(N)cc(=O)n(CC=C)c1=O | C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O | null | null | O | Functional Group Addition | OtherReaction | 37b5dbf927322d4de54944b07579e1c735be607324387f2bb7b266fb591d966b | c852dfd7a307035d7b21dc79db1d13bba1cfffe7578c3caa265be3f4f0c038c5 | O=c1cc[nH]c(=O)[nH]1 | [C;D1;H2:1]=[C:2]-[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C:7]-[C:8]=[C;D1;H2:9]):[c:10](-[N;D1;H2:11]):[cH;D2;+0:12]:[c:13]:1=[O;D1;H0:14]>>[C;D1;H2:1]=[C:2]-[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C:7]-[C:8]=[C;D1;H2:9]):[c:10](-[N;D1;H2:11]):[c;H0;D3;+0:12](-[#7:15]=[O;D1;H0:16]):[c:13]:1=[O;D1;H0:14] | 87 | [{"value": 87.0, "product": "C(C=C)N1C(=O)N(C(=O)C(=C1N)N=O)CC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "C(C=C)N1C(=O)N(C(=O)C(=C1N)N=O)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1,3-Diallyl-6-aminouracil (5 g) was suspended in 400 ml of water in a one-liter round bottom flask with overhead stirring. Acetic acid (6.7 ml of a 20% solution) was added, followed by intermittent addition of 2 ml of concentrated hydrochloric acid and a sodium nitrite solution (1.53 g in 7 ml water). After 4 hours, th... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitroso | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | O | null | 4 | C=CCn1c(N)cc(=O)n(CC=C)c1=O>O>C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8f15eb953a84aa19e1130c014edb8b2 | C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O>>C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O | C(C=C)N1C(=O)N(C(=O)C(=C1N)N=O)CC=C.S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>C(C=C)N1C(=O)N(C(=O)C(=C1N)N)CC=C | O=[N:8][c:7]1[c:5]([NH2:6])[n:4]([CH2:3][CH:2]=[CH2:1])[c:15](=[O:16])[n:11]([CH2:12][CH:13]=[CH2:14])[c:9]1=[O:10]>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([NH2:6])[c:7]([NH2:8])[c:9](=[O:10])[n:11]([CH2:12][CH:13]=[CH2:14])[c:15]1=[O:16] | C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O | C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O | null | null | O.C(C)(=O)OCC | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | O=c1cc[nH]c(=O)[nH]1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](-[N;D1;H2:4]):[#7;a:5](-[C:6]-[C:7]=[C;D1;H2:8]):[c:9]:[#7;a:10](-[C:11]-[C:12]=[C;D1;H2:13]):[c:14]:1=[O;D1;H0:15]>>[C;D1;H2:13]=[C:12]-[C:11]-[#7;a:10]1:[c:9]:[#7;a:5](-[C:6]-[C:7]=[C;D1;H2:8]):[c:3](-[N;D1;H2:4]):[c:2](-[NH2;D1;+0:1]):[c:14]:1=[O;D1;H0:15] | 104.2 | [{"value": 104.2, "product": "C(C=C)N1C(=O)N(C(=O)C(=C1N)N)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The 1,3-diallyl-5-nitroso-6-aminouracil (4.5 g) was suspended in 150 ml of ethyl acetate and treated with 23.6 g of sodium dithionite in 64 ml of water. After 1 hour, the layers were separated and the aqueous phase was extracted with ethyl acetate (4×100 ml). The combined organic extracts were dried over magnesium sulf... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1cncnc1 | Other | O.C(C)(=O)OCC | null | 1 | C=CCn1c(N)c(N=O)c(=O)n(CC=C)c1=O>O.C(C)(=O)OCC>C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee021fa8c0fc47e48b1fbf4ceb821807 | C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O>>C=CCC1C(=O)C([NH-])=C(N)C(CC=C)C1=O | ClC(=O)OCC(C)C.CN1CCOCC1.C1(=CC=CC=C1)[C@H]1[C@@H](CCC1)C(=O)O.C(C=C)N1C(=O)N(C(=O)C(=C1N)N)CC=C>>C1(=CC=CC=C1)[C@H]1[C@@H](CCC1)C(=O)O.C(C=C)C1C(=C(C(C(C1=O)CC=C)=O)[NH-])N | n1([CH2:3][CH:2]=[CH2:1])[c:5](=[O:6])n([CH2:12][CH:13]=[CH2:14])[c:15](=[O:16])[c:11]([NH2:8])[c:9]1[NH2:10]>>[CH2:1]=[CH:2][CH2:3][CH:4]1[C:5](=[O:6])[C:7]([NH-:8])=[C:9]([NH2:10])[CH:11]([CH2:12][CH:13]=[CH2:14])[C:15]1=[O:16] | C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O | C=CCC1C(=O)C([NH-])=C(N)C(CC=C)C1=O | null | null | O1CCCC1.C(C)OCC | Miscellaneous | OtherReaction | e889cd2367de801ea04c858b42e0e75c0983312b78829811d7f4022b3350eda3 | d4911dd9231cb2495232c541c84a116045819d01caa0160725ed247452c439ad | O=C1C=CCC(=O)C1 | [C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-n1:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c;H0;D3;+0:6](-[NH2;D1;+0:7]):[c;H0;D3;+0:8](-[N;D1;H2:9]):n(-[CH2;D2;+0:10]-[C:11]=[C;D1;H2:12]):[c;H0;D3;+0:13]:1=[O;D1;H0:14]>>[C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:6]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:15](-[CH2;D2;+0:10]-[C:11]=[C;D1;H2:12])-[C;H0;... | 87.8 | [{"value": 87.8, "product": "C(C=C)C1C(=C(C(C(C1=O)CC=C)=O)[NH-])N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve trans-2-phenyl-cyclopentanecarboxylic acid (1.0 g, 5.3 mmol), prepared according to F. G. Bordwell and J. Almy, J. Org. Chem., 38, 571 (1973), in tetrahydrofuran (20 ml) and add N-methylmorpholine (0.58 ml, 5.3 mmol). Cool the reaction to -20° C. and add isobutyl chloroformate (0.69 ml, 5.3 mmol). Stir the rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Allyl.Allyl | Enamine.Ketone.Ketone.Allyl.Allyl | c1cncnc1 | C1=CCCCC1 | C1=CCCCC1 | null | O1CCCC1.C(C)OCC | null | null | C=CCn1c(N)c(N)c(=O)n(CC=C)c1=O>O1CCCC1.C(C)OCC>C=CCC1C(=O)C([NH-])=C(N)C(CC=C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8fa4707b7f14f039824c58e9cb46488 | C=CCC1C(=O)C(NC(=O)[C@@H]2CCC[C@H]2c2ccccc2)=C(N)C(CC=C)C1=O>>C=CCC1C(=O)c2nc(C3CCCC3c3ccccc3)[nH]c2C(CC=C)C1=O | C(C=C)C1C(=C(C(C(C1=O)CC=C)=O)NC(=O)[C@H]1[C@@H](CCC1)C1=CC=CC=C1)N.[OH-].[K+]>>C(C=C)C1C(C2=C(NC(=N2)C2C(CCC2)C2=CC=CC=C2)C(C1=O)CC=C)=O | O=[C:9]([NH:8][C:7]1=[C:22]([NH2:21])[CH:23]([CH2:24][CH:25]=[CH2:26])[C:27](=[O:28])[CH:4]([CH2:3][CH:2]=[CH2:1])[C:5]1=[O:6])[C@@H:10]1[CH2:11][CH2:12][CH2:13][C@H:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH:4]1[C:5](=[O:6])[c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH:14]3[c:15]3... | C=CCC1C(=O)C(NC(=O)[C@@H]2CCC[C@H]2c2ccccc2)=C(N)C(CC=C)C1=O | C=CCC1C(=O)c2nc(C3CCCC3c3ccccc3)[nH]c2C(CC=C)C1=O | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | d09968330c08fb4dffb0211fb7bbb3b5ca8e00b99ed353f27f9f103af4cf5d5a | ba46e582b0ccb13494cab36c11ab176ac32f471b77c782fcf5ef31b2be2bfd37 | O=C1CC(=O)c2nc(C3CCCC3c3ccccc3)[nH]c2C1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[NH2;D1;+0:5])-[C:6](-[C:7]-[C:8]=[C;D1;H2:9])-[C:10](=[O;D1;H0:11])-[C:12]-[C:13]-1=[O;D1;H0:14])-[C@@H;D3;+0:15]1-[C:16]-[C:17]-[C:18]-[C@H;D3;+0:19]-1-[c:20](:[c:21]):[c:22]>>[C;D1;H2:9]=[C:8]-[C:7]-[C:6]1-[C:10](=[O;D1;H0:11])-[C:12]-[C:13](=[O;D1;H0:14... | 52.4 | [{"value": 52.4, "product": "C(C=C)C1C(C2=C(NC(=N2)C2C(CCC2)C2=CC=CC=C2)C(C1=O)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve trans-2-phenylcyclopentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enyl)amide (300 mg, 0.76 mmol) in ethanol (100 ml), add 10% potassium hydroxide (100 ml) and heat the reaction to 60° C. for 4 hours. Cool the reaction and dilute with water (200 ml). Acidify with concentrated hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ketone.Secondary amide | Ketone | C1=CCCCC1 | c1nc2c([nH]1)CCCC2 | c1nc2c([nH]1)CCCC2.C1CCCC1.c1ccccc1 | HO- | C(C)O.O | null | null | C=CCC1C(=O)C(NC(=O)[C@@H]2CCC[C@H]2c2ccccc2)=C(N)C(CC=C)C1=O>C(C)O.O>C=CCC1C(=O)c2nc(C3CCCC3c3ccccc3)[nH]c2C(CC=C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6efe1ee7b8454d5381cd919bc39975fa | O=S(Cl)Cl.OC(=S)Cc1cc(Cl)ccc1Cl>>S=C(Cl)Cc1cc(Cl)ccc1Cl | ClC1=C(C=C(C=C1)Cl)CC(=S)O.S(=O)(Cl)Cl>>ClC1=C(C=C(C=C1)Cl)CC(=S)Cl | O=S(Cl)[Cl:3].O[C:2](=[S:1])[CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[Cl:12]>>[S:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[Cl:12] | O=S(Cl)Cl.OC(=S)Cc1cc(Cl)ccc1Cl | S=C(Cl)Cc1cc(Cl)ccc1Cl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | e3e7eb3511d75cc9b7008c826aaaa8b4366e22a02097643e8cf39eea9f81047c | e438533efbf2459408e0cff61c39d9bdcef2fe0fc4e698464b18d7590879cc9a | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[S;D1;H0:3])-[C:4]-[c:5]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[S;D1;H0:3])-[C:4]-[c:5] | 106.5 | [{"value": 100.0, "product": "ClC1=C(C=C(C=C1)Cl)CC(=S)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.5, "product": "ClC1=C(C=C(C=C1)Cl)CC(=S)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,5-dichlorophenylthioacetic acid (13.0 g, 54.9 mmol) in methylene chloride (55 mL) and thionyl chloride (10 mL, 137 mmol) was heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The residue was evaporated two times from toluene to give 14 ... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Alkenyl halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | null | O=S(Cl)Cl.OC(=S)Cc1cc(Cl)ccc1Cl>C(Cl)Cl>S=C(Cl)Cc1cc(Cl)ccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b901239143da4037bbabfa55e775adfc | O=C([O-])C1=C(CI)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12.Sc1ccncc1>>O=C(OCSc1ccncc1)C1=CCSC2C(NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 | SC1=CC=NC=C1.N1=C(C=CC=C1C)C.CCOCC.ICC1=C(N2C([C@H]([C@H]2SC1)NC(CC1=C(C=CC(=C1)Cl)Cl)=S)=O)C(=O)[O-]>>N1=CC=C(C=C1)SCOC(=O)C=1N2C(C(C2SCC1)NC(CC1=C(C=CC(=C1)Cl)Cl)=S)=O | I[CH2:4][C:13]1=[C:12]([C:2](=[O:1])[O-:3])[N:32]2[C@H:16]([S:15][CH2:14]1)[C@H:17]([NH:18][C:19](=[S:20])[CH2:21][c:22]1[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]1[Cl:29])[C:30]2=[O:31].[SH:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[O:1]=[C:2]([O:3][CH2:4][S:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[C:12]1=[CH:13][CH2... | O=C([O-])C1=C(CI)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12.Sc1ccncc1 | O=C(OCSc1ccncc1)C1=CCSC2C(NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 | null | null | C1CCOC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 84a0347f1081e9ad7bf7283ae33fc8b336fbe93bb9310a66a48477ce04762686 | 6738b49e6402204fa1cc0054e66a38aa7624ee83b342fb7189e9c54b2cacfd8a | O=C(OCSc1ccncc1)C1=CCSC2C(NC(=S)Cc3ccccc3)C(=O)N12 | I-[CH2;D2;+0:1]-[C;H0;D3;+0:2]1=[C:3](-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6])-[#7:7](-[C:8]-[#16:9]-[C:10]-1)-[C:11]=[O;D1;H0:12].[SH;D1;+0:13]-[c:14]1:[c:15]:[c:16]:[#7;a:17]:[c:18]:[c:19]:1>>[O;D1;H0:6]=[C:4](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[S;H0;D2;+0:13]-[c:14]1:[c:15]:[c:16]:[#7;a:17]:[c:18]:[c:19]:1)-[C:3]1=[CH;D2;+0:2]... | 49 | [{"value": 49.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | (6R)-trans-3-Iodomethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, diphenylmethyl ester (3.00 g, 4.14 mmol) was dissolved in THF (50 mL) at 0° C. and treated with 4-mercaptopyridine (0.504 g, 4.54 mmol). A solution of 2,6-lutidine (0.576 g, 5.38 mmol) in THF (1 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Aromatic thiol | Enamine.Ester.Monosulfide | C1=CN2CC[C@H]2SC1 | C1=CN2CCC2SC1 | c1ccncc1.c1ccccc1.C1=CN2CCC2SC1 | I- | C1CCOC1.C(C)(=O)OCC | 0 | 0.5 | O=C([O-])C1=C(CI)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12.Sc1ccncc1>C1CCOC1.C(C)(=O)OCC>O=C(OCSc1ccncc1)C1=CCSC2C(NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c37ebe36c3e740b7b55727694727316c | O=C([O-])C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12>>O=C(O)C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 | FC(C(=O)O)(F)F.ClCC1=C(N2C([C@H]([C@H]2SC1)NC(CC1=C(C=CC(=C1)Cl)Cl)=S)=O)C(=O)[O-].C1(=CC=CC=C1)OC>>ClCC1=C(N2C([C@H]([C@H]2SC1)NC(CC1=C(C=CC(=C1)Cl)Cl)=S)=O)C(=O)O | [O:1]=[C:2]([O-:3])[C:4]1=[C:5]([CH2:6][Cl:7])[CH2:8][S:9][C@@H:10]2[C@H:11]([NH:12][C:13](=[S:14])[CH2:15][c:16]3[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:22]3[Cl:23])[C:24](=[O:25])[N:26]12>>[O:1]=[C:2]([OH:3])[C:4]1=[C:5]([CH2:6][Cl:7])[CH2:8][S:9][C@@H:10]2[C@H:11]([NH:12][C:13](=[S:14])[CH2:15][c:16]3[cH:17][c:18]([C... | O=C([O-])C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 | O=C(O)C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 | null | null | C(Cl)Cl | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | O=C1[C@@H](NC(=S)Cc2ccccc2)[C@H]2SCC=CN12 | [#16:1]-[C:2]-[C:3](-[C:4])=[C:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8])-[#7:9]-[C:10]=[O;D1;H0:11]>>[#16:1]-[C:2]-[C:3](-[C:4])=[C:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7])-[#7:9]-[C:10]=[O;D1;H0:11] | 70 | [{"value": 70.0, "product": "ClCC1=C(N2C([C@H]([C@H]2SC1)NC(CC1=C(C=CC(=C1)Cl)Cl)=S)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A slurry of (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, diphenylmethyl ester (10.0 g, 15.8 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with anisole (24 mL) and then trifluoroacetic acid (80 mL). The resulting solution was stirred for 1 h at ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.C1=CN2CC[C@H]2SC1 | null | C(Cl)Cl | 0 | 1 | O=C([O-])C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12>C(Cl)Cl>O=C(O)C1=C(CCl)CS[C@@H]2[C@H](NC(=S)Cc3cc(Cl)ccc3Cl)C(=O)N12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3e51c74c8ae2432e999cbab6081867a5 | CC(C)(C)OC(=O)NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1>>NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1 | [Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CNC(=O)OC(C)(C)C.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>[Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CN | CC(C)(C)OC(=O)[NH:1][CH2:2][CH:3]([OH:4])[CH2:5][n+:6]1[cH:7][cH:8][c:9]([S:10][CH2:11][C:12]2=[C:13]([C:14](=[O:15])[OH:16])[N:17]3[C:18](=[O:19])[C@@H:20]([NH:21][C:22](=[O:23])[CH2:24][S:25][c:26]4[cH:27][c:28]([Cl:29])[cH:30][cH:31][c:32]4[Cl:33])[C@H:34]3[S:35][CH2:36]2)[cH:37][cH:38]1>>[NH2:1][CH2:2][CH:3]([OH:4]... | CC(C)(C)OC(=O)NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1 | NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CSc1ccccc1)N[C@@H]1C(=O)N2C=C(CSc3cc[nH+]cc3)CS[C@H]12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 127.2 | [{"value": 54.0, "product": "[Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 127.2, "product": "[Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CN", "details": "CALCULATE... | 0 | CELSIUS | 30 | MINUTE | A slurry of 1-(2-hydroxy-3-t-butoxycarbonylamino-1-propyl)-4-[[(6R)trans-2-carboxy-8-oxo-7-[(2,5- dichlorophenylthio)acetamido]-5- thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium chloride (1.19 g, 1.58 mmol) in methylene chloride (22 mL) was cooled to 0° C. Anisole (3.4 mL) was added followed by trifluoroa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1=CC=[NH+]C=C1.C1=CN2CC[C@H]2SC1.c1ccccc1 | HO- | C(Cl)Cl | 0 | 0.5 | CC(C)(C)OC(=O)NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1>C(Cl)Cl>NCC(O)C[n+]1ccc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)CSc4cc(Cl)ccc4Cl)[C@H]3SC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e9f35d9308c4443ac4377883641dd28 | CC(C)C(=O)Cl.Nc1ccc(I)cc1>>CC(C)C(=O)Nc1ccc(I)cc1 | C(C(C)C)(=O)Cl.IC1=CC=C(N)C=C1.N1=CC=CC=C1.O.C(C(C)C)(=O)Cl>>IC1=CC=C(C=C1)NC(C(C)C)=O | Cl[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1 | CC(C)C(=O)Cl.Nc1ccc(I)cc1 | CC(C)C(=O)Nc1ccc(I)cc1 | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 97.4 | [{"value": 97.0, "product": "IC1=CC=C(C=C1)NC(C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "IC1=CC=C(C=C1)NC(C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a dispersion of p-iodoaniline (219.0 g, 1 mol) in acetonitrile(1000 ml) was added pyridine (81.0 ml, 1 mol). Isobutyryl chloride (100.5 ml, 1 mol) was added dropwise to the mixture over 1 hour in an ice bath. The mixture was further stirred for one hour following the addition of isobutyryl chloride and to the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(C)#N | null | 1 | CC(C)C(=O)Cl.Nc1ccc(I)cc1>C(C)#N>CC(C)C(=O)Nc1ccc(I)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58a8141f935a45458cf7a40ae4224d27 | CCCC(=O)CCC.CCOC(=O)CC#N>>CCCC(CCC)=C(C#N)C(=O)OCC | CCCC(CCC)=O.C(#N)CC(=O)OCC.CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C>>C(#N)C(C(=O)OCC)=C(CCC)CCC | O=[C:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7].[CH2:8]([C:9]#[N:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][C:4]([CH2:5][CH2:6][CH3:7])=[C:8]([C:9]#[N:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15] | CCCC(=O)CCC.CCOC(=O)CC#N | CCCC(CCC)=C(C#N)C(=O)OCC | null | null | C1CCCCC1.C(C)(=O)OCC | C-C Coupling | Aldol condensation | 2357b320f8650e3d2d4ab36462f2f41aea7962d3026be19ede573264cdbf06cd | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | null | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](-[C:11]#[N;D1;H0:12])=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5] | 80,000 | [{"value": 80.0, "product": "C(#N)C(C(=O)OCC)=C(CCC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80000.0, "product": "C(#N)C(C(=O)OCC)=C(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 100 mL round-bottom flask was dissolved 4-heptanone (11.4 g, 0.10 mmole) and ethyl cyanoacetate (11.30 g, 0.100 mole) in cyclohexane (25 mL). Acetic add (1.0 mL) and NH4OAc (2.0 g) were added. The solution was magnetically stirred and heated to reflux with a Dean-Stark trap in place overnight under N2. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | null | null | null | HO- | C1CCCCC1.C(C)(=O)OCC | null | null | CCCC(=O)CCC.CCOC(=O)CC#N>C1CCCCC1.C(C)(=O)OCC>CCCC(CCC)=C(C#N)C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa9e36ab9df044eca0ae8f17c3acb777 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O>>Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 | ON1C(CCC1=O)=O.C(C)N(CC)CC.C1(=CC=C(C=C1)C(=O)O)C.P(=O)(OC1=CC=CC=C1)(OC1=CC=CC=C1)Cl>>C1(CCC(N1OC(=O)C1=CC=C(C=C1)C)=O)=O | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)=[O:7].[OH:8][N:9]1[C:10](=[O:11])[CH2:12][CH2:13][C:14]1=[O:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[O:8][N:9]2[C:10](=[O:11])[CH2:12][CH2:13][C:14]2=[O:15])[cH:16][cH:17]1 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O | Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 | null | null | C(C)(C)(C)OC.C(C)(=O)OCC | Acylation | OtherReaction | db5387e6a0a70df402c1de47d784ebd77c0df6ea444556bcb68e6c99ac233dfc | d6b6da3f4e6a1bff80118626f0eda39fc948645429a79c2af70ffd0ea7000442 | O=C(ON1C(=O)CCC1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[OH;D1;+0:13]>>[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 94 | [{"value": 94.0, "product": "C1(CCC(N1OC(=O)C1=CC=C(C=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.42 g (0.021 mol) of N-hydroxysuccinimide and 5.06 g (0.050 mol) of triethylamine were initially introduced into 5 ml of ethyl acetate and the suspension was stirred at room temperature. 2.72 g (0.020 mol) of solid 4-toluic acid were added to this suspension in the course of 5 min. and then a solution of 5.64 g (0.21 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.C1CC[NH]C1 | HO- | C(C)(C)(C)OC.C(C)(=O)OCC | null | null | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O>C(C)(C)(C)OC.C(C)(=O)OCC>Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46ef6b3fdcb74f75b3a22e357525e9cd | CC(=O)O.O=C1CCC(=O)N1O>>CC(=O)ON1C(=O)CCC1=O | C(C)(=O)O.C(C)N(CC)CC.P(=O)(OC1=CC=CC=C1)(OC1=CC=CC=C1)Cl.ON1C(CCC1=O)=O>>C1(CCC(N1OC(C)=O)=O)=O | O[C:2]([CH3:1])=[O:3].[OH:4][N:5]1[C:6](=[O:7])[CH2:8][CH2:9][C:10]1=[O:11]>>[CH3:1][C:2](=[O:3])[O:4][N:5]1[C:6](=[O:7])[CH2:8][CH2:9][C:10]1=[O:11] | CC(=O)O.O=C1CCC(=O)N1O | CC(=O)ON1C(=O)CCC1=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | db5387e6a0a70df402c1de47d784ebd77c0df6ea444556bcb68e6c99ac233dfc | d6b6da3f4e6a1bff80118626f0eda39fc948645429a79c2af70ffd0ea7000442 | O=C1CCC(=O)N1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]1-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[#7:10]-1-[OH;D1;+0:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:11]-[#7:10]1-[C:5](=[O;D1;H0:4])-[C:6]-[C:7]-[C:8]-1=[O;D1;H0:9] | 70 | [{"value": 70.0, "product": "C1(CCC(N1OC(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "C1(CCC(N1OC(C)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.27 g (0.011 mol) of N-hydroxysuccinimide were initially introduced into 10 ml of ethyl acetate, a solution of 3.22 g (0.012 mol) of diphenyl chlorophosphate in 10 ml of ethyl acetate was added and then a solution of 2.53 g (0.025 mol) of triethylamine in 10 ml of ethyl acetate was added dropwise in the course of 10 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CC[NH]C1 | HO- | C(C)(=O)OCC | null | 0.5 | CC(=O)O.O=C1CCC(=O)N1O>C(C)(=O)OCC>CC(=O)ON1C(=O)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd19c881eac941828954e215ecddc363 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O>>Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 | P(=O)(OCC)(OCC)Cl.ON1C(CCC1=O)=O.C1(=CC=C(C=C1)C(=O)O)C.C(C)N(CC)CC>>C1(CCC(N1OC(=O)C1=CC=C(C=C1)C)=O)=O | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)=[O:7].[OH:8][N:9]1[C:10](=[O:11])[CH2:12][CH2:13][C:14]1=[O:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[O:8][N:9]2[C:10](=[O:11])[CH2:12][CH2:13][C:14]2=[O:15])[cH:16][cH:17]1 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O | Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | db5387e6a0a70df402c1de47d784ebd77c0df6ea444556bcb68e6c99ac233dfc | d6b6da3f4e6a1bff80118626f0eda39fc948645429a79c2af70ffd0ea7000442 | O=C(ON1C(=O)CCC1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[OH;D1;+0:13]>>[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Analogous example 3 2,76 g (0.024 mol) of N-hydroxysuccinimide and 5.06 g (0,050 mol) of triethylamine were initially introduced into 5 ml of ethyl acetate and stirred at room temperature. 2.72 g (0.020 mol) of solid 4-toluic acid were added to this suspension in the course of 5 min. and then a solution of 3.47 g (0,02... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.C1CC[NH]C1 | HO- | C(C)(=O)OCC | null | null | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1O>C(C)(=O)OCC>Cc1ccc(C(=O)ON2C(=O)CCC2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-608e80bb9092458b8ead7e8d78854485 | NC(Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1>>O=C(NC(Cc1cccs1)C(=O)O)OCc1ccccc1 | S1C(=CC=C1)CC(N)C(=O)O.C([O-])([O-])=O.[K+].[K+].C(=O)(OCC1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)OC(=O)NC(CC=1SC=CC1)C(=O)O | [NH2:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][s:10]1)[C:11](=[O:12])[OH:13].Cl[C:2](=[O:1])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][s:10]1)[C:11](=[O:12])[OH:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NC(Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1 | O=C(NC(Cc1cccs1)C(=O)O)OCc1ccccc1 | null | null | O.O1CCOCC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCCc1cccs1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | 98 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC=1SC=CC1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC=1SC=CC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 3.0 g (16.9 mmol) of β-thienyl-D,L-alanine in 75 mL of water and 60 mL of dioxane, was added 5.6 g (40.6 mmol) of anhydrous potassium carbonate, followed by 2.85 mL (20 mmol) of carbobenzyloxychloride. The resulting mixture was stirred rapidly for approximately one hour. When the reaction was substantia... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccsc1.c1ccccc1 | HCl | O.O1CCOCC1 | null | 1 | NC(Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1>O.O1CCOCC1>O=C(NC(Cc1cccs1)C(=O)O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df1c9357898a4614b9ce145323b84ad8 | C=CC#N.CNCCO>>CN(CCO)CCC#N | C(C=C)#N.C(C=C)#N.CNCCO.C(C=C)#N.C(C=C)#N>>C(#N)CCN(C)CCO | [CH2:6]=[CH:7][C:8]#[N:9].[CH3:1][NH:2][CH2:3][CH2:4][OH:5]>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[CH2:6][CH2:7][C:8]#[N:9] | C=CC#N.CNCCO | CN(CCO)CCC#N | null | null | O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 8acf647a588bdc7347506dcd3290904024f41acb450fe55eb6c0af193ad82ab8 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4] | null | [] | 75 | CELSIUS | 2.75 | HOUR | 1000.0 grams (13.31 moles) of 2-methylaminoethanol was placed in a 3000 milliliter 3-neck flask equipped with a stirrer, a condenser, an addition funnel, and a thermometer. 50.0 grams of distilled water was charged to the flask, and 705.4 grams (13.31 moles) of acrylonitrile was charged to the addition funnel (875.2 ml... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | null | null | null | null | O | 75 | 2.75 | C=CC#N.CNCCO>O>CN(CCO)CCC#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-664817258c1d475a9aa4855277b7c19b | NC(=O)[C@H](Cc1ccccc1)NN1C(=O)c2ccccc2C1=O.O=CCCCC=O>>O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 | C1(=CC=C(C=C1)S(=O)(=O)O)C.O1CCCC1.ClCCl.C1(C=2C(C(N1N[C@@H](CC1=CC=CC=C1)C(=O)N)=O)=CC=CC2)=O.C(CC=O)CC=O.O>>O=C1N(C(C2=CC=CC=C12)=O)[C@H](C(=O)N1C=CCC=C1)CC1=CC=CC=C1 | N1([NH:11][C@H:3]([C:2](=[O:1])[NH2:22])[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21].O=[CH:23][CH2:24][CH2:25][CH2:26][CH:27]=O>>[O:1]=[C:2]([C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][c... | NC(=O)[C@H](Cc1ccccc1)NN1C(=O)c2ccccc2C1=O.O=CCCCC=O | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 | null | null | ClCCl | Acylation | OtherReaction | eb0357b231fadb383e7c0743bd7b61ed556ca36310e864da652b60f8868ccc09 | 12c4a7b540175553e1ac5271d7afd9b06d4196e08ca58f502c62b2c89b622a4a | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 | O=[CH;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-[CH;D2;+0:5]=O.[C:6]-[C:7](-[NH;D2;+0:8]-N1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:15]-1=[O;D1;H0:16])-[C:17](-[NH2;D1;+0:18])=[O;D1;H0:19]>>[C:6]-[C:7](-[C:17](=[O;D1;H0:19])-[N;H0;D3;+0:18]1-[CH;D2;+0:1]=[CH;D2;+0:2]-[C:3]-[CH;D2;+0:4... | null | [] | null | null | 4 | DAY | Combine phthalimido-(S)-phenyalanine amide (3.0 g, 10 mmol) and a solution of glutaric dialdehyde (2.0 g; 50% by weight in water) in dichloromethane (200 mL). Heat to reflux with azeotropic removal of water from the refluxate. Add p-toluenesulfonic acid (60 mg). Continue heating at reflux. Pass the refluxate through ov... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Aldehyde.Aldehyde.Primary amide | Enamine.Enamine.Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1=C[NH]C=CC1 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1=C[NH]C=CC1 | HO- | ClCCl | null | 96 | NC(=O)[C@H](Cc1ccccc1)NN1C(=O)c2ccccc2C1=O.O=CCCCC=O>ClCCl>O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a578e8b392e4d4384fa2f1bad0efe35 | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1>>O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | C(C)(=O)OCC.CCCCCC.C(C)(=O)OCC.CCCCCC.O=C1N(C(C2=CC=CC=C12)=O)[C@H](C(=O)N1C=CCC=C1)CC1=CC=CC=C1.FC(S(=O)(=O)O)(F)F.FC(S(=O)(=O)O)(F)F>>O=C1N(C(C2=CC=CC=C12)=O)[C@@H]1C(N2C(C3=C(C1)C=CC=C3)CCC=C2)=O | [O:1]=[C:2]([C@@H:3]([N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[N:27]1[CH:22]=[CH:23][CH2:24][CH:25]=[CH:26]1>>[O:1]=[C:2]1[C@@H:3]([N:4]2[C:5](=[O:6])[c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[C:13]2=[O:14])[CH2:15][c:16]2[cH:17][cH:18][cH... | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | null | null | ClCCl | C-C Coupling | OtherReaction | d18fcdd83ea4f34bc411bfc970998921caf3702209b406e1715c6346e9a255d1 | 638e72fa85e9a6f961a3ec4bd9661dad3d0f2347468aed1bc6b1f4d9792c0889 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | [O;D1;H0:1]=[C:2](-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])-[#7:10]1-[C:11]=[C:12]-[C:13]-[CH;D2;+0:14]=[CH;D2;+0:15]-1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[CH;D3;+0:15]2-[CH2;D2;+0:14]-[C:13]-[C:12]=[C:11]-[#7:10]-1-2 | null | [] | null | null | 2.5 | HOUR | Add a solution of (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.1 g, 3.1 mmol) in dichloromethane (2 mL) to trifluoromethanesulfonic acid (1.2 mL). After 2.5 hours, add trifluoromethanesulfonic acid (1.2 mL). After 4 hours, partition the reaction mixture between ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | null | c1ccccc1.C1=C[NH]C=CC1 | C1=CN2CCCc3ccccc3C2CC1 | c1ccc2c(c1)C[NH]C2.C1=CN2CCCc3ccccc3C2CC1 | null | ClCCl | null | 2.5 | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1>ClCCl>O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f3c835216c0344d1af2af2f75940e898 | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1>>O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | C([O-])(O)=O.[Na+].S(O)(O)(=O)=O.FC(C(=O)OC(C(F)(F)F)=O)(F)F.O=C1N(C(C2=CC=CC=C12)=O)[C@H](C(=O)N1C=CCC=C1)CC1=CC=CC=C1>>O=C1N(C(C2=CC=CC=C12)=O)[C@@H]1C(N2C(C3=C(C1)C=CC=C3)CCC=C2)=O | [O:1]=[C:2]([C@@H:3]([N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[N:27]1[CH:22]=[CH:23][CH2:24][CH:25]=[CH:26]1>>[O:1]=[C:2]1[C@@H:3]([N:4]2[C:5](=[O:6])[c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[C:13]2=[O:14])[CH2:15][c:16]2[cH:17][cH:18][cH... | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | null | null | C(C)(=O)OCC.CCCCCC | C-C Coupling | OtherReaction | d18fcdd83ea4f34bc411bfc970998921caf3702209b406e1715c6346e9a255d1 | 638e72fa85e9a6f961a3ec4bd9661dad3d0f2347468aed1bc6b1f4d9792c0889 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 | [O;D1;H0:1]=[C:2](-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])-[#7:10]1-[C:11]=[C:12]-[C:13]-[CH;D2;+0:14]=[CH;D2;+0:15]-1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[CH;D3;+0:15]2-[CH2;D2;+0:14]-[C:13]-[C:12]=[C:11]-[#7:10]-1-2 | null | [] | null | null | 30 | MINUTE | Combine sulfuric acid (3.0 mL, 96%) and trifluoroacetic anhydride (300 mL). Add (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.0 mmol). After 30 minutes, pour the reaction mixture into a mixture of saturated aqueous sodium bicarbonate and ice. Extract with ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | null | c1ccccc1.C1=C[NH]C=CC1 | C1=CN2CCCc3ccccc3C2CC1 | c1ccc2c(c1)C[NH]C2.C1=CN2CCCc3ccccc3C2CC1 | null | C(C)(=O)OCC.CCCCCC | null | 0.5 | O=C([C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O)N1C=CCC=C1>C(C)(=O)OCC.CCCCCC>O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fbd154b2d6e642c8b3af3f1af09e77e0 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | O.O=C1N(C(C2=CC=CC=C12)=O)[C@@H]1C(N2C(C3=C(C1)C=CC=C3)CCC=C2)=O.S(O)(O)(=O)=O.C(=O)O>>O=C1N(C(C2=CC=CC=C12)=O)C1C(N2C(C3=C(C1)C=CC=C3)CCC[C@H]2C(=O)O)=O | [CH:4]1=[CH:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15][C@H:16]([N:17]3[C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]4[C:26]3=[O:27])[C:28](=[O:29])[N:30]12.[O:1]=[CH:2][OH:3]>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15... | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO | O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | null | null | C(C)(=O)OCC.CCCCCC | C-C Coupling | Acylation of olefines by aldehydes | 3a21f12377cb8c09c940df604a05cec2fea4223f56cb56c1ba3cb45c8753c803 | a07c08b10c207ce8329ed9f3df9ebbc8346d1dd55a4c78853ad588c1db0b3fc1 | O=C1C(N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCCCN12 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-1.[O;D1;H0:10]=[CH;D2;+0:11]-[O;D1;H1:12]>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-[C@H;D3;+0:9]-1-[C;H0;D3;+0:11](=[O;D1;H0:10])-[O;D1;H1:12] | null | [] | null | null | 18 | HOUR | Combine (S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine (32 mg, 0.09 mmol) and sulfuric acid (1.0 mL, 95-98%) in a pressure vessel. Add 96% formic acid (200 μL) and quickly seal the vessel. After 18 hours, add water (10 mL). Extract the reaction mixture with eth... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid | Carboxylic acid | C1=CN2CCCc3ccccc3C2CC1 | c1ccc2c(c1)CCCN1CCCCC21 | c1ccc2c(c1)CCCN1CCCCC21.c1ccc2c(c1)C[NH]C2 | null | C(C)(=O)OCC.CCCCCC | null | 18 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>C(C)(=O)OCC.CCCCCC>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-85424ad23e3e44a495e94c72983ed679 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | O=C1N(C(C2=CC=CC=C12)=O)[C@@H]1C(N2C(C3=C(C1)C=CC=C3)CCC=C2)=O.S(O)(O)(=O)=O.C(=O)O>>O=C1N(C(C2=CC=CC=C12)=O)C1C(N2C(C3=C(C1)C=CC=C3)CCC[C@H]2C(=O)O)=O | [CH:4]1=[CH:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15][C@H:16]([N:17]3[C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]4[C:26]3=[O:27])[C:28](=[O:29])[N:30]12.[O:1]=[CH:2][OH:3]>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15... | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO | O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | null | null | C(C)(=O)OCC.CCCCCC.C(C)(=O)O | C-C Coupling | Acylation of olefines by aldehydes | 3a21f12377cb8c09c940df604a05cec2fea4223f56cb56c1ba3cb45c8753c803 | a07c08b10c207ce8329ed9f3df9ebbc8346d1dd55a4c78853ad588c1db0b3fc1 | O=C1C(N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCCCN12 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-1.[O;D1;H0:10]=[CH;D2;+0:11]-[O;D1;H1:12]>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-[C@H;D3;+0:9]-1-[C;H0;D3;+0:11](=[O;D1;H0:10])-[O;D1;H1:12] | null | [] | null | null | 18 | HOUR | Combine (S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine (67 mg, 0.19 mmol) and sulfuric acid (2.0 mL, 95-98%) in a pressure vessel. Add 96% formic acid (400 μL) and quickly seal the vessel. After 18 hours, open the vessel cautiously and add ice-cold water (5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid | Carboxylic acid | C1=CN2CCCc3ccccc3C2CC1 | c1ccc2c(c1)CCCN1CCCCC21 | c1ccc2c(c1)CCCN1CCCCC21.c1ccc2c(c1)C[NH]C2 | null | C(C)(=O)OCC.CCCCCC.C(C)(=O)O | null | 18 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>C(C)(=O)OCC.CCCCCC.C(C)(=O)O>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58615e62df594250977665f017188dc0 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | [C]=O.O=C1N(C(C2=CC=CC=C12)=O)[C@@H]1C(N2C(C3=C(C1)C=CC=C3)CCC=C2)=O.S(O)(O)(=O)=O.[C]=O.C(=O)O>>O=C1N(C(C2=CC=CC=C12)=O)C1C(N2C(C3=C(C1)C=CC=C3)CCC[C@H]2C(=O)O)=O | [CH:4]1=[CH:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15][C@H:16]([N:17]3[C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]4[C:26]3=[O:27])[C:28](=[O:29])[N:30]12.[O:1]=[CH:2][OH:3]>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15... | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO | O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | null | null | null | C-C Coupling | Acylation of olefines by aldehydes | 3a21f12377cb8c09c940df604a05cec2fea4223f56cb56c1ba3cb45c8753c803 | a07c08b10c207ce8329ed9f3df9ebbc8346d1dd55a4c78853ad588c1db0b3fc1 | O=C1C(N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCCCN12 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-1.[O;D1;H0:10]=[CH;D2;+0:11]-[O;D1;H1:12]>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-[C@H;D3;+0:9]-1-[C;H0;D3;+0:11](=[O;D1;H0:10])-[O;D1;H1:12] | null | [] | null | null | 16 | HOUR | Combine (S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine (800 mg, 2.2 mmol) and sulfuric acid (24 mL) in a pressure vessel. Carefully, add formic acid (4.0 mL, 87 mmol) to minimize mixing and thereby the formation of carbon monoxide. Seal the pressure vessel and ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid | Carboxylic acid | C1=CN2CCCc3ccccc3C2CC1 | c1ccc2c(c1)CCCN1CCCCC21 | c1ccc2c(c1)CCCN1CCCCC21.c1ccc2c(c1)C[NH]C2 | null | null | null | 16 | O=C1[C@@H](N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCC=CN12.O=CO>>O=C(O)[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7404f2b9601b4073b13d1d8a134a80dc | N#CC1CCC=CN1C(=O)[C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O>>N#C[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | O=C1N(C(C2=CC=CC=C12)=O)[C@H](C(=O)N1C(CCC=C1)C#N)CC1=CC=CC=C1.S(O)(O)(=O)=O.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>C(#N)[C@@H]1CCCC2N1C(C(CC1=C2C=CC=C1)N1C(C2=CC=CC=C2C1=O)=O)=O | [N:1]#[C:2][CH:3]1[CH2:4][CH2:5][CH:6]=[CH:7][N:29]1[C:27]([C@H:15]([CH2:14][c:13]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:16]1[C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]1=[O:26])=[O:28]>>[N:1]#[C:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH:7]2[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[CH2:14][CH:15]([N:16]3[C:... | N#CC1CCC=CN1C(=O)[C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O | N#C[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 | null | null | null | C-C Coupling | OtherReaction | d5e137af20319d81b6121bb540f73ae62f4ba7f0ac0519e0c866f3dd8c22297c | 638e72fa85e9a6f961a3ec4bd9661dad3d0f2347468aed1bc6b1f4d9792c0889 | O=C1C(N2C(=O)c3ccccc3C2=O)Cc2ccccc2C2CCCCN12 | [O;D1;H0:1]=[C:2](-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])-[#7:10]1-[C:11]-[C:12]-[C:13]-[CH;D2;+0:14]=[CH;D2;+0:15]-1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[CH;D3;+0:15]2-[CH2;D2;+0:14]-[C:13]-[C:12]-[C:11]-[#7:10]-1-2 | null | [] | null | null | 24 | HOUR | Combine N-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-2-cyano-1,2,3,4-tetrahydro-pyridine (100 mg, 0.26 mmol), sulfuric acid (3 mL, 99.999%), and trifluoroacetic anhydride (0.03 mL). After 24 hours, the title compound is obtained as a solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Enamine | null | C1=C[NH]CCC1.c1ccccc1 | c1ccc2c(c1)CCCN1CCCCC21 | c1ccc2c(c1)CCCN1CCCCC21.c1ccc2c(c1)C[NH]C2 | null | null | null | 24 | N#CC1CCC=CN1C(=O)[C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O>>N#C[C@@H]1CCCC2c3ccccc3CC(N3C(=O)c4ccccc4C3=O)C(=O)N21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ed77840c3734a39844b39f7948bc2ab | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCBr)cc1.CCOC(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-]>>BrBr.CCOC(=O)CCCCOc1ccc(OCCCO)cc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Br-].CC(CCCOC1=CC=C(OCCC[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1)(C(=O)OCC)C.CC(C(=O)OCC)(CCCOC1=CC=C(C=C1)OCCCBr)C>>OCCCOC1=CC=C(OCCCCC(=O)OCC)C=C1.BrBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C[C:8](C)([C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][Br:1])[cH:22][cH:23]1.CC[O:21]C(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-:2]>>[Br:1][Br:2].[CH3:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]... | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCBr)cc1.CCOC(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | BrBr.CCOC(=O)CCCCOc1ccc(OCCCO)cc1 | null | null | C(C)#N | Functional Group Addition | OtherReaction | 0963c76c9fcb4095648c164a3f9df17a4d4b02242078c0ed22f8a246242ce785 | 983c0bc69ec135e3e613b6c5d57b7923e7181c4a74d571e83604c65fe138c490 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-C(=O)-C(-C)(-C)-C-C-C-O-c1:c:c:c(-O-C-C-C-[P+](-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):c:c:1.C-[C;H0;D4;+0:2](-C)(-[C:3]-[C:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[Br;H0;D1;+0:9]-[CH2;D2;+0:10]-[C:11]-[C:12].[Br-;H0;D0:13]>>[Br;H0;D1;+0:9]-[Br;H0;D1;+0:13].[C:4]-[C:3]-[CH2;D2;+0:2]-[C:5](=[O;... | null | [] | null | null | null | null | The 3-[4-(4,4-dimethyl-4-ethoxycarbonylbutoxy)phenoxy]propyltriphenylphosphonium bromide used as starting material was prepared by reacting triphenylphosphine in acetonitrile, at reflux, with ethyl 2,2-dimethyl-5-[4-(3-bromopropyloxy)phenoxy]pentanoate, itself obtained from ethyl 5-[4-(3-hydroxypropyloxy)phenoxy]pentan... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Ether.Ether | Ester.Primary alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C(C)#N | null | null | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCBr)cc1.CCOC(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-]>C(C)#N>BrBr.CCOC(=O)CCCCOc1ccc(OCCCO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4abd6c40e154847ac62183456b57efd | CC(=O)c1ccccc1Br.COc1cccc(O)c1OC>>COc1cccc(OCC(=O)c2ccccc2)c1OC | C(CCCC)O.COC1=C(C=CC=C1OC)O.BrC1=C(C=CC=C1)C(C)=O.C([O-])([O-])=O.[K+].[K+]>>COC1=C(OCC(=O)C2=CC=CC=C2)C=CC=C1OC | Br[c:17]1[c:12]([C:10]([CH3:9])=[O:11])[cH:13][cH:14][cH:15][cH:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[c:18]1[O:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH2:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[O:19][CH3:20] | CC(=O)c1ccccc1Br.COc1cccc(O)c1OC | COc1cccc(OCC(=O)c2ccccc2)c1OC | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | a992275e23cb5227b4d5eccf868fd52665a05715ad04ec0ef240f68d23c4e0a8 | f6c7fa7ba6219ad4cbab6ca16559eea73bb2ead486d62a35ca063b3cb7ec8967 | O=C(COc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[CH3;D1;+0:6])=[O;D1;H0:7]):[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:5](-[CH2;D2;+0:6]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | 87 | [{"value": 87.0, "product": "COC1=C(OCC(=O)C2=CC=CC=C2)C=CC=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "COC1=C(OCC(=O)C2=CC=CC=C2)C=CC=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 8 | HOUR | Amyl alcohol (44 ml) was added to 2,3-dimethoxyphenol (5 g), 2'-bromoacetophenone (7 g), potassium carbonate (6.7 g) and copper acetate (1.1 g), followed by heating and stirring at 150° C. for 8 hours for reacting them together. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)OCC | 150 | 8 | CC(=O)c1ccccc1Br.COc1cccc(O)c1OC>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)OCC>COc1cccc(OCC(=O)c2ccccc2)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a54143023c8447f1b5e3531d3b260f2e | COc1ccc(C=O)c(OC)c1OC>>COc1ccc(O)c(OC)c1OC | COC1=C(C=O)C=CC(=C1OC)OC.ClC1=CC(=CC=C1)C(=O)OO>>COC1=C(C=CC(=C1OC)OC)O | O=C[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH3:13])[c:8]1[O:9][CH3:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([O:9][CH3:10])[c:11]1[O:12][CH3:13] | COc1ccc(C=O)c(OC)c1OC | COc1ccc(O)c(OC)c1OC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 659bdf700aa189a2a9389f31eb68406ea47a032243ab8e9e00a61645412a9c19 | c759f926c3e97e5d1aec68154208997a6cce50cebe875125c17b3c0b6382138e | c1ccccc1 | O=C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;D1;H1:7]):[c:2]:[c:3] | 51.1 | [{"value": 51.0, "product": "COC1=C(C=CC(=C1OC)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.1, "product": "COC1=C(C=CC(=C1OC)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | HOUR | 2,3,4-Trimethoxybenzaldehyde (5 g) was suspended in anhydrous methylene chloride (50 ml), followed by addition of m-chloroperbenzoic acid (10 g; purity of 70%) to heat and stir the resulting mixture at 50° C. for 3 hours. After distilling off the solvents under reduced pressure, the residue was dissolved in ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(Cl)Cl | 50 | 3 | COc1ccc(C=O)c(OC)c1OC>C(Cl)Cl>COc1ccc(O)c(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd7bd30d38484bb09e3a0ae03fe39a9e | CBr.O=Cc1cc(F)ccc1F>>CC(=O)c1cc(F)ccc1F | CBr.[Mg].FC1=C(C=O)C=C(C=C1)F>>FC1=C(C=C(C=C1)F)C(C)=O | Br[CH3:1].[CH:2](=[O:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[F:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[F:11] | CBr.O=Cc1cc(F)ccc1F | CC(=O)c1cc(F)ccc1F | null | null | O1CCCC1 | C-C Coupling | C-methylation | 63e7e3b4270d44304e15e93c2d13d22887bfb567ee4a77e26c495339213249c2 | 375877964803faf905d6fcbb6176fcec6dc4e543ddfd549316ffc37d5a7cd261 | c1ccccc1 | Br-[CH3;D1;+0:1].[O;D1;H0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[CH3;D1;+0:1]-[C;H0;D3;+0:3](=[O;D1;H0:2])-[c:4](:[c:5]):[c:6] | 84 | [{"value": 84.0, "product": "FC1=C(C=C(C=C1)F)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution (100 ml) of 2,5-difluorobenzaldehyde (24.6 g) in tetrahydrofuran was dropwise added to an ice-cooled solution (207 ml) of 0.92N magnesium methylbromide in tetrahydrofuran. The resulting solution was stirred at room temperature for 1.5 hours, and the organic phase was washed in a saturated sodium chloride sol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ketone | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 1.5 | CBr.O=Cc1cc(F)ccc1F>O1CCCC1>CC(=O)c1cc(F)ccc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b95cd72edf0492b9e7ff218eee8d726 | CCBr.COc1cc(O)c(C=O)c(OC)c1>>CCCc1c(O)cc(OC)cc1OC | C(C)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Na+].CS(=O)C.COC1=CC(=C(C=O)C(=C1)OC)O>>COC=1C(=C(C=C(C1)OC)O)CCC | Br[CH2:2][CH3:1].O=[CH:3][c:4]1[c:5]([OH:6])[cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([OH:6])[cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]1[O:13][CH3:14] | CCBr.COc1cc(O)c(C=O)c(OC)c1 | CCCc1c(O)cc(OC)cc1OC | null | null | null | C-C Coupling | OtherReaction | fb64cfe49b9d38dd70c244824abc3c1ad6b2e83874a0083fb9c9a3476b827743 | a3dca447376ff0c6fe3968bb1ab0785c8926c417c53ba2b61f8ebdb52a7e5a2a | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].O=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 46.4 | [{"value": 46.0, "product": "COC=1C(=C(C=C(C1)OC)O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "COC=1C(=C(C=C(C1)OC)O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Triphenylphosphine ethylbromide (4.1 g) was added to a 2N sodium hydride/dimethyl sulfoxide solution (11 ml), prior to agitation at 50° C. for 30 minutes. To the mixture was added 4,6-dimethoxy-2-hydroxybenzaldehyde (1 g), for agitation at 50° C. overnight. After the termination of the reaction, the resulting solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | null | null | null | c1ccccc1 | Br- | null | null | 0.5 | CCBr.COc1cc(O)c(C=O)c(OC)c1>>CCCc1c(O)cc(OC)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f74f21c59b2540efaaa12d148ca12e15 | CCBr.COc1cc(O)cc(OC)c1C=O>>CCCc1c(OC)cc(O)cc1OC | CC(C)([O-])C.[K+].C(C)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COC1=C(C=O)C(=CC(=C1)O)OC>>COC=1C=C(C=C(C1CCC)OC)O | Br[CH2:2][CH3:1].O=[CH:3][c:4]1[c:5]([O:6][CH3:7])[cH:8][c:9]([OH:10])[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([O:6][CH3:7])[cH:8][c:9]([OH:10])[cH:11][c:12]1[O:13][CH3:14] | CCBr.COc1cc(O)cc(OC)c1C=O | CCCc1c(OC)cc(O)cc1OC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | fb64cfe49b9d38dd70c244824abc3c1ad6b2e83874a0083fb9c9a3476b827743 | a3dca447376ff0c6fe3968bb1ab0785c8926c417c53ba2b61f8ebdb52a7e5a2a | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].O=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 55.7 | [{"value": 55.0, "product": "COC=1C=C(C=C(C1CCC)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.7, "product": "COC=1C=C(C=C(C1CCC)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Anhydrous tetrahydrofuran (36 ml) was added to triphenylphosphine ethyl bromide (12.3 g) prior to stirring at room temperature for 20 minutes. To the resulting mixture was added potassium tert-butoxide (4.5 g), for stirring at room temperature for 30 minutes. Then, 2,6-dimethoxy-4-hydroxybenzaldehyde (3.0 g) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | null | null | null | c1ccccc1 | Br- | O1CCCC1 | null | 0.333333 | CCBr.COc1cc(O)cc(OC)c1C=O>O1CCCC1>CCCc1c(OC)cc(O)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83441b5019214471922280f5515c2e22 | COc1cc(O)cc(OC)c1.O=C(O)Cc1c(F)cccc1Cl>>COc1cc(OC)cc(Oc2cccc(F)c2CC(=O)O)c1 | ClC1=C(C(=CC=C1)F)CC(=O)O.COC=1C=C(C=C(C1)OC)O.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C(OC2=C(C(=CC=C2)F)CC(=O)O)C=C(C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([OH:10])[cH:22]1.Cl[c:11]1[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]1[CH2:18][C:19](=[O:20])[OH:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[CH2:18][C:19](=[O:20])[OH:21])[cH:22]1 | COc1cc(O)cc(OC)c1.O=C(O)Cc1c(F)cccc1Cl | COc1cc(OC)cc(Oc2cccc(F)c2CC(=O)O)c1 | null | [Cu](I)I.[Cu] | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[C:5]-[c:4](:[c:9]):[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2]:[c:3] | 86.1 | [{"value": 86.0, "product": "COC=1C=C(OC2=C(C(=CC=C2)F)CC(=O)O)C=C(C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "COC=1C=C(OC2=C(C(=CC=C2)F)CC(=O)O)C=C(C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 20 | HOUR | N,N-Dimethylformamide (20 ml) was added to 2-chloro-6-fluorophenyl acetic acid (3.77 g), 3,5-dimethoxyphenol (3.08 g), potassium carbonate (5.52 g), copper iodide (950 mg) and copper (250 mg), for stirring at 120° C. for 20 hours. The resulting reaction solution was partitioned with ethyl acetate and dilute hydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [Cu](I)I.[Cu].CN(C=O)C | 120 | 20 | COc1cc(O)cc(OC)c1.O=C(O)Cc1c(F)cccc1Cl>[Cu](I)I.[Cu].CN(C=O)C>COc1cc(OC)cc(Oc2cccc(F)c2CC(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-24790d511c784f0cb5c8390c2b1741e2 | Cc1sc([Si](C)(C)C)cc1C1=C(c2cc([Si](C)(C)C)sc2C)C(F)(F)C(F)(F)C1(F)F>>Cc1sccc1C1=C(c2ccsc2C)C(F)(F)C(F)(F)C1(F)F | CC=1SC(=CC1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)[Si](C)(C)C)C)[Si](C)(C)C.Br>>CC=1SC=CC1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC=C1)C | C[Si](C)(C)[c:4]1[s:3][c:2]([CH3:1])[c:6]([C:7]2=[C:8]([c:9]3[cH:10][c:11]([Si](C)(C)C)[s:12][c:13]3[CH3:14])[C:15]([F:16])([F:17])[C:18]([F:19])([F:20])[C:21]2([F:22])[F:23])[cH:5]1>>[CH3:1][c:2]1[s:3][cH:4][cH:5][c:6]1[C:7]1=[C:8]([c:9]2[cH:10][cH:11][s:12][c:13]2[CH3:14])[C:15]([F:16])([F:17])[C:18]([F:19])([F:20])[... | Cc1sc([Si](C)(C)C)cc1C1=C(c2cc([Si](C)(C)C)sc2C)C(F)(F)C(F)(F)C1(F)F | Cc1sccc1C1=C(c2ccsc2C)C(F)(F)C(F)(F)C1(F)F | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | b4f95afb484b33e308ab008c6f093f7b6d0911e1867fa00e64fa29d5eb8fb909 | 28fd0e3907aba95760fb0c8ef9c1ab1afc9130d426157659fd8807eab7cfdc29 | c1cc(C2=C(c3ccsc3)CCC2)cs1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4](-[C:5]=[C:6]-[c:7]2:[c:8]:[#16;a:9]:[c;H0;D3;+0:10](-[Si](-C)(-C)-C):[c:11]:2):[c:12]:1>>[#16;a:2]1:[c:3]:[c:4](-[C:5]=[C:6]-[c:7]2:[c:8]:[#16;a:9]:[cH;D2;+0:10]:[c:11]:2):[c:12]:[cH;D2;+0:1]:1 | 98 | [{"value": 98.0, "product": "CC=1SC=CC1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,2-bis(2-methyl-5-trimethylsilyl-3-thienyl)hexafluorocyclopentene (2.16 g, 0.005 mol) was dissolved in chloroform (200 ml) and was allowed to react for 6 hours under refluxing conditions by adding concentrated hydrobromic acid (10 ml) to the solution. After the completion of the reaction, the chloroform layer was wash... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group.Silyl protective group | null | c1ccsc1.c1ccsc1 | c1ccsc1.c1ccsc1 | c1ccsc1.c1ccsc1.C1=CCCC1 | Other | C(Cl)(Cl)Cl | null | null | Cc1sc([Si](C)(C)C)cc1C1=C(c2cc([Si](C)(C)C)sc2C)C(F)(F)C(F)(F)C1(F)F>C(Cl)(Cl)Cl>Cc1sccc1C1=C(c2ccsc2C)C(F)(F)C(F)(F)C1(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4ed8d077a2e4b55a7f88a3b17be86f8 | COCCOC.Cc1csc(OB(O)O)c1.Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F>>Cc1csc(-c2cc(C3=C(c4cc(-c5cc(C)cs5)sc4C)C(F)(F)C(F)(F)C3(F)F)c(C)s2)c1 | BrC1=CC(=C(S1)C)C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)Br)C.C(OC)COC.CC=1C=C(SC1)OB(O)O.C([O-])([O-])=O.[K+].[K+]>>CC=1SC(=CC1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC=C(C1)C)C)C=1SC=C(C1)C | O([CH2:16][CH2:18]O[CH3:15])[CH3:17].OB(O)O[c:5]1[s:4][cH:3][c:2]([CH3:1])[cH:35]1.Br[c:6]1[cH:7][c:8]([C:9]2=[C:10]([c:11]3[cH:12][c:13](Br)[s:20][c:21]3[CH3:22])[C:23]([F:24])([F:25])[C:26]([F:27])([F:28])[C:29]2([F:30])[F:31])[c:32]([CH3:33])[s:19]1>>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[cH:7][c:8]([C:9]3=[C:10]([c:... | COCCOC.Cc1csc(OB(O)O)c1.Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F | Cc1csc(-c2cc(C3=C(c4cc(-c5cc(C)cs5)sc4C)C(F)(F)C(F)(F)C3(F)F)c(C)s2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | null | Aromatic Heterocycle Formation | OtherReaction | 3fea609e7dae8772d52976120b9c97976a584e8e9d03ec007d4ef06a8f996450 | a7fd6a75b5f2a4c7a794b82fac2561476a46093a10a5f5c711da3a9da5f607c3 | c1csc(-c2cc(C3=C(c4csc(-c5cccs5)c4)CCC3)cs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4](-[C:5](=[C:6](-[c:7]2:[c:8]:[c;H0;D3;+0:9](-Br):[s;H0;D2;+0:10]:[c;H0;D3;+0:11]:2-[C;D1;H3:12])-[C:13])-[C:14]):[c:15]:1.O-B(-O)-O-[c;H0;D3;+0:16]1:[#16;a:17]:[c:18]:[c:19]:[c:20]:1.[CH3;D1;+0:21]-O-[CH2;D2;+0:22]-[CH2;D2;+0:23]-O-[CH3;D1;+0:24]>>[C:14]-[C:5](-[c:4]1:[c:15]:[c;H... | null | [] | null | null | 5 | MINUTE | 1,2-Bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene (1.0 g 0.002 mol) was dissolved in dimethoxyethane (50 ml), and palladium tetra(triphenylphosphine) (120 mg) was added to the mixture which was stirred for 5 minutes under argon atmosphere. With 4-methyl-2-thienyl boric acid (852 mg, 0.006 mol) and an aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether | null | c1ccsc1.c1ccsc1.c1ccsc1 | c1ccsc1.c1ccsc1.c1ccsc1.c1ccsc1 | c1ccsc1.c1ccsc1.c1ccsc1.c1ccsc1.C1=CCCC1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | null | 0.083333 | COCCOC.Cc1csc(OB(O)O)c1.Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]>Cc1csc(-c2cc(C3=C(c4cc(-c5cc(C)cs5)sc4C)C(F)(F)C(F)(F)C3(F)F)c(C)s2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-197bcc85a93f490aae992086e3528101 | Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F>>FC1(F)C=CC(F)(F)C1(F)F | BrC1=CC(=C(S1)C)C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)Br)C.C[Si](C1=CC=C(S1)C1=CC=C(S1)OB(O)O)(C)C.C([O-])([O-])=O.[K+].[K+]>>FC1(C(C(C=C1)(F)F)(F)F)F | Cc1sc(Br)cc1[C:4]1=[C:5](c2cc(Br)sc2C)[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:2]1([F:1])[F:3]>>[F:1][C:2]1([F:3])[CH:4]=[CH:5][C:6]([F:7])([F:8])[C:9]1([F:10])[F:11] | Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F | FC1(F)C=CC(F)(F)C1(F)F | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | C(OC)COC | Reduction | OtherReaction | 354e485efb55b58f1ddb0c5d00bac09bb4f327e22bee9a164c742689187f3962 | 0ecff68b4ffbd9fa417ba42b220387f06d93399a1e61c4d05eaeeacbdad5d93b | C1=CCCC1 | Br-c1:c:c(-[C;H0;D3;+0:1]2=[C;H0;D3;+0:2](-c3:c:c(-Br):s:c:3-C)-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6]-[C:7]-2(-[F;D1;H0:8])-[F;D1;H0:9]):c(-C):s:1>>[F;D1;H0:8]-[C:7]1(-[F;D1;H0:9])-[C:6]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[CH;D2;+0:2]=[CH;D2;+0:1]-1 | 35 | [{"value": 35.0, "product": "FC1(C(C(C=C1)(F)F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 1,2-bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene (1.0 g, 0.002 mol) was dissolved in dimethoxyethane (50 ml), and palladium tetra(triphenylphosphine) (120 mg) was added to the mixture which was stirred for 5 minutes under argon atmosphere. With 5-(5-trimethylsilyl-2-thienyl)-2-thienyl boric acid (1.4 g, 0.006 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccsc1.c1ccsc1.C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | HBr | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(OC)COC | null | 0.083333 | Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(OC)COC>FC1(F)C=CC(F)(F)C1(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-715eda2fd48842e6980bb6bc0bfdb8f4 | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O>>CCC(C)C(C(=O)O)n1sc2ccccc2c1=O | C(=O)(O)C(C(CC)C)NC(=O)C1=C(C(=O)N(C(C(=O)O)C(CC)C)SSC2=CC=CC=C2)C=CC=C1.BrBr>>CC(C(C(=O)O)N1SC2=C(C1=O)C=CC=C2)CC | CCC(C)C(NC(=O)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([N:9]([CH:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[C:6](=[O:7])[OH:8])[S:10]Sc1ccccc1)=[O:18])C(=O)O>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]([C:6](=[O:7])[OH:8])[n:9]1[s:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[c:17]1=[O:18] | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O | CCC(C)C(C(=O)O)n1sc2ccccc2c1=O | null | null | ClCCl | Miscellaneous | OtherReaction | e2926d905a02e34c58aa119038113df327a8b0c9b951a9c6c07d2367edb1d58e | 95efc4ecf4ace74c5432ec55a35221782e607c11c8e2bcb5f206d10c974b4c9d | O=c1[nH]sc2ccccc12 | C-C-C(-C)-C(-N-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[S;H0;D2;+0:8]-S-c1:c:c:c:c:c:1)-[C:9](-[C:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c:14])-C(-O)=O>>[C:10]-[C:9](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[n;H0;D3;+0:7]1:[s;H0;D2;+0:8]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:... | null | [] | null | null | 2 | HOUR | A stirred, room temperature suspension of 5.3 g (10.0 mmol) of [S-(R*,R*)]-2-[2-[2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulfanyl benzoylamino]-3-methylpentanoic acid (prepared by the general method of Example 5) in 200 mL of dichloromethane was treated dropwise with 2.4 g (15.0 mmol) of liquid bromine. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Tertiary amide.Disulfide | null | c1ccccc1.c1ccccc1 | c1ccc2sncc2c1 | c1ccc2sncc2c1 | Other | ClCCl | null | 2 | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O>ClCCl>CCC(C)C(C(=O)O)n1sc2ccccc2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-206a6fa334884220975b99cf576fbf83 | CON(C)C(=O)c1ccccc1.Sc1ccccc1>>O=C(c1ccccc1)c1ccccc1S | CON(C(C1=CC=CC=C1)=O)C.Cl.CN(CCN(C)C)C.C1(=CC=CC=C1)S.C(CCC)[Li]>>SC1=C(C(=O)C2=CC=CC=C2)C=CC=C1 | CON(C)[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[cH:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[SH:15]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[SH:15] | CON(C)C(=O)c1ccccc1.Sc1ccccc1 | O=C(c1ccccc1)c1ccccc1S | null | null | C1CCCCC1 | C-C Coupling | OtherReaction | 41ea75cfa140a7d6447e321e352b483a34b34c40b5181472890e2641a35b9c4c | 4113f0e803c7e6f9f731016c87e547bd597c0045514b87ca0ff3566df8b4b2c4 | O=C(c1ccccc1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[S;D1;H1:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[S;D1;H1:6]):[c:8] | 59.6 | [{"value": 59.6, "product": "SC1=C(C(=O)C2=CC=CC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of N,N,N',N'-tetramethylethylene diamine (4.4 g, 0.038 mol) and thiophenol (2 g, 0.018 mol) in cyclohexane (40 mL) was added dropwise n-butyllithium (24 mL, 0.038 mol) at room temperature. The suspension was stirred under nitrogen for 16 hours, followed by the dropwise addition of N-methoxy-N-methylbenzam... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C1CCCCC1 | null | 16 | CON(C)C(=O)c1ccccc1.Sc1ccccc1>C1CCCCC1>O=C(c1ccccc1)c1ccccc1S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18a0ff4af7384269a935d5430d7f8ca8 | NS(=O)(=O)c1cc(Cl)ccc1Cl.S>>NS(=O)(=O)c1cc(Cl)ccc1S | ClC1=C(C=C(C=C1)Cl)S(=O)(=O)N.S.[Na]>>SC1=C(C=C(C=C1)Cl)S(=O)(=O)N | Cl[c:11]1[c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:6][c:7]([Cl:8])[cH:9][cH:10]1.[SH2:12]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[SH:12] | NS(=O)(=O)c1cc(Cl)ccc1Cl.S | NS(=O)(=O)c1cc(Cl)ccc1S | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a68a9f190548bfb055191578c24b0de54c85f8443714e35747c2990bf0f973bd | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6].[SH2;D0;+0:7]>>[#16:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[SH;D1;+0:7]):[c:2]:[c:3] | 30.1 | [{"value": 30.1, "product": "SC1=C(C=C(C=C1)Cl)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 34.0 g (0.15 mol) of 2,5-dichloro-benzene sulfonamide in 200 mL of DMF was added 16.0 g (0.28 mol) of sodium hydrogensulfide. The mixture was refluxed for 18 hours, then cooled, concentrated, and the solids collected by filtration. The solids were dissolved in hot water, the pH adjusted to 4.0 and the precipitate fi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CN(C)C=O | null | null | NS(=O)(=O)c1cc(Cl)ccc1Cl.S>CN(C)C=O>NS(=O)(=O)c1cc(Cl)ccc1S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c2bf9e31bb848cdbaf04402697bce42 | O=C(O)c1cc([N+](=O)[O-])ccc1Cl>>NC(=O)c1cc([N+](=O)[O-])ccc1Cl | ClC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].C(C(=O)Cl)(=O)Cl.CN(C=O)C>>ClC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-] | O[C:2](=[O:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[Cl:13]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[Cl:13] | O=C(O)c1cc([N+](=O)[O-])ccc1Cl | NC(=O)c1cc([N+](=O)[O-])ccc1Cl | null | null | ClCCl | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 3 | HOUR | A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) in 200 mL of dichloromethane was reacted at 24° C. with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. After 3 hours, the solvent was removed in vacuo, and the residue was redissolved in 200 mL of fresh dichloromethane. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1 | null | ClCCl | 0 | 3 | O=C(O)c1cc([N+](=O)[O-])ccc1Cl>ClCCl>NC(=O)c1cc([N+](=O)[O-])ccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71cd525c3da84d9d811cf5b361bea38c | CC(=O)N(C)[Si](C)(C)C.NCc1ccc(S(N)(=O)=O)cc1.O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>NS(=O)(=O)c1ccc(CNC(=O)c2ccccc2SSc2ccccc2C(=O)NCc2ccc(S(N)(=O)=O)cc2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.O.Cl.NCC1=CC=C(C=C1)S(=O)(=O)N.CN(C(C)=O)[Si](C)(C)C>>NS(=O)(=O)C1=CC=C(C=C1)CNC(C1=C(C=CC=C1)SSC1=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)N)C=CC=C1)=O | [Si]([N:1]([C:5](=[O:4])[CH3:8])[CH3:7])([CH3:6])([CH3:41])[CH3:42].[NH2:29][CH2:30][c:31]1[cH:32][cH:33][c:34]([S:35]([NH2:36])(=[O:37])=[O:38])[cH:39][cH:40]1.[OH2:3].Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[S:19][S:2][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[C:27](Cl)=[O:28]>>[NH2:1][S:2](=[O:3])... | CC(=O)N(C)[Si](C)(C)C.NCc1ccc(S(N)(=O)=O)cc1.O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | NS(=O)(=O)c1ccc(CNC(=O)c2ccccc2SSc2ccccc2C(=O)NCc2ccc(S(N)(=O)=O)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2f737d920337492f33c2b5ce9afc4d8bd2bf7db12b4af7aa86720425ee244a67 | dc91b49c857e5aff637fc9b7c11116c009ac8f0dae5b155540816db72ea542a0 | O=C(NCc1ccccc1)c1ccccc1SSc1ccccc1C(=O)NCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[S;H0;D2;+0:6]-[S;H0;D2;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;H0;D3;+0:12](-Cl)=[O;D1;H0:13]):[c:14]):[c:15].[CH3;D1;+0:16]-[Si](-[CH3;D1;+0:17])(-[CH3;D1;+0:18])-[N;H0;D3;+0:19](-[CH3;D1;+0:20])-[C;H0;D3;+0:21](-[CH3;D1;+0:22])=[O;H0;D1;+0:23].[NH2;D1;+0:24... | 35.4 | [{"value": 35.4, "product": "NS(=O)(=O)C1=CC=C(C=C1)CNC(C1=C(C=CC=C1)SSC1=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)N)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 g, 29 mmol) in 100 mL pyridine was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (13.4 mL, 83.0 mmol) until a homogenous solution occurred. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobisbenzoyl chloride (4.0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Tertiary amide.Primary amine.Disulfide.Silyl protective group | Sulfonamide.Secondary amide.Secondary amide.Disulfide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | 18 | CC(=O)N(C)[Si](C)(C)C.NCc1ccc(S(N)(=O)=O)cc1.O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>NS(=O)(=O)c1ccc(CNC(=O)c2ccccc2SSc2ccccc2C(=O)NCc2ccc(S(N)(=O)=O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d4b3e2d8b104f55b15cbffa0a456209 | Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1>>N1=C(N=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC2=NC=CC=N2)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:39][c:40]([S:41](=[O:9])(=[O:10])[NH:44][c:45]2[n:11][cH:14][cH:15][cH:49][n:50]2)[cH:51][cH:52]1.Cl[C:2](=[O:1])[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[S:26][S:8][c:7]1[cH:6][cH:12][cH:31][cH:32][c:33]1[C:34](Cl)=[O:35]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][... | Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | a66a35ba2fc480812910f775ea5d06975512d00d8307eeff4c17a5984239f179 | 237c94f9bfeb760408a4fe8675c80a8ef696736e818eb00c99939b94b6dc2129 | O=C(Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[S;H0;D2;+0:6]-[S;H0;D2;+0:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c;H0;D3;+0:13]:1-[C;H0;D3;+0:14](-Cl)=[O;D1;H0:15]):[c:16].[NH2;D1;+0:17]-[c;H0;D3;+0:18]1:[cH;D2;+0:19]:[c:20]:[c:21](-[S;H0;D4;+0:22](=[O;H0;D1;+0:23])(=[O;H0;D1;+0:24])-... | 58.2 | [{"value": 58.2, "product": "N1=C(N=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC2=NC=CC=N2)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general methods described in Example 1 using 2,2'-dithiobisbenzoyl chloride (3.0 g, 8.7 mmol) in 30 mL dichloromethane and 4-amino-N-(2-pyrimidinyl) benzenesulfonamide (5.3 g, 21.7 mmol) in 100 mL pyridine. The crude product was recrystallized from a mixture of dimethylformam... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Sulfonamide.Primary amine.Disulfide | Sulfonamide.Sulfonamide.Secondary amide.Secondary amide.Disulfide | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cncnc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-45e1e2f32fac4e2c92640fb69c3a608f | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.N[C@@H](CO)c1ccccc1>>O=C(NC(CO)c1ccccc1)c1ccccc1 | CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C.N[C@@H](CO)C1=CC=CC=C1.CN(C(C)=O)[Si](C)(C)C>>OCC(C1=CC=CC=C1)NC(C1=CC=CC=C1)=O | CC(=O)OCc1c2ccccc2c(CO[C:2](C)=[O:1])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.[NH2:3][C@@H:4]([CH2:5][OH:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[C:2]([NH:3][CH:4]([CH2:5][OH:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.N[C@@H](CO)c1ccccc1 | O=C(NC(CO)c1ccccc1)c1ccccc1 | null | null | ClCCl | Acylation | OtherReaction | 1f4385245df9155d5d7b9085759e7cd4f1a70fa0f7ff9e1db687c4f785a3c76c | 2045625a573697f90685b6f2edaef3bd39413d8546c2cd555781f1d7e040b9e9 | O=C(NCc1ccccc1)c1ccccc1 | C-C(=O)-O-C-c1:[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:2:c(-C-O-[C;H0;D3;+0:7](-C)=[O;D1;H0:8]):c2:c:c:c:c:c:1:2.[NH2;D1;+0:9]-[C@@H;D3;+0:10](-[C:11]-[O;D1;H1:12])-[c:13](:[c:14]):[c:15]>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[NH;D2;+0:9]-[CH;D3;+0:10](-[C:11]-[O;D1;H1:12])-[c:13](:[c:14]):[c:15])-[c;H0;D3;+0:6]1... | null | [] | null | null | 2 | HOUR | A slurry of (R)-2-amino-2-phenylethanol (1.0 g, 7.4 mmol) in 50 mL dichloromethane was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (3.4 mL, 21.1 mmol) until a homogenous solution occured. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobis[benzoyl chloride] (1.0 g, 2.9 mmol) in 20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Secondary amide | c1ccc2cc3ccccc3cc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 2 | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.N[C@@H](CO)c1ccccc1>ClCCl>O=C(NC(CO)c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58247be6c9cf4f31b764ec27ffb99a3b | CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)C(=O)OC(C)(C)C>>CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)O)C(C)CC)C(=O)O | C1(=CC=CC=C1)C.C(C)(C)(C)OC(C(C(CC)C)NC(C1=C(C(=CC=C1)F)SSC1=C(C=CC=C1F)C(NC(C(CC)C)C(=O)OC(C)(C)C)=O)=O)=O.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(=O)(O)C(C(CC)C)NC(=O)C1=C(C(=CC=C1)F)SSC1=C(C(=O)NC(C(=O)O)C(CC)C)C=CC=C1F | CC(C)(C)[O:31][C:29]([CH:28]([NH:27][C:25]([c:24]1[c:18]([S:17][S:16][c:15]2[c:9]([C:7]([NH:6][CH:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[C:36](=[O:37])[O:38]C(C)(C)C)=[O:8])[cH:10][cH:11][cH:12][c:13]2[F:14])[c:19]([F:20])[cH:21][cH:22][cH:23]1)=[O:26])[CH:32]([CH3:33])[CH2:34][CH3:35])=[O:30]>>[CH3:1][CH2:2][CH:3]([CH3:4])... | CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)C(=O)OC(C)(C)C | CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)O)C(C)CC)C(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 44 | [{"value": 44.0, "product": "C(=O)(O)C(C(CC)C)NC(=O)C1=C(C(=CC=C1)F)SSC1=C(C(=O)NC(C(=O)O)C(CC)C)C=CC=C1F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-2-methyl-butylcarbamoyl)-6-fluorophenyldisulfanyl]-3-fluoro- benzoylamino]-3-methylpentanoic acid tert butyl ester (0.6 g ,0.8 mmol) and anisole (1 ml) in 10 mL dichloromethane at 0° C., was added dropwise 10 mL trifluoroacetic acid. The mixture was allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | 4 | CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)C(=O)OC(C)(C)C>ClCCl>CCC(C)C(NC(=O)c1cccc(F)c1SSc1c(F)cccc1C(=O)NC(C(=O)O)C(C)CC)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b2fa86f98d3442e988c60a6a17094fb | CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=C(C=C1)F)SSC1=C(C=CC(=C1)F)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)F)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)F | CC(C)(C)[O:35][C:33]([CH:28]([NH:27][C:25]([c:24]1[c:18]([S:17][S:16][c:15]2[c:9]([C:7]([NH:6][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:36](=[O:37])[O:38]C(C)(C)C)=[O:8])[cH:10][cH:11][c:12]([F:13])[cH:14]2)[cH:19][c:20]([F:21])[cH:22][cH:23]1)=[O:26])[CH2:29][CH:30]([CH3:31])[CH3:32])=[O:34]>>[CH3:1][CH:2]([CH3:3])[CH2:... | CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 62.5 | [{"value": 62.5, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)F)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-fluoro-phenyldisulfanyl]-4-fluorobenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (3.1 g, 4.5 mmol) from Example 27, 30 mL dichloromethane, 30 mL trifluoroaceti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl>CC(C)CC(NC(=O)c1ccc(F)cc1SSc1cc(F)ccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5076d4109d134b4ea10232263e62da0c | CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=CC(=C1)F)SSC1=C(C=C(C=C1)F)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)F)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=C(C=C1)F | CC(C)(C)[O:35][C:33]([CH:28]([NH:27][C:25]([c:24]1[c:18]([S:17][S:16][c:15]2[c:9]([C:7]([NH:6][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:36](=[O:37])[O:38]C(C)(C)C)=[O:8])[cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:19][cH:20][c:21]([F:22])[cH:23]1)=[O:26])[CH2:29][CH:30]([CH3:31])[CH3:32])=[O:34]>>[CH3:1][CH:2]([CH3:3])[CH2:... | CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 17.6 | [{"value": 17.6, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)F)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R R*)-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-4-fluoro-phenyldisulfanyl]-5-fluorobenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (2.1 g, 3.0 mmol) from Example 28, 25 mL dichloromethane, 25 mL trifluoroacetic ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl>CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e25215ee60094b58ac72c52a0aebb599 | COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>>COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=CC(=C1)OC)SSC1=C(C=C(C=C1)OC)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)OC)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=C(C=C1)OC | CC(C)(C)[O:27][C:25]([CH:20]([NH:19][C:17]([c:16]1[c:9]([S:8][S:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][c:28]2[C:29](=[O:30])[NH:31][CH:32]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:37](=[O:38])[O:39]C(C)(C)C)[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15]1)=[O:18])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:26]>>[CH3:1][O:2][... | COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1 | COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 34.7 | [{"value": 34.7, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)OC)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl- butylcarbamoyl)-4-methoxy-phenyldisulfanyl]-5-methoxybenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (2.4 g, 3.4 mmol) from Example 31, 25 mL dichloromethane, 25 mL trifluoroac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>ClCCl>COc1ccc(SSc2ccc(OC)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6ce76bad70b40cc9115ea80cc9c91d4 | Cc1cccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C>>Cc1cccc(C(=O)NC(CC(C)C)C(=O)O)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)O | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C(=CC=C1)C)SSC1=C(C=CC=C1C)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C(=CC=C1)C)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC=C1C | CC(C)(C)[O:17][C:15]([CH:10]([NH:9][C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:18]1[S:19][S:20][c:21]1[c:22]([CH3:23])[cH:24][cH:25][cH:26][c:27]1[C:28](=[O:29])[NH:30][CH:31]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:36](=[O:37])[O:38]C(C)(C)C)=[O:8])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:16]>>[CH3:1][c:2]1[cH:3][cH:4][c... | Cc1cccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C | Cc1cccc(C(=O)NC(CC(C)C)C(=O)O)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 54.9 | [{"value": 54.9, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C(=CC=C1)C)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-6-methyl-phenyldisulfanyl]-3-methylbenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (0.9 g, 1.3 mmol) from Example 32, 10 mL dichloromethane, and 10 mL trifluoroa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | Cc1cccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C>ClCCl>Cc1cccc(C(=O)NC(CC(C)C)C(=O)O)c1SSc1c(C)cccc1C(=O)NC(CC(C)C)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e21f9e4f9b6c43e9a6bef3b86579a4ee | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>>Cc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=C(C=C1)C)SSC1=C(C=CC(=C1)C)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)C)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)C | CC(C)(C)[O:16][C:14]([CH:9]([NH:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:38][c:17]1[S:18][S:19][c:20]1[cH:21][c:22]([CH3:23])[cH:24][cH:25][c:26]1[C:27](=[O:28])[NH:29][CH:30]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:35](=[O:36])[O:37]C(C)(C)C)=[O:7])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:15]>>[CH3:1][c:2]1[cH:3][cH:4][c... | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1 | Cc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 89.2 | [{"value": 89.2, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)C)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5 -methyl-phenyldisulfanyl]-4-methylbenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (1.9 g, 2.8 mmol) from Example 33, 20 mL dichloromethane, 20 mL trifluoroacet... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>ClCCl>Cc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-264b85044b034d0ba81c2947a44108fd | CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>>CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=CC(=C1)NC(C)=O)SSC1=C(C=C(C=C1)NC(C)=O)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F>>C(C)(=O)NC=1C=CC(=C(C(=O)NC(C(=O)O)CC(C)C)C1)SSC1=C(C=C(C=C1)NC(C)=O)C(NC(CC(C)C)C(=O)O)=O | CC(C)(C)[O:31][C:29]([CH:24]([NH:23][C:21]([c:20]1[c:11]([S:10][S:9][c:8]2[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:44][c:32]2[C:33](=[O:34])[NH:35][CH:36]([CH2:37][CH:38]([CH3:39])[CH3:40])[C:41](=[O:42])[O:43]C(C)(C)C)[cH:12][cH:13][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:19]1)=[O:22])[CH2:25][CH:26]([CH3:27]... | CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1 | CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 77.3 | [{"value": 77.3, "product": "C(C)(=O)NC=1C=CC(=C(C(=O)NC(C(=O)O)CC(C)C)C1)SSC1=C(C=C(C=C1)NC(C)=O)C(NC(CC(C)C)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]2-{5-acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester (0.2 g, 0.2 mmol) from Example 44, 10 mL dichloromethane, and 10 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>ClCCl>CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8655bb3b290949c98eac8596befecd66 | CCNc1ccc(SSc2ccc(NCC)cc2C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c(C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c1>>CCNc1ccc(SSc2ccc(NCC)cc2C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c(C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c1 | C(C)(C)(C)OC(C(C(CC)C)NC(C1=C(C=CC(=C1)NCC)SSC1=C(C=C(C=C1)NCC)C(NC(C(CC)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F>>C(C)NC=1C=CC(=C(C1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)O)SSC1=C(C=C(C=C1)NCC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)O | CC(C)(C)[O:25][C:23]([CH:22]([NH:21][C:19]([c:18]1[c:10]([S:9][S:8][c:7]2[cH:6][cH:5][c:4]([NH:3][CH2:2][CH3:1])[cH:42][c:30]2[C:31](=[O:32])[NH:33][CH:34]([C:35](=[O:36])[O:37]C(C)(C)C)[CH:38]([CH3:39])[CH2:40][CH3:41])[cH:11][cH:12][c:13]([NH:14][CH2:15][CH3:16])[cH:17]1)=[O:20])[CH:26]([CH3:27])[CH2:28][CH3:29])=[O:... | CCNc1ccc(SSc2ccc(NCC)cc2C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c(C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c1 | CCNc1ccc(SSc2ccc(NCC)cc2C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c(C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c1 | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | null | [] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]2-{5-ethylamino-2-[4-ethylamino-2-(1-tert-butoxy carbonyl-2-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-3-methyl-pentanoic acid tert-butyl ester (0.8 g, 1.1 mmol) from Example 45, 10 mL dichloromethane, and 10 mL t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CCNc1ccc(SSc2ccc(NCC)cc2C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c(C(=O)NC(C(=O)OC(C)(C)C)C(C)CC)c1>ClCCl>CCNc1ccc(SSc2ccc(NCC)cc2C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c(C(=O)N[C@H](C(=O)O)[C@@H](C)CC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0c63113194641109ceb64f308eed198 | CC(C)(C)OC(=O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>O=C(O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)O)C(=O)O)C(=O)O | C(C)(C)(C)OC(C(CCCC(=O)OC(C)(C)C)NC(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(NC(CCCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C(=O)(O)C(CCCC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NC(C(=O)O)CCCC(=O)O)C=CC=C1 | CC(C)(C)[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH:7]([NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](=[O:26])[NH:27][CH:28]([CH2:29][CH2:30][CH2:31][C:32](=[O:33])[O:34]C(C)(C)C)[C:35](=[O:36])[O:37]C(C)(C)C)[C:38](=[O:39])[O:40]C(C)(C)C>>[O:1]... | CC(C)(C)OC(=O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | O=C(O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)O)C(=O)O)C(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ffd747b208ee9d9178a9ed853830179ed0fd8da3f4916bf7a2ba3d05b0c4580a | 160e34dc880ed6d7d713a596527bbe74b68c919fb5536505ec345c6927256c13 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8].C-C(-C)(-C)-[O;H0;D2;+0:9]-[C:10](-[C:11])=[O;D1;H0:12].C-C(-C)(-C)-[O;H0;D2;+0:13]-[C:14](-[C:15])=[O;D1;H0:16]>>[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:11]-[C:10](=[O;D1;H... | null | [] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-{2-[2-(1,4-bis-tert-butoxycarbonyl-butylcarbamoyl)phenyldisulfanyl]-benzoylamino}-hexanedioic acid di-tert-butyl ester (1.1 g, 1.4 mmol) from Example 10 mL dichloromethane, 10 mL trifluoroacetic acid, and 1 mL anisole. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester.Boc.Boc.Boc.Boc | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CC(C)(C)OC(=O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl>O=C(O)CCCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(CCCC(=O)O)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f5ac2919a37f4d268e8ee62516c10df4 | CC(C)(C)OC(=O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)OC(C)(C)C>>O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O | CC(C)(C)OC(CCCNC(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)NCCCC(=O)OC(C)(C)C)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)NCCCC(=O)O)C(=O)NCCCC(=O)O | CC(C)(C)[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24](=[O:25])[NH:26][CH2:27][CH2:28][CH2:29][C:30](=[O:31])[O:32]C(C)(C)C>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][... | CC(C)(C)OC(=O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)OC(C)(C)C | O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 139.9 | [{"value": 139.9, "product": "C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)NCCCC(=O)O)C(=O)NCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using 4,4'-[dithiobis(2,1-phenylenecarbonylimino)]bis butanoic acid bis (1,1-dimethylethyl) ester (0.5 g, 0.9 mmol) from Example 43, 10 mL dichloromethane, 10 mL trifluoroacetic acid, and 1 mL anisole. The crude product was recrystallized fro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CC(C)(C)OC(=O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)OC(C)(C)C>ClCCl>O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90c1ac43b2814299a03384dc402e2956 | CC(C)(C)OC(=O)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)OC(C)(C)C)c1ccccc1)c1ccccc1>>O=C(NC(C(=O)O)c1ccccc1)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)c1ccccc1 | C(C)(C)(C)OC(C(C1=CC=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(NC(C1=CC=CC=C1)C(=O)OC(C)(C)C)=O)=O)=O.ClCCl.FC(C(=O)O)(F)F>>C(=O)(O)C(C1=CC=CC=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NC(C(=O)O)C2=CC=CC=C2)C=CC=C1 | CC(C)(C)[O:7][C:5]([CH:4]([NH:3][C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[S:20][S:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28](=[O:29])[NH:30][CH:31]([C:32](=[O:33])[O:34]C(C)(C)C)[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1)[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:6]>>[O:1]=[C:2]([NH:3][CH:4](... | CC(C)(C)OC(=O)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)OC(C)(C)C)c1ccccc1)c1ccccc1 | O=C(NC(C(=O)O)c1ccccc1)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)c1ccccc1 | null | null | CCOCC.CCCCCC | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | O=C(NCc1ccccc1)c1ccccc1SSc1ccccc1C(=O)NCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 42.5 | [{"value": 42.5, "product": "C(=O)(O)C(C1=CC=CC=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NC(C(=O)O)C2=CC=CC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the procedure described in Example 50 using [R-(R*,R*)] (2-{2-[(tert-butoxycarbonyl-phenyl-methyl)-carbamoyl]-phenyldisulfanyl}-benzoylamino)-phenyl-acetic acid tert-butyl ester (0.2 g, 0.3 mmol) from Example 38, 10 mL dichloromethane, and 10 mL trifluoroacetic acid. The crude pr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CCOCC.CCCCCC | null | null | CC(C)(C)OC(=O)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)OC(C)(C)C)c1ccccc1)c1ccccc1>CCOCC.CCCCCC>O=C(NC(C(=O)O)c1ccccc1)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a67bdc641f8e4f39ae974ec2f00e4563 | O=C(N[C@@H](CO)C(=O)O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CO)C(=O)O>>CC(C)(C)OCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(COC(C)(C)C)C(=O)O)C(=O)O | C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N[C@@H](CO)C(=O)O)C(=O)N[C@@H](CO)C(=O)O.[OH-].[Na+]>>C(C)(C)(C)OCC(C(=O)O)NC(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(NC(COC(C)(C)C)C(=O)O)=O)=O | [cH:1]1[cH:21][cH:20][c:19]([S:18][S:17][c:16]2[c:11]([C:9]([NH:8][C@@H:7]([CH2:6][OH:5])[C:38](=[O:39])[OH:40])=[O:10])[cH:12][cH:13][cH:14][cH:15]2)[c:24]([C:25](=[O:26])[NH:27][C@@H:28]([CH2:29][OH:30])[C:35](=[O:36])[OH:37])[cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH:7]([NH:8][C:9](=[O:10])[c:11]1[cH:12... | O=C(N[C@@H](CO)C(=O)O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CO)C(=O)O | CC(C)(C)OCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(COC(C)(C)C)C(=O)O)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 2b242633f15fd939e014127c5e4cbf2e9e6b7fd425c2b851bc70e0b6c0a0b54f | c43f1fd9a286578779dd421b544e0d21b4ff22c398f56b345fdd016e4eec452f | c1ccc(SSc2ccccc2)cc1 | [O;D1;H0:1]=[C:2](-[#7:3]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])-[c:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1.[O;D1;H0:16]=[C:17](-[O;D1;H1:18])-[C:19]-[C:20]-[OH;D1;+0:21]>>[C;D1;H3:22]-[C:23](-[C;D1;H3:24])(-[C;D1;H3:25])-[O;H0;D2;+0:6]-[C:5]-[C:4](-[#7:3]-[C:2](=[O;D1;H0:1])... | null | [] | null | null | 18 | HOUR | A solution of N,N'-[dithiobis(2,1-phenylene carbonyl)]bis L-serine bis[O(1,1-dimethylethyl) bis (1,1-dimethylethyl)ester (1.0 g, 1.4 mmol) from Example 39, in 30 mL methanol was treated with 8 mL of 1N NaOH and allowed to stir for 18 hours. The methanol was removed in vacuo and the residual was diluted with 5 water and... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ether.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CO | null | 18 | O=C(N[C@@H](CO)C(=O)O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CO)C(=O)O>CO>CC(C)(C)OCC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(COC(C)(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-633d84603ffe4743a9aba35936f4eeaa | CC(C)(C)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CC(C)(C)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C(C)(C)C)cc2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.C(C)(C)(C)C1=CC=C(N)C=C1>>CC(C)(C)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C(C)(C)C)C=CC=C1)=O | [CH3:1][C:2]([c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:39][cH:40]1)([CH3:29])[CH3:33].Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](Cl)=[O:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:1... | CC(C)(C)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CC(C)(C)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C(C)(C)C)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 5e7dfe57baccae2b9f8237d28bb05b03f973be38ed0d1e13108e5b3f0bc6e511 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[c:15]1:[c:16]:[c:17]:[c:18](-[NH2;D1;+0:19]):[c:20]:[c:21]:1>>[C;D1;H3:22]-[C;H0;D4;+0:14](-[C;D1;H3:23])(-[C;D1;H3:24])-[c:25]1:[c:26]:[c:27]:[c;H0;D3... | 12.1 | [{"value": 12.1, "product": "CC(C)(C)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C(C)(C)C)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 18 | HOUR | A solution of 2,2'-dithiobisbenzoyl chloride (1.20 g, 3.50 mmol) in 25 mL of dichloromethane was added to a solution of 4-tert-butylaniline (1.04 g, 6.99 mmol) in 8 mL of pyridine at 23° C. The reaction mixture was stirred for 18 hours at 23° C. under nitrogen atmosphere. The mixture was concentrated, the residue tritu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | 23 | 18 | CC(C)(C)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CC(C)(C)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C(C)(C)C)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-99ded9ee638c4e8e8ae32c49527a72c9 | Cc1cccc(N)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>Cc1cccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2cccc(C)c2)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=CC(=CC=C1)C>>CC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)C)C=CC=C1)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:34]1.Cl[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24](Cl)=[O:25]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[S:16][S:17][c:18]2[cH:19][cH:20][cH:2... | Cc1cccc(N)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | Cc1cccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2cccc(C)c2)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 5e7dfe57baccae2b9f8237d28bb05b03f973be38ed0d1e13108e5b3f0bc6e511 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 42 | [{"value": 42.0, "product": "CC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)C)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and m-toluidine (1.24 g, 11.6 mmol) in 10 mL of pyridine. The crude product was recrystallized from ethyl ether-ethyl acetate to yield 1.18 g of the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Cc1cccc(N)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>Cc1cccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2cccc(C)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13c2d40238f04e09ad2c43fc65c95f17 | Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.[N+](=O)([O-])C1=C(C=C(N)C=C1)C(F)(F)F>>[N+](=O)([O-])C1=C(C=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C=CC=C1)=O)C(F)(F)F | [NH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1.Cl[C:2](=[O:1])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[S:23][S:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]1[C:31](Cl)=[O:32]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([C:12]([F:13])([F:14]... | Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | b163e875372378d1d028ea4cd7d647886a8a6c0f7c85c6359b9bacf7ead938ae | faa2f590cb6fe8321b08f10ffb778d02b3a22ddfe9af0e788d658aa8ed54717e | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[#7:15]-[c:16])-[c:8](:[c:9]):[c:10].[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:3](:[c:4]):[c:5] | 6.3 | [{"value": 6.3, "product": "[N+](=O)([O-])C1=C(C=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C=CC=C1)=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-nitro-3-(trifluoromethyl)aniline (2.39 g, 11.6 mmol) in 19 mL of pyridine. The crude product was recrystallized from ethyl ether to yield 0.25 g of the titl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Trifluoro group.Nitro group.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b72f28adf1044fce8dbba03ec99cbcd2 | Nc1cccc(Br)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cccc(Br)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(Br)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.BrC=1C=C(N)C=CC1>>BrC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)Br)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](Cl)=[O:26]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:2... | Nc1cccc(Br)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cccc(Br)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(Br)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 0b7f4098d290755c90a886d0c252e496f0da36f344c58467b3815e0aa364cb08 | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 55.8 | [{"value": 55.8, "product": "BrC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)Br)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 3-bromoaniline (1.98 g, 11.6 mmol) in 16 mL of pyridine. The crude product was recrystallized from ethyl acetate-hexanes to yield 1.99 g of the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cccc(Br)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cccc(Br)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d69713b0abd4540ba7707592879c8e1 | Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.FC(C=1C=C(N)C=C(C1)C(F)(F)F)(F)F>>FC(C=1C=C(C=C(C1)C(F)(F)F)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C=CC=C1)=O)(F)F | [NH2:3][c:4]1[cH:17][c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][c:35]([C:5]([F:8])([F:10])[F:47])[cH:36]1.Cl[C:2](=[O:1])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[S:24][S:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[C:32](Cl)=[O:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([... | Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 3af4a80b9f477945a35669e39ac3d6d34656dcab74bbf530e1dd4e5d3e557110 | e16cf9ca3cc19e012f47c13758aab8b39d59e0e372ede8756b43a41ab0d6cae0 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[F;D1;H0:11]-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[c:15]1:[c:16]:[c;H0;D3;+0:17](-[NH2;D1;+0:18]):[cH;D2;+0:19]:[c;H0;D3;+0:20](-[C;H0;D4;+0:21](-[F;H0;D1;+0:22])(-[F;H0;D1;+0:23])-[F;H0;D1;+0:24]):[cH;D2;+0:25]:1>>... | 8 | [{"value": 8.0, "product": "FC(C=1C=C(C=C(C1)C(F)(F)F)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C=CC=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 3,5-bis(trifluoromethyl)aniline (2.66 g, 11.6 mmol) in 21 mL of pyridine. The crude product was recrystallized from ethyl acetate-hexanes (1:9) to yield 0.34 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Trifluoro group.Primary amine | Trifluoro group.Trifluoro group.Trifluoro group.Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
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