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-0c41a886f892437a80e1ebfc69bc8999 | CCO.CSc1nc(Cl)cc(Cl)n1.Oc1cccc(C(F)(F)F)c1>>CCOc1cc(Oc2cccc(C(F)(F)F)c2)nc(SC)n1 | C(C)O.[H-].[Na+].FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].ClC1=NC(=NC(=C1)Cl)SC>>C(C)OC1=NC(=NC(=C1)OC1=CC(=CC=C1)C(F)(F)F)SC | [CH3:1][CH2:2][OH:3].Cl[c:4]1[cH:5][c:6](Cl)[n:18][c:19]([S:20][CH3:21])[n:22]1.[OH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]2)[n:18][c:19]([S:20][CH3:21])[n:22]1 | CCO.CSc1nc(Cl)cc(Cl)n1.Oc1cccc(C(F)(F)F)c1 | CCOc1cc(Oc2cccc(C(F)(F)F)c2)nc(SC)n1 | null | null | CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 29a438eea1e56cb3e58f97b3a65584b92c6780a20719e4a18d7d224393cebeb2 | d37fb640deee362662d550188dc8afd00e30441a55a467542ae6bf66e47599da | c1ccc(Oc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c;H0;D3;+0:6](-Cl):[c:7]:1.[C;D1;H3:8]-[C:9]-[OH;D1;+0:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#16:4]-[c:3]1:[#7;a:5]:[c;H0;D3;+0:6](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:7]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[C:9]-[C;D1;H3:8]):[#7;a:2]:1 | null | [] | null | null | 30 | MINUTE | Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary alcohol.Aromatic alcohol | Ether.Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CN(C)C=O.C1CCOC1 | null | 0.5 | CCO.CSc1nc(Cl)cc(Cl)n1.Oc1cccc(C(F)(F)F)c1>CN(C)C=O.C1CCOC1>CCOc1cc(Oc2cccc(C(F)(F)F)c2)nc(SC)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-779700042b074f55b42f3a2202e7c555 | CSc1nc(Cl)cc(C(F)(F)F)n1.Oc1cccc(C(F)(F)F)c1>>CSc1nc(Oc2cccc(C(F)(F)F)c2)cc(C(F)(F)F)n1 | FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].ClC1=NC(=NC(=C1)C(F)(F)F)SC>>CSC1=NC(=CC(=N1)C(F)(F)F)OC1=CC(=CC=C1)C(F)(F)F | Cl[c:5]1[n:4][c:3]([S:2][CH3:1])[n:23][c:18]([C:19]([F:20])([F:21])[F:22])[cH:17]1.[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[CH3:1][S:2][c:3]1[n:4][c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[n:23]1 | CSc1nc(Cl)cc(C(F)(F)F)n1.Oc1cccc(C(F)(F)F)c1 | CSc1nc(Oc2cccc(C(F)(F)F)c2)cc(C(F)(F)F)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]):[c:10]:1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:7]-[C:6](-[F;D1;H0:8])(-[F;D1;H0:9])-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1 | null | [] | null | null | null | null | m-(Trifluoromethyl)phenol (1.06 g, 0.0044×1.5 mol) and NaH (0.26 g (ca.60% in mineral oil), 0.0044×1.5 mol) were dissolved in THF, and then 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (Compound No. VII-17) (1.0 g, 0.0044 mol) was added thereto. The resulting solution was refluxed for about 7 hours. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | null | null | CSc1nc(Cl)cc(C(F)(F)F)n1.Oc1cccc(C(F)(F)F)c1>C1CCOC1>CSc1nc(Oc2cccc(C(F)(F)F)c2)cc(C(F)(F)F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3df2c010cc0541928156900e8959ed27 | CSc1nc(Br)cc(Br)n1.Oc1cccc(C(F)(F)F)c1>>CSc1nc(Br)cc(Oc2cccc(C(F)(F)F)c2)n1 | FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].BrC1=NC(=NC(=C1)Br)SC>>BrC1=NC(=NC(=C1)OC1=CC(=CC=C1)C(F)(F)F)SC | Br[c:8]1[cH:7][c:5]([Br:6])[n:4][c:3]([S:2][CH3:1])[n:20]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1>>[CH3:1][S:2][c:3]1[n:4][c:5]([Br:6])[cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]2)[n:20]1 | CSc1nc(Br)cc(Br)n1.Oc1cccc(C(F)(F)F)c1 | CSc1nc(Br)cc(Oc2cccc(C(F)(F)F)c2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncn2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[Br;D1;H0:7]):[c:8]:1.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:8]:[c:6](-[Br;D1;H0:7]):[#7;a:5]:1 | null | [] | null | null | null | null | In THF, a phenoxide was prepared from m-(trifluoromethyl)phenol (1.30 g, 0.00794×1.0 mol) and NaH (0.32 g (ca. 60% in mineral oil), 0.00794×1.0 mol), and 4,6-dibromo-2-(methylthio)pyrimidine (Compound No. VII-22) (2.0 g, 0.00794 mol) was added thereto, and the mixture was then allowed to react for 5 hours at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | C1CCOC1 | null | null | CSc1nc(Br)cc(Br)n1.Oc1cccc(C(F)(F)F)c1>C1CCOC1>CSc1nc(Br)cc(Oc2cccc(C(F)(F)F)c2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1754134a9e1b4ab5a610540df5e81abc | CC(=O)OC(C)=O.Cc1cccc(N)c1C(=O)O>>CC(=O)Nc1cccc(C)c1C(=O)O | Cl.CC=1C=CC=C(C1C(=O)O)N.[OH-].[Na+].C(C)(=O)OC(C)=O>>CC1=C(C(=O)O)C(=CC=C1)NC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]1[C:12](=[O:13])[OH:14]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]1[C:12](=[O:13])[OH:14] | CC(=O)OC(C)=O.Cc1cccc(N)c1C(=O)O | CC(=O)Nc1cccc(C)c1C(=O)O | null | null | O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | null | [] | null | null | 1 | HOUR | 90.6 g (0.6 mol) of 6-methylanthranilic acid are added to a solution of 24.8 g (0.62 mol) of NaOH in 500 ml of water and 63.4 g (0.62 mol) of acetic anhydride are then added dropwise. After stirring for one hour, the mixture is acidified to pH 3 with conc. HCl with cooling, and the precipitate which deposits is filtere... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O | null | 1 | CC(=O)OC(C)=O.Cc1cccc(N)c1C(=O)O>O>CC(=O)Nc1cccc(C)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-036dc1bd98f447088e22557193b51876 | CC(=O)Nc1cccc(C)c1C(=O)O.O=[N+]([O-])O>>CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O | [N+](=O)(O)[O-].CC1=C(C(=O)O)C(=CC=C1)NC(C)=O>>CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])NC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:12]([CH3:13])[c:14]1[C:15](=[O:16])[OH:17].O[N+:9](=[O:10])[O-:11]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([CH3:13])[c:14]1[C:15](=[O:16])[OH:17] | CC(=O)Nc1cccc(C)c1C(=O)O.O=[N+]([O-])O | CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:4]-[c:5](:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c;H0;D3;+0:10](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:11]:[c:12] | null | [] | 10 | CELSIUS | 1 | HOUR | 271 ml of 98% nitric acid are initially taken at -5° C. and 106 g (0.55 mol) of the 2-methyl-6-acetamidobenzoic acid prepared in 1. are added in portions. After stirring at 10° C. for one hour, the reaction mixture is poured into a mixture of 540 g of ice and 270 ml of water. The deposited precipitate is filtered off w... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | 10 | 1 | CC(=O)Nc1cccc(C)c1C(=O)O.O=[N+]([O-])O>O>CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36a2a540166a44e2ae3ef4e91516ef3a | CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O>>Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O | CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])NC(C)=O.Cl>>CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N | CC(=O)[NH:10][c:9]1[cH:8][cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[c:11]1[C:12](=[O:13])[OH:14]>>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9]([NH2:10])[c:11]1[C:12](=[O:13])[OH:14] | CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O | Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O | null | null | [OH-].[Na+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | 95 | CELSIUS | 1 | HOUR | 450 ml of 2N NaOH are initially taken and 75.6 g (0.317 mol) of 2-methyl-3-nitro-6-acetamidobenzoic acid are added. The reaction mixture is then warmed to 95° C. and is stirred at this temperature for one hour. After cooling to 10° C., it is acidified by addition of 425 ml of 2N HCl, and the precipitate which deposits ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | [OH-].[Na+] | 95 | 1 | CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O>[OH-].[Na+]>Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-24a3ddd0c4da4019a874af8b0e5c2e2d | COS(=O)(=O)OC.Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O>>COC(=O)c1c(N)ccc([N+](=O)[O-])c1C | C(=O)=O.S(=O)(=O)(OC)OC.[Na].CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N.C(O)([O-])=O.[Na+].CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N>>CC1=C(C(=O)OC)C(=CC=C1[N+](=O)[O-])N | COS(=O)(=O)O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[CH3:15] | COS(=O)(=O)OC.Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O | COC(=O)c1c(N)ccc([N+](=O)[O-])c1C | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | null | null | null | null | 49.7 g (0.253 mol) of 2-methyl-3-nitro-6-aminobenzoic acid are dissolved in 380 ml of acetone and 43 g (0.51 mol) of sodium hydrogen carbonate are added. The mixture is then heated to boiling until evolution of CO2 is complete. 35.3 g (0.28 mol) of dimethyl sulfate are then added dropwise in the course of two hours at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HO- | O.CC(=O)C | null | null | COS(=O)(=O)OC.Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O>O.CC(=O)C>COC(=O)c1c(N)ccc([N+](=O)[O-])c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9750ebabdd9f4e72aa5a98408ce4247f | COC(=O)c1c(S(=O)(=O)Cl)ccc([N+](=O)[O-])c1C.N>>Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O | N.O.COC(=O)C1=C(C=CC(=C1C)[N+](=O)[O-])S(=O)(=O)Cl>>CC1=C2C(NS(=O)(=O)C2=CC=C1[N+](=O)[O-])=O | CO[C:11]([c:10]1[c:2]([CH3:1])[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9]1[S:14](Cl)(=[O:15])=[O:16])=[O:12].[NH3:13]>>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9]2[c:10]1[C:11](=[O:12])[NH:13][S:14]2(=[O:15])=[O:16] | COC(=O)c1c(S(=O)(=O)Cl)ccc([N+](=O)[O-])c1C.N | Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O | null | null | O1CCCC1 | Acylation | OtherReaction | 22faaebb6d2314e97dbe234804447317ab111ce22357071da0f15828073371ea | 7ccbb14edacd0055aec1ed6cfa3ce7113dc484df701274a79504003cfe511064 | O=C1NS(=O)(=O)c2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[S;H0;D4;+0:6](-Cl)(=[O;D1;H0:7])=[O;D1;H0:8]):[c:9].[NH3;D0;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:10]-[S;H0;D4;+0:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:5](:[c:9]):[c:3]-1:[c:4] | null | [] | 25 | CELSIUS | 3 | HOUR | 104 ml of 25% ammonia solution are initially taken, 100 ml of water are added and a solution of 48.7 g (0.166 mol) of 2-methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride in 70 ml of tetrahydrofuran is then added dropwise at 10° C. After stirring at 25° C. for three hours, the mixture is concentrated on a rotary ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Sulfonyl halide | Sulfonamide.Secondary amide | null | c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2 | HCl | O1CCCC1 | 25 | 3 | COC(=O)c1c(S(=O)(=O)Cl)ccc([N+](=O)[O-])c1C.N>O1CCCC1>Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-67ec3bcdf85a4cd095b46cc07afa68ed | Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O>>Cc1c(N)ccc2c1C(=O)NS2(=O)=O | CC1=C2C(NS(=O)(=O)C2=CC=C1[N+](=O)[O-])=O.[H][H]>>CC1=C2C(NS(=O)(=O)C2=CC=C1N)=O | O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[c:8]2[c:7]([cH:6][cH:5]1)[S:12](=[O:13])(=[O:14])[NH:11][C:9]2=[O:10]>>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[NH:11][S:12]2(=[O:13])=[O:14] | Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O | Cc1c(N)ccc2c1C(=O)NS2(=O)=O | null | [Pd] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1NS(=O)(=O)c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 45 | CELSIUS | null | null | 33.6 g (0.13 mol) of 4-methyl-5-nitrosaccharin are dissolved in 1.2 l of water with warming to 45° C. and 5 g of Pd/C (10% on active carbon) are added. Hydrogen gas is then passed in with vigorous stirring (pressureless hydrogenation). 9 l of H2 are absorbed in the course of 4.5 hours. After cooling to 25° C., the cata... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CNS2 | Other | [Pd].O | 45 | null | Cc1c([N+](=O)[O-])ccc2c1C(=O)NS2(=O)=O>[Pd].O>Cc1c(N)ccc2c1C(=O)NS2(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64895c5b03224120a7cbd0bc650559fc | Cc1c(N)ccc2c1C(=O)NS2(=O)=O.[I-]>>Cc1c(I)ccc2c1C(=O)NS2(=O)=O | Cl.[I-].[K+].CC1=C2C(NS(=O)(=O)C2=CC=C1N)=O.N(=O)[O-].[Na+]>>CC1=C2C(NS(=O)(=O)C2=CC=C1I)=O | N[c:3]1[c:2]([CH3:1])[c:8]2[c:7]([cH:6][cH:5]1)[S:12](=[O:13])(=[O:14])[NH:11][C:9]2=[O:10].[I-:4]>>[CH3:1][c:2]1[c:3]([I:4])[cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[NH:11][S:12]2(=[O:13])=[O:14] | Cc1c(N)ccc2c1C(=O)NS2(=O)=O.[I-] | Cc1c(I)ccc2c1C(=O)NS2(=O)=O | null | null | C(C)(=O)O.O | Functional Group Interconversion | OtherReaction | 02cafa9f779ee5940bd93b8230c881189907d1a0ec609fabd90735eb4159b16d | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | O=C1NS(=O)(=O)c2ccccc21 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6]-[C:7](=[O;D1;H0:8])-[#7:9].[I-;H0;D0:10]>>[#7:9]-[C:7](=[O;D1;H0:8])-[c:6]:[c:4](-[C;D1;H3:5]):[c;H0;D3;+0:1](-[I;H0;D1;+0:10]):[c:2]:[c:3] | null | [] | 50 | CELSIUS | null | null | A mixture of 205 ml of glacial acetic acid, 160 ml of water and 40 ml of conc. HCl is initially taken and 23.4 g (0.11 mol) of 4-methyl-5-aminosaccharin are introduced with stirring at 15°-20° C. 7.9 g (0.115 mol) of sodium nitrite are added dropwise to the resulting suspension at 5°-10° C. and it is stirred at 5° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2 | Other | C(C)(=O)O.O | 50 | null | Cc1c(N)ccc2c1C(=O)NS2(=O)=O.[I-]>C(C)(=O)O.O>Cc1c(I)ccc2c1C(=O)NS2(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5bfe10bbdded406ba8ad3cc28a98a377 | C#CCC(C(=O)OCC)C(=O)c1ccccc1.CNO>>C#CCC1C(=O)N(C)OC1c1ccccc1 | [OH-].[Na+].CNO.C(C1=CC=CC=C1)(=O)C(C(=O)OCC)CC#C.[OH-].[Na+].Cl>>CN1OC(C(C1=O)CC#C)C1=CC=CC=C1 | CCO[C:5]([CH:4]([CH2:3][C:2]#[CH:1])[C:10](=O)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:6].[NH:7]([CH3:8])[OH:9]>>[CH:1]#[C:2][CH2:3][CH:4]1[C:5](=[O:6])[N:7]([CH3:8])[O:9][CH:10]1[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C#CCC(C(=O)OCC)C(=O)c1ccccc1.CNO | C#CCC1C(=O)N(C)OC1c1ccccc1 | null | null | CCOCC.CO.O | Acylation | OtherReaction | 2d3f69240c936c3c2fd9b8f8d3a2721f6df50ac8b98a3bd09cab262d447fc586 | 56154730fca33738cbd11bdaa7691b6c08e53702809fef7babac3ec4bfd050ad | O=C1CC(c2ccccc2)ON1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5]#[C;D1;H1:6])-[C;H0;D3;+0:7](=O)-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[NH;D2;+0:12]-[OH;D1;+0:13]>>[C;D1;H1:6]#[C:5]-[C:4]-[C:3]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12](-[C;D1;H3:11])-[O;H0;D2;+0:13]-[CH;D3;+0:7]-1-[c:8](:[c:9]):[c:10] | 34.5 | [{"value": 34.5, "product": "CN1OC(C(C1=O)CC#C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 10 | MINUTE | A stirred solution of 0.28 g (7.0 mmol) of NaOH in 3 mL of water and 7 mL of methanol was cooled to -30° C. and and a solution of 1.42 g (6.2 mmol) of ethyl α-benzoyl-α-propargylacetate in 2 mL of methanol was added dropwise over 2 min. The mixture was stirred at -30° C. for 10 min and a precooled slurry of 0.54 g (13.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Secondary amine | Tertiary amide | null | C1C[NH]OC1 | C1C[NH]OC1.c1ccccc1 | HO- | CCOCC.CO.O | -30 | 0.166667 | C#CCC(C(=O)OCC)C(=O)c1ccccc1.CNO>CCOCC.CO.O>C#CCC1C(=O)N(C)OC1c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c014829738084401b0a152f2e7cdf4bb | CC(C)(C)NS(=O)(=O)c1cc[nH]c1.CI>>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | CC(C)(C)NS(=O)(=O)C1=CNC=C1.CI.CC(C)([O-])C.[K+]>>CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C | [nH:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]1.I[CH3:1]>>[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]1 | CC(C)(C)NS(=O)(=O)c1cc[nH]c1.CI | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9ead09c93a8a9d57f887a48202e25076c1ec25be9e5b61e0648504d88c26cda6 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1cc[nH]c1 | I-[CH3;D1;+0:1].[c:2]1:[c:3]:[c:4]:[c:5]:[nH;D2;+0:6]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:6]1:[c:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | 60 | CELSIUS | 2 | HOUR | A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3 -sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15° C. under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60° C. for 2 hours the... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HI | CN(C=O)C.C(C)(=O)OCC | 60 | 2 | CC(C)(C)NS(=O)(=O)c1cc[nH]c1.CI>CN(C=O)C.C(C)(=O)OCC>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a32d55e896f94ee09bb5a13e0797fb99 | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.ClC(=O)OC.Cl.C(CCC)[Li]>>CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | Cl[C:3]([O:2][CH3:1])=[O:4].[cH:5]1[c:6]([S:7](=[O:8])(=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][n:17]1[CH3:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([S:7](=[O:8])(=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][n:17]1[CH3:18] | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | null | [Au].[Au] | C1CCOC1 | C-C Coupling | Friedel-Crafts acylation | 5a20a43a2af69e0af226cfafc54d8480b0d90b850454abf46c572d6de72c336e | 25d9bd8621b941df428c033fedc648334f6dc6f4157dff30f33212e6bac7f1de | c1cc[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#16:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9](-[C;D1;H3:10]):[cH;D2;+0:11]:1>>[#16:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9](-[C;D1;H3:10]):[c;H0;D3;+0:11]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of I g (4.62 mol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 4.1 mL (9.48 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was st... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ester | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | HCl | [Au].[Au].C1CCOC1 | -78 | 0.5 | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>[Au].[Au].C1CCOC1>COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-476d1b77fb1f4defbab1a8181428d9b8 | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | Cl.CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.C(CCC)[Li].ClC(=O)OC>>CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | Cl[C:3]([O:2][CH3:1])=[O:4].[cH:5]1[c:6]([S:7](=[O:8])(=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][n:17]1[CH3:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([S:7](=[O:8])(=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][n:17]1[CH3:18] | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | null | [Au].[Au] | C1CCOC1 | C-C Coupling | Friedel-Crafts acylation | 5a20a43a2af69e0af226cfafc54d8480b0d90b850454abf46c572d6de72c336e | 25d9bd8621b941df428c033fedc648334f6dc6f4157dff30f33212e6bac7f1de | c1cc[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#16:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9](-[C;D1;H3:10]):[cH;D2;+0:11]:1>>[#16:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9](-[C;D1;H3:10]):[c;H0;D3;+0:11]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 55.9 | [{"value": 55.9, "product": "CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 5 g (23 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 20 mL (47.4 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ester | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | HCl | [Au].[Au].C1CCOC1 | -78 | 0.5 | COC(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>[Au].[Au].C1CCOC1>COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-740719404b1e4815a4a77e34574adcd7 | COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C>>COC(=O)c1c(S(N)(=O)=O)ccn1C | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC.FC(C(=O)O)(F)F>>NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | CC(C)(C)[NH:8][S:7]([c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:13]([CH3:14])[cH:12][cH:11]1)(=[O:9])=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11][cH:12][n:13]1[CH3:14] | COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | COC(=O)c1c(S(N)(=O)=O)ccn1C | null | [Au] | C(Cl)Cl | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1cc[nH]c1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | To a solution of 3.53 g of methyl 3-[[(1,1-dimethylethyl)amino]-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate in 40 mL, of methylene chloride under an nitrogen atmosphere was added 80 mL of trifluoroacetic acid (TFA). The gold solution was stirred at room temperature overnight ca. 16 hours. The gold solution was concentr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1c[nH]cc1 | Other | [Au].C(Cl)Cl | null | null | COC(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C>[Au].C(Cl)Cl>COC(=O)c1c(S(N)(=O)=O)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec291f168e3d4ab6bc17d0209ef33361 | CSSC.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C | Cl.C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CSSC>>CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)SC | CS[S:2][CH3:1].[cH:3]1[c:4]([S:5](=[O:6])(=[O:7])[NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14][n:15]1[CH3:16]>>[CH3:1][S:2][c:3]1[c:4]([S:5](=[O:6])(=[O:7])[NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14][n:15]1[CH3:16] | CSSC.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | ecf0720e800804680a16cf0e555235641ea38e58156d36aab76023a793ee6569 | 19099c5abc7af7f1b3d32ffaaaa6b84236f3e8c2bf9cb204008fe61bb9aa47e2 | c1cc[nH]c1 | C-S-[S;H0;D2;+0:1]-[C;D1;H3:2].[#16:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[cH;D2;+0:9]:1>>[#16:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c;H0;D3;+0:9]:1-[S;H0;D2;+0:1]-[C;D1;H3:2] | 58.8 | [{"value": 58.8, "product": "CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 25.52 mL (61.5 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Disulfide | Monosulfide | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | Other | C1CCOC1 | -78 | 0.5 | CSSC.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>C1CCOC1>CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee7d05a9975a483f9332d56b8ce092a7 | CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C>>CSc1c(S(N)(=O)=O)ccn1C | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)SC.FC(C(=O)O)(F)F>>CN1C(=C(C=C1)S(=O)(=O)N)SC | CC(C)(C)[NH:6][S:5]([c:4]1[c:3]([S:2][CH3:1])[n:11]([CH3:12])[cH:10][cH:9]1)(=[O:7])=[O:8]>>[CH3:1][S:2][c:3]1[c:4]([S:5]([NH2:6])(=[O:7])=[O:8])[cH:9][cH:10][n:11]1[CH3:12] | CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C | CSc1c(S(N)(=O)=O)ccn1C | null | null | C(Cl)Cl | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1cc[nH]c1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | 79.6 | [{"value": 79.6, "product": "CN1C(=C(C=C1)S(=O)(=O)N)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 4.63 g (17.66 mmol) N-(1,1-dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide in 50 mL of methylene chloride was added 50 mL of trifluoroacetic acid (TFA) under a nitrogen atmosphere. The orange reaction mixture was stirred at room temperature overnight ca. 16 hours. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1c[nH]cc1 | Other | C(Cl)Cl | null | 16 | CSc1c(S(=O)(=O)NC(C)(C)C)ccn1C>C(Cl)Cl>CSc1c(S(N)(=O)=O)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d425205828e434aa8465064fdc60f2d | BrBr.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br | Cl.CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.C(CCC)[Li].BrBr>>BrC=1N(C=CC1S(=O)(=O)NC(C)(C)C)C | Br[Br:15].[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[Br:15] | BrBr.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br | null | null | C(C)OCC | Functional Group Interconversion | Bromination | ff11be9c465e8e0b713e91d635a470a31e4b520eecced5f40078ac699b959435 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cc[nH]c1 | Br-[Br;H0;D1;+0:1].[#16:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[cH;D2;+0:8]:1>>[#16:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c;H0;D3;+0:8]:1-[Br;H0;D1;+0:1] | 58.7 | [{"value": 58.7, "product": "BrC=1N(C=CC1S(=O)(=O)NC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | To a solution of 8.85 g (41 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 200 mL diethyl ether under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 36.0 mL (85 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | HBr | C(C)OCC | -78 | 0.25 | BrBr.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>C(C)OCC>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-952e75b6acac43568991fc07fe11133a | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br>>Cn1ccc(S(N)(=O)=O)c1Br | BrC=1N(C=CC1S(=O)(=O)NC(C)(C)C)C.C(=O)(C(F)(F)F)O>>BrC=1N(C=CC1S(=O)(=O)N)C | CC(C)(C)[NH:7][S:6]([c:5]1[cH:4][cH:3][n:2]([CH3:1])[c:10]1[Br:11])(=[O:8])=[O:9]>>[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[c:10]1[Br:11] | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br | Cn1ccc(S(N)(=O)=O)c1Br | null | null | C(Cl)Cl | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1cc[nH]c1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | 21.4 | [{"value": 21.4, "product": "BrC=1N(C=CC1S(=O)(=O)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 7.11 g (24 mmol) of 2-bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 50 mL methylene chloride under a nitrogen atmosphere was added 50 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1c[nH]cc1 | Other | C(Cl)Cl | null | 16 | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1Br>C(Cl)Cl>Cn1ccc(S(N)(=O)=O)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1689ec83ac2b4e2e9bc10359a96a617b | CN(C)C=O.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O | CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CN(C=O)C.Cl>>CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C=O | CN(C)[CH:15]=[O:16].[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[CH:15]=[O:16] | CN(C)C=O.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | d9d66c0383111c39672c6f97615b03ec6c6d4177c1f7428c4be4b53020a617e2 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1cc[nH]c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#16:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[cH;D2;+0:9]:1>>[#16:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 39 | [{"value": 39.0, "product": "CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 12.96 g (60 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 52.35 mL (123 mmol) 2.35M n-butylithium in hexanes. The reaction was stirred at -78° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | Other | C1CCOC1 | -78 | 0.5 | CN(C)C=O.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>C1CCOC1>Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b75f1f1033143b794c5a9db7bc6a994 | CON.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O>>CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C | O.C(C)(=O)[O-].[Na+].Cl.CON.CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C=O>>CC(C)(C)NS(=O)(=O)C1=C(NC=C1)C=NOC | [CH3:1][O:2][NH2:3].C[n:6]1[c:5]([CH:4]=O)[c:9]([S:10](=[O:11])(=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:8][cH:7]1>>[CH3:1][O:2][N:3]=[CH:4][c:5]1[nH:6][cH:7][cH:8][c:9]1[S:10](=[O:11])(=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CON.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O | CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 6615c49504af75b4b6922f41afffb4a5b99652fa7cae8476b66064dff8f82dfd | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | c1cc[nH]c1 | C-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1-[CH;D2;+0:6]=O.[C;D1;H3:7]-[#8:8]-[NH2;D1;+0:9]>>[C;D1;H3:7]-[#8:8]-[N;H0;D2;+0:9]=[CH;D2;+0:6]-[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 96.2 | [{"value": 96.2, "product": "CC(C)(C)NS(=O)(=O)C1=C(NC=C1)C=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 3.91 g (46.8 mmol) of methoxyamine hydrochloride in 60 mL of methanol was added 3.84 g (46.8 mmol) of sodium acetate. After stirring the white suspension for ca. 15 minutes 5.72 g (23 mmol) of N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide was added in one portion. The white suspens... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | c1c[nH]cc1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | CO | null | null | CON.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1C=O>CO>CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d13730de7524a88a677102766469c81 | CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C>>CON=Cc1c(S(N)(=O)=O)ccn1C | CC(C)(C)NS(=O)(=O)C1=C(NC=C1)C=NOC.C(=O)(C(F)(F)F)O>>CON=CC=1N(C=CC1S(=O)(=O)N)C | C[C:14](C)(C)[NH:8][S:7]([c:6]1[c:5]([CH:4]=[N:3][O:2][CH3:1])[nH:13][cH:12][cH:11]1)(=[O:9])=[O:10]>>[CH3:1][O:2][N:3]=[CH:4][c:5]1[c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11][cH:12][n:13]1[CH3:14] | CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C | CON=Cc1c(S(N)(=O)=O)ccn1C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 20cc103add3cd1e006adea631b88681acfdc5c9577152885a8f7e1af33d45e2d | 28816b3b9482e4d163df59e58124d148a1ad8c4cd722815a1176060bd8f7cbeb | c1cc[nH]c1 | C-[C;H0;D4;+0:1](-C)(-C)-[NH;D2;+0:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1-[C:11]=[#7:12]>>[#7:12]=[C:11]-[c:10]1:[c:6](-[#16:3](-[NH2;D1;+0:2])(=[O;D1;H0:4])=[O;D1;H0:5]):[c:7]:[c:8]:[n;H0;D3;+0:9]:1-[CH3;D1;+0:1] | null | [] | null | null | 16 | HOUR | To a solution of 5.74 g (21.9 mmol) of N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide in 75 mL methylene chloride under a nitrogen atmosphere was add 75 mL of TFA. The clear orange reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The orange reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | Other | C(Cl)Cl | null | 16 | CON=Cc1[nH]ccc1S(=O)(=O)NC(C)(C)C>C(Cl)Cl>CON=Cc1c(S(N)(=O)=O)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-00887c12283747658f3f8ff3622cc7d7 | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1.O=S=O>>CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C | ClN1C(CCC1=O)=O.C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.O1CCCC1.S(=O)=O>>CC(C)(C)C=1C(=C(N(C1)C)S(=O)(=O)N(C)C)S(=O)(=O)N | [cH:7]1[c:8]([S:9]([NH:10][C:14]([CH3:15])([CH3:16])[CH3:17])(=[O:11])=[O:12])[cH:13][cH:18][n:19]1[CH3:20].[S:4](=[O:5])=[O:6]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][n:19]1[CH3:20] | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1.O=S=O | CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dd02c072c1999fa8686995b4042f04e221b8deebf71bf2d4552560d128d10b13 | 93bbbd43c2c285e6277a373ccd60ddc62a63bc9ef6f7404d9d43a73dd3e65412 | c1cc[nH]c1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12](-[C;D1;H3:13]):[cH;D2;+0:14]:1.[O;D1;H0:15]=[S;H0;D2;+0:16]=[O;D1;H0:17]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12](-[C;D1;H3:13]):... | null | [] | null | null | 1 | HOUR | A solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL of anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -78° C. The colorless reaction was treated with 61.5 mmol of 2.38M n-butyllithium in hexanes dropwise at such a rate as to keep the temperature b... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide.Tertiary amine | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | null | null | null | 1 | Cn1ccc(S(=O)(=O)NC(C)(C)C)c1.O=S=O>>CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bce13e6e0f2b4556bf712059577ecdcd | CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C>>CN(C)S(=O)(=O)c1c(S(N)(=O)=O)ccn1C | CC(C)(C)C=1C(=C(N(C1)C)S(=O)(=O)N(C)C)S(=O)(=O)N.C(=O)(C(F)(F)F)O>>CN(S(=O)(=O)C=1N(C=CC1S(=O)(=O)N)C)C | CC(C)(C)[c:13]1[c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[c:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[n:15]([CH3:16])[cH:14]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[cH:13][cH:14][n:15]1[CH3:16] | CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C | CN(C)S(=O)(=O)c1c(S(N)(=O)=O)ccn1C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | f537e285e05ca146260582b82dd7145f92fed17d878e360c64814f979252e9c0 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc[nH]c1 | C-C(-C)(-C)-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C;D1;H3:4]):[c:5](-[#16:6]):[c:7]:1-[#16:8]>>[#16:6]-[c:5]1:[#7;a:3](-[C;D1;H3:4]):[c:2]:[cH;D2;+0:1]:[c:7]:1-[#16:8] | null | [] | null | null | 16 | HOUR | To a solution of 6.95 g (21 mmol) of N3 -(1,1-dimethylethyl)-N2,N2,1-trimethyl-1H-pyrrole-2,3-disulfonamide in 75 mL of methylene chloride under a nitrogen atmosphere was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vac... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | Other | C(Cl)Cl | null | 16 | CN(C)S(=O)(=O)c1c(S(N)(=O)=O)c(C(C)(C)C)cn1C>C(Cl)Cl>CN(C)S(=O)(=O)c1c(S(N)(=O)=O)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-acf44331951a4df6acd00502ec327265 | CN(C)C(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>>CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | [Cl-].[NH4+].C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CN(C(=O)Cl)C.Cl>>CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[cH:6]1[c:7]([S:8](=[O:9])(=[O:10])[NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17][n:18]1[CH3:19]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[c:7]([S:8](=[O:9])(=[O:10])[NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17][n:18]1[CH3:19] | CN(C)C(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1 | CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts acylation | c62ead7f39f71b7724860484b46753891098edf9d1881789884a9b80b0963d93 | 5aa1746bf699ea29bafc1c026df78788a454dbf70414dd42e98cfe9c89871a23 | c1cc[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#16:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10](-[C;D1;H3:11]):[cH;D2;+0:12]:1>>[#16:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10](-[C;D1;H3:11]):[c;H0;D3;+0:12]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5] | 50.2 | [{"value": 50.2, "product": "CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -60° C., 25 mL (61.5 mmol) 2.46M n-butyllithium in hexanes. The reaction mixture was stirred at -78... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide | Tertiary amide | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1 | HCl | C1CCOC1 | -78 | 0.5 | CN(C)C(=O)Cl.Cn1ccc(S(=O)(=O)NC(C)(C)C)c1>C1CCOC1>CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d0fbf7c4db24ef2820d2d87a9754e6c | CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C>>CN(C)C(=O)c1c(S(N)(=O)=O)ccn1C | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C.C(=O)(C(F)(F)F)O>>NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C | CC(C)(C)[NH:9][S:8]([c:7]1[c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[n:14]([CH3:15])[cH:13][cH:12]1)(=[O:10])=[O:11]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[c:7]([S:8]([NH2:9])(=[O:10])=[O:11])[cH:12][cH:13][n:14]1[CH3:15] | CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C | CN(C)C(=O)c1c(S(N)(=O)=O)ccn1C | null | null | C(Cl)Cl | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1cc[nH]c1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | 92.9 | [{"value": 92.9, "product": "NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 5.63 g of 3-[[(1,1-dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide in 75 mL of methylene chloride was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1c[nH]cc1 | Other | C(Cl)Cl | null | 16 | CN(C)C(=O)c1c(S(=O)(=O)NC(C)(C)C)ccn1C>C(Cl)Cl>CN(C)C(=O)c1c(S(N)(=O)=O)ccn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66c80b7eb0654eda89cb0773db258c7f | CC(C)(C)N.Cn1cccc1.O=S=O>>Cn1cccc1S(=O)(=O)NC(C)(C)C | S(=O)=O.C(CCC)[Li].CN1C=CC=C1.C(C)(C)(C)N>>CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C | [NH2:10][C:11]([CH3:12])([CH3:13])[CH3:14].[CH3:1][n:2]1[cH:3][cH:4][cH:5][cH:6]1.[S:7](=[O:8])=[O:9]>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1[S:7](=[O:8])(=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14] | CC(C)(C)N.Cn1cccc1.O=S=O | Cn1cccc1S(=O)(=O)NC(C)(C)C | null | null | C1CCOC1 | Protection | OtherReaction | 7e3b061ab6a31649fa6a371fc4433b0fe652714813be2bfca8beb3fa97e8bfe0 | 95f9bec41996e1d6385bdfda8a285b8770de8952829289a8e8fac2bb61b0a5ce | c1cc[nH]c1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11].[O;D1;H0:12]=[S;H0;D2;+0:13]=[O;D1;H0:14]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH;D2;+0:11]-[S;H0;D4;+0:13](=[O;D1;H0:12])(=[O;D1;H0:14])-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[#7;a:2]:1-[C;D1;H3... | 28.5 | [{"value": 28.5, "product": "CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 10 g (0.12 mol) of N-methyl-pyrrole in 120 mL of anhydrous THF under nitrogen atmosphere was cooled to below -70° C. then treated with 56 mL of 2.4M n-butyllithium in hexanes (0.13 mol) dropwise at such a rate as to keep the temperature below -60° C. The resulting brown colored mixture was stirred for 16 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1 | null | C1CCOC1 | null | 16 | CC(C)(C)N.Cn1cccc1.O=S=O>C1CCOC1>Cn1cccc1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eaa9d1d720194b459594019c4118fe86 | COC(=O)Cl.Cn1cccc1S(=O)(=O)NC(C)(C)C>>COC(=O)c1ccn(C)c1S(=O)(=O)NC(C)(C)C | ClC(=O)OC.CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C.C(CCC)[Li]>>CC(C)(C)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C | Cl[C:3]([O:2][CH3:1])=[O:4].[cH:5]1[cH:6][cH:7][n:8]([CH3:9])[c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8]([CH3:9])[c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[CH3:18] | COC(=O)Cl.Cn1cccc1S(=O)(=O)NC(C)(C)C | COC(=O)c1ccn(C)c1S(=O)(=O)NC(C)(C)C | null | null | C1CCOC1.C(C)(=O)OCC | C-C Coupling | Friedel-Crafts acylation | 50a128be0ecdfa440a20704024d0efb90098e7c5cc7f1747307f8056462cd7b3 | 25d9bd8621b941df428c033fedc648334f6dc6f4157dff30f33212e6bac7f1de | c1cc[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#16:5]-[c:6]1:[cH;D2;+0:7]:[c:8]:[c:9]:[#7;a:10]:1-[C;D1;H3:11]>>[#16:5]-[c:6]1:[#7;a:10](-[C;D1;H3:11]):[c:9]:[c:8]:[c;H0;D3;+0:7]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 14.3 | [{"value": 14.3, "product": "CC(C)(C)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2.5 g (11.5 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-2-sulfonamide in 50 mL THF under nitrogen atmosphere cooled to below -70° C. was added dropwise 13 mL (32.5 mmol) of 2.5M n-butyllithium at such a rate as to keep the temperature below -58° C. After stirring at -20° C. to -10° C. for 30 min... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ester | c1ccc[nH]1 | c1c[nH]cc1 | c1c[nH]cc1 | HCl | C1CCOC1.C(C)(=O)OCC | null | 0.5 | COC(=O)Cl.Cn1cccc1S(=O)(=O)NC(C)(C)C>C1CCOC1.C(C)(=O)OCC>COC(=O)c1ccn(C)c1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5a19d2e3ccc4cb7bff13f06f043ffc0 | COC(=O)c1ccn(C)c1S(N)(=O)=O.COc1nc(C)nc(NC(=O)Oc2ccccc2)n1>>COC(=O)c1ccn(C)c1S(=O)(=O)NC(=O)NC1=NC(OC)=CN(C)N1 | Cl.NS(=O)(=O)C=1N(C=CC1C(=O)OC)C.COC1=NC(=NC(=N1)C)NC(OC1=CC=CC=C1)=O.C1CCC2=NCCCN2CC1>>COC=1N=C(NN(C1)C)NC(=O)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8]([CH3:9])[c:10]1[S:11](=[O:12])(=[O:13])[NH2:14].c1ccc(O[C:15](=[O:16])[NH:17][c:18]2[n:19][c:20]([O:21][CH3:22])[n:24][c:23]([CH3:25])[n:26]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8]([CH3:9])[c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][C:18]1... | COC(=O)c1ccn(C)c1S(N)(=O)=O.COc1nc(C)nc(NC(=O)Oc2ccccc2)n1 | COC(=O)c1ccn(C)c1S(=O)(=O)NC(=O)NC1=NC(OC)=CN(C)N1 | null | null | C(C)#N.O | Acylation | OtherReaction | f988767444e9fb806a783801e95d85a36d79f56e5189ed5c36171ed46c73d7c8 | d4aa065d3dd6b2eb9aa239fb936ebd84810693bbeac61ec007c62593188be20b | O=C(NC1=NC=CNN1)NS(=O)(=O)c1ccc[nH]1 | [#7;a:1]:[c:2]-[#16:3](-[NH2;D1;+0:4])(=[O;D1;H0:5])=[O;D1;H0:6].[C;D1;H3:7]-[#8:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[#7:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-c2:c:c:c:c:c:2):[n;H0;D2;+0:15]:[c;H0;D3;+0:16](-[CH3;D1;+0:17]):[n;H0;D2;+0:18]:1>>[#7;a:1]:[c:2]-[#16:3](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:4... | null | [] | null | null | 30 | MINUTE | Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate were combined in 2 mL of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Ether.Ether | Enamine.Sulfonamide.Hydrazine.Ether.Urea | c1ccccc1.c1ncncn1 | C1=C[NH]NC=N1 | c1c[nH]cc1.C1=C[NH]NC=N1 | HO- | C(C)#N.O | null | 0.5 | COC(=O)c1ccn(C)c1S(N)(=O)=O.COc1nc(C)nc(NC(=O)Oc2ccccc2)n1>C(C)#N.O>COC(=O)c1ccn(C)c1S(=O)(=O)NC(=O)NC1=NC(OC)=CN(C)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-819df65591774363bb9b76f5effae47b | CC(=O)c1c(F)cccc1F.Nc1ncccc1C=O>>Fc1cccc(F)c1-c1ccc2cccnc2n1 | NC1=C(C=O)C=CC=N1.CC(=O)C1=C(C=CC=C1F)F.[OH-].[K+]>>FC1=C(C(=CC=C1)F)C1=NC2=NC=CC=C2C=C1 | O=[C:9]([c:8]1[c:2]([F:1])[cH:3][cH:4][cH:5][c:6]1[F:7])[CH3:10].O=[CH:11][c:12]1[cH:13][cH:14][cH:15][n:16][c:17]1[NH2:18]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1-[c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[n:18]1 | CC(=O)c1c(F)cccc1F.Nc1ncccc1C=O | Fc1cccc(F)c1-c1ccc2cccnc2n1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 3936808456ac378e4397a3dafa777312a8f9677e9b37312d1a52d94356865178 | 08667cf58f28cec17f3f2604bf85c92e5fab0f09949cef6990e380a70b99d0bf | c1ccc(-c2ccc3cccnc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3](:[c:4](-[F;D1;H0:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].O=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[#7;a:15]:[c:16]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:3](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13](:[#7;a:15]:[c:16]):[n;H0;D2;+0:14]:1... | 79 | [{"value": 79.0, "product": "FC1=C(C(=CC=C1)F)C1=NC2=NC=CC=C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "FC1=C(C(=CC=C1)F)C1=NC2=NC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Aminonicotinaldehyde (2.44 g, 20 mmol) and 2,6-difluoroacetophenone (3.28 g, 21 mmol) are dissolved in 20 ml of MeOH. The mixture is treated dropwise with 3 ml of 40% KOH and, after the exothermic reaction has subsided, it is poured onto water and the residue which is deposited is filtered off with suction. 3.8 g (79... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine | null | c1ccncc1 | c1cnc2ncccc2c1 | c1ccccc1.c1cnc2ncccc2c1 | HO- | CO | null | null | CC(=O)c1c(F)cccc1F.Nc1ncccc1C=O>CO>Fc1cccc(F)c1-c1ccc2cccnc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6da8fccbc46d48d9b47085df7224e0c2 | CC(=O)c1nccs1.Nc1ncccc1C=O>>c1cnc2nc(-c3nccs3)ccc2c1 | NC1=C(C=O)C=CC=N1.C(C)(=O)C=1SC=CN1.[OH-].[K+]>>S1C(=NC=C1)C1=NC2=NC=CC=C2C=C1 | O=[C:6]([c:7]1[n:8][cH:9][cH:10][s:11]1)[CH3:12].O=[CH:13][c:14]1[c:4]([NH2:5])[n:3][cH:2][cH:1][cH:15]1>>[cH:1]1[cH:2][n:3][c:4]2[n:5][c:6](-[c:7]3[n:8][cH:9][cH:10][s:11]3)[cH:12][cH:13][c:14]2[cH:15]1 | CC(=O)c1nccs1.Nc1ncccc1C=O | c1cnc2nc(-c3nccs3)ccc2c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 3936808456ac378e4397a3dafa777312a8f9677e9b37312d1a52d94356865178 | 08667cf58f28cec17f3f2604bf85c92e5fab0f09949cef6990e380a70b99d0bf | c1cnc2nc(-c3nccs3)ccc2c1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1.O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]>>[c:10]:[c:9]1:[cH;D2;+0:8]:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:3]2:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:2):[n;H0;D2;+0:12]:[c:11]:1:[#7;a:13]:[c:14] | 46.5 | [{"value": 46.0, "product": "S1C(=NC=C1)C1=NC2=NC=CC=C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.5, "product": "S1C(=NC=C1)C1=NC2=NC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-Aminonicotinaldehyde (1.5 g, 12.3 mmol) and 2-acetylthiazole (1.64 g, 12.9 mmol) are dissolved in 12 ml of MeOH and the mixture is treated with 1.5 ml of 40% KOH. After 3 h, the reaction is complete and the mixture is poured onto water. The solid which is deposited is filtered off with suction, washed and dried. 1.22... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine | null | c1ccncc1 | c1cnc2ncccc2c1 | c1cnc2ncccc2c1.c1cscn1 | HO- | CO | null | 3 | CC(=O)c1nccs1.Nc1ncccc1C=O>CO>c1cnc2nc(-c3nccs3)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4fe7e7b0295444c08046dd75241f89c9 | C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12.NO>>CC(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=NO)C(=NO)C[C@]4(C)[C@H]3CC[C@]12C | ON=C1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)O)=O.NO.Cl.CC(=O)[O-].[Na+].O>>C(C)(=O)O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(C(C[C@]3(C)[C@H]1CC2)=NO)=NO | O=[C:14]1[CH2:13][C@@H:12]2[CH2:11][CH2:10][C@H:9]3[C@@H:8]4[CH2:7][CH2:6][C@H:5]([OH:4])[C@@:26]4([CH3:27])[CH2:25][CH2:24][C@@H:23]3[C@@:21]2([CH3:22])[CH2:20][C:17]1=[N:18][OH:19].[NH2:15][OH:16]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@H:8]2[C@@H:9]3[CH2:10][CH2:11][C@H:12]4[CH2:13][C:14](=[N:15][OH:16])[... | C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12.NO | CC(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=NO)C(=NO)C[C@]4(C)[C@H]3CC[C@]12C | null | null | O | Acylation | OtherReaction | b4a23b040d618e2b4c65b8ca220b611623f5b0d1aab9edd43720ddfd6dc65183 | 11bb0537b70e084630323c94e955c7bfcb0b78dbd257b5953e091be00486ff45 | N=C1CC2[C@@H](CC[C@H]3[C@@H]4CCCC4CC[C@H]23)CC1=N | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[#7:5]-[O;D1;H1:6])-[C:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11].[NH2;D1;+0:12]-[O;D1;H1:13]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[C:14](-[C;D1;H3:15])=[O;D1;H0:16])-[C:11].[C:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[O;D1;H1:13])-[C:4](=[#7:5]-[O;D1;H1:6])-[C:7] | null | [] | null | null | null | null | A suspension of steroid 7, NH2OH.HCl and NaOAc/H2O was refluxed for 20 minutes. The reaction was cooled to room temperature and poured into H2O. The precipitate was collected by filtration. The resulting solid 8 was washed with H2O and air and dried; wt. 23.4 g.
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Primary amine | Ester.Oxime | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | null | O | null | null | C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12.NO>O>CC(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=NO)C(=NO)C[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c0049ffd5bd4c2597bd8dc1da4f9125 | N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-].Sc1ccccc1>>N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C#N)C(=CC=C1)[N+](=O)[O-].C1(=CC=CC=C1)S.C(=O)([O-])[O-].[K+].[K+].N1=CC=CC=C1>>[N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1 | O=[N+]([O-])[c:4]1[c:3]([C:2]#[N:1])[c:15]([N+:16](=[O:17])[O-:18])[cH:14][cH:13][cH:12]1.[SH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[N:1]#[C:2][c:3]1[c:4]([S:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13][cH:14][c:15]1[N+:16](=[O:17])[O-:18] | N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-].Sc1ccccc1 | N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-] | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | OtherReaction | a4feeb0224c95b591ffae5f38900a0e1c2efd3e17e75ff223366faab4cc7a260 | 124c5e2fa17ef87ad2270619dfa07e40ca83ae69e72cfb81a511ef39c15c3695 | c1ccc(Sc2ccccc2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:2]:[c:3] | 89 | [{"value": 89.0, "product": "[N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "[N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | An ice water bath-cooled mixture of 2.0 g (0.01 mol) of 2,6-dinitrobenzonitrile (Lancaster Synthesis, Inc., Windham, N.H. 03087), 1.06 ml (0.01 mol) of thiophenol, and 1.44 g (0.01 mol) of anhydrous K2CO3 in 50 mL of DMF was stirred for 0.5 h. Pyridine was added to the reaction mixture until it became basic, and was fo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic thiol | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.O | null | 0.5 | N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-].Sc1ccccc1>CN(C)C=O.O>N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d850da0197e245649bff3ba3999f661f | N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-]>>N#Cc1c(N)cccc1Sc1ccccc1 | O.[N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1.Cl[Sn]Cl>>NC1=C(C#N)C(=CC=C1)SC1=CC=CC=C1 | O=[N+:5]([O-])[c:4]1[c:3]([C:2]#[N:1])[c:9]([S:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:8][cH:7][cH:6]1>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][cH:8][c:9]1[S:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-] | N#Cc1c(N)cccc1Sc1ccccc1 | null | null | COCCOCCOC.Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Sc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a water bath-cooled solution of 3.9 g (0.015 mol) of 2-nitro-6-(phenylthio)benzonitrile (Example 1) in 85 mL of diglyme was added dropwise, with stirring, 11.53 g (0.045 mol) of SnCl2.2H2 O in 35 mL of conc. HCl. The water bath was removed, and the reaction was stirred at room temperature for 0.5 h. This reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | COCCOCCOC.Cl | null | null | N#Cc1c(Sc2ccccc2)cccc1[N+](=O)[O-]>COCCOCCOC.Cl>N#Cc1c(N)cccc1Sc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-942c876021324f25bb9887685a674993 | Cc1cc(C)cc(S)c1.N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-]>>Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1 | O.[N+](=O)([O-])C1=C(C#N)C(=CC=C1)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+].CC=1C=C(C=C(C1)C)S>>CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([SH:8])[cH:20]1.O=[N+]([O-])[c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]1[C:18]#[N:19]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8][c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]2[C:18]#[N:19])[cH:20]1 | Cc1cc(C)cc(S)c1.N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-] | Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a4feeb0224c95b591ffae5f38900a0e1c2efd3e17e75ff223366faab4cc7a260 | 124c5e2fa17ef87ad2270619dfa07e40ca83ae69e72cfb81a511ef39c15c3695 | c1ccc(Sc2ccccc2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:2]:[c:3] | 73,011.2 | [{"value": 80.0, "product": "CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73011.2, "product": "CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was pour... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic thiol | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 0 | null | Cc1cc(C)cc(S)c1.N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-]>CN(C)C=O>Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8c04216a28bb4609b9208e0d1a14c091 | Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1>>Cc1cc(C)cc(Sc2cccc(N)c2C#N)c1 | CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-].[OH-].[Na+]>>NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)C)C | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][cH:10][c:9]([S:8][c:7]2[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:18]2)[c:15]1[C:16]#[N:17]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:15]2[C:16]#[N:17])[cH:18]1 | Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1 | Cc1cc(C)cc(Sc2cccc(N)c2C#N)c1 | null | null | COCCOCCOC.O.Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Sc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": "NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrile (Example 5) (1.0 g, 0.0035 mol) was dissolved in 50 ml of diglyme. A solution of stannous chloride-2H2O (3.16 g, 0.014 mol) in 15 ml of concentrated HCl was added dropwise with stirring. After stirring 1 h and 15 min, the reaction mixture was poured into a solution of 12... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | COCCOCCOC.O.Cl | null | null | Cc1cc(C)cc(Sc2cccc([N+](=O)[O-])c2C#N)c1>COCCOCCOC.O.Cl>Cc1cc(C)cc(Sc2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a610715a9a2049339b2b5008fb407eed | COc1cccc(Sc2cccc(F)c2C#N)c1.O=C(OO)c1cccc(Cl)c1.O=C(OO)c1cccc(Cl)c1>>COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1 | ClC1=CC(=CC=C1)C(=O)OO.S([O-])(O)=O.[Na+].O.FC1=C(C#N)C(=CC=C1)SC1=CC(=CC=C1)OC.ClC1=CC(=CC=C1)C(=O)OO>>FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8][c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]#[N:19])[cH:20]1.O=C(O[OH:10])c1cccc(Cl)c1.OOC(c1cccc(Cl)c1)=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]#[N:19])[cH:20]1 | COc1cccc(Sc2cccc(F)c2C#N)c1.O=C(OO)c1cccc(Cl)c1.O=C(OO)c1cccc(Cl)c1 | COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1 | null | null | null | Oxidation | OtherReaction | fa9379080be52796ca8aad2066720360879b6743ff6ce008e4ef793c8196487b | 00d01750cba21c0937a6facb86295b3305f6895167f97bd162720af7670b1a25 | O=S(=O)(c1ccccc1)c1ccccc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:2])-O-O):c:1.[c:3]:[c:4](-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:9]>>[O;H0;D1;+0:1]=[S;H0;D4;+0:5](=[O;H0;D1;+0:2])(-[c:4](:[c:3]):[c:9])-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | To a solution of 2 g (7.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile (Example 13) was added 2.93 g (17 mmol) of m-chloroperbenzoic acid. The resultant mixture was stirred for 24 h. Additional 0.29 g of m-chloroperbenzoic acid was added and the resultant mixture was stirred for 15 min. Excess sodium bisulfi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Peroxide.Peroxide.Monosulfide | Sulfone | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1cccc(Sc2cccc(F)c2C#N)c1.O=C(OO)c1cccc(Cl)c1.O=C(OO)c1cccc(Cl)c1>>COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70d2fe8819214856a573963ea6b87bb1 | COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1.[NH4+]>>COc1cccc(S(=O)(=O)c2cccc(N)c2C#N)c1 | FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC.[NH4+].[OH-]>>NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC | F[c:15]1[cH:14][cH:13][cH:12][c:11]([S:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]2)(=[O:9])=[O:10])[c:17]1[C:18]#[N:19].[NH4+:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([NH2:16])[c:17]2[C:18]#[N:19])[cH:20]1 | COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1.[NH4+] | COc1cccc(S(=O)(=O)c2cccc(N)c2C#N)c1 | null | null | CO.CCO | Functional Group Interconversion | OtherReaction | 0b3f36c6e96a844ac8c671a85ab317446ee29bfa735a32d39184f4616cac3a55 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | O=S(=O)(c1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH4+;D0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | null | [] | 130 | CELSIUS | null | null | To a solution of 0.7 g (2.4 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile (Example 14) in 110 ml of MeOH/EtOH (7:4) was added 20 mL of concentrated NH4OH, This mixture was sealed in a glass-lined bomb and heated at 130° C. for 3 h. After solvent removal, the resultant concentrate was purified by flash col... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CO.CCO | 130 | null | COc1cccc(S(=O)(=O)c2cccc(F)c2C#N)c1.[NH4+]>CO.CCO>COc1cccc(S(=O)(=O)c2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f52f628e55bf48349560d5f7350120df | COc1cccc(Sc2cccc(F)c2C#N)c1>>COc1cccc(S(=O)c2cccc(F)c2C#N)c1 | ClC1=CC(=CC=C1)C(=O)OO.S([O-])(O)=O.[Na+].FC1=C(C#N)C(=CC=C1)SC1=CC(=CC=C1)OC.ClC1=CC(=CC=C1)C(=O)OO>>FC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]#[N:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]#[N:18])[cH:19]1 | COc1cccc(Sc2cccc(F)c2C#N)c1 | COc1cccc(S(=O)c2cccc(F)c2C#N)c1 | null | null | O | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]):[c:7]>>[O;D1;H0:8]=[S;H0;D3;+0:3](-[c:2](:[c:1]):[c:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | To a solution of 2 g (7.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile (Example 13) was added portionwise 1.6 g (9.3 mmol) of m-chloroperbenzoic acid. The resultant mixture was stirred for 24 h. Additional 0.16 g of m-chloroperbenzoic acid was added and the resultant mixture was stirred for 15 min. Excess so... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1 | null | O | null | null | COc1cccc(Sc2cccc(F)c2C#N)c1>O>COc1cccc(S(=O)c2cccc(F)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-efbec65196ea4c25a91fe4f5f0f30b06 | COc1cccc(S(=O)c2cccc(F)c2C#N)c1.[NH4+]>>COc1cccc(S(=O)c2cccc(N)c2C#N)c1 | FC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC.[NH4+].[OH-]>>NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC | F[c:14]1[cH:13][cH:12][cH:11][c:10]([S:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]2)=[O:9])[c:16]1[C:17]#[N:18].[NH4+:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([S:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[c:16]2[C:17]#[N:18])[cH:19]1 | COc1cccc(S(=O)c2cccc(F)c2C#N)c1.[NH4+] | COc1cccc(S(=O)c2cccc(N)c2C#N)c1 | null | null | CO.CCO | Functional Group Interconversion | OtherReaction | 0b3f36c6e96a844ac8c671a85ab317446ee29bfa735a32d39184f4616cac3a55 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | O=S(c1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH4+;D0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | null | [] | 130 | CELSIUS | null | null | To a solution of 0.73 g (2.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile (Example 16) in 65 ml of MeOH/EtOH (2.5:4) was added 20 mL of concentrated NH4OH. This mixture was sealed in a glass-lined bomb and heated at 130° C. for 3 h. After solvent removal, the resultant concentrate was purified by flash c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CO.CCO | 130 | null | COc1cccc(S(=O)c2cccc(F)c2C#N)c1.[NH4+]>CO.CCO>COc1cccc(S(=O)c2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ddfb59c25f34fe781aa3d4f78fc3efa | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1>>Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1 | CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F.OOS(=O)[O-].[K+]>>CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]#[N:18])[cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]#[N:18])[cH:19]1 | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1 | Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1 | null | null | CO.O | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]):[c:7]>>[O;D1;H0:8]=[S;H0;D3;+0:3](-[c:2](:[c:1]):[c:7])-[c:4](:[c:5]):[c:6] | 47 | [{"value": 47.0, "product": "CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile (Example 18) (1.0 g, 3.9 mmol) was dissolved in 100 ml of methanol. A solution of OXONE®.dagger. (2.63 g, 4.3 mmol) in 15 ml of water was added dropwise with stirring. After stirring 1.5 h, the solid was removed by vacuum filtration and washed with 3×50 ml of methanol. ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1 | null | CO.O | null | null | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1>CO.O>Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a63765ce57f4be88697886cd8f75569 | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1>>Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1 | O.OOS(=O)[O-].[K+].CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F.OOS(=O)[O-].[K+]>>CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8][c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]#[N:19])[cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]#[N:19])[cH:20]1 | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1 | Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1 | null | null | CO | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S(=O)(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]):[c:7]>>[O;D1;H0:8]=[S;H0;D4;+0:3](=[O;D1;H0:9])(-[c:2](:[c:1]):[c:7])-[c:4](:[c:5]):[c:6] | 65 | [{"value": 65.0, "product": "CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile (Example 18) (1.0 g 3.9 mmol) was dissolved in 100 ml of methanol. A solution of OXONE®.dagger. (5.26 g, 8.6 mmol) in 30 ml of water was added dropwise with stirring. After stirring 1 h, another 1.5 equivalents of OXONE® (3.60 g 5.9 mmol) was added. The reaction was sti... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccccc1 | null | CO | null | null | Cc1cc(C)cc(Sc2cccc(F)c2C#N)c1>CO>Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba9711ed922e47f3840d3a080575bd49 | Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1.N>>Cc1cc(C)cc(S(=O)c2cccc(N)c2C#N)c1 | CCOC(=O)C.CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F.N>>NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC(=C1)C)C | F[c:14]1[cH:13][cH:12][cH:11][c:10]([S:8]([c:7]2[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:19]2)=[O:9])[c:16]1[C:17]#[N:18].[NH3:15]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[c:16]2[C:17]#[N:18])[cH:19]1 | Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1.N | Cc1cc(C)cc(S(=O)c2cccc(N)c2C#N)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | O=S(c1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH3;D0;+0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | 61 | [{"value": 61.0, "product": "NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.2, "product": "NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 2-[(3,5-Dimethylphenyl)sulfinyl]-6-fluorobenzonitrile (Example 19) (0.4 g, 1.5 mmol) was dissolved in 40 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to 150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CO | -78 | null | Cc1cc(C)cc(S(=O)c2cccc(F)c2C#N)c1.N>CO>Cc1cc(C)cc(S(=O)c2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5f73f3ea0a54afca47617c9e6b59c43 | Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N>>Cc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 | CCOC(=O)C.CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F.N>>NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)C)C | F[c:15]1[cH:14][cH:13][cH:12][c:11]([S:8]([c:7]2[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:20]2)(=[O:9])=[O:10])[c:17]1[C:18]#[N:19].[NH3:16]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([NH2:16])[c:17]2[C:18]#[N:19])[cH:20]1 | Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N | Cc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | O=S(=O)(c1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH3;D0;+0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | 57.5 | [{"value": 56.0, "product": "NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 24 | HOUR | 2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzonitrile (Example 20) (0.5 g 1.7 mmol) was dissolved in 80 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CO | -78 | 24 | Cc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N>CO>Cc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c9f5721435e410ba7c84870a32cbc44 | COc1cc(C)cc(Br)c1.N#Cc1c(F)cccc1F.[S]>>COc1cc(C)cc(Sc2cccc(F)c2C#N)c1 | FC1=C(C#N)C(=CC=C1)F.CS(=O)C.BrC=1C=C(C=C(C1)OC)C.[Li]C(C)CC.[S]>>FC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C | Br[c:8]1[cH:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[cH:19]1.F[c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]1[C:17]#[N:18].[S:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([S:9][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]#[N:18])[cH:19]1 | COc1cc(C)cc(Br)c1.N#Cc1c(F)cccc1F.[S] | COc1cc(C)cc(Sc2cccc(F)c2C#N)c1 | null | null | C1CCOC1.O.C(=O)=O.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d40080b381033c26189f34d56f4f0aa776c9f43bbed3a9779aed3a120ca17904 | 204c5e15c927a46727388dfb8648dd74e8e697ddbafa15dfb583665a12d53930 | c1ccc(Sc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].F-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10]#[N;D1;H0:11]):[c:12].[S;H0;D0;+0:13]>>[N;D1;H0:11]#[C:10]-[c:9](:[c:12]):[c;H0;D3;+0:6](-[S;H0;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | 20 | MINUTE | A solution of 1 g (0.005 mol) of 3-bromo-5-methoxytoluene in 10 mL of freshly distilled THF was cooled in dry ice/acetone and stirred under a N2 atmosphere. To this was added dropwise via a syringe 8.46 mL (0.011 mol) of sec-BuLi (1.3M in cyclohexane). The resultant mixture was stirred for 10 min after which 0.19 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | Monosulfide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C1CCOC1.O.C(=O)=O.CC(=O)C | null | 0.333333 | COc1cc(C)cc(Br)c1.N#Cc1c(F)cccc1F.[S]>C1CCOC1.O.C(=O)=O.CC(=O)C>COc1cc(C)cc(Sc2cccc(F)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a88c0d5212446d3b4c2d1662ded1557 | COc1cc(C)cc(Sc2cccc(F)c2C#N)c1.N>>COc1cc(C)cc(Sc2cccc(N)c2C#N)c1 | FC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C.N>>NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C | F[c:14]1[cH:13][cH:12][cH:11][c:10]([S:9][c:8]2[cH:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[cH:19]2)[c:16]1[C:17]#[N:18].[NH3:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([S:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[c:16]2[C:17]#[N:18])[cH:19]1 | COc1cc(C)cc(Sc2cccc(F)c2C#N)c1.N | COc1cc(C)cc(Sc2cccc(N)c2C#N)c1 | null | null | C(C)O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(Sc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH3;D0;+0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | null | [] | 145 | CELSIUS | null | null | A solution of 0.1 g (0.00037 mol) of 2-fluoro-6-[(3-methyl-5-methoxyphenyl)thio]benzonitrile (Example 23) in 10 mL of absolute ethanol and ca. 2 mL of THF was saturated with ammonia. The resultant solution was sealed in a glass-lined Parr bomb and heated to 145° C. for 48 h. The solvent was removed in vacuo. 20 mL of 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C(C)O.C1CCOC1 | 145 | null | COc1cc(C)cc(Sc2cccc(F)c2C#N)c1.N>C(C)O.C1CCOC1>COc1cc(C)cc(Sc2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b52dd58a1564476b8012385c8b071efd | COc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N>>COc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 | FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)OC)C.N>>NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)OC)C | F[c:16]1[cH:15][cH:14][cH:13][c:12]([S:9]([c:8]2[cH:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[cH:21]2)(=[O:10])=[O:11])[c:18]1[C:19]#[N:20].[NH3:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[c:18]2[C:19]#[N:20])[cH:21]1 | COc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N | COc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 | null | null | C(C)O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | O=S(=O)(c1ccccc1)c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[NH3;D0;+0:8]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[NH2;D1;+0:8]):[c:2]:[c:3] | 34 | [{"value": 34.0, "product": "NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | A solution of 0.3 g (0.00098 mol) of 2-fluoro-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile (Example 25) in 10 mL of absolute ethanol and ca. 2 mL of THF was saturated with ammonia. The resultant solution was sealed in a glass-lined Parr bomb and heated to 130° C. for 4 h. The solvent was removed in vacuo. 20 mL o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C(C)O.C1CCOC1 | 130 | null | COc1cc(C)cc(S(=O)(=O)c2cccc(F)c2C#N)c1.N>C(C)O.C1CCOC1>COc1cc(C)cc(S(=O)(=O)c2cccc(N)c2C#N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-57d496f8cfa74e14b0b60ed9b08a5969 | CCC(N)C(=O)O.CCOCC.O=S(Cl)Cl>>CCOC(=O)C(N)CC.Cl | NC(C(=O)O)CC.S(=O)(Cl)Cl.C(C)OCC>>Cl.NC(C(=O)OCC)CC | [OH:3][C:4](=[O:5])[CH:6]([NH2:7])[CH2:8][CH3:9].CCO[CH2:2][CH3:1].O=S(Cl)[Cl:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH2:7])[CH2:8][CH3:9].[ClH:10] | CCC(N)C(=O)O.CCOCC.O=S(Cl)Cl | CCOC(=O)C(N)CC.Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 51b8a6656c0a2b883c9ef3d6e10f16e7a23403a54025d10a356d536fd60cd751 | c9da2d501363e26e3362b4d92445c316ae4db0a7128a4caa823650c7a4fa5893 | null | C-C-O-[CH2;D2;+0:1]-[C;D1;H3:2].Cl-S(=O)-[Cl;H0;D1;+0:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C;D1;H3:2].[ClH;D0;+0:3] | null | [] | 0 | CELSIUS | 8 | HOUR | A slurry of 2-aminobutyric acid (100 g, Aldrich) in absolute ethanol (300 ml) was stirred under nitrogen at 0° C. and thionyl chloride (120.8 g) was added dropwise. The reaction was stirred overnight at 0° C. and then gradually warmed to room temperature. The resulting white slurry was heated under reflux for 3 hours, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester | null | null | null | HCl | C(C)O | 0 | 8 | CCC(N)C(=O)O.CCOCC.O=S(Cl)Cl>C(C)O>CCOC(=O)C(N)CC.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-968da5d345074707bd8ae7f036b4987e | CCOC(=O)C(N)CC.O=Cc1ccccc1>>CCOC(=O)C(CC)N=Cc1ccccc1 | C(C1=CC=CC=C1)=O.Cl.NC(C(=O)OCC)CC.S(=O)(=O)([O-])[O-].[Mg+2].C(C)N(CC)CC>>C(C1=CC=CC=C1)=NC(C(=O)OCC)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH3:8])[NH2:9].O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH3:8])[N:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CCOC(=O)C(N)CC.O=Cc1ccccc1 | CCOC(=O)C(CC)N=Cc1ccccc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH2;D1;+0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[N;H0;D2;+0:11]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 88.9 | [{"value": 88.9, "product": "C(C1=CC=CC=C1)=NC(C(=O)OCC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of the product from step (a) (149.6 g), magnesium sulphate (74.3 g), and triethylamine (246 ml) in dichloromethane (1500 ml) was stirred at room temperature under nitrogen and benzaldehyde (94.9 g, Aldrich) was added dropwise. The mixture was stirred at room temperature for 3 hours then filtered. The filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1ccccc1 | HO- | ClCCl | null | 3 | CCOC(=O)C(N)CC.O=Cc1ccccc1>ClCCl>CCOC(=O)C(CC)N=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8bc8a5b260b5493c8773ed6d142bea7c | CC=CCC(N)(CC)C(=O)OCC>>CC=CCC(N)(CC)CO | [OH-].[Na+].NC(C(=O)OCC)(CC=CC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NC(CO)(CC=CC)CC | CCO[C:9]([C:5]([CH2:4][CH:3]=[CH:2][CH3:1])([NH2:6])[CH2:7][CH3:8])=[O:10]>>[CH3:1][CH:2]=[CH:3][CH2:4][C:5]([NH2:6])([CH2:7][CH3:8])[CH2:9][OH:10] | CC=CCC(N)(CC)C(=O)OCC | CC=CCC(N)(CC)CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[N;D1;H2:5])-[C:6]-[C:7]=[C:8]>>[C:8]=[C:7]-[C:6]-[C:3](-[C:4])(-[N;D1;H2:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 32.5 | [{"value": 32.5, "product": "NC(CO)(CC=CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of the product from step (d) (116.7 g) in THF (100 ml) was added to a 1M solution of lithium aluminium hydride in THF (800 ml) at about 0° C. When addition was complete, the mixture was stirred overnight at room temperature, then 50% w/v aqu. NaOH (200 ml) was added. The organic phase was separated, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | HO- | C1CCOC1 | null | 8 | CC=CCC(N)(CC)C(=O)OCC>C1CCOC1>CC=CCC(N)(CC)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-031db419b85e49eb8266022d09028e45 | CC=CCC(N)(CC)CO>>CC=CCC1(CC)CN1 | ClS(=O)(=O)O.NC(CO)(CC=CC)CC>>C(C=CC)C1(NC1)CC | O[CH2:8][C:5]([CH2:4][CH:3]=[CH:2][CH3:1])([CH2:6][CH3:7])[NH2:9]>>[CH3:1][CH:2]=[CH:3][CH2:4][C:5]1([CH2:6][CH3:7])[CH2:8][NH:9]1 | CC=CCC(N)(CC)CO | CC=CCC1(CC)CN1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2f512f4c744a197f9864da73637475e2ab4d1fc6062fe9117a472495e3ed9f33 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | C1CN1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[NH2;D1;+0:4])-[C:5]-[C:6]=[C:7]>>[C:7]=[C:6]-[C:5]-[C:2]1(-[C:3])-[CH2;D2;+0:1]-[NH;D2;+0:4]-1 | 57 | [{"value": 57.0, "product": "C(C=CC)C1(NC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Chlorosulphonic acid (18 mL) was added to a solution of the product from step (e) (32.3 g) in acetonitrile (100 ml) at least 9° C. When addition was complete, the mixture was warmed to room temperature. The resulting crystals were filtered off, washed with acetonitrile/pet. ether, dried, taken up in a mixture of 50% w/... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | C1CN1 | C1CN1 | HO- | C(C)#N | null | null | CC=CCC(N)(CC)CO>C(C)#N>CC=CCC1(CC)CN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70a686d8594848a0be625406e5a5cefa | CCC(N)(CO)CO.CCO>>CCN1C(=O)OCC1CO | NC(CO)(CO)CC.C(OCC)(OCC)=O.CCO>>C(C)N1C(OCC1CO)=O | C[CH2:7][C:8](CO)([NH2:3])[CH2:9][OH:10].O[CH2:2][CH3:1]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[O:6][CH2:7][CH:8]1[CH2:9][OH:10] | CCC(N)(CO)CO.CCO | CCN1C(=O)OCC1CO | null | C[O-].[Na+] | null | Heteroatom Alkylation and Arylation | OtherReaction | 121a8d904936bec16350b8eebf12af85b76bb2c1f851c4c39d775e2c2fc4c968 | 70fae35b1445ca2d187982b205c3f1487be400228313b6151d1080f84e72b95e | O=C1NCCO1 | C-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[NH2;D1;+0:3])(-C-O)-[C:4]-[O;D1;H1:5].O-[CH2;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:7]-[CH2;D2;+0:6]-[N;H0;D3;+0:3]1-[C:8](=[O;D1;H0:9])-[#8:10]-[CH2;D2;+0:1]-[CH;D3;+0:2]-1-[C:4]-[O;D1;H1:5] | null | [] | null | null | null | null | Sodium methoxide (2.2 g, Aldrich) was added to a solution of 2-amino-2-ethyl-1,3-propanediol (100.0 g, Aldrich) and diethyl carbonate (169.0 g, Aldrich) This solution was refluxed in a Dean Stark apparatus until no more EtOH was collected. The reaction mixture was cooled, added acetone (200 ml) and allowed to stand ove... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Primary amine | Carbamic ester.Ether | null | C1COC[NH]1 | C1COC[NH]1 | HO- | C[O-].[Na+] | null | null | CCC(N)(CO)CO.CCO>C[O-].[Na+]>CCN1C(=O)OCC1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-85a305aeebfc4263a0d5dfa4da2ff2f2 | CCN1C(=O)OCC1CO.Cc1ccc(S(=O)(=O)Cl)cc1>>CCC1(COS(=O)(=O)c2ccc(C)cc2)COC(=O)N1 | Cl.N1=CC=CC=C1.S(=O)(=O)(C1=CC=C(C)C=C1)Cl.C(C)N1C(OCC1CO)=O>>C(C)C1(NC(OC1)=O)COS(=O)(=O)C1=CC=C(C)C=C1 | [CH3:1][CH2:2][N:20]1[CH:3]([CH2:4][OH:5])[CH2:16][O:17][C:18]1=[O:19].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][C:3]1([CH2:4][O:5][S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]2)[CH2:16][O:17][C:18](=[O:19])[NH:20]1 | CCN1C(=O)OCC1CO.Cc1ccc(S(=O)(=O)Cl)cc1 | CCC1(COS(=O)(=O)c2ccc(C)cc2)COC(=O)N1 | null | null | [Cl-].[Na+].O | Acylation | OtherReaction | 2e658918820e0aff0c94124acfe4b050c7bb3a642a4c42bb6e5512913bf1e286 | 7b9c64df079876ee957c060f58afdc2308aed15454df820ab7c4cc2d6b7661b2 | O=C1NC(COS(=O)(=O)c2ccccc2)CO1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[CH2;D2;+0:8]-[N;H0;D3;+0:9]1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]-[CH;D3;+0:14]-1-[C:15]-[OH;D1;+0:16]>>[C;D1;H3:7]-[CH2;D2;+0:8]-[C;H0;D4;+0:14]1(-[C:15]-[O;H0;D2;+0:16]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:13]... | null | [] | null | null | 6 | HOUR | Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a sol... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Carbamic ester.Primary alcohol.Sulfonyl halide | Tosylate.Carbamic ester | C1COC[NH]1 | C1COCN1 | c1ccccc1.C1COCN1 | HCl | [Cl-].[Na+].O | null | 6 | CCN1C(=O)OCC1CO.Cc1ccc(S(=O)(=O)Cl)cc1>[Cl-].[Na+].O>CCC1(COS(=O)(=O)c2ccc(C)cc2)COC(=O)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05670d53f7f64813b11aec885e767cda | FC(F)(F)CCI.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>FC(F)(F)CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[I-] | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.FC(CCI)(F)F>>[I-].FC(CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F | [F:1][C:2]([F:3])([F:4])[CH2:5][CH2:6][I:26].[P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[F:1][C:2]([F:3])([F:4])[CH2:5][CH2:6][P+:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20... | FC(F)(F)CCI.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | FC(F)(F)CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc([PH+](c2ccccc2)c2ccccc2)cc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[CH2;D2;+0:6]-[I;H0;D1;+0:7].[c:8]:[c:9](-[P;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:14](:[c:15]):[c:16]):[c:17]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[CH2;D2;+0:6]-[P+;H0;D4:10](-[c:11](:[c:12]):[c:13])(-[c:14](:[c:15]):[c:16])-[c:9](:[c:8]):[c:17].[I... | 76.5 | [{"value": 76.5, "product": "[I-].FC(CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of triphenylphosphine (Aldrich, 11.7 g) and 3,3,3-trifluoropropyl iodid (Lancaster, 10 g) was vigorously refluxed in xylenes (75 mL) for 2 days. The solid which formed was filtered and washed with xylenes then air dried to yield a white solid (16.6 g). 1H NMR and elemental analysis are consistent with the pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)CCI.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>FC(F)(F)CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[I-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4b47970bbbd496493b0100b353ff70e | N#Cc1ccc(CBr)cc1.[N-]=[N+]=[N-]>>N#Cc1ccc(CN=[N+]=[N-])cc1 | [N-]=[N+]=[N-].[Na+].C(#N)C1=CC=C(CBr)C=C1>>C(#N)C1=CC=C(CN=[N+]=[N-])C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:12][cH:11]1.[N-:8]=[N+:9]=[N-:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]=[N+:9]=[N-:10])[cH:11][cH:12]1 | N#Cc1ccc(CBr)cc1.[N-]=[N+]=[N-] | N#Cc1ccc(CN=[N+]=[N-])cc1 | null | null | CN(C)C=O.C1(=CC=CC=C1)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 20.23 g (0.31 mol) sodium azide in 50 ml water was added to 49.15 g (251 mmol) 4-cyanobenzyl bromide in 200 ml DMF at ambient temperature. An exothermic reaction took place and after 1.5 h the reaction mixture was diluted with 200 ml toluene(caution: In order to avoid separation of potentially explosive a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1 | Br- | CN(C)C=O.C1(=CC=CC=C1)C.O | null | null | N#Cc1ccc(CBr)cc1.[N-]=[N+]=[N-]>CN(C)C=O.C1(=CC=CC=C1)C.O>N#Cc1ccc(CN=[N+]=[N-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8c0bae38a8294d0e9674fa88542622fe | O=C(Cl)OCc1ccccc1.[N-]=[N+]=NCc1ccc(C(=N)N)cc1>>[N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1 | ClC(=O)OCC1=CC=CC=C1.C(N)(=N)C1=CC=C(CN=[N+]=[N-])C=C1.C(C)N(CC)CC.Cl.ClC(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)NC(=N)C1=CC=C(CN=[N+]=[N-])C=C1 | Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[NH:10])[NH2:11])[cH:22][cH:23]1>>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[NH:10])[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][c... | O=C(Cl)OCc1ccccc1.[N-]=[N+]=NCc1ccc(C(=N)N)cc1 | [N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1 | null | null | C(Cl)Cl.O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | N=C(NC(=O)OCc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[N;D1;H1:5]=[C:6](-[NH2;D1;+0:7])-[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](=[N;D1;H1:5])-[c:8] | null | [] | null | null | 30 | MINUTE | The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an add... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl.O | null | 0.5 | O=C(Cl)OCc1ccccc1.[N-]=[N+]=NCc1ccc(C(=N)N)cc1>C(Cl)Cl.O>[N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91be128b9742407397cb2ab366a4130b | [N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1>>N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | 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.C(C1=CC=CC=C1)OC(=O)NC(=N)C1=CC=C(CN=[N+]=[N-])C=C1.C(C1=CC=CC=C1)OC(=O)NC(=N)C1=CC=C(CN=[N+]=[N-])C=C1.C(#N)C(C1=CC=CC=C1)Br>>NCC1=CC=C(C=C1)C(NC(=O)OCC1=CC=CC=C1)=N | [N-]=[N+]=[N:19][CH2:18][c:17]1[cH:16][cH:15][c:14]([C:2](=[NH:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:21][cH:20]1>>[NH:1]=[C:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([CH2:18][NH2:19])[cH:20][cH:21]1 | [N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1 | N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | null | null | C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | N=C(NC(=O)OCc1ccccc1)c1ccccc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | 26.3 g (100 mmol) triphenylphosphine was added at room temperature to the 4-(benzyloxycarbonylamidino) benzyl azide from (iii) above dissolved in 160 ml THF. After 16 h an additional 6.6 g (25 mmol) triphenylphosphine was added and the solution was allowed to stand for 4 h before removal of the solvent in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | [N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1>C1CCOC1>N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b5d6ed5aa3144caa92cff165e2d40f8 | CC(C)(C)OC(=O)NCC1CCNCC1.CSC(=N)NC(=O)OCc1ccccc1>>CC(C)(C)OC(=O)NCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 | C(C)(C)(C)OC(=O)NCC1CCNCC1.C(C1=CC=CC=C1)OC(=O)NC(SC)=N>>C(C)(C)(C)OC(=O)NCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][NH:13][CH2:27][CH2:28]1.CS[C:14](=[NH:15])[NH:16][C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:14](=[NH:15])[NH... | CC(C)(C)OC(=O)NCC1CCNCC1.CSC(=N)NC(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1b47623bd99949b4cf4f2fee4856128f888eea2f61ec86d31845b541c33c66e1 | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | N=C(NC(=O)OCc1ccccc1)N1CCCCC1 | C-S-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | 37 | [{"value": 37.0, "product": "C(C)(C)(C)OC(=O)NCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "C(C)(C)(C)OC(=O)NCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60°-70° C. for six hours and left at room temperature for two days. The solvent was evaporated and the residue was dissolved in C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | C(C)O | null | 48 | CC(C)(C)OC(=O)NCC1CCNCC1.CSC(=N)NC(=O)OCc1ccccc1>C(C)O>CC(C)(C)OC(=O)NCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38cb457f7729445685e412a4fffa8894 | CSC(=N)NC(=O)OCc1ccccc1.OCCC1CCNCC1>>N=C(NC(=O)OCc1ccccc1)N1CCC(CCO)CC1 | OCCC1CCNCC1.C(C1=CC=CC=C1)OC(=O)NC(SC)=N>>C(C1=CC=CC=C1)OC(=O)NC(=N)N1CCC(CC1)CCO | CS[C:2](=[NH:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[NH:14]1[CH2:15][CH2:16][CH:17]([CH2:18][CH2:19][OH:20])[CH2:21][CH2:22]1>>[NH:1]=[C:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[N:14]1[CH2:15][CH2:16][CH:17]([CH2:18][CH2:19][OH:20])[CH2:21][CH2:22... | CSC(=N)NC(=O)OCc1ccccc1.OCCC1CCNCC1 | N=C(NC(=O)OCc1ccccc1)N1CCC(CCO)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b47623bd99949b4cf4f2fee4856128f888eea2f61ec86d31845b541c33c66e1 | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | N=C(NC(=O)OCc1ccccc1)N1CCCCC1 | C-S-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | 41 | [{"value": 41.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CCC(CC1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.9, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CCC(CC1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6.2 g (0.028 mol) of 4-hydroxyethyl piperidine and 3.6 g (0.028 mol) of N-benzyloxycarbonyl-S-methyl isothiourea in 50 ml of acetonitrile was refluxed overnight. Evaporation and flash chromatography on silica gel with ethyl acetate gave 3.5 g (41%) of the title compound.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | C(C)#N | null | null | CSC(=N)NC(=O)OCc1ccccc1.OCCC1CCNCC1>C(C)#N>N=C(NC(=O)OCc1ccccc1)N1CCC(CCO)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d3631dc5ac684ec9b01dd5b9b7ce5987 | CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 | C(C1=CC=CC=C1)OC(=O)NC(=N)N1CCC(CC1)CCOS(=O)(=O)C.[N-]=[N+]=[N-].[Na+].O>>N(=[N+]=[N-])CCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N | CS(=O)(=O)O[CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[NH:11])[NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[NH:11])[NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19... | CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1.[N-]=[N+]=[N-] | [N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 341eb24906c58cd9cfdeec13febaf0724780d7854e6b6d7ec703218c4bcbe27b | 5f2cb2b9819a73a6855f5277f7fe9d5ce3871340baaebb59d42e38e1ca145c0a | N=C(NC(=O)OCc1ccccc1)N1CCCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[N-;H0;D1:4]=[#7;+:5]=[N;-;D1;H0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:4]=[#7;+:5]=[N;-;D1;H0:6] | null | [] | 100 | CELSIUS | null | null | In 100 ml of dimethylformamide was dissolve (0.0115 mol) of crude 1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine and 4.5 g (0.069 mol) of sodium azide was added. The mixture was heated at 100° C. for 2.5 h. It was then poured into water and extracted with ethyl acetate three times. The combined organic phase was... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Azide | null | null | C1CC[NH]CC1.c1ccccc1 | MsOH.HO- | CN(C=O)C | 100 | null | CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2080a877db5f4bf4b20e375ca34bad46 | [N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1>>N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)CC1 | Cl.[BH4-].[Na+].N(=[N+]=[N-])CCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N>>NCCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N | [N-]=[N+]=[N:20][CH2:19][CH2:18][CH:17]1[CH2:16][CH2:15][N:14]([C:2](=[NH:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:22][CH2:21]1>>[NH:1]=[C:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[N:14]1[CH2:15][CH2:16][CH:17]([CH2:18][CH2:19][NH2:20])[CH2:21][... | [N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1 | N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)CC1 | null | [Pd].[Pd] | O.O1CCCC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | N=C(NC(=O)OCc1ccccc1)N1CCCCC1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | null | [] | null | null | null | null | To 30 ml of water was added 0.40 g of 10% Pd/C. Sodium borohydride, 1.0 g (0.031 mol), was dissolved in 30 ml of water and was added carefully to the stirred and ice-cooled slurry of Pd/C and water. 4-Azidoethyl-1-benzyloxycarbonylamidino piperidine, 2.9 g (8.8 mmol), was dissolved in 80 ml of tetrahydrofurane and this... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | Other | [Pd].[Pd].O.O1CCCC1 | null | null | [N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1>[Pd].[Pd].O.O1CCCC1>N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66270614c8d046a8af9a342eb13c4b24 | COC(=N)NC(=O)OCc1ccccc1.OCC1CCNC1>>N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1 | OCC1CNCC1.C(C1=CC=CC=C1)OC(=O)NC(OC)=N>>C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CO | CO[C:2](=[NH:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[NH:14]1[CH2:15][CH2:16][CH:17]([CH2:18][OH:19])[CH2:20]1>>[NH:1]=[C:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[N:14]1[CH2:15][CH2:16][CH:17]([CH2:18][OH:19])[CH2:20]1 | COC(=N)NC(=O)OCc1ccccc1.OCC1CCNC1 | N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b0f97014035cf0d99b32a42bcb79ab87c0cd49b39ff30f05a7ff00b27a74c06 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | N=C(NC(=O)OCc1ccccc1)N1CCCC1 | C-O-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1 | 25.2 | [{"value": 25.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1.01 g (0.01 mole) (3RS)-3-hydroxymethyl pyrrolidine and 2.29 g (0.011 mole) N-benzyloxycarbonyl-O-methylisourea was dissolved (the amine not very soluble) in toluene and heated to 60° C. for three hours followed by stirring at room temperature over night. The mixture was evaporated and the 1H-NMR showed that the react... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | C1(=CC=CC=C1)C | 60 | null | COC(=N)NC(=O)OCc1ccccc1.OCC1CCNC1>C1(=CC=CC=C1)C>N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50d2591cf07947e7ab725904f4df96f4 | CS(=O)(=O)Cl.N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1>>CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 | CS(=O)(=O)Cl.C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CO.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[NH:12])[NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[NH:12])[NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20]... | CS(=O)(=O)Cl.N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1 | CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 | null | null | C(C)(=O)OCC.CCCCCCC.C(C)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | N=C(NC(=O)OCc1ccccc1)N1CCCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | 0.7 g (2.53 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethyl pyrrolidine and 0.70 ml (5.05 mmole) triethylamine was dissolved in 15 ml diethyl ether/CH2Cl2 1/1 and the mixture was cooled to 0° C. 0.25 ml (3.29 mmole) methanesulphonyl chloride in 3 ml diethyl ether was slowly added and the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1.c1ccccc1 | HCl | C(C)(=O)OCC.CCCCCCC.C(C)OCC | 0 | 3 | CS(=O)(=O)Cl.N=C(NC(=O)OCc1ccccc1)N1CCC(CO)C1>C(C)(=O)OCC.CCCCCCC.C(C)OCC>CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f9821df03a7466091a3423b9a248655 | CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C.[N-]=[N+]=[N-].[Na+].O>>C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CN=[N+]=[N-] | CS(=O)(=O)O[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:9](=[NH:10])[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:9](=[NH:10])[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)... | CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-] | [N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 341eb24906c58cd9cfdeec13febaf0724780d7854e6b6d7ec703218c4bcbe27b | 5f2cb2b9819a73a6855f5277f7fe9d5ce3871340baaebb59d42e38e1ca145c0a | N=C(NC(=O)OCc1ccccc1)N1CCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[N-;H0;D1:6]=[#7;+:7]=[N;-;D1;H0:8]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8])-[C:3] | 68.2 | [{"value": 68.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CN=[N+]=[N-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CN=[N+]=[N-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 0.450 g (1.27 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine and 0.124 g (1.9 mmole) of sodium azide were dissolved in 10 ml dimethylformamide and heated to 60° C. for four hours followed by stirring at room temperature over night. Water was added and the mixture was extracted twice with tolue... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Azide | null | null | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | CN(C=O)C | 60 | null | CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1537debbdfcd4c9fb2d97af472b6fc7c | O=S(Cl)Cl.OCC1CCN(Cc2ccccc2)C1>>ClCC1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)CO.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)N1CC(CC1)CCl | O=S(Cl)[Cl:1].O[CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1>>[Cl:1][CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1 | O=S(Cl)Cl.OCC1CCN(Cc2ccccc2)C1 | ClCC1CCN(Cc2ccccc2)C1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(CN2CCCC2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C:4])-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1])-[C:4] | null | [] | null | null | 1 | HOUR | To a refluxing solution of 15.3 g (0.08 mole) (3RS)-1-benzyl-3-hydroxymethyl pyrrolidine in 220 ml CHCl3 was slowly added a solution of 330 ml thionyl chloride in 60 ml CHCl3, and the reflux was continued for one hour. The mixture was evaporated and the residue was dissolved in water.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | C1CC[NH]C1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 1 | O=S(Cl)Cl.OCC1CCN(Cc2ccccc2)C1>C(Cl)(Cl)Cl>ClCC1CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-56818a6d757b4766865fa51ce27de994 | ClCC1CCN(Cc2ccccc2)C1.[C-]#N>>N#CCC1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)CCl.[C-]#N.[Na+].O>>C(C1=CC=CC=C1)N1CC(CC1)CC#N | Cl[CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | ClCC1CCN(Cc2ccccc2)C1.[C-]#N | N#CCC1CCN(Cc2ccccc2)C1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(CN2CCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[C-;H0;D1:6]#[N;D1;H0:7]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[C;H0;D2;+0:6]#[N;D1;H0:7])-[C:3] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)N1CC(CC1)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "C(C1=CC=CC=C1)N1CC(CC1)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | DAY | 16.8 g (0.08 mole) (3RS)-1-benzyl-3-chloromethyl pyrrolidine and 5.88 g (0.12 mole) of sodium cyanide was dissolved in 250 ml dimethyl sulfoxide. The mixture was stirred at 60° C. for two days and at room temperature for one week. Water was added and the mixture was extracted three times with ethyl acetate. The combine... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | C1CC[NH]C1.c1ccccc1 | Other | CS(=O)C | 60 | 48 | ClCC1CCN(Cc2ccccc2)C1.[C-]#N>CS(=O)C>N#CCC1CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-355bf43961874334b0dd644d901cbbcf | N#CCC1CCN(Cc2ccccc2)C1>>NCCC1CCN(Cc2ccccc2)C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O.C(C1=CC=CC=C1)N1CC(CC1)CC#N>>C(C1=CC=CC=C1)N1CC(CC1)CCN | [N:1]#[C:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>>[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | N#CCC1CCN(Cc2ccccc2)C1 | NCCC1CCN(Cc2ccccc2)C1 | null | null | C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(CN2CCCC2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)N1CC(CC1)CCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "C(C1=CC=CC=C1)N1CC(CC1)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 14.7 g (0.0734 mole) (3RS)-1-benzyl-3-cyanomethyl pyrrolidine dissolved in 220 ml diethyl ether was slowly added to a slurry of 2.94 g of lithium aluminium hydride in 74 ml diethyl ether under an argon atmosphere. The mixture was stirred over night,and 6 ml water, 18 ml 3.75M NaOH-solution and 6 ml water was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC[NH]C1.c1ccccc1 | null | C(C)OCC | null | null | N#CCC1CCN(Cc2ccccc2)C1>C(C)OCC>NCCC1CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2326e4f1e4844936a51646b96ee23d0d | CC(C)(C)OC(=O)NCCC1CCN(Cc2ccccc2)C1>>CC(C)(C)OC(=O)NCCC1CCNC1 | C(C1=CC=CC=C1)N1CC(CC1)CCNC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)NCCC1CNCC1 | c1ccc(C[N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][NH:14][CH2:15]1 | CC(C)(C)OC(=O)NCCC1CCN(Cc2ccccc2)C1 | CC(C)(C)OC(=O)NCCC1CCNC1 | null | [OH-].[OH-].[Pd+2] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | 846a35f8c83fa58d2c714915319a8bc96745602a4dd9ac20dbad14bc1e16a470 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CCNC1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | null | [] | null | null | null | null | 3.1 g (0.0t mol) (3RS)-1-benzyl-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine was hydrogenated at 0.28 MPa over 0.6 g of Pearlman's catalyst (Pd(OH)2) in 40 ml ethanol (95%) over night. After filtration of the catalyst through cellite and evaporation of the solvent 1H-NMR showed that the reaction was not completed.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | Other | [OH-].[OH-].[Pd+2].C(C)O | null | null | CC(C)(C)OC(=O)NCCC1CCN(Cc2ccccc2)C1>[OH-].[OH-].[Pd+2].C(C)O>CC(C)(C)OC(=O)NCCC1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d42f48a7d3fc473aba6c5139093935b5 | CC(C)(C)OC(=O)NCCC1CCNC1.CSC(=N)NC(=O)OCc1ccccc1>>N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)C1 | C(C)(C)(C)OC(=O)NCCC1CNCC1.C(C1=CC=CC=C1)OC(=O)NC(SC)=N.OS(=O)(=O)[O-].[K+]>>C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CCN | CC(C)(C)OC(=O)[NH:20][CH2:19][CH2:18][CH:17]1[CH2:16][CH2:15][NH:14][CH2:21]1.CS[C:2](=[NH:1])[NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[NH:1]=[C:2]([NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[N:14]1[CH2:15][CH2:16][CH:17]([CH2:18][CH2:19][NH2:20])[CH2:21]1 | CC(C)(C)OC(=O)NCCC1CCNC1.CSC(=N)NC(=O)OCc1ccccc1 | N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)C1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e41463d89a0c3093b9e549b0fd45908e8b91cfc217a44320d33492e3fcab5e4f | 403a59c8b6e9766a4301d1da3109f0687a3485a98c4d8eacd70e1f338293189c | N=C(NC(=O)OCc1ccccc1)N1CCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-1.C-S-[C;H0;D3;+0:9](=[N;D1;H1:10])-[#7:11]-[C:12](-[#8:13])=[O;D1;H0:14]>>[#8:13]-[C:12](=[O;D1;H0:14])-[#7:11]-[C;H0;D3;+0:9](=[N;D1;H1:10])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:4](-[C:3]-[C:2]-[NH2;D1;+0:1])-[C:8]-1 | 67.5 | [{"value": 51.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | 2.18 g (0.0102 mole) (3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60°-70° C. for eight hours followed by stirring at room temperature for one day. 0.3M KHSO4 -solution was added and the water layer w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amine.Monosulfide.Boc | Primary amine.Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | Other | C1(=CC=CC=C1)C | null | 24 | CC(C)(C)OC(=O)NCCC1CCNC1.CSC(=N)NC(=O)OCc1ccccc1>C1(=CC=CC=C1)C>N=C(NC(=O)OCc1ccccc1)N1CCC(CCN)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ecbc4c566e744d9b960cfaf350b242df | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)NCC1CNC1 | C(C)(C)(C)OC(=O)NCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)NCC1CNC1 | c1ccc(C(c2ccccc2)[N:12]2[CH2:11][CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][NH:12][CH2:13]1 | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1 | CC(C)(C)OC(=O)NCC1CNC1 | null | [OH-].[OH-].[Pd+2] | CO | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CNC1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | 67.1 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)NCC1CNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "C(C)(C)(C)OC(=O)NCC1CNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.4 g (9.6 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine was dissolved in 170 mL MeOH and hydrogenated over 0.30 g Pd(OH)2 at 5 MPa over night. The catalyst was filtered off and the solvent evaporated. The crude product was purified by flash chromatography using MeOH/CH2Cl2, 1/9, followed by Me... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | C1CNC1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1>[OH-].[OH-].[Pd+2].CO>CC(C)(C)OC(=O)NCC1CNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d13e77736d347fc8d7ecd3394515558 | CC(C)(C)OC(=O)NCC1CNC1.COC(=N)NC(=O)OCc1ccccc1>>CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 | C(C)(C)(C)OC(=O)NCC1CNC1.C(C1=CC=CC=C1)OC(=O)NC(OC)=N>>C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][NH:12][CH2:26]1.CO[C:13](=[NH:14])[NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][N:12]([C:13](=[NH:14])[NH:15][C:16](=[O:17])[O:18... | CC(C)(C)OC(=O)NCC1CNC1.COC(=N)NC(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | df9d7c4a76f1544cef1093b3238ae3b2a5398bdd8f2dfa35c3397eb37c957b67 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | N=C(NC(=O)OCc1ccccc1)N1CCC1 | C-O-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:10]-1 | 38.5 | [{"value": 38.0, "product": "C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.5, "product": "C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 72 | HOUR | 0.9 g (4.8 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl) azetidine and 1.3 g (6.3 mmol) of N-benzyloxycarbonyl-O-methylisourea was mixed in 6.5 mL toluene and heated to 70° C. for 72 h and then left at room temperature for another 72 h. Evaporation followed by flash chromatography using EtOAc followed by MeOH (satura... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 70 | 72 | CC(C)(C)OC(=O)NCC1CNC1.COC(=N)NC(=O)OCc1ccccc1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df1a0a7ecbb7442b9ee9a9bf29ebf6f4 | N#CCC1CN(C(c2ccccc2)c2ccccc2)C1>>NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | C(#N)CC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-]>>NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1 | [N:1]#[C:2][CH2:3][CH:4]1[CH2:5][N:6]([CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20]1>>[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:5][N:6]([CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20]1 | N#CCC1CN(C(c2ccccc2)c2ccccc2)C1 | NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(C(c2ccccc2)N2CCC2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 87 | [{"value": 87.0, "product": "NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.7 g (21.7 mmol) of 3-cyanomethyl-1-benzhydryl azetidine was added slowly to a suspension of 2.9 g (76.0 mmol) of LiAlH4 in 80 mL of dry THF at roomtemperature. The reaction mixture was refluxed for 4 h. Excess hydride reagent was hydrolyzed by careful addition, with cooling, of NH4 Cl(aq), the gelatinous mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | null | N#CCC1CN(C(c2ccccc2)c2ccccc2)C1>C1CCOC1>NCCC1CN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f30681c7d0b3464187d3580e892ca811 | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1.NCCC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)NCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1 | c1ccc(C(c2ccccc2)N2CC([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])C2)cc1.NC[CH2:10][CH:11]1[CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][N:1... | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1.NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | null | null | null | C-C Coupling | Boc amine protection of primary amine | d521418afe2b27744aa0853d3dbd8c645ea76c2c7dd653b84e848b47bf48524a | add7b52e4edbeac1e43fd32b2de1efd36d163c3f3297283b5665fda49bd05248 | c1ccc(C(c2ccccc2)N2CCC2)cc1 | N-C-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[CH2;D2;+0:14]-C1-C-N(-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-C-1>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[CH2;D2;+0:14]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[... | null | [] | null | null | null | null | The title compound was prepared from 3-aminoethyl-1-benzhydryl azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine, in a yield of 6.5 g (95%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | null | c1ccccc1.c1ccccc1.C1CNC1 | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1.NCCC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b116e8105ba1433db653190ba3814a43 | CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)NCCC1CNC1 | C(C)(C)(C)OC(=O)NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)NCC1CNC1>>C(C)(C)(C)OC(=O)NCCC1CNC1 | c1ccc(C(c2ccccc2)[N:13]2[CH2:12][CH:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:14]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][NH:13][CH2:14]1 | CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1 | CC(C)(C)OC(=O)NCCC1CNC1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CNC1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | The title compound was prepared from 3-(N-tert-butyloxycarbonylaminoethyl)-1-benzhydryl azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl) azetidine, in a yield of 1.2 g (70%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | C1CNC1 | Other | null | null | null | CC(C)(C)OC(=O)NCCC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)NCCC1CNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f3a40523b2f4c598bcdee0f2ca4642e | CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1.CC(C)(C)OC(=O)NCCC1CNC1>>CC(C)(C)OC(=O)NCCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 | C(C)(C)(C)OC(=O)NCCC1CNC1.C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N>>C(C)(C)(C)OC(=O)NCCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N | CC(C)(C)OC(=O)N[CH2:10][CH:11]1[CH2:12][N:13]([C:14](=[NH:15])[NH:16][C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1.C1NCC1C[CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][N:13]([C:14]... | CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1.CC(C)(C)OC(=O)NCCC1CNC1 | CC(C)(C)OC(=O)NCCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 | null | null | null | C-C Coupling | OtherReaction | 1d7ac5a0e7f04e0106eb9b0e5a3a46be2ebfbf5433f9d9401383a34517b64867 | 6ace98d3c3046eaaa61eca3c25430e6bc592d0da17160c18a7110f07cdb4d09d | N=C(NC(=O)OCc1ccccc1)N1CCC1 | C-C(-C)(-C)-O-C(=O)-N-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[CH2;D2;+0:14]-C-C1-C-N-C-1>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[CH2;D2;+0:14]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1 | null | [] | null | null | null | null | The title compound was prepared from 3-(N-tert-butyloxycarbonylaminoethyl) azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl)-1-(N-benzyloxycarbon ylamidino) azetidine, in a yield of 0.090 g (34%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amine.Boc | null | C1CNC1 | null | C1C[NH]C1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NCC1CN(C(=N)NC(=O)OCc2ccccc2)C1.CC(C)(C)OC(=O)NCCC1CNC1>>CC(C)(C)OC(=O)NCCC1CN(C(=N)NC(=O)OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f2917c57d8924daa80ca9144336b9913 | CSC[C@H](N)C(=O)O.O=[N+]([O-])c1ccc(F)cc1F>>CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O | CSC[C@H](N)C(=O)O.C(C)N(CC)CC.FC1=C(C=CC(=C1)F)[N+](=O)[O-]>>FC=1C=CC(=C(C1)N[C@@H](CSC)C(=O)O)[N+](=O)[O-] | [CH3:1][S:2][CH2:3][C@H:4]([NH2:5])[C:16](=[O:17])[OH:18].F[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[CH3:1][S:2][CH2:3][C@H:4]([NH:5][c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15])[C:16](=[O:17])[OH:18] | CSC[C@H](N)C(=O)O.O=[N+]([O-])c1ccc(F)cc1F | CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:2]:[c:3] | null | [] | null | null | null | null | 16.2 g of (-)-S-Methyl-L-cysteine (0.1 mol) are suspended in a mixture of 120 ml of water and 120 ml of acetone in a four-necked flask under N2. 30.4 ml (22.2 g) of triethylamine (0.22 mol) are added rapidly while stirring. 15.9 g of 2,4-difluoronitrobenzene (0.1 mol) are added, with further stirring, to the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CC(=O)C | null | null | CSC[C@H](N)C(=O)O.O=[N+]([O-])c1ccc(F)cc1F>O.CC(=O)C>CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49f2d19dd08c44a6a1032e78dc4359e1 | CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O.C[O-]>>COc1ccc([N+](=O)[O-])c(N[C@@H](CSC)C(=O)O)c1 | FC=1C=CC(=C(C1)N[C@@H](CSC)C(=O)O)[N+](=O)[O-].C[O-].[Na+]>>COC=1C=CC(=C(C1)N[C@@H](CSC)C(=O)O)[N+](=O)[O-] | F[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][C@@H:12]([CH2:13][S:14][CH3:15])[C:16](=[O:17])[OH:18])[cH:19]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][C@@H:12]([CH2:13][S:14][CH3:15])[C:16](=[O:17])[OH:18])[cH:19]1 | CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O.C[O-] | COc1ccc([N+](=O)[O-])c(N[C@@H](CSC)C(=O)O)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 39d5ff1cd4e8c0faf94cc5b2ad4bb50293cf15e9a5e1331d02f5731b7900363c | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[O-;H0;D1:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 27 g of N-(5-fluoro-2-nitrophenyl)-S-methyl-L-cysteine (0.1 mol) from Example 1 are dissolved in 150 ml of absolute methanol in a four-necked flask, and 14.4 g of 95% sodium methoxide (0.25 mmol) are added in portions, within the space of 20 minutes and under argon, to this solution while stirring well and while coolin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CO | null | null | CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O.C[O-]>CO>COc1ccc([N+](=O)[O-])c(N[C@@H](CSC)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-acafbcbe9a2a44309d2b4dd92b3f58bb | OCCCCc1ccccc1>>O=CCCCc1ccccc1 | C1(=CC=CC=C1)CCCCO.[Cr](=O)(=O)([O-])Cl.C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl>>C1(=CC=CC=C1)CCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | OCCCCc1ccccc1 | O=CCCCc1ccccc1 | null | null | CCOCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 22.7 | [{"value": 22.7, "product": "C1(=CC=CC=C1)CCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 3.2 mL (20.8 mmol) of 4-phenyl-1-butanol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at 0° C. was added 3.2 g of powdered 3 Å molecular sieves and then 5.37 g (24.9 mmol) of pyridinum chlorochromate (PCC). The resulting suspension was stirred at 0° C. for 1 h at which time an additional 2.16 g (10.0 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | CCOCC.C(Cl)Cl | null | 0.5 | OCCCCc1ccccc1>CCOCC.C(Cl)Cl>O=CCCCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76f829bb3ada43dbb9e69131f368da79 | O=CCCCc1ccccc1.[Br][Mg][CH2]CCc1ccccc1>>OC(CCCc1ccccc1)CCCc1ccccc1 | C1(=CC=CC=C1)CCCC=O.C1(=CC=CC=C1)CCC[Mg]Br>>C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O | [O:1]=[CH:2][CH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[Br][Mg][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[OH:1][CH:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[CH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=CCCCc1ccccc1.[Br][Mg][CH2]CCc1ccccc1 | OC(CCCc1ccccc1)CCCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard from aldehyde to alcohol | fec51c6fbcca146daa523566f7e8d93ddaee19549cd7ca45d0ef939f0a2ea2fd | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(CCCCCCCc2ccccc2)cc1 | [Br]-[Mg]-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C:4]-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[CH2;D2;+0:1]-[C:2]-[C:3] | 88.8 | [{"value": 88.8, "product": "C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | To a solution of 700 mg (4.7 mmol) of 4-phenyl-1-butanal (119) in 5.0 mL of THF at 0° C. was added 10.0 mL (5.0 mmol) of 3-phenyl-1-propylmagnesium bromide (120) and the resulting mixture was stirred at 0° C. for 0.5 h. The mixture was then quenched by the dropwise addition of saturated NH4Cl and diluted with ether. Th... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | Br-.Mg | C1CCOC1 | 0 | 0.5 | O=CCCCc1ccccc1.[Br][Mg][CH2]CCc1ccccc1>C1CCOC1>OC(CCCc1ccccc1)CCCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1489d72d83a3432b8980d4f94eed3de6 | OCc1cccc(Oc2ccccc2)c1>>O=Cc1cccc(Oc2ccccc2)c1 | O(C1=CC=CC=C1)C=1C=C(CO)C=CC1>>O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1 | OCc1cccc(Oc2ccccc2)c1 | O=Cc1cccc(Oc2ccccc2)c1 | null | O=[Mn]=O.O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(Oc2ccccc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.1 | [{"value": 90.1, "product": "O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 1.8mL (10.3 mmol) of 3-phenoxybenzyl alcohol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at room temperature was added 1.5 g of powdered 4 Å molecular sieves and 2.5 g of activated MnO2. The resulting suspension was stirred at room temperature for 0.5 h, at which time an additional 2.5 g of MnO2 was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | O=[Mn]=O.O=[Mn]=O.C(Cl)Cl | null | 0.5 | OCc1cccc(Oc2ccccc2)c1>O=[Mn]=O.O=[Mn]=O.C(Cl)Cl>O=Cc1cccc(Oc2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a5760aaa3d049789dc0038907f707bb | C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)CO>>C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1 | C(C)N(CC)CC.[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/CO)\C.C(C(=O)Cl)(=O)Cl.CS(=O)C>>[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/C=O)\C | [CH3:1]/[C:2]([CH2:3][OH:4])=[CH:5]\[C@H:6]1[CH2:7][CH2:8][C@H:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:1]/[C:2]([CH:3]=[O:4])=[CH:5]\[C@H:6]1[CH2:7][CH2:8][C@H:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)CO | C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCCCC1 | [C:1]-[C:2](/[C:3]=[C:4](\[C;D1;H3:5])-[CH2;D2;+0:6]-[OH;D1;+0:7])-[C:8]>>[C:1]-[C:2](/[C:3]=[C:4](\[C;D1;H3:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7])-[C:8] | null | [] | null | null | 5 | MINUTE | To a -78° C. solution of oxalyl chloride (105 μL, 1.2 mmol) in 1.0 mL of methylene chloride was added dimethylsulfoxide (170 μL, 2.4 mmol). The resulting solution was stirred for 5 min and then 170 mg (0.6 mmol) of the alcohol 135 was added in 1.0 mL of methylene chloride. The reaction mixture was stirred at -78° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCCCC1 | null | C(Cl)Cl | null | 0.083333 | C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)CO>C(Cl)Cl>C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6be5895ebf2488a874923e3878acfbe | C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1.OC(CCCc1ccccc1)CCCc1ccccc1>>C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)C(O)CCCc1ccccc1 | [Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/C=O)\C.C1(=CC=CC=C1)CCC[Mg]Br.C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O>>[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)\C=C(\C(CCCC1=CC=CC=C1)O)/C | [CH3:1]/[C:2](=[CH:3]\[C@H:4]1[CH2:5][CH2:6][C@H:7]([O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1)[CH:18]=[O:19].OC(CCCc1ccccc1)[CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1]/[C:2](=[CH:3]\[C@H:4]1[CH2:5][CH2:6][C@H:7]([O:8][Si:9]([CH3:10])([CH3:11])[C... | C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1.OC(CCCc1ccccc1)CCCc1ccccc1 | C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)C(O)CCCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 745e9d5550f1bc5d8f9663a93679046bd7d0fca4f985bc640e2b19519b4d19c5 | a3560394ead03d025274020cb23d2d580daa991ec04104aa7a504d5ac71e3ae6 | C(=CC1CCCCC1)CCCCc1ccccc1 | O-C(-C-C-C-c1:c:c:c:c:c:1)-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](/[C:6]=[C:7](\[C;D1;H3:8])-[CH;D2;+0:9]=[O;H0;D1;+0:10])-[C:11]>>[C:4]-[C:5](/[C:6]=[C:7](\[C;D1;H3:8])-[CH;D3;+0:9](-[OH;D1;+0:10])-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:11] | null | [] | null | null | null | null | The alcohol 137 was prepared from the crude aldehyde 136. and 1.5 mL (0.75 mmol) of 120 in 2.0 mL of THF as described above for the synthesis of alcohol 121 in Example 1 to give 220 mg of the crude diastereomeric alcohol 137. Flash chromatography (elution with 20% ethyl acetate in hexane) afforded 146 mg of the alcohol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol | Secondary alcohol | c1ccccc1 | null | C1CCCCC1.c1ccccc1 | HO- | C1CCOC1 | null | null | C/C(C=O)=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1.OC(CCCc1ccccc1)CCCc1ccccc1>C1CCOC1>C/C(=C\[C@@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1)C(O)CCCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ab94114d8b645e082906ef9a74075cf | CN(C)O.O=C(O)CCCc1c[nH]c2ccccc12>>CON(C)C(=O)CCCc1c[nH]c2ccccc12 | N1C=C(C2=CC=CC=C12)CCCC(=O)O.C(C)(C)N(C(C)C)CC.Cl.CN(O)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>CN(C(CCCC1=CNC2=CC=CC=C12)=O)OC | [CH3:1][N:3]([OH:2])[CH3:4].O[C:5](=[O:6])[CH2:7][CH2:8][CH2:9][c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[CH2:7][CH2:8][CH2:9][c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CN(C)O.O=C(O)CCCc1c[nH]c2ccccc12 | CON(C)C(=O)CCCc1c[nH]c2ccccc12 | null | null | C(C)#N | Acylation | OtherReaction | d8b2983456520e04d3c60473cdb132720f2fe2d412f78ff14b19d4ff149b7970 | 24bc53ff5c10681d8cc73a1bb4d5e3f184958ea20e029afafa8ff123b17ea76c | c1ccc2[nH]ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:7])-[OH;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[O;H0;D2;+0:8]-[CH3;D1;+0:7] | 94.3 | [{"value": 94.3, "product": "CN(C(CCCC1=CNC2=CC=CC=C12)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Tertiary amide | null | null | c1ccc2[nH]ccc2c1 | HO- | C(C)#N | null | 8 | CN(C)O.O=C(O)CCCc1c[nH]c2ccccc12>C(C)#N>CON(C)C(=O)CCCc1c[nH]c2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70019092bb2c48d18020b5be4b31c9ad | CON(C)C(=O)CCCc1c[nH]c2ccccc12.[Cl][Mg][CH2]c1ccccc1>>O=C(CCC(Cc1ccccc1)c1c[nH]c2ccccc12)CCC(Cc1ccccc1)c1c[nH]c2ccccc12 | CN(C(CCCC1=CNC2=CC=CC=C12)=O)OC.C(C1=CC=CC=C1)[Mg]Cl>>C(C1=CC=CC=C1)C(CCC(=O)CCC(CC1=CC=CC=C1)C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12 | O([CH3:3])[N:15]([C:2](=[O:1])[CH2:22][CH2:23][CH2:24][c:32]1[cH:33][nH:34][c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]12)[CH3:14].[Cl][Mg][CH2:6][c:7]1[cH:8][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][cH:... | CON(C)C(=O)CCCc1c[nH]c2ccccc12.[Cl][Mg][CH2]c1ccccc1 | O=C(CCC(Cc1ccccc1)c1c[nH]c2ccccc12)CCC(Cc1ccccc1)c1c[nH]c2ccccc12 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 298d2d31c7f84c015c10da15c1d39cea10099f6fc8aa5162a1e949dce4f10daa | 81f865b55a0aa641c7c58099315544d18d237b86f0e3509b1685b149b9ab86dc | O=C(CCC(Cc1ccccc1)c1c[nH]c2ccccc12)CCC(Cc1ccccc1)c1c[nH]c2ccccc12 | [CH3;D1;+0:1]-[N;H0;D3;+0:2](-O-[CH3;D1;+0:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7]-[CH2;D2;+0:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:1.[Cl]-[Mg]-[CH2;D2;+0:14]-[c;H0;D3;+0:15]1:[cH;D2;+0:16]:[c:17]:[c:18]:[cH;D2;+0:19]:[cH;D2;+0:20]:1>>[O;D1;H0:5]=[C;H0;D3;+0:4](-[C:6]-[C:7]-[CH;D3;+0:8](-[C:21]-[c:22])-[c:9]1:[... | 68.6 | [{"value": 68.6, "product": "C(C1=CC=CC=C1)C(CCC(=O)CCC(CC1=CC=CC=C1)C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 147 mg (0.60 mmol) of amide 139 in 4.0 mL of THF at -78° C. was added 1.31 mL (1.31 mmol) of benzylmagnesium chloride (1.0M in Et2O) and the reaction mixture was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with 5% KHSO4 and extracted into ether. The combined ethereal... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amide | Ketone | c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1.c1ccc2[nH]ccc2c1 | Mg | C1CCOC1 | null | 3 | CON(C)C(=O)CCCc1c[nH]c2ccccc12.[Cl][Mg][CH2]c1ccccc1>C1CCOC1>O=C(CCC(Cc1ccccc1)c1c[nH]c2ccccc12)CCC(Cc1ccccc1)c1c[nH]c2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-741882d51dc940da96a4eb974652c9bb | O.O=Cc1ccccn1.[Li][CH2]CCC.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1>>C(=C/c1ccccn1)\CC1OCCCO1.C(=C\c1ccccn1)\CC1OCCCO1 | N1=C(C=CC=C1)C=O.O.[Br-].O1C(OCCC1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li]>>O1C(OCCC1)C/C=C/C1=NC=CC=C1.O1C(OCCC1)C\C=C/C1=NC=CC=C1 | [OH2:26].[CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1)=[O:30].[Li][CH2:27][CH2:28][CH2:25][CH3:24].c1ccc([P+]([CH2:1][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15]2)([c:16]2ccc[cH:29]c2)[c:18]2[cH:17][cH:22][cH:21][cH:20][cH:19]2)cc1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1)\[CH2:9][CH:10]1[O:11][CH2:12... | O.O=Cc1ccccn1.[Li][CH2]CCC.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1 | C(=C/c1ccccn1)\CC1OCCCO1.C(=C\c1ccccn1)\CC1OCCCO1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7c66045ce7194fe655427ea5fa5c0dc6b626153f1009577225bfd7aa7dca8e9d | 334880a3e534bf94c21ad10a2154b5e8216acf3dd3844c5e35907ff9e6afe03a | C(=C/c1ccccn1)\CC1OCCCO1.C(=C\c1ccccn1)\CC1OCCCO1 | [#8:1]-[C:2](-[C:3]-[CH2;D2;+0:4]-[P+](-[c;H0;D3;+0:5]1:c:[cH;D2;+0:6]:c:c:c:1)(-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1)-c1:c:c:c:c:c:1)-[#8:13].[CH3;D1;+0:14]-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[CH2;D2;+0:17]-[Li].[O;H0;D1;+0:18]=[CH;D2;+0:19]-[c:20](:[c:21]):[#7;a:22]:[c:23].[OH2;D0;+0:24]>>[#7;a... | null | [] | 0 | CELSIUS | 0.5 | HOUR | To a suspension of 4.6 g (10.2 mmol) of [2-(1,3-dioxan-2yl)ethyl]triphenylphosphonium bromide (Aldrich Chemical Co.) in 50 mL of THF at 0° C. was added 6.4 mL (10.2 mmol) of n-butyl lithium (1.6M in hexanes) and the resulting red solution was allowed to stir at 0° C. for 0.5 h. To this solution was added 880 μL (9.3 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Alkyl lithium | Ether.Ether | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1.C1COCOC1 | c1ccncc1.C1COCOC1.c1ccncc1.C1COCOC1 | Li | C1CCOC1 | 0 | 0.5 | O.O=Cc1ccccn1.[Li][CH2]CCC.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1>C1CCOC1>C(=C/c1ccccn1)\CC1OCCCO1.C(=C\c1ccccn1)\CC1OCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-600c0203d0174eabae949b47eb4ee810 | C(=C\c1ccccn1)\CC1OCCCO1>>c1ccc(CCCC2OCCCO2)nc1 | O1C(OCCC1)C\C=C/C1=NC=CC=C1>>O1C(OCCC1)CCCC1=NC=CC=C1 | [cH:1]1[cH:2][cH:3][c:4](/[CH:5]=[CH:6]\[CH2:7][CH:8]2[O:9][CH2:10][CH2:11][CH2:12][O:13]2)[n:14][cH:15]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][CH:8]2[O:9][CH2:10][CH2:11][CH2:12][O:13]2)[n:14][cH:15]1 | C(=C\c1ccccn1)\CC1OCCCO1 | c1ccc(CCCC2OCCCO2)nc1 | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCCC2OCCCO2)nc1 | [#8:1]-[C:2](-[C:3]/[CH;D2;+0:4]=[CH;D2;+0:5]\[c:6](:[c:7]):[#7;a:8]:[c:9])-[#8:10]>>[#8:1]-[C:2](-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9])-[#8:10] | 92.5 | [{"value": 92.5, "product": "O1C(OCCC1)CCCC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Through a suspension of 800 mg (4.2 mmol) of olefin 149 and 100 mg of 10% palladium on carbon was bubbled a steady stream of hydrogen gas for a period of 10 min. The reaction mixture was then filtered through celite and concentrated to give 805 mg of the acetal 150 as a colorless oil. 1H NMR consistent with structure.
... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1COCOC1 | null | [Pd] | null | null | C(=C\c1ccccn1)\CC1OCCCO1>[Pd]>c1ccc(CCCC2OCCCO2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dec073da1f4d41b387cb25d85d14d5f1 | C[Si](C)(C)C=[N+]=[N-].O=Cc1ccc(C(=O)O)cc1>>COC(=O)c1ccc(C=O)cc1 | C(=O)(O)C1=CC=C(C=O)C=C1.C[Si](C)(C)C=[N+]=[N-].C(=O)(O)[O-].[Na+]>>COC(C1=CC=C(C=C1)C=O)=O | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:11][cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:11][cH:12]1 | C[Si](C)(C)C=[N+]=[N-].O=Cc1ccc(C(=O)O)cc1 | COC(=O)c1ccc(C=O)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | To a suspension of 9.6 g (63.6 mmol) of 4-carboxybenzaldehyde (Aldrich Chemical Co.) in 100 mL of CH2Cl2 at 0° C. was added excess trimethylsilyldiazomethane and the resulting mixture was allowed to stir at 0° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted three times with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | C(Cl)Cl | 0 | 1 | C[Si](C)(C)C=[N+]=[N-].O=Cc1ccc(C(=O)O)cc1>C(Cl)Cl>COC(=O)c1ccc(C=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6120ae4e516c4335a3f2eb3671f18da1 | CC(C1OCCCO1)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1>>COC(=O)c1ccc(C=CCC2OCCO2)cc1 | COC(C1=CC=C(C=C1)C=O)=O.[Br-].O1C(OCCC1)C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Li]CCCC>>COC(C1=CC=C(C=C1)C=CCC1OCCO1)=O | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:11]([CH3:10])[CH:12]2[O:13]C[CH2:14][CH2:15][O:16]2)cc1.O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH:10][CH2:11][CH:12]2[O:13][CH2:14][CH2:15][O:16]2)[cH:17][cH:18]1 | CC(C1OCCCO1)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1 | COC(=O)c1ccc(C=CCC2OCCO2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | e9b81df9c146ee18d35392a14925db0bee8ab8848c8cf94f2ebdbc4d1c5e0096 | 77f70c88f5781565bbef978a13aa26af9cfeac78f7ee0eea1b4ee8e9b7684280 | C(=Cc1ccccc1)CC1OCCO1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[CH;D3;+0:6](-[C:7]1-[#8:8]-[C:9]-[CH2;D2;+0:10]-C-[O;H0;D2;+0:11]-1)-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:3]:[c:2](-[CH;D2;+0:1]=[CH;D2;+0:5]-[CH2;D2;+0:6]-[C:7]1-[#8:8]-[C:9]-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1):[c:4] | 50.3 | [{"value": 50.3, "product": "COC(C1=CC=C(C=C1)C=CCC1OCCO1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The olefin was prepared from 4.3 g (26.2 mmol) of the aldehyde 167, 13.94 g of [1-(1,3-dioxan-2-yl)ethyl]triphenylphosphoniumbromide and 12.6 mL (32.0 mmol) of n-BuLi in 75 mL of THF as described for the synthesis of 156 in Example 8. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.27 g of the ol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Acetal/Ketal | Ether.Acetal/Ketal | c1ccccc1.c1ccccc1.c1ccccc1.C1COCOC1 | C1COCO1 | c1ccccc1.C1COCO1 | HO- | C1CCOC1 | null | null | CC(C1OCCCO1)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1>C1CCOC1>COC(=O)c1ccc(C=CCC2OCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e4b7283463484f78b8ff3e4f5af4a115 | COC(=O)c1ccc(CCCC2OCCO2)cc1>>OCc1ccc(CCCC2OCCCO2)cc1 | COC(C1=CC=C(C=C1)CCCC1OCCO1)=O.[H-].C(C(C)C)[Al+]CC(C)C>>O1C(OCCC1)CCCC1=CC=C(C=C1)CO | O([C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:13][CH2:14][O:15]2)[cH:16][cH:17]1)[CH3:12]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(CCCC2OCCO2)cc1 | OCc1ccc(CCCC2OCCCO2)cc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 11ad31eb5e15c19b6b0bf870375e0b2b1b523d97d63cb564c0ec774ecdc4a360 | 60cbd0cdeedbe0df3b69ed77da0b18c75ba37a82153e9e68a6e5664d36d6e6bb | c1ccc(CCCC2OCCCO2)cc1 | [CH3;D1;+0:1]-O-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]1-[#8:9]-[C:10]-[CH2;D2;+0:11]-[O;H0;D2;+0:12]-1>>[C:7]-[C:8]1-[#8:9]-[C:10]-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-1.[OH;D1;+0:3]-[CH2;D2;+0:2]-[c:4](:[c:5]):[c:6] | 95.8 | [{"value": 95.8, "product": "O1C(OCCC1)CCCC1=CC=C(C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a solution of 2.85 g (11.4 mmol) of ester 169 in 25 mL of THF at 0° C. was added 4.4 mL (24.7 mmol) of diisobutylaluminum hydride and the resulting mixture was allowed to stir at 0° C. for 15 min. The reaction was quenched with saturated potassium sodium tartrate and extracted three times with ethyl acetate. The com... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ether.Primary alcohol.Acetal/Ketal | C1COCO1 | C1COCOC1 | c1ccccc1.C1COCOC1 | Other | C1CCOC1 | 0 | 0.25 | COC(=O)c1ccc(CCCC2OCCO2)cc1>C1CCOC1>OCc1ccc(CCCC2OCCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c93e9ea79a9405d9591cb8af2288670 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OCc1ccc(CCCC2OCCCO2)cc1>>CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1 | O1C(OCCC1)CCCC1=CC=C(C=C1)CO.N1C=NC=C1.C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC1OCCO1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.C1[O:16][CH:15]([CH2:14][CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([CH2:7][OH:6])[cH:21][cH:20]2)[O:19][CH2:18][CH2:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][c:8]1[cH:9][cH:10][c... | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OCc1ccc(CCCC2OCCCO2)cc1 | CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 9e413bc0d07ca62059d4b17c7c667341998c537dcec7980d48da74e43f2bda95 | ac2b248fc44a91755024346efa1d4ec06dc3f9520fa06d3fd61d67db934b24ce | c1ccc([SiH](OCc2ccc(CCCC3OCCO3)cc2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]1-[#8:14]-[C:15]-[CH2;D2;+0:16]-C-[O;H0;D2;+0:17]-1.[OH;D1;+0:18]-[C:19]-[c:20]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[Si;H0;D4;+0:1](-[O;H0;D2;+0:18]-[C:19]-[c:20])(-[c:2](:[c:3]):[c:4... | 102.9 | [{"value": 102.9, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2.58 g (11.6 mmol) of alcohol 170 and 1.19 g (17.5 mmol) of imidazole in 50 mL of CH2Cl2 was added 3.4 mL (13.1 mmol) of tert-butylchlorodiphenyl silane and the resulting mixture was allowed to stir at room temperature for 1 h. The mixture was then diluted with ethyl acetate and washed with 0.5N HCl. T... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Silyl protective group.Acetal/Ketal | Ether.Silyl protective group.Acetal/Ketal | C1COCOC1 | C1COCO1 | c1ccccc1.C1COCO1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 1 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OCc1ccc(CCCC2OCCCO2)cc1>C(Cl)Cl.C(C)(=O)OCC>CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-991308a13d764cc0817ac696051b408e | CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1>>CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1 | Cl.[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC1OCCO1.Cl.N1C=NC=C1.C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl.C(=O)([O-])[O-].[K+].[K+]>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC=O | C1C[O:16][CH:15]([CH2:14][CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([CH2:7][O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:18][cH:17]2)O1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH... | CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1 | CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(CO[SiH](c2ccccc2)c2ccccc2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 42.8 | [{"value": 42.8, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5.5 g (11.9 mmol) of the dioxolane 171 in 40 mL of THF at room temperature was added 40 mL of 4.0N HCl and the resulting solution was allowed to stir for 1 h. The mixture was neutralized with solid K2CO3, extracted with ethyl acetate and concentrated. The crude mixture was dissolved into 25 mL of CH2Cl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | CC(C)(C)[Si](OCc1ccc(CCCC2OCCO2)cc1)(c1ccccc1)c1ccccc1>C1CCOC1>CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-796ad571c9a54fe982b77146ea41a2af | CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1.OC(CCCc1ccccc1)CCCc1ccccc1>>CC(C)(C)[Si](OCc1ccc(CCCC(O)CCCc2ccccc2)cc1)(c1ccccc1)c1ccccc1 | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC=O.C1(=CC=CC=C1)CCC[Mg]Br.C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC(CCCC1=CC=CC=C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][CH:15]=[O:16])[cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.OC(CCCc1ccccc1)[CH2:17][CH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3... | CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1.OC(CCCc1ccccc1)CCCc1ccccc1 | CC(C)(C)[Si](OCc1ccc(CCCC(O)CCCc2ccccc2)cc1)(c1ccccc1)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 745e9d5550f1bc5d8f9663a93679046bd7d0fca4f985bc640e2b19519b4d19c5 | a3560394ead03d025274020cb23d2d580daa991ec04104aa7a504d5ac71e3ae6 | c1ccc(CCCCCCCc2ccc(CO[SiH](c3ccccc3)c3ccccc3)cc2)cc1 | O-C(-C-C-C-c1:c:c:c:c:c:1)-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C:4]-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[CH2;D2;+0:1]-[C:2]-[C:3] | 122.9 | [{"value": 122.9, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC(CCCC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The alcohol 173 was prepared from 2.12 g (5.0 mmol) of 172 and 9.0 mL (9 mmol) of 120 in 50 mL of THF as described for the synthesis of 121 in Example 1. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.3 g of the alcohol 173. 1H NMR consistent with the product.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol | Secondary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | null | CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1.OC(CCCc1ccccc1)CCCc1ccccc1>C1CCOC1>CC(C)(C)[Si](OCc1ccc(CCCC(O)CCCc2ccccc2)cc1)(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-696b27b131f24c17a8f31b09f5726b28 | C[C@H](CO)Nc1ccccn1.O=S(Cl)Cl>>CC1CO[S@@](=O)N1c1ccccn1 | N1=C(C=CC=C1)N[C@@H](CO)C.C(C)(C)N(C(C)C)CC.S(=O)(Cl)Cl>>CC1N([S@@](OC1)=O)C1=NC=CC=C1 | [CH3:1][C@H:2]([CH2:3][OH:4])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.Cl[S:5](Cl)=[O:6]>>[CH3:1][CH:2]1[CH2:3][O:4][S@@:5](=[O:6])[N:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1 | C[C@H](CO)Nc1ccccn1.O=S(Cl)Cl | CC1CO[S@@](=O)N1c1ccccn1 | null | null | ClCCl | Acylation | OtherReaction | 3d2c53a666fb5a577b1313e56f6be1ee5645334dca79c4f10831a331b18034d8 | b742aca93543b8e281f953dd08553590c1a12f1562393e6d8aed2fc78e477c3c | O=[S@@]1OCCN1c1ccccn1 | Cl-[S;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C;D1;H3:3]-[C@H;D3;+0:4](-[C:5]-[OH;D1;+0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:3]-[CH;D3;+0:4]1-[C:5]-[O;H0;D2;+0:6]-[S@@;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7]-1-[c:8](:[c:9]):[#7;a:10]:[c:11] | 599.1 | [{"value": 599.1, "product": "CC1N([S@@](OC1)=O)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of (R)-N-(2-pyridyl)-2-aminopropanol (20.0 g, 0.13 moles) and N,N-diisopropylethylamine (33.6 g, 0.13 moles) in dichloromethane (500 ml) was cooled to 5° C. Then thionyl chloride (15.5 g, 0.13 moles) in dichloromethane (100 ml) was added slowly whilst the temperature was kept below 10° C. The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine.Sulfinate | null | C1COS[NH]1 | C1COS[NH]1.c1ccncc1 | HCl | ClCCl | null | 0.5 | C[C@H](CO)Nc1ccccn1.O=S(Cl)Cl>ClCCl>CC1CO[S@@](=O)N1c1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-894fd0022b9d41c08eca3c3e063480b8 | CC1CO[S@@](=O)N1c1ccccn1.[O-][I+3]([O-])([O-])[O-]>>C[C@@H]1COS(=O)(=O)N1c1ccccn1 | C(C)(=O)OCC.I(=O)(=O)(=O)[O-].[Na+].CC1N([S@@](OC1)=O)C1=NC=CC=C1>>C[C@H]1N(S(OC1)(=O)=O)C1=NC=CC=C1 | [CH3:1][CH:2]1[CH2:3][O:4][S@@:5](=[O:7])[N:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.[O-][I+3]([O-])([O-])[O-:6]>>[CH3:1][C@@H:2]1[CH2:3][O:4][S:5](=[O:6])(=[O:7])[N:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1 | CC1CO[S@@](=O)N1c1ccccn1.[O-][I+3]([O-])([O-])[O-] | C[C@@H]1COS(=O)(=O)N1c1ccccn1 | null | [Ru](Cl)(Cl)Cl | C(C)#N.O | Oxidation | OtherReaction | 92d5ffa8b213dca13ca6074410126311038742783dec16e6a8042db63b59a05b | af0860f95582a26dccf6319bcb57e674f568c8c484a6a567b7d7bc738c3a91e4 | O=S1(=O)OCCN1c1ccccn1 | [#7;a:1]:[c:2]-[#7:3]1-[C:4]-[C:5]-[#8:6]-[S@;H0;D3;+0:7]-1=[O;D1;H0:8].[O-;H0;D1:9]-[I+3](-[O-])(-[O-])-[O-]>>[#7;a:1]:[c:2]-[#7:3]1-[C:4]-[C:5]-[#8:6]-[S;H0;D4;+0:7]-1(=[O;D1;H0:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | A solution of sodium periodate (21 g, 0.10 moles) in water (150 ml) was added slowly to a solution of (R)-4-methyl-3-pyridin-2-yl-[1,2,3]oxathiazolidine-2-oxide (15.4 g, 0.78 moles) and ruthenium(III)chloride (20 mg) in acetonitrile (1540 ml) whilst the temperature was kept below 5° C. A heavy precipitate developed. Th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfinate | Sulfamate | C1COS[NH]1 | C1COS[NH]1 | C1COS[NH]1.c1ccncc1 | I- | [Ru](Cl)(Cl)Cl.C(C)#N.O | null | null | CC1CO[S@@](=O)N1c1ccccn1.[O-][I+3]([O-])([O-])[O-]>[Ru](Cl)(Cl)Cl.C(C)#N.O>C[C@@H]1COS(=O)(=O)N1c1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-094501f6e5574d25af8d8557ebfc848e | C[C@@H]1COS(=O)(=O)N1c1ccccn1.c1cc(N2CCNCC2)c2cc[nH]c2c1>>C[C@H](CN1CCN(c2cccc3[nH]ccc23)CC1)Nc1ccccn1 | C[C@H]1N(S(OC1)(=O)=O)C1=NC=CC=C1.N1(CCNCC1)C1=C2C=CNC2=CC=C1>>N1C=CC2=C(C=CC=C12)N1CCN(CC1)C[C@H](NC1=NC=CC=C1)C | O=S1(=O)O[CH2:3][C@@H:2]([CH3:1])[N:19]1[c:20]1[cH:21][cH:22][cH:23][cH:24][n:25]1.[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[nH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1>>[CH3:1][C@H:2]([CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[nH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1... | C[C@@H]1COS(=O)(=O)N1c1ccccn1.c1cc(N2CCNCC2)c2cc[nH]c2c1 | C[C@H](CN1CCN(c2cccc3[nH]ccc23)CC1)Nc1ccccn1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 8f41d66678295c8bc94d7c54b6d59ad5ffb6169c1fa057a13b5d9d5cf8cd6ac9 | 599291d464aa192b54fe88259a98d054ef3f70cbce75e19456bd40be9dc0bc7b | c1ccc(NCCN2CCN(c3cccc4[nH]ccc34)CC2)nc1 | O=S1(=O)-O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:4]-1-[c:5](:[c:6]):[#7;a:7]:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C;D1;H3:3]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1)-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 67.5 | [{"value": 67.5, "product": "N1C=CC2=C(C=CC=C12)N1CCN(CC1)C[C@H](NC1=NC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of (R)-4-methyl-3-pyridin-2-yl-[1,2,3]-oxathiazolidine-2,2-dioxide (4.04 g 0.019 moles) and 4-piperazinoindole (3.80 g 0.019 moles) in acetonitrile (200 ml) was heated to 60° C. for 0.5 h then evaporated in vacuo. The residue was taken up into dilute HCl (100 ml), warmed to 60° C. for 0.5 h, cooled, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tertiary amine.Sulfamate | Secondary amine.Tertiary amine | C1COS[NH]1.C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.c1ccncc1 | Other | C(C)#N | 60 | null | C[C@@H]1COS(=O)(=O)N1c1ccccn1.c1cc(N2CCNCC2)c2cc[nH]c2c1>C(C)#N>C[C@H](CN1CCN(c2cccc3[nH]ccc23)CC1)Nc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1d28f93300e04c54af211412e745642b | C[C@H](O)CN.Clc1ccccn1>>C[C@H](O)CNc1ccccn1 | NC[C@H](C)O.CC(C)([O-])C.[K+].ClC1=NC=CC=C1>>N1=C(C=CC=C1)NC[C@H](C)O | [CH3:1][C@H:2]([OH:3])[CH2:4][NH2:5].Cl[c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1>>[CH3:1][C@H:2]([OH:3])[CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1 | C[C@H](O)CN.Clc1ccccn1 | C[C@H](O)CNc1ccccn1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 84.4 | [{"value": 84.4, "product": "N1=C(C=CC=C1)NC[C@H](C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-1-amino-2-propanol (43 g, 0.57M) was added to a stirred solution of potassium tertiary butoxide (64.2 g, 0.66M) in tetrahydrofuran (500 ml). 2-Chloropyridine (65.1 g 0.66M) was then added dropwise. After the exothermic reaction had subsided, the reaction was heated under reflux overnight, filtered to remove the pot... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | O1CCCC1 | null | null | C[C@H](O)CN.Clc1ccccn1>O1CCCC1>C[C@H](O)CNc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3287b7f0e07644e393371b77d33adaf0 | Nc1ccccn1.O=C(Cl)CCl>>O=C(CCl)Nc1ccccn1 | ClCC(=O)Cl.NC1=NC=CC=C1.C(C)(C)N(CC)C(C)C>>ClCC(=O)NC1=NC=CC=C1 | [NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1 | Nc1ccccn1.O=C(Cl)CCl | O=C(CCl)Nc1ccccn1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | 80.1 | [{"value": 80.1, "product": "ClCC(=O)NC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Chloroacetylchloride (60 g, 0.53M) was added with stirring to a mixture of 2-aminopyridine (50 g, 0.53M) and diisopropylethylamine (75 ml, 0.53M) in dichloromethane (500 ml) keeping the temperature below 5° C. After the reaction mixture was warmed to room temperature it was filtered and washed with water. The organic l... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | ClCCl | null | null | Nc1ccccn1.O=C(Cl)CCl>ClCCl>O=C(CCl)Nc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d2aea31453084c8dba037f866c0833b5 | C1CNCCN1.COc1ccccc1C=CCO>>COc1ccccc1/C=C/CN1CCN(C/C=C/c2ccccc2OC)CC1 | COC1=C(C=CCO)C=CC=C1.S(=O)(Cl)Cl.N1CCNCC1>>COC1=C(C=CC=C1)/C=C/CN1CCN(CC1)C\C=C\C1=C(C=CC=C1)OC | [CH2:1]1[CH2:8][NH:12][CH2:9][CH2:10][NH:15]1.[OH:2][CH2:16][CH:17]=[CH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1/[CH:9]=[CH:10]/[CH2:11][N:12]1[CH2:13][CH2:14][N:15]([CH2:16]/[CH:17]=[CH:18]/[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[O:25][CH3:26])[CH... | C1CNCCN1.COc1ccccc1C=CCO | COc1ccccc1/C=C/CN1CCN(C/C=C/c2ccccc2OC)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ae38299a0dc1b7d9b40bbb5e2efe189375071b36bd4710814491a861f49ebbcd | 67bf8e269000e5e8ec7808c6cda59bc0898ee178a898a68ad64a0f0c67a170be | C(=C/c1ccccc1)\CN1CCN(C/C=C/c2ccccc2)CC1 | [CH2;D2;+0:1]1-[CH2;D2;+0:2]-[NH;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[NH;D2;+0:6]-1.[OH;D1;+0:7]-[CH2;D2;+0:8]-[C:9]=[C:10]-[c:11]>>[CH3;D1;+0:5]-[O;H0;D2;+0:7]-[c:12](:[c:13]):[c;H0;D3;+0:4](/[CH;D2;+0:2]=[CH;D2;+0:1]/[C:14]-[N;H0;D3;+0:3]1-[C:15]-[C:16]-[N;H0;D3;+0:6](-[CH2;D2;+0:8]/[C:9]=[C:10]/[c:11])-[C:17]-[C:18... | null | [] | null | null | null | null | 2-Methoxy-cinnamylalcohol (1.44 g) was chlorinated using thionylchloride. Subsequently, reaction with piperazine and other treatments were performed as described in Preparation Example 2, to thereby obtain 314 mg of a salt as colorless prisms.
Conditions: See reaction.notes.procedure_details.
Workup: as described in Pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine.Secondary amine | Ether.Tertiary amine.Tertiary amine | C1CNCCN1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | C1CNCCN1.COc1ccccc1C=CCO>>COc1ccccc1/C=C/CN1CCN(C/C=C/c2ccccc2OC)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-754d50c008364ac9b11186dee1fd24b1 | CCOC(=O)C(=O)CBr.O=C1CCCCC1=O>>O=C(O)c1coc2c1C(=O)CCC2 | [OH-].[Na+].[OH-].[K+].C1(C(CCCC1)=O)=O.BrCC(C(=O)OCC)=O>>O=C1CCCC2=C1C(=CO2)C(=O)O | CC[O:3][C:2](=[O:1])[C:4]([CH2:5]Br)=[O:6].O=[C:8]1[CH2:7][CH2:13][CH2:12][CH2:11][C:9]1=[O:10]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][o:6][c:7]2[c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13]2 | CCOC(=O)C(=O)CBr.O=C1CCCCC1=O | O=C(O)c1coc2c1C(=O)CCC2 | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 12c523d95bc989e82a3c117bb5c0da9972d3a2503b927240d48f0eb0564d3e74 | 8131734fe6d69265d1a032be994ef2ac858280264b2f94ca2c209f0c391853b1 | O=C1CCCc2occc21 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-C.O=[C;H0;D3;+0:7]1-[CH2;D2;+0:8]-[C:9]-[C:10]-[C:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:13]=[C:12]1-[C:11]-[C:10]-[C:9]-[c;H0;D3;+0:8]2:[o;H0;D2;+0:3]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]):[c;H0;D3;+0:7]:2-1 | null | [] | 0 | CELSIUS | 0.5 | HOUR | 4-Oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid was prepared as follows: To a stirred solution of potassium hydroxide (28.06 g, 0.5 mol) in methyl alcohol (100 mL) under nitrogen at 0° C. was added dropwise a solution of cyclohexanedione (56.07 g, 0.5 mol) in methyl alcohol (100 mL). The mixture was stirred at 0° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Ketone.Ester | Carboxylic acid.Ketone | C1CCCCC1 | c1cc2c(o1)CCCC2 | c1cc2c(o1)CCCC2 | HBr | CO.O | 0 | 0.5 | CCOC(=O)C(=O)CBr.O=C1CCCCC1=O>CO.O>O=C(O)c1coc2c1C(=O)CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ac1973ef2f974d578c8e88e00c27d930 | CC(=O)Cl.O=C(O)c1coc2c1C(=O)CCC2>>CCOC(=O)c1coc2c1C(=O)CCC2 | O=C1CCCC2=C1C(=CO2)C(=O)O.C(C)(=O)Cl>>O=C1CCCC2=C1C(=CO2)C(=O)OCC | O=[C:2](Cl)[CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][o:8][c:9]2[c:10]1[C:11](=[O:12])[CH2:13][CH2:14][CH2:15]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][o:8][c:9]2[c:10]1[C:11](=[O:12])[CH2:13][CH2:14][CH2:15]2 | CC(=O)Cl.O=C(O)c1coc2c1C(=O)CCC2 | CCOC(=O)c1coc2c1C(=O)CCC2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e4e418517831e68b0ae6eff0e20954e6373d72ef6db8a62429d10c826be6ea2e | b1bbfb03e48869c16300667505b58de6f6c5a435aa2a615a319deee7cf33326a | O=C1CCCc2occc21 | Cl-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[#8;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[#8;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 1 | HOUR | To a stirred suspension of 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid (28.2 g, 157 mmol) in ethyl alcohol (500 mL) under nitrogen at ambient temperature was added acetyl chloride(56 mL, 783 mmol) dropwise. After stirring 1 h, the solution was then heated at reflux for 1 h. The solution was cooled and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid | Ester | null | null | c1cc2c(o1)CCCC2 | Other | C(C)O | null | 1 | CC(=O)Cl.O=C(O)c1coc2c1C(=O)CCC2>C(C)O>CCOC(=O)c1coc2c1C(=O)CCC2 |
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