dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7527eb69678f4b00afc468a3bbc062ef | CCOC(=O)CSc1nccc(O)n1.O=C1CCC(=O)N1Br>>CCOC(=O)CSc1nccc(Br)n1 | O.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC1=NC(=NC=C1)SCC(=O)OCC>>BrC1=NC(=NC=C1)SCC(=O)OCC | O[c:12]1[cH:11][cH:10][n:9][c:8]([S:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:14]1.O=C1CCC(=O)N1[Br:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][S:7][c:8]1[n:9][cH:10][cH:11][c:12]([Br:13])[n:14]1 | CCOC(=O)CSc1nccc(O)n1.O=C1CCC(=O)N1Br | CCOC(=O)CSc1nccc(Br)n1 | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 332ca0722220d19160e856a3c9921806297eda6eb032daa7cbfeb3336780bf81 | 8ff2e5788c87c98c6b186fc8768ca8b9a470fb4896e8bf2306b275978aaa9be3 | c1cncnc1 | O-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:8]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[Br;H0;D1;+0:8]):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | null | null | 30 | MINUTE | Under argon, 52.5 g (0.20 mol) of triphenylphosphine are initially charged in 600 ml of dioxane, and 35.6 g (0.20 mol) of N-bromosuccinimide are added a little at a time, with cooling. The mixture is stirred at RT for 30 min. 8.6 g (0.04 mol) of ethyl [(4-hydroxy-2-pyrimidinyl)thio]acetate are then added and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Aromatic alcohol | Aromatic halide | c1cncnc1.C1CCNC1 | c1cncnc1 | c1cncnc1 | HO- | O1CCOCC1 | null | 0.5 | CCOC(=O)CSc1nccc(O)n1.O=C1CCC(=O)N1Br>O1CCOCC1>CCOC(=O)CSc1nccc(Br)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-083c6a63c5cf4ef4a1d50b8a2e104444 | CCOC(=O)CC(=O)C(OCC)OCC.N=C(N)N>>CCOC(OCC)c1cc(=O)[nH]c(N)n1 | C(C)OC(CC(C(OCC)OCC)=O)=O.C(O)(O)=O.NC(=N)N>>NC1=NC(=CC(N1)=O)C(OCC)OCC | CCO[C:10]([CH2:9][C:8](=O)[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])=[O:11].[NH2:12][C:13]([NH2:14])=[NH:15]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][c:10](=[O:11])[nH:12][c:13]([NH2:14])[n:15]1 | CCOC(=O)CC(=O)C(OCC)OCC.N=C(N)N | CCOC(OCC)c1cc(=O)[nH]c(N)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e1086e09babe9a6eadacd25aedc6500fef83912c69ad4a008a7c15c97bbc10be | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | O=c1ccnc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](-[#8:6])-[#8:7].[N;D1;H2:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[#8:6]-[C:5](-[#8:7])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:10]:[c;H0;D3;+0:9](-[N;D1;H2:8]):[n;H0;D2;+0:11]:1 | null | [] | null | null | null | null | A solution of 4,4-diethoxy-3-oxo-butyric acid ethyl ester [Johnson, T. B. and Mikeska, L. A. J. Am. Chem. Soc. 41, 810 (1919)] (18.0 g, 82.5 mol) in ethanol (300 mL) was treated with guanidine carbonate (14.8 g, 82.5 mol) and this was stirred under reflux until no solid remained (˜4 hours). The mixture was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | null | c1ccncn1 | c1ccncn1 | HO- | C(C)O | null | null | CCOC(=O)CC(=O)C(OCC)OCC.N=C(N)N>C(C)O>CCOC(OCC)c1cc(=O)[nH]c(N)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-764d1c4e0aa144ca945e165640b2174a | CCOC(=O)CC(=O)C(=O)OCC.N=C(N)N>>CCOC(=O)c1cc(=O)[nH]c(N)n1 | C(C)OC(CC(=O)C(=O)OCC)=O.C(O)(O)=O.NC(=N)N>>C(C)OC(=O)C=1N=C(NC(C1)=O)N | CCO[C:8]([CH2:7][C:6](=O)[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:9].[NH2:10][C:11]([NH2:12])=[NH:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](=[O:9])[nH:10][c:11]([NH2:12])[n:13]1 | CCOC(=O)CC(=O)C(=O)OCC.N=C(N)N | CCOC(=O)c1cc(=O)[nH]c(N)n1 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | cbab3679912241313f5fbc643aa0f3885595e68e8b36752540418f04a59a2151 | 1f7cfbf178b989a5dc61b8bb4fcd61ce54e19d0cd6c69f55ae836eb22030509b | O=c1ccnc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[N;D1;H2:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:11]:[c;H0;D3;+0:10](-[N;D1;H2:9]):[n;H0;D2;+0:12]:1 | null | [] | null | null | null | null | A solution of oxalacetic acid diethyl ester (8.5 g, 45.2 mmol) in ethanol (100 mL) was treated with guanidine carbonate (8.1 g, 45.2 mmol) and this was stirred under reflux for 2 hours. The mixture was diluted with water, concentrated to removed ethanol, and the solid was collected by filtration. The solid was then sus... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Primary amine | Ester | null | c1ccncn1 | c1ccncn1 | HO- | O.C(C)O | null | null | CCOC(=O)CC(=O)C(=O)OCC.N=C(N)N>O.C(C)O>CCOC(=O)c1cc(=O)[nH]c(N)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b695f5fa5646402185bd99e6f5509a2f | COC(=O)Cc1ccc(F)cc1.CSc1nccc(C=O)n1>>COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1 | C(C)(C)[N-]C(C)C.[Li+].FC1=CC=C(C=C1)CC(=O)OC.CSC1=NC=CC(=N1)C=O>>COC(C(C(O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.[CH:13](=[O:14])[c:15]1[cH:16][cH:17][n:18][c:19]([S:20][CH3:21])[n:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[CH:13]([OH:14])[c:15]1[cH:16][cH:17][n:18][c:19]([S:20][CH3:21])[n:22]1 | COC(=O)Cc1ccc(F)cc1.CSc1nccc(C=O)n1 | COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccc(CCc2ccncn2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;H0;D1;+0:9]=[CH;D2;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[CH;D3;+0:10](-[OH;D1;+0:9])-[c:11]1:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1)-[c:6](:[c:7]):[c:8] | 76 | [{"value": 76.0, "product": "COC(C(C(O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a cold (−78° C.) solution of lithium diisopropylamide (21.4 mL of 2M solution in THF, 42.8 mmol) in THF (70 mL) is added dropwise a solution of methyl 4-fluorophenyl-acetate (6.0 g, 35.7 mmol) in THF (30 mL). The solution is stirred for 1 hour at −78° C. after which a solution of 2-methylsulfanyl-pyrimidine-4-carbal... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1.c1cncnc1 | null | C1CCOC1 | null | 0.75 | COC(=O)Cc1ccc(F)cc1.CSc1nccc(C=O)n1>C1CCOC1>COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92abac6eebe740f68af133ca116b4187 | COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1>>COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1 | N1=CC=CC=C1.COC(C(C(O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O>>COC(C(C(=O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH:6]([OH:7])[c:8]1[cH:9][cH:10][n:11][c:12]([S:13][CH3:14])[n:15]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][n:11][c:12]([S:13][CH3:14])[n:15]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1 | COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1 | COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1 | null | [Cr] | C(Cl)Cl.CCOCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(Cc1ccccc1)c1ccncn1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[c:6])-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[c:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 43 | [{"value": 43.0, "product": "COC(C(C(=O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of CrO3 in CH2Cl2 (300 mL) is added pyridine. The mixture is stirred vigorously for 1 hour at room temp. A solution of the crude 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester, 2, prepared above in CH2Cl2 (50 mL) is added dropwise to the chromium suspension. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1cncnc1.c1ccccc1 | null | [Cr].C(Cl)Cl.CCOCC | null | 1 | COC(=O)C(c1ccc(F)cc1)C(O)c1ccnc(SC)n1>[Cr].C(Cl)Cl.CCOCC>COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac24702ae6f64a9aaf0f876ca8221ebb | C1CNNC1.COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1>>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 | N1NCCC1.COC(C(C(=O)C1=NC(=NC=C1)SC)C1=CC=C(C=C1)F)=O>>FC1=CC=C(C=C1)C1=C(N2N(CCC2)C1=O)C1=NC(=NC=C1)SC | [NH:19]1[NH:20][CH2:21][CH2:22][CH2:23]1.CO[C:17]([CH:9]([C:8](=O)[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:24]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1)=[O:18]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[c:17](=[O:18])[n:19]3[n:20]2[CH2:21][... | C1CNNC1.COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 10bf19095ad5fcc0a8a4a67ab60977b506cad07f365a67f5cbd1154439a3fca8 | f32fac81dfdb000dc8678b0df4fe3b0a64c38caab136205f41649f692b09b3bd | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7](-[#16:8]):[#7;a:9]:[c:10]:[c:11]:1)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[C:17]1-[C:18]-[C:19]-[NH;D2;+0:20]-[NH;D2;+0:21]-1>>[#16:8]-[c:7]1:[#7;a:6]:[c;H0;D3;+0:5](-[c;H0;D3;+0:4]2:[c;H0;D3;+0:3](-[c;H0;D3;+0:12](... | 37 | [{"value": 37.0, "product": "FC1=CC=C(C=C1)C1=C(N2N(CCC2)C1=O)C1=NC(=NC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of pyrazolidine (7.8 g, 54.16 mmol) in pyridine (100 mL) is added 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester, 3, (11.5 g, 36.1 mmol). The reaction mixture is heated to 90° C. for 16 hours. The solvent is removed in vacuo and the resulting residue purified over... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | null | C1CNNC1 | c1cn2n(c1)CCC2 | c1cncnc1.c1ccccc1.c1cn2n(c1)CCC2 | HO- | N1=CC=CC=C1 | 90 | null | C1CNNC1.COC(=O)C(C(=O)c1ccnc(SC)n1)c1ccc(F)cc1>N1=CC=CC=C1>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-245f887f4b944d7aa69c92de847409da | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1>>CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 | FC1=CC=C(C=C1)C1=C(N2N(CCC2)C1=O)C1=NC(=NC=C1)SC.CO.OOS(=O)[O-].[K+].S(=O)(=O)(O[O-])[O-].[K+].[K+]>>FC1=CC=C(C=C1)C1=C(N2N(CCC2)C1=O)C1=NC(=NC=C1)S(=O)(=O)C | [CH3:1][S:2][c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[c:19](=[O:20])[n:21]3[n:22]2[CH2:23][CH2:24][CH2:25]3)[n:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[c:19](=[O:20])[n:21]3[n... | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 | null | null | C(=O)(O)[O-].[Na+].C1CCOC1.O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 1 | HOUR | To a solution of 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 4, (1.3 g, 3.8 mmol) in THF:methanol (56 mL of a 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (9.34 g, 15.2 mmol) in water (42 mL). The reaction is stirred 1 hour at ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cncnc1.c1ccccc1.c1cn2n(c1)CCC2 | null | C(=O)(O)[O-].[Na+].C1CCOC1.O | null | 1 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1>C(=O)(O)[O-].[Na+].C1CCOC1.O>CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16ce0de6403640198e3f969730ca292f | C=C(CCl)CCl.CC(C)(C)OC(=O)NNC(=O)OCc1ccccc1>>C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1 | [H-].[Na+].C(=O)(OCC1=CC=CC=C1)NNC(=O)OC(C)(C)C.ClCC(=C)CCl>>C(C)(C)(C)OC(=O)N1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1 | Cl[CH2:3][C:2](=[CH2:1])[CH2:23]Cl.[NH:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH2:1]=[C:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:2... | C=C(CCl)CCl.CC(C)(C)OC(=O)NNC(=O)OCc1ccccc1 | C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | ce17673b84aa11a03e75dacc9ab89456d374efca0573321a46e3315bc85b6e5a | 9b2df4ffc85c3bfa472caf43fa08b1e61cbf4a7b843972afe9671fab932acf35 | C=C1CNN(C(=O)OCc2ccccc2)C1 | Cl-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[CH2;D2;+0:4]-Cl.[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9]1-[CH2;D2;+0:4]-[C:2](=[C;D1;H2:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:10]-1-[C:11](=[O... | null | [] | null | null | 20 | MINUTE | To a suspension of NaH (3.81 g, 95.4 mmol) in DMF (80 mL) is add dropwise a solution of N-Cbz-N′-Boc-hydrazine (12.1 g, 45.4 mmol) in DMF (20 mL). The reaction mixture is stirred about 20 minutes and 3-chloro-2-chloromethyl-propene (5.8 mL, 50 mmol) is added dropwise and the reaction is allowed to stir at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Primary halide.Primary halide | Acylhydrazine.Acylhydrazine.Carbamic ester.Carbamic ester | null | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1 | HCl | CN(C)C=O | null | 0.333333 | C=C(CCl)CCl.CC(C)(C)OC(=O)NNC(=O)OCc1ccccc1>CN(C)C=O>C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f5a1084af704e6c96cab63ed63b299d | C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1>>C=C1CNN(C(=O)OCc2ccccc2)C1 | Cl.C(C)(C)(C)OC(=O)N1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC(=O)N1NCC(C1)=C | CC(C)(C)OC(=O)[N:4]1[CH2:3][C:2](=[CH2:1])[CH2:16][N:5]1[C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH2:1]=[C:2]1[CH2:3][NH:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1 | C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1 | C=C1CNN(C(=O)OCc2ccccc2)C1 | null | null | CO | Reduction | Boc amine deprotection | 9578cd18bbcfcfca88169fdd3d6ff34423e5564f7f0c7e002990a08b9dceabe2 | b8e1e75e4199725018e8cff61fd2fde98c56b629bbf185579b99364e52c966a1 | C=C1CNN(C(=O)OCc2ccccc2)C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](=[C;D1;H2:4])-[C:5]-[#7:6]-1-[C:7](-[#8:8])=[O;D1;H0:9]>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7:6]1-[C:5]-[C:3](=[C;D1;H2:4])-[C:2]-[NH;D2;+0:1]-1 | 97 | [{"value": 97.0, "product": "C(C1=CC=CC=C1)OC(=O)N1NCC(C1)=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of crude 4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 8, (30 g) in methanol (300 mL) is added thionyl chloride dropwise at 0° C. The reaction is warmed to room temperature and stirred an additional 18 hours. Concentration of the reaction in vacuo affords a yellow oil wh... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether.Boc | Acylhydrazine | C1C[NH][NH]C1 | C1CN[NH]C1 | C1CN[NH]C1.c1ccccc1 | HO- | CO | null | 18 | C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1>CO>C=C1CNN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-500db76911fe4a4ead497cd52689022e | C=C1CNN(C(=O)OCc2ccccc2)C1.O=C(Cl)Cc1ccc(F)cc1>>C=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | [OH-].[Na+].C(C1=CC=CC=C1)OC(=O)N1NCC(C1)=C.FC1=CC=C(C=C1)CC(=O)Cl>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)=C)C(CC1=CC=C(C=C1)F)=O | [CH2:1]=[C:2]1[CH2:3][NH:4][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1.Cl[C:5](=[O:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH2:1]=[C:2]1[CH2:3][N:4]([C:5](=[O:6])[CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[N:15]([C:16](=[O:17])[O:18][CH2:19... | C=C1CNN(C(=O)OCc2ccccc2)C1.O=C(Cl)Cc1ccc(F)cc1 | C=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | null | null | O.C(Cl)Cl.O | Acylation | N-alkylation of secondary amines with alkyl halides | 0459b87e660679b8d69960c66dd0cc11b0e7482cd47b28c08235e8ee831fe8c9 | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | C=C1CN(C(=O)Cc2ccccc2)N(C(=O)OCc2ccccc2)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[C;D1;H2:11])-[C:12]-[NH;D2;+0:13]-1>>[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[C;D1;H2:11])-[C:12]-[N;H0;D3;+0:13]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 62 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)=C)C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydroxide (0.12 g, 3 mmol) is dissolved in a 1:2 water/methylene chloride solution (30 mL) with rapid stirring followed by the addition of 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester, 9, (0.62 g, 2.8 mmol) at room temperature. (4-Fluorophenyl)acetyl chloride (0.39 mL, 4.2 mmol) is added and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | C1CN[NH]C1 | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1.c1ccccc1 | HCl | O.C(Cl)Cl.O | null | null | C=C1CNN(C(=O)OCc2ccccc2)C1.O=C(Cl)Cc1ccc(F)cc1>O.C(Cl)Cl.O>C=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-248d1db259c542e7a6fada3be8fed337 | C1COCCN1.O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>>O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)=O)C(CC1=CC=C(C=C1)F)=O.N1CCOCC1.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].CC(=O)O.Cl.Cl>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)N1CCOCC1)C(CC1=CC=C(C=C1)F)=O | [NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.O=[C:13]1[CH2:12][N:11]([C:2](=[O:1])[CH2:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[N:21]([C:22](=[O:23])[O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:20]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([N:14... | C1COCCN1.O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | reductive amination | 239d9774f3fe4f3fbd9f65460249ac64af6187c5db1fef94a4c7dce1b76462c4 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | O=C(Cc1ccccc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[#7:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-1.[#8:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7:6]1-[C:10]-[CH;D3;+0:1](-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#8:11]-[C:16]-[C:15]-2)-[C:2]-[#7:3]-1-[C:4]=[O;D1;H0:5] | 60 | [{"value": 60.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)N1CCOCC1)C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (0.14 g, 0.4 mmol) and morpholine (0.038 mL, 0.43 mmol) in THF at room temperature is added Na(OAc)3BH (0.125 g, 0.6 mmol) and HOAc (0.022 mL, 0.4 mmol). The solution is stirred 12 hours then partitioned between diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1COCCN1.C1C[NH][NH]C1 | C1C[NH][NH]C1.C1COCC[NH]1 | c1ccccc1.C1C[NH][NH]C1.C1COCC[NH]1.c1ccccc1 | Other | C1CCOC1 | null | 12 | C1COCCN1.O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>C1CCOC1>O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa397fb612df4793addb6b2f66766d69 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1>>O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1 | Cl.C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)N1CCOCC1)C(CC1=CC=C(C=C1)F)=O>>FC1=CC=C(C=C1)CC(=O)N1NCC(C1)N1CCOCC1 | O=C(OCc1ccccc1)[N:21]1[N:11]([C:2](=[O:1])[CH2:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[CH2:12][CH:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH2:20]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH2:20][NH:21]1 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | 3760f8f0fb3cef0386fcc2bd25df2d075a94ea9bbd4272b04d35720969303b49 | 1f0012c5850764dd3cc9db449445325c9a813ec816b1ff7d035254ab8b2a88de | O=C(Cc1ccccc1)N1CC(N2CCOCC2)CN1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[#7:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 81 | [{"value": 81.0, "product": "FC1=CC=C(C=C1)CC(=O)N1NCC(C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 2-[2-(4-Fluorophenyl)acetyl]-4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester HCl salt, 12, (100 mg, 0.2 mmol) is dissolved in methanol and Pd/C (5 mg) is added. The solution is then hydrogenated in a Parr® Hydrogenation Apparatus for 3 days after which time the catalyst is removed by filtration and the fil... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether | Acylhydrazine | c1ccccc1.C1C[NH][NH]C1 | C1C[NH]NC1 | c1ccccc1.C1C[NH]NC1.C1COCC[NH]1 | HO- | [Pd].CO | null | 72 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)OCc1ccccc1>[Pd].CO>O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dead07a44f7a4bb99af3704ce3bf4d5d | CO.COC(=O)c1nc(C)ncc1S>>COC(=O)c1ccnc(S(C)(=O)=O)n1 | OOS(=O)[O-].[K+].COC(=O)C1=NC(=NC=C1S)C.CO.C1CCOC1>>COC(=O)C1=NC(=NC=C1)S(=O)(=O)C | O[CH3:11].C[c:9]1[n:8][cH:7][c:6]([SH:10])[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[n:14]1 | CO.COC(=O)c1nc(C)ncc1S | COC(=O)c1ccnc(S(C)(=O)=O)n1 | null | null | null | Oxidation | OtherReaction | bcd1859bec8d3a8ad1dea782a6e554ffe84f48b7d3bf31a1dc4adcd13e362dae | 6ca7a09e7728948227217f1d9332dd5ee0a2e7ded0c37f985a512a03a6969c11 | c1cncnc1 | C-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]):[c;H0;D3;+0:8](-[SH;D1;+0:9]):[c:10]:[#7;a:11]:1.O-[CH3;D1;+0:12]>>[C;D1;H3:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D4;+0:9](-[CH3;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]):[#7;a:11]:[c:10]:[cH;D2;+0:8]:1 | null | [] | null | null | 1.5 | HOUR | An aqueous solution (1 L) of Oxone® (211.7 g, 344 mmol) is added dropwise at 0° C. to a solution of 2-methyl-sulfanyl-pyrimidine-4-carboxylic acid methyl ester, 14, (19 9,86.1 mmol) in 1:1 methanol/THF (1 L). The reaction solution is allowed to warm to room temperature and stir for 1.5 hours. The resulting suspension i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Methanol | Sulfone | c1cncnc1 | c1cncnc1 | c1cncnc1 | null | null | null | 1.5 | CO.COC(=O)c1nc(C)ncc1S>>COC(=O)c1ccnc(S(C)(=O)=O)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-276c3050d37d4414aee78dca75b07f0e | COC(=O)c1ccnc(Oc2ccccc2)n1>>O=C(O)c1ccnc(Oc2ccccc2)n1 | COC(=O)C1=NC(=NC=C1)OC1=CC=CC=C1.[OH-].[Na+]>>O(C1=CC=CC=C1)C1=NC=CC(=N1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1 | COC(=O)c1ccnc(Oc2ccccc2)n1 | O=C(O)c1ccnc(Oc2ccccc2)n1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Oc2ncccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 60 | [{"value": 60.0, "product": "O(C1=CC=CC=C1)C1=NC=CC(=N1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 2-phenoxy-pyrimidine-4-carboxylic acid methyl ester, 16, (1.72 g, 74.8 mmol) in methanol (50 mL) is added a 50% NaOH solution (10 mL) at room temperature. After stirring for 1.5 hours the solvent is removed in vacuo and the remaining aqueous phase is extracted with ethyl acetate. The aqueous phase can ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | CO | null | 1.5 | COC(=O)c1ccnc(Oc2ccccc2)n1>CO>O=C(O)c1ccnc(Oc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b5716b643fe46a79cfea718435d5ecd | O=C(Cl)C(=O)Cl.O=C(O)c1ccnc(Oc2ccccc2)n1>>O=C(Cl)c1ccnc(Oc2ccccc2)n1 | O(C1=CC=CC=C1)C1=NC=CC(=N1)C(=O)O.C(C(=O)Cl)(=O)Cl>>O(C1=CC=CC=C1)C1=NC=CC(=N1)C(=O)Cl | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccnc(Oc2ccccc2)n1 | O=C(Cl)c1ccnc(Oc2ccccc2)n1 | null | CN(C)C=O | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc(Oc2ncccn2)cc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | null | [] | null | null | 2 | HOUR | To a solution of 2-phenoxy-pyrimidine-4-carboxylic acid, 17, (0.19 g, 0.89 mmol) in methylene chloride (10 mL) containing a few drops of DMF is added oxalyl chloride (0.1 mL). The solution is stirred for 2 hours at room temperature and concentrated in vacuo to afford the desired product which is used without further pu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cncnc1.c1ccccc1 | HCl | CN(C)C=O.C(Cl)Cl | null | 2 | O=C(Cl)C(=O)Cl.O=C(O)c1ccnc(Oc2ccccc2)n1>CN(C)C=O.C(Cl)Cl>O=C(Cl)c1ccnc(Oc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3c1f90257b1404d8bd653259f3abe9b | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)c1ccnc(Oc2ccccc2)n1>>O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(N1CCOCC1)C2 | FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)N1CCOCC1)C(=O)C1=NC(=NC=C1)OC1=CC=CC=C1.[H-].[Na+]>>FC1=CC=C(C=C1)C1=C(N2N(CC(C2)N2CCOCC2)C1=O)C1=NC(=NC=C1)OC1=CC=CC=C1 | O=[C:11]([c:12]1[cH:13][cH:14][n:15][c:16]([O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1)[N:25]1[N:26]([C:2](=[O:1])[CH2:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[CH2:27][CH:28]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH2:35]1>>[O:1]=[c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[c... | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)c1ccnc(Oc2ccccc2)n1 | O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(N1CCOCC1)C2 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 94a3c5df15e7ffb45c1fa6d50c33222438b5fcad2d4caebb8ef877690bb303e3 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=c1c(-c2ccccc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(N1CCOCC1)C2 | O=[C;H0;D3;+0:1](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#8:18]):[#7;a:19]:[c:20]:[c:21]:1>>[#8:18]-[c:17]1:[#7;a:19]:[c:20]:[c:21]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c;H0;D3;+0:9](-[... | 20 | [{"value": 20.0, "product": "FC1=CC=C(C=C1)C1=C(N2N(CC(C2)N2CCOCC2)C1=O)C1=NC(=NC=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-(4-fluorophenyl)-1-[4-morpholin-4-yl-2-(2-phenoxy-pyrimidine-4-carbonyl)pyrazolidine-1-yl]ethanone, 19, (0.2 g, 0.4 mmol) in DMF (10 mL) at 0° C. is added NaH (0.024 g, 0.6 mmol) and the resulting solution is stirred 2 hours. The solvent is removed in vacuo the residue dissolved in methylene chloride... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | C1C[NH][NH]C1 | c1cn2n(c1)C[CH]C2 | c1ccccc1.c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2.C1COCC[NH]1 | HO- | CN(C)C=O | null | 2 | O=C(Cc1ccc(F)cc1)N1CC(N2CCOCC2)CN1C(=O)c1ccnc(Oc2ccccc2)n1>CN(C)C=O>O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(N1CCOCC1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a24a25d742e340afb3d8dcefa39dd1b3 | CN(C)C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>>CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1 | Cl.C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)N(C)C)C(CC1=CC=C(C=C1)F)=O>>CN(C1CNN(C1)C(CC1=CC=C(C=C1)F)=O)C | O=C(OCc1ccccc1)[N:6]1[CH2:5][CH:4]([N:2]([CH3:1])[CH3:3])[CH2:18][N:7]1[C:8](=[O:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][NH:6][N:7]([C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1 | CN(C)C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | 5a07e2f524012d2f6f80c5a0d06ac6c177e8d13feb1f4c081828f9a230490fd7 | 1f0012c5850764dd3cc9db449445325c9a813ec816b1ff7d035254ab8b2a88de | O=C(Cc1ccccc1)N1CCCN1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[#7:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | 4-dimethylamino-2-[2-(4-fluorophenyl)acetyl]-pyrazolidine-1-carboxylic acid benzyl ester HCl salt, 21, (4.22 g, 10 mmol) is dissolved in methanol and Pd/C (100 mg) is added. The solution is then hydrogenated of a Parr® Hydrogenation Apparatus 18 hours after which time the catalyst is removed by filtration and the filtr... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether | Acylhydrazine | c1ccccc1.C1C[NH][NH]C1 | C1CN[NH]C1 | C1CN[NH]C1.c1ccccc1 | HO- | [Pd].CO | null | null | CN(C)C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>[Pd].CO>CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0ea4dd15bca4f30812abbf21b6d7a4f | CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>>CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | [OH-].[Na+].CN(C1CNN(C1)C(CC1=CC=C(C=C1)F)=O)C.CS(=O)(=O)C1=NC=CC(=N1)C(=O)Cl>>CN(C1CN(N(C1)C(CC1=CC=C(C=C1)F)=O)C(=O)C1=NC(=NC=C1)SC)C | [NH:10]1[CH2:11][CH:12]([N:13]([CH3:14])[CH3:15])[CH2:16][N:17]1[C:18](=[O:19])[CH2:20][c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.O=[S:2](=O)([CH3:1])[c:3]1[n:4][cH:5][cH:6][c:7]([C:8](Cl)=[O:9])[n:28]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH:12]([N:13]([CH3:14])[CH3:15])[CH2:1... | CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1 | CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | null | null | ClCCl | Acylation | OtherReaction | 5340a2176b1efc202a6178caa3249457e15c6ad066db75952b45d7d8b88c57f7 | 83a4e54509ac96555933260450599bd02024dc81a021eaa4d7252893ae767d9e | O=C(Cc1ccccc1)N1CCCN1C(=O)c1ccncn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[S;H0;D4;+0:6](=O)(=O)-[C;D1;H3:7]):[#7;a:8]:[c:9]:[c:10]:1.[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[N;H0;D3;+0:18]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-... | null | [] | null | null | 12 | HOUR | To a solution of 1-(4-dimethylamino-pyrazolidin-1-yl)-2-(4-fluorophenyl)-ethanone, 22, (2.5 g, 10 mmol) in dichloromethane (20 mL) is added 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (3.7 g, 20 mmol) followed by dropwise addition of a 1.0 N aqueous solution of sodium hydroxide (35 mL). The mixture is vigorously st... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine.Sulfone | Acylhydrazine.Acylhydrazine.Monosulfide | C1CN[NH]C1 | C1C[NH][NH]C1 | c1cncnc1.C1C[NH][NH]C1.c1ccccc1 | HCl | ClCCl | null | 12 | CN(C)C1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>ClCCl>CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08396a805534465c9d2391dc3eb2f269 | CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1>>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1 | CN(C1CN(N(C1)C(CC1=CC=C(C=C1)F)=O)C(=O)C1=NC(=NC=C1)SC)C.[H-].[Na+]>>CN(C1CN2N(C1)C(C(=C2C2=NC(=NC=C2)SC)C2=CC=C(C=C2)F)=O)C | O=[C:8]([c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:27]1)[N:20]1[N:19]([C:17]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)=[O:18])[CH2:26][CH:22]([N:23]([CH3:24])[CH3:25])[CH2:21]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[c:17](=[O:18])[n... | CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 94a3c5df15e7ffb45c1fa6d50c33222438b5fcad2d4caebb8ef877690bb303e3 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | O=[C;H0;D3;+0:1](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#16:18]):[#7;a:19]:[c:20]:[c:21]:1>>[#16:18]-[c:17]1:[#7;a:16]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c;H0;D3;+0:9](-[c;H0;D3;+0:1... | null | [] | 0 | CELSIUS | null | null | 1-[4-Dimethylamino-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)-pyrazolidin-1-yl]-2-(4-fluorophenyl)-ethanone, 23, (4.0 g, 10 mmol) is dissolved in THF (75 mL). This solution is then added dropwise via cannula to a suspension of NaH (0.440 g of a 60% dispersion in mineral oil, 11 mmol) at −30° C. The reaction is allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | C1C[NH][NH]C1 | c1cn2n(c1)C[CH]C2 | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | HO- | C1CCOC1 | 0 | null | CSc1nccc(C(=O)N2CC(N(C)C)CN2C(=O)Cc2ccc(F)cc2)n1>C1CCOC1>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44ea1d306de34253b4e25e3d6de8ac32 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1>>CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | CN(C1CN2N(C1)C(C(=C2C2=NC(=NC=C2)SC)C2=CC=C(C=C2)F)=O)C.CO.OOS(=O)[O-].[K+].S(=O)(=O)(O[O-])[O-].[K+].[K+]>>CN(C1CN2N(C1)C(C(=C2C2=NC(=NC=C2)S(=O)(=O)C)C2=CC=C(C=C2)F)=O)C | [CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][n:6]2[c:7](-[c:8]3[cH:9][cH:10][n:11][c:12]([S:13][CH3:14])[n:17]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[c:26](=[O:27])[n:28]2[CH2:29]1>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][n:6]2[c:7](-[c:8]3[cH:9][cH:10][n:11][c:12]([S:13]([CH3:14])(=[O:15])=[O:16])[n:17]3)[c:1... | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1 | CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | null | null | C(=O)(O)[O-].[Na+].C1CCOC1.O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 1 | HOUR | To a solution of 6-dimethylamino-2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 24, (3.9 g, 10 mmol) in THF:methanol (150 mL of a 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (24.3 g, 39.5 mmol) in water (100 mL). The reaction is ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | null | C(=O)(O)[O-].[Na+].C1CCOC1.O | null | 1 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1>C(=O)(O)[O-].[Na+].C1CCOC1.O>CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d25374737a9e4104a2fb69a179eedfcd | CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.C[C@H](N)c1ccccc1>>C[C@H](Nc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1)c1ccccc1 | CN(C1CN2N(C1)C(C(=C2C2=NC(=NC=C2)S(=O)(=O)C)C2=CC=C(C=C2)F)=O)C.C[C@@H](C1=CC=CC=C1)N>>CN(C1CN2N(C1)C(C(=C2C2=NC(=NC=C2)N[C@@H](C)C2=CC=CC=C2)C2=CC=C(C=C2)F)=O)C | CS(=O)(=O)[c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18](=[O:19])[n:20]3[n:21]2[CH2:22][CH:23]([N:24]([CH3:25])[CH3:26])[CH2:27]3)[n:28]1.[CH3:1][C@H:2]([NH2:3])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][C@H:2]([NH:3][c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[c... | CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.C[C@H](N)c1ccccc1 | C[C@H](Nc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1c(-c2ccccc2)c(-c2ccnc(NCc3ccccc3)n2)n2n1CCC2 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C;D1;H3:6]-[C:7](-[c:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 140 | CELSIUS | null | null | A solution of the crude 6-dimethylamino-2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 25, prepared as described herein above (4.2 g, 10 mmol) and (S)-(−)-α-methyl-benzyl amine (45.2 mL, 351 mmol) are dissolved in toluene (100 mL). The resulting mixture is heated to... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 140 | null | CN(C)C1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.C[C@H](N)c1ccccc1>C1(=CC=CC=C1)C>C[C@H](Nc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(N(C)C)C3)n1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dda017fe43b8478fafb3335b9df58960 | CC(C)(C)OC(=O)N1CC(=O)CN1C(=O)OCc1ccccc1>>CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1 | C(C)(C)(C)OC(=O)N1N(CC(C1)=O)C(=O)OCC1=CC=CC=C1.CCOCC>>C(C)(C)(C)OC(=O)N1N(CC(C1)O)C(=O)OCC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C:10](=[O:11])[CH2:12][N:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:12][N:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22... | CC(C)(C)OC(=O)N1CC(=O)CN1C(=O)OCc1ccccc1 | CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 3dd83949fcebb64c5c1352998f55ceea6b2269108640ce89731dc06f95107868 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(OCc1ccccc1)N1CCCN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[#7:9]-1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[C:8]-[#7:9]-1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-... | 93 | [{"value": 93.0, "product": "C(C)(C)(C)OC(=O)N1N(CC(C1)O)C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 40 | MINUTE | 4-Oxo-pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 27, (5.0 g, 15.6 mmol) is dissolved in tetrahydrofuran (150 mL) and the solution cooled to −78° C. A 5.0 M solution of borane-dimethyl sulfide complex in ether (6.24 mL, 31.2 mmol) is added dropwise via syringe. After 40 minutes at −78° C., the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1C[NH][NH]C1 | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1 | null | O1CCCC1 | -78 | 0.666667 | CC(C)(C)OC(=O)N1CC(=O)CN1C(=O)OCc1ccccc1>O1CCCC1>CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd9ac4cd0e8844958d4762bd71e90a7b | CC(C)(C)C(=O)Cl.CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1>>CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1 | C(C)(C)(C)OC(=O)N1N(CC(C1)O)C(=O)OCC1=CC=CC=C1.CC(C(=O)Cl)(C)C.ClCCl>>C(C)(C)(C)OC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)OCC1=CC=CC=C1 | Cl[C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:18][N:19]1[C:20](=[O:21])[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][C:12](=[O:13])[C:14]([CH3:... | CC(C)(C)C(=O)Cl.CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1 | CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(OCc1ccccc1)N1CCCN1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[OH;D1;+0:7]-[C:8]1-[C:9]-[#7:10]-[#7:11]-[C:12]-1>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:8]1-[C:9]-[#7:10]-[#7:11]-[C:12]-1 | 98 | [{"value": 98.0, "product": "C(C)(C)(C)OC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 4-Hydroxypyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 28, (1.42 mg, 4.40 mmol) is dissolved in pyridine (22 mL). 4-Dimethylamino-pyridine (10 mg) is added followed by trimethylacetyl chloride (1.63 mL, 13.2 mmol). The reaction is stirred at ambient temperature for 12 hours. The cloudy reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1C[NH][NH]C1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | null | 12 | CC(C)(C)C(=O)Cl.CC(C)(C)OC(=O)N1CC(O)CN1C(=O)OCc1ccccc1>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95bc99090f3e498c8ea0e5f42c1b5fc5 | CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1>>CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1 | C(C)(C)(C)OC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)OCC1=CC=CC=C1.S(=O)(Cl)Cl.Cl>>C(C1=CC=CC=C1)OC(=O)N1NCC(C1)OC(C(C)(C)C)=O | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH:8]([O:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[CH2:22][N:11]1[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH:8]1[CH2:9][NH:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]... | CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1 | CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1 | null | null | CO | Reduction | Boc amine deprotection | 9578cd18bbcfcfca88169fdd3d6ff34423e5564f7f0c7e002990a08b9dceabe2 | b8e1e75e4199725018e8cff61fd2fde98c56b629bbf185579b99364e52c966a1 | O=C(OCc1ccccc1)N1CCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C:6](-[#8:7])=[O;D1;H0:8]>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 98 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)OC(=O)N1NCC(C1)OC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 12 | HOUR | 4-(2,2-Dimethylpropionyloxy)pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 29, (1.76 g, 4.33 mmol) is dissolved in methanol (40 mL) and the solution cooled to 0° C. Thionyl chloride (3.16 mL, 43.3 mmol) is added dropwise and the reaction allowed to warm to room temperature and continue stirring 1... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether.Boc | Acylhydrazine | C1C[NH][NH]C1 | C1CN[NH]C1 | C1CN[NH]C1.c1ccccc1 | HO- | CO | 0 | 12 | CC(C)(C)OC(=O)N1CC(OC(=O)C(C)(C)C)CN1C(=O)OCc1ccccc1>CO>CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14ac32702a034893b50ffce1ffb8e2fb | CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1.O=C(O)Cc1ccc(F)cc1>>CC(C)(C)C(=O)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | Cl.C(C)N=C=NCCCN(C)C.C(C)N(CC)CC.C(C1=CC=CC=C1)OC(=O)N1NCC(C1)OC(C(C)(C)C)=O.FC1=CC=C(C=C1)CC(=O)O>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(CC1=CC=C(C=C1)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH:8]1[CH2:9][NH:10][N:21]([C:22](=[O:23])[O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32]1.O[C:11](=[O:12])[CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH:8]1[CH2:9][N:10]([C:11](=[O:12])[... | CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1.O=C(O)Cc1ccc(F)cc1 | CC(C)(C)C(=O)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 1e91ccb6d8e6d29c5edad331cfd72fffb3c076f5aa2586f8fccb4c6fa28b60c5 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | O=C(Cc1ccccc1)N1CCCN1C(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 91 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | 4-(2,2-Dimethylpropionyloxy)-pyrazolidine-1-carboxylic acid 1-benzyl ester, 30, (1.45 g, 4.23 mmol) is dissolved in dichloromethane (21 mL). The solution is cooled to 0° C. and triethylamine (1.30 mL, 9.31 mmol) added dropwise via syringe. The cold bath is removed and the reaction allowed to warm to room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | C1CN[NH]C1 | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1.c1ccccc1 | HO- | ClCCl | 0 | 0.333333 | CC(C)(C)C(=O)OC1CNN(C(=O)OCc2ccccc2)C1.O=C(O)Cc1ccc(F)cc1>ClCCl>CC(C)(C)C(=O)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c321a4c7a244437b81f8d587db912124 | CC(C)(C)C(=O)OC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>>CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | [OH-].[Na+].FC1=CC=C(C=C1)CC(=O)N1NCC(C1)OC(C(C)(C)C)=O.CS(=O)(=O)C1=NC=CC(=N1)C(=O)Cl>>FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)C1=NC(=NC=C1)SC | [NH:10]1[CH2:11][CH:12]([O:13][C:14](=[O:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][N:21]1[C:22](=[O:23])[CH2:24][c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1.O=[S:2](=O)([CH3:1])[c:3]1[n:4][cH:5][cH:6][c:7]([C:8](Cl)=[O:9])[n:32]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH:12](... | CC(C)(C)C(=O)OC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1 | CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | null | null | ClCCl | Acylation | OtherReaction | 5340a2176b1efc202a6178caa3249457e15c6ad066db75952b45d7d8b88c57f7 | 83a4e54509ac96555933260450599bd02024dc81a021eaa4d7252893ae767d9e | O=C(Cc1ccccc1)N1CCCN1C(=O)c1ccncn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[S;H0;D4;+0:6](=O)(=O)-[C;D1;H3:7]):[#7;a:8]:[c:9]:[c:10]:1.[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[N;H0;D3;+0:18]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-... | 96.6 | [{"value": 96.6, "product": "FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)C1=NC(=NC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 2,2-dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 32, (427 mg, 1.79 mmol) in dichloromethane (3 mL) is added 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (676 mg, 3.58 mmol) followed by dropwise addition of a 1.0 N aqueous solution of sodium hydroxide (6 mL). The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine.Sulfone | Acylhydrazine.Acylhydrazine.Monosulfide | C1CN[NH]C1 | C1C[NH][NH]C1 | c1cncnc1.C1C[NH][NH]C1.c1ccccc1 | HCl | ClCCl | null | 12 | CC(C)(C)C(=O)OC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>ClCCl>CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d18676ed547c49bbba7e0ace1b5f3389 | CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1>>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(OC(=O)C(C)(C)C)C3)n1 | FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(C(C)(C)C)=O)C(=O)C1=NC(=NC=C1)SC.[H-].[Na+]>>FC1=CC=C(C=C1)C=1C(N2N(C1C1=NC(=NC=C1)SC)CC(C2)OC(C(C)(C)C)=O)=O | O=[C:8]([c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:31]1)[N:20]1[N:19]([C:17]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)=[O:18])[CH2:30][CH:22]([O:23][C:24](=[O:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:21]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[c... | CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1 | CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(OC(=O)C(C)(C)C)C3)n1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 94a3c5df15e7ffb45c1fa6d50c33222438b5fcad2d4caebb8ef877690bb303e3 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | O=[C;H0;D3;+0:1](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#16:18]):[#7;a:19]:[c:20]:[c:21]:1>>[#16:18]-[c:17]1:[#7;a:16]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c;H0;D3;+0:9](-[c;H0;D3;+0:1... | 30 | [{"value": 30.0, "product": "FC1=CC=C(C=C1)C=1C(N2N(C1C1=NC(=NC=C1)SC)CC(C2)OC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 2,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-2-(methylsulfany-pyrimidine-4-carbonyl)-pyrazolidin-4-yl ester, 33, (300 mg, 0.651 mmol) is dissolved in THF (6 mL). This solution is then added dropwise via cannula to a suspension of NaH (29 mg of a 60% dispersion in mineral oil, 0.716 mmol) at −30° C. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | C1C[NH][NH]C1 | c1cn2n(c1)C[CH]C2 | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | HO- | C1CCOC1 | 0 | null | CSc1nccc(C(=O)N2CC(OC(=O)C(C)(C)C)CN2C(=O)Cc2ccc(F)cc2)n1>C1CCOC1>CSc1nccc(-c2c(-c3ccc(F)cc3)c(=O)n3n2CC(OC(=O)C(C)(C)C)C3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e9769098a8441dabd3195fa66d61c8f | CC(C)(C)C(=O)OC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.[O-]c1ccccc1>>O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(O)C2 | FC1=CC=C(C=C1)C=1C(N2N(C1C1=NC(=NC=C1)S(=O)(=O)C)CC(C2)OC(C(C)(C)C)=O)=O.C1(=CC=CC=C1)[O-].[Na+]>>FC1=CC=C(C=C1)C1=C(N2N(CC(C2)O)C1=O)C1=NC(=NC=C1)OC1=CC=CC=C1 | CC(C)(C)C(=O)[O:29][CH:28]1[CH2:27][n:26]2[c:2](=[O:1])[c:3](-[c:4]3[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]3)[c:11](-[c:12]3[cH:13][cH:14][n:15][c:16](S(C)(=O)=O)[n:24]3)[n:25]2[CH2:30]1.[O-:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)[c:11](-[c:12]2[cH:... | CC(C)(C)C(=O)OC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.[O-]c1ccccc1 | O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(O)C2 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 7a36d85b6073af3fd0f94a94db660dd991f14a912e4a0a2443e258fb99931769 | b9969328bd7472b5c57c9b3874c8a2da2f1c45bda94fbc8bd514a1e538069aa9 | O=c1c(-c2ccccc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CCC2 | C-C(-C)(-C)-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#7;a:4]:[#7;a:5]-[C:6]-1.C-S(=O)(=O)-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11].[O-;H0;D1:12]-[c:13](:[c:14]):[c:15]>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#7;a:4]:[#7;a:5]-[C:6]-1.[c:11]:[#7;a:10]:[c;H0;D3;+0:7](-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:8]:[c:9] | 21 | [{"value": 21.0, "product": "FC1=CC=C(C=C1)C1=C(N2N(CC(C2)O)C1=O)C1=NC(=NC=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2,2-dimethyl-propionic acid 6-(4-fluorophenyl)-7-(2-methane-sulfonyl-pyrimidin-4-yl)-5-oxo-2,3-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl ester, 35, (50 mg, 0.105 mmol) in THF (1 mL) is slowly cannulated into a solution of sodium phenolate in THF (1 mL) at 0° C. The cooling bath is removed and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Sulfone | Ether.Secondary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | HO- | C1CCOC1 | null | 1 | CC(C)(C)C(=O)OC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1.[O-]c1ccccc1>C1CCOC1>O=c1c(-c2ccc(F)cc2)c(-c2ccnc(Oc3ccccc3)n2)n2n1CC(O)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84b12dc39c894768b6b9c583103a0eff | O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>>O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)=O)C(CC1=CC=C(C=C1)F)=O.CCOCC>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)O)C(CC1=CC=C(C=C1)F)=O | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][C:13](=[O:14])[CH2:15][N:16]1[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([OH:14])[CH2:15][N:16]1[C:17](=[O:18])[O:19][CH2:2... | O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 3dd83949fcebb64c5c1352998f55ceea6b2269108640ce89731dc06f95107868 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(Cc1ccccc1)N1CCCN1C(=O)OCc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[#7:9]-1-[C:10]=[O;D1;H0:11]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[C:8]-[#7:9]-1-[C:10]=[O;D1;H0:11] | 73 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)O)C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | 2-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (1.0 g, 2.81 mmol) is dissolved in THF (30 mL) and the solution cooled to −78° C. A 5.0 M solution of borane-dimethyl sulfide complex in ether (1.2 mL, 5.61 mmol) is added dropwise. After 1 hour at −78° C., the reaction is quenched by s... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1C[NH][NH]C1 | C1C[NH][NH]C1 | c1ccccc1.C1C[NH][NH]C1.c1ccccc1 | null | C1CCOC1 | -78 | 1 | O=C1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>C1CCOC1>O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07899571ac004176a04f3732b5db25f0 | O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)O)C(CC1=CC=C(C=C1)F)=O.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-].N1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(CC1=CC=C(C=C1)F)=O | [OH:13][CH:14]1[CH2:15][N:16]([C:17](=[O:18])[CH2:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[N:27]([C:28](=[O:29])[O:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:38]1.Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][c:7]([N... | O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | null | null | ClCCl.O | Acylation | Schotten-Baumann to ester | 9d3813d6d0fea128d006be246c91a81540a6fda22070dabe99cbd137dd931f94 | bf61d3d2f28b6503a73eb3548c26cb203a24f8622ebddd1c0211172cf3f6ae1d | O=C(Oc1ccccc1)OC1CN(C(=O)Cc2ccccc2)N(C(=O)OCc2ccccc2)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[OH;D1;+0:5]-[C:6]1-[C:7]-[#7:8]-[#7:9]-[C:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#8:3]-[c:4])-[O;H0;D2;+0:5]-[C:6]1-[C:7]-[#7:8]-[#7:9]-[C:10]-1 | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 2-[2-(4-Fluorophenyl)acetyl]-4-hydroxy-pyrazolidine-1-carboxylic acid benzyl ester, 38, (366 mg, 1.02 mmol) is dissolved in dichloromethane (10 mL). The solution is cooled to 0° C. and p-nitrophenyl chloroformate (411 mg, 2.04 mmol) is added in one portion. The solution is stirred at 0° C., and pyridine (198 μL, 2.45 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Ether.Ether | null | null | c1ccccc1.C1C[NH][NH]C1.c1ccccc1.c1ccccc1 | HCl | ClCCl.O | 0 | 1 | O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>ClCCl.O>O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eec4b42b5c084c3bb52c9fd508719ce2 | C1COCCN1.O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>>O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(CC1=CC=C(C=C1)F)=O.N1CCOCC1>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(=O)N1CCOCC1)C(CC1=CC=C(C=C1)F)=O | [NH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.O=[N+]([O-])c1ccc(O[C:2](=[O:1])[O:3][CH:4]2[CH2:5][N:6]([C:7](=[O:8])[CH2:9][c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[N:17]([C:18](=[O:19])[O:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[CH2:28]2)cc1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][N:6]([C:7](=[O:8]... | C1COCCN1.O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 90888210e2a5e69f4c438ead6ba299d790b433d2e7a797a13239d00576df8fe5 | eddc3613d84ded08d7123d12e66f453518c88f1e99fc781f123cfee7c1f9d958 | O=C(OC1CN(C(=O)Cc2ccccc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1 | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]):c:c:1.[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | null | [] | null | null | 1.5 | HOUR | 2-[2-(4-Fluorophenyl)acetyl]-4-(4-nitro-phenoxycarbonyloxy)-pyrazolidine-1-carboxylic acid benzyl ester, 39, (462 mg, 0.882 mmol) is dissolved in dichloromethane (9 mL). Morpholine (770 μL, 8.82 mmol) is added and the reaction immediately develops a light yellow color. After stirring about 1.5 hours at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitro group.Secondary amine | Carbamic ester | C1COCCN1.c1ccccc1 | C1COCC[NH]1 | C1C[NH][NH]C1.c1ccccc1.c1ccccc1.C1COCC[NH]1 | HO- | ClCCl | null | 1.5 | C1COCCN1.O=C(Oc1ccc([N+](=O)[O-])cc1)OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1>ClCCl>O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-213fc392fbf14d7a9f55a86e23cd71e9 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1>>O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC(=O)N1CCOCC1)C(CC1=CC=C(C=C1)F)=O>>FC1=CC=C(C=C1)CC(=O)N1NCC(C1)OC(=O)N1CCOCC1 | O=C(OCc1ccccc1)[N:6]1[CH2:5][CH:4]([O:3][C:2](=[O:1])[N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[CH2:18][N:7]1[C:8](=[O:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][NH:6][N:7]([C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1)[N:19]1[... | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1 | O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | 5a07e2f524012d2f6f80c5a0d06ac6c177e8d13feb1f4c081828f9a230490fd7 | 1f0012c5850764dd3cc9db449445325c9a813ec816b1ff7d035254ab8b2a88de | O=C(OC1CNN(C(=O)Cc2ccccc2)C1)N1CCOCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[#7:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 2.5 | HOUR | morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 40, (512 mg, 1.09 mmol) is dissolved in methanol (10 mL) and the flask flushed with nitrogen then charged with 10% palladium on carbon (103 mg). The reaction mixture is vigorously stirred and hydrogenated at 1 atmosphe... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether | Acylhydrazine | c1ccccc1.C1C[NH][NH]C1 | C1CN[NH]C1 | C1CN[NH]C1.c1ccccc1.C1COCC[NH]1 | HO- | CO | null | 2.5 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1)N1CCOCC1>CO>O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7d30b541628c4d209e47355cf4b279db | O=C(Cl)c1ccnc(Oc2ccccc2)n1.O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1>>O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1 | FC1=CC=C(C=C1)CC(=O)N1NCC(C1)OC(=O)N1CCOCC1.O(C1=CC=CC=C1)C1=NC=CC(=N1)C(=O)Cl.[OH-].[Na+]>>FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(=O)N1CCOCC1)C(=O)C1=NC(=NC=C1)OC1=CC=CC=C1 | Cl[C:18](=[O:19])[c:20]1[cH:21][cH:22][n:23][c:24]([O:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32]1.[O:1]=[C:2]([O:3][CH:4]1[CH2:5][N:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[NH:17][CH2:33]1)[N:34]1[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][N:6]([... | O=C(Cl)c1ccnc(Oc2ccccc2)n1.O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 91de36b9dc9e6325ec180011ce317f011da9829041c7fa633c471469801d11e6 | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C(OC1CN(C(=O)Cc2ccccc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]1-[C:13]-[C:14]-[C:15]-[N;H0;D3;+0:16]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 61 | [{"value": 61.0, "product": "FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(=O)N1CCOCC1)C(=O)C1=NC(=NC=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 41, (354 mg, 1.05 mmol) and 2-phenoxypyrimidine-4-carbonyl chloride, 18, (345 mg, 1.47 mmol) are dissolved in dichloromethane (2 mL). 1.0 N NaOH (3 mL) is added dropwise at room temperature while vigorously stirring. The reaction is allow... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | C1C[NH]NC1 | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1.c1cncnc1.c1ccccc1.C1COCC[NH]1 | HCl | ClCCl | null | 12 | O=C(Cl)c1ccnc(Oc2ccccc2)n1.O=C(OC1CNN(C(=O)Cc2ccc(F)cc2)C1)N1CCOCC1>ClCCl>O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c544afb083bd431097b42993f61f5952 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1>>O=C(OC1Cn2c(-c3ccnc(Oc4ccccc4)n3)c(-c3ccc(F)cc3)c(=O)n2C1)N1CCOCC1 | FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC(=O)N1CCOCC1)C(=O)C1=NC(=NC=C1)OC1=CC=CC=C1.[H-].[Na+]>>FC1=CC=C(C=C1)C=1C(N2N(C1C1=NC(=NC=C1)OC1=CC=CC=C1)CC(C2)OC(=O)N2CCOCC2)=O | O=[C:7]([N:6]1[CH2:5][CH:4]([O:3][C:2](=[O:1])[N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[CH2:32][N:31]1[C:29]([CH2:21][c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1)=[O:30])[c:8]1[cH:9][cH:10][n:11][c:12]([O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][n:6]2[c:7](-[c:... | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1 | O=C(OC1Cn2c(-c3ccnc(Oc4ccccc4)n3)c(-c3ccc(F)cc3)c(=O)n2C1)N1CCOCC1 | null | null | CN(C=O)C.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 94a3c5df15e7ffb45c1fa6d50c33222438b5fcad2d4caebb8ef877690bb303e3 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=C(OC1Cn2c(-c3ccnc(Oc4ccccc4)n3)c(-c3ccccc3)c(=O)n2C1)N1CCOCC1 | O=[C;H0;D3;+0:1](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#8:18]):[#7;a:19]:[c:20]:[c:21]:1>>[#8:18]-[c:17]1:[#7;a:19]:[c:20]:[c:21]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c;H0;D3;+0:9](-[... | 32 | [{"value": 32.0, "product": "FC1=CC=C(C=C1)C=1C(N2N(C1C1=NC(=NC=C1)OC1=CC=CC=C1)CC(C2)OC(=O)N2CCOCC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-2-(2-phenoxypyrimidine-4-carbonyl)-pyrazolidin-4-yl ester, 42, (154 mg, 0.287 mmol) in dimethylformamide (3 mL) is added dropwise to a −10° C. suspension of sodium hydride (16.4 mg of a 60% dispersion in mineral oil, 0.410 mmol) in tetrahydrofuran ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | C1C[NH][NH]C1 | c1cn2n(c1)C[CH]C2 | c1cncnc1.c1ccccc1.c1ccccc1.c1cn2n(c1)C[CH]C2.C1COCC[NH]1 | HO- | CN(C=O)C.O1CCCC1 | 0 | 1 | O=C(OC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(Oc3ccccc3)n2)C1)N1CCOCC1>CN(C=O)C.O1CCCC1>O=C(OC1Cn2c(-c3ccnc(Oc4ccccc4)n3)c(-c3ccc(F)cc3)c(=O)n2C1)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-655bf75cb9f346c6bda87fc87af5a863 | CI.O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1>>COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)O)C(CC1=CC=C(C=C1)F)=O.CI.CCOCC>>C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC)C(CC1=CC=C(C=C1)F)=O | I[CH3:1].[OH:2][CH:3]1[CH2:4][N:5]([C:6](=[O:7])[CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[N: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>>[CH3:1][O:2][CH:3]1[CH2:4][N:5]([C:6](=[O:7])[CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[N:16]([C:17](=[O:18])... | CI.O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1 | COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 | null | [Ag]=O | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | O=C(Cc1ccccc1)N1CCCN1C(=O)OCc1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[C:3]1-[C:4]-[#7:5]-[#7:6]-[C:7]-1>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[C:3]1-[C:4]-[#7:5]-[#7:6]-[C:7]-1 | 97 | [{"value": 97.0, "product": "C(C1=CC=CC=C1)OC(=O)N1N(CC(C1)OC)C(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-[2-(4-Fluorophenyl)acetyl]-4-hydroxy-pyrazolidine-1-carboxylic acid benzyl ester, 28, (2.55 g, 7.91 mmol) is dissolved in dimethylformamide (40 mL). Methyl iodide (1.97 mL, 31.6 mmol) is added followed by silver oxide (3.67 g, 15.8 mmol). The flask is cover with foil and stirred overnight in the absence of light. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | C1C[NH][NH]C1.c1ccccc1.c1ccccc1 | HI | [Ag]=O.CN(C=O)C | null | 8 | CI.O=C(Cc1ccc(F)cc1)N1CC(O)CN1C(=O)OCc1ccccc1>[Ag]=O.CN(C=O)C>COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6940eccead1d4814aab7d5708d0adac2 | COC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>>COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1 | FC1=CC=C(C=C1)CC(=O)N1NCC(C1)OC.CS(=O)(=O)C1=NC=CC(=N1)C(=O)Cl.[OH-].[Na+]>>FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC)C(=O)C1=NC(=NC=C1)SC | [CH3:1][O:2][CH:3]1[CH2:4][N:5]([C:6](=[O:7])[CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[NH:16][CH2:27]1.O=[S:24](=O)([c:23]1[n:22][cH:21][cH:20][c:19]([C:17](Cl)=[O:18])[n:26]1)[CH3:25]>>[CH3:1][O:2][CH:3]1[CH2:4][N:5]([C:6](=[O:7])[CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[N:16]([C:17](=[... | COC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1 | COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1 | null | null | ClCCl.C([O-])([O-])=O.[Na+].[Na+] | Acylation | OtherReaction | 635bdbce5dbfbf5e4318ca853132979fea09f3235e6671d6f20e3bb4d7eb89bb | 83a4e54509ac96555933260450599bd02024dc81a021eaa4d7252893ae767d9e | O=C(Cc1ccccc1)N1CCCN1C(=O)c1ccncn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[S;H0;D4;+0:6](=O)(=O)-[C;D1;H3:7]):[#7;a:8]:[c:9]:[c:10]:1.[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C:16]-[C:17]-[N;H0;D3;+0:18]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-... | null | [] | null | null | 4 | HOUR | 2-(4-Fluorophenyl)-1-(4-methoxy-pyrazolidin-1-yl)-ethanone, 47, (7.67 g, 32.2 mmol) and 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (9.11 g, 48.3 mmol) are dissolved in dichloromethane (150 mL). A 0.5 N aqueous solution of sodium hydroxide (150 mL) is added steadily via addition funnel and the mixture is stirred vi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine.Sulfone | Acylhydrazine.Acylhydrazine.Monosulfide | C1C[NH]NC1 | C1C[NH][NH]C1 | C1C[NH][NH]C1.c1ccccc1.c1cncnc1 | HCl | ClCCl.C([O-])([O-])=O.[Na+].[Na+] | null | 4 | COC1CNN(C(=O)Cc2ccc(F)cc2)C1.CS(=O)(=O)c1nccc(C(=O)Cl)n1>ClCCl.C([O-])([O-])=O.[Na+].[Na+]>COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0529cd6038664d1a9b461b16a65a887a | COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1>>COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | FC1=CC=C(C=C1)CC(=O)N1N(CC(C1)OC)C(=O)C1=NC(=NC=C1)SC.CN(C=O)C.O1CCCC1.[H-].[Na+]>>FC1=CC=C(C=C1)C1=C(N2N(CC(C2)OC)C1=O)C1=NC(=NC=C1)SC | O=[C:6]([N:5]1[CH2:4][CH:3]([O:2][CH3:1])[CH2:26][N:25]1[C:23]([CH2:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)=[O:24])[c:7]1[cH:8][cH:9][n:10][c:11]([S:12][CH3:13])[n:14]1>>[CH3:1][O:2][CH:3]1[CH2:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][n:10][c:11]([S:12][CH3:13])[n:14]3)[c:15](-[c:16]3[cH:17][cH:18][c:19]([F:20]... | COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1 | COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 94a3c5df15e7ffb45c1fa6d50c33222438b5fcad2d4caebb8ef877690bb303e3 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | O=[C;H0;D3;+0:1](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#16:18]):[#7;a:19]:[c:20]:[c:21]:1>>[#16:18]-[c:17]1:[#7;a:19]:[c:20]:[c:21]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c;H0;D3;+0:9](... | 57 | [{"value": 57.0, "product": "FC1=CC=C(C=C1)C1=C(N2N(CC(C2)OC)C1=O)C1=NC(=NC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 2-(4-fluorophenyl)-1-[4-methoxy-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)pyrazolidine-1-yl]-ethanone, 48, (2.04 g, 5.22 mmol) in 1:1 dimethylformamide/tetrahydrofuran (30 mL) is added dropwise to a 0° C. suspension of sodium hydride (230 mg of a 60% dispersion in mineral oil, 5.75 mmol) in dimethylformam... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | C1C[NH][NH]C1 | c1cn2n(c1)C[CH]C2 | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | HO- | CN(C=O)C | null | 2 | COC1CN(C(=O)Cc2ccc(F)cc2)N(C(=O)c2ccnc(SC)n2)C1>CN(C=O)C>COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9376f5d373fb4f039f78d34ca6b522f9 | COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1.O=C(OO)c1cccc(Cl)c1>>COC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | FC1=CC=C(C=C1)C1=C(N2N(CC(C2)OC)C1=O)C1=NC(=NC=C1)SC.ClC1=CC(=CC=C1)C(=O)OO.S([O-])(O)=O.[Na+].ClC1=CC(=CC=C1)C(=O)OO>>FC1=CC=C(C=C1)C1=C(N2N(CC(C2)OC)C1=O)C1=NC(=NC=C1)S(=O)(=O)C | [CH3:1][O:2][CH:3]1[CH2:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][n:10][c:11]([S:12][CH3:13])[n:16]3)[c:17](-[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[c:25](=[O:26])[n:27]2[CH2:28]1.O=C(O[OH:15])c1cccc(Cl)c1>>[CH3:1][O:2][CH:3]1[CH2:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][n:10][c:11]([S:12]([CH3:13])(=[O:14])=[O:15])[n:16]... | COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1.O=C(OO)c1cccc(Cl)c1 | COC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 | null | null | ClCCl | Oxidation | OtherReaction | 84855dd3f46d7f633669ce7b0a2d1343353729d5975dd53fd20abc6eb43ece69 | dc6f43112eef310adb122ebf81e1733b34eff292ed27058fb45445842d61d3da | O=c1c(-c2ccccc2)c(-c2ccncn2)n2n1CCC2 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:3](=[O;D1;H0:9])(=[O;H0;D1;+0:1])-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | 20 | MINUTE | 2-(4-Fluorophenyl)-6-methoxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 49, (1.10 g, 2.95 mmol) is diluted with dichloromethane (60 mL). 3-Chloroperbenzoic acid (662 mg of ˜77% purity, 2.95 mmol) is added all at once to the yellow suspension. After 20 min, additional 3-chloroperben... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfone | c1ccccc1 | null | c1cncnc1.c1ccccc1.c1cn2n(c1)C[CH]C2 | HCl | ClCCl | null | 0.333333 | COC1Cn2c(-c3ccnc(SC)n3)c(-c3ccc(F)cc3)c(=O)n2C1.O=C(OO)c1cccc(Cl)c1>ClCCl>COC1Cn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)c(=O)n2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0224c20f2e144680a90e3f6f2a7fd373 | NCC(=O)OCc1ccccc1>>CC(=O)OCc1ccccc1 | CN(C)[P+](N(C)C)(N(C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC(CN)=O.Cl>>C(C1=CC=CC=C1)OC(C)=O | N[CH2:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | NCC(=O)OCc1ccccc1 | CC(=O)OCc1ccccc1 | null | null | CCOC(=O)C.CN(C)C=O | Reduction | OtherReaction | 0cd4ae4500561d2b43ed94481c8df711dd015696c792f8f157ca86736635c7a1 | fc38e660a3e677b2dbb29a39046e330adf15c8ad92e29b7f76466fb7196336ff | c1ccccc1 | N-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]>>[C:5]-[#8:4]-[C:2](-[CH3;D1;+0:1])=[O;D1;H0:3] | 215.4 | [{"value": 215.4, "product": "C(C1=CC=CC=C1)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 96 | HOUR | Glycine benzyl ester p-toluenesulfonate salt (6.03 g) was dissolved in DMF prior to the addition of Hunig's base (12.4 mL) and 2-(tert-butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6 g) (Takagishi et al., Synlett 1992, 360). After cooling to 0° C., BOP Reagent (8.69 g) was added. The resulting mixture was warmed ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Ester | null | null | c1ccccc1 | Other | CCOC(=O)C.CN(C)C=O | 0 | 96 | NCC(=O)OCc1ccccc1>CCOC(=O)C.CN(C)C=O>CC(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c8013b1e4334c0ea13274b312c754f1 | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>>CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F>>C(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F | C[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20] | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | null | null | O1CCOCC1.Cl | Miscellaneous | OtherReaction | 47ee087222cc986f9fb1ced28c92ac84f92f81e26297f2d960a13936e28e91e9 | 1b4ed01a2f690ab7de22ff29ffe33634aafc80d6e4fc163123671460c5372d70 | c1ccccc1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[#8:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[#8:4]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | 14 | [{"value": 14.0, "product": "C(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6.0 g) was dissolved in 4M HCl (4 mL) in dioxane. After 3 h, the solution was concentrated to a white solid. A portion of this material (900 mg) was dissolved in THF (10 mL), water (2 mL), and Et3N (1.8 mL) prior to the addition of 1M i-propyl chloroformate (4... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | Ether | null | null | c1ccccc1 | Other | O1CCOCC1.Cl | null | 3 | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>O1CCOCC1.Cl>CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49117191fe304ac4a8e3e2f12b232b4f | C=CCBr.CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>>CC(C)NC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | C(=O)([O-])[O-].[K+].[K+].C(C=C)Br.C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F.CN(C)C=O.CCOC(=O)C>>C(C)(C)NC(NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F)=O | Br[CH2:3]C=[CH2:1].CC(C)(C)O[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20]>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20] | C=CCBr.CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | CC(C)NC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | null | null | O | Acylation | OtherReaction | f235f6338c06b05897387d80e39338de7425c291773d7166f74c5256da9fc1cb | 9cfcd3456014bfd73349ee4c910289d23ccdeaed699e848ca705172afed75519 | c1ccccc1 | Br-[CH2;D2;+0:1]-C=[CH2;D1;+0:2].C-C(-C)(-C)-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:5]-[c:6]>>[CH3;D1;+0:2]-[C:7](-[CH3;D1;+0:1])-[#7:8]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:5]-[c:6] | null | [] | null | null | 1 | HOUR | 2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (2 g) was dissolved in DMF prior to the addition of K2CO3 (1.08 g) and allyl bromide (0.68 mL). The mixture was stirred for 18 h before EtOAc and water were added. The organic layer was washed with brine, dried, filtered, and concentrated (2.05 g). The resultin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Allyl.Boc | Urea | null | null | c1ccccc1 | HBr | O | null | 1 | C=CCBr.CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>O>CC(C)NC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5512a38e6e4242e797c233f92c35932b | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>>CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F>>C(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F | C[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20] | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O | null | null | O1CCOCC1.Cl | Miscellaneous | OtherReaction | 47ee087222cc986f9fb1ced28c92ac84f92f81e26297f2d960a13936e28e91e9 | 1b4ed01a2f690ab7de22ff29ffe33634aafc80d6e4fc163123671460c5372d70 | c1ccccc1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[#8:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[#8:4]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | 5.3 | [{"value": 5.3, "product": "C(C)(C)OC(=O)NC1=C(C(=O)O)C=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6.0 g) was dissolved in 4M HCl (4 mL) in dioxane. After 3 h, the solution was concentrated to a white solid. A portion of this material (200 mg) was dissolved in THF (2.5 mL) and 2M K2CO3 (1.46 mL) was added followed by cyclohexanecarbonyl chloride (0.2 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | Ether | null | null | c1ccccc1 | Other | O1CCOCC1.Cl | null | 3 | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O>O1CCOCC1.Cl>CC(C)OC(=O)Nc1ccc(C(F)(F)F)cc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d12f0fca81cd4ef483d82118f4d47080 | CSc1ccc(S(C)(=O)=O)cc1.c1ccc(CO[C@H]2CC[C@@H]3O[C@@H]3C2)cc1>>CSc1ccc(S(=O)(=O)C[C@@H]2CC[C@H](OCc3ccccc3)C[C@H]2O)cc1 | [NH4+].[Cl-].B(F)(F)F.CCOCC.C(C1=CC=CC=C1)O[C@@H]1C[C@@H]2[C@H](CC1)O2.CS(=O)(=O)C1=CC=C(C=C1)SC.[Li]CCCC>>C(C1=CC=CC=C1)O[C@H]1CC[C@H]([C@@H](C1)O)CS(=O)(=O)C1=CC=C(C=C1)SC | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH3:10])[cH:26][cH:27]1.[C@H:11]12[CH2:12][CH2:13][C@H:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23][C@H:24]1[O:25]2>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][C@@H:11]2[CH2:12][CH2:13][C@H:14]([O:15][CH2:16][c:17... | CSc1ccc(S(C)(=O)=O)cc1.c1ccc(CO[C@H]2CC[C@@H]3O[C@@H]3C2)cc1 | CSc1ccc(S(=O)(=O)C[C@@H]2CC[C@H](OCc3ccccc3)C[C@H]2O)cc1 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | OtherReaction | 51819a7923b1c5dbdee1645270bdebf414da27dfeec7464b16c6d05c2f8ca2a2 | 3f6b269d3a99a15a69c35a864bf12ee50f8d35e815861bb36518e2ffe01eeb4e | O=S(=O)(C[C@H]1CC[C@@H](OCc2ccccc2)CC1)c1ccccc1 | [CH3;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[C@H;D3;+0:10]2-[O;H0;D2;+0:11]-[C@@H;D3;+0:12]-1-2>>[O;D1;H0:3]=[#16:2](=[O;D1;H0:4])(-[c:5])-[CH2;D2;+0:1]-[C@@H;D3;+0:12]1-[C:6]-[C:7]-[C:8]-[C:9]-[C@H;D3;+0:10]-1-[OH;D1;+0:11] | 80.3 | [{"value": 80.3, "product": "C(C1=CC=CC=C1)O[C@H]1CC[C@H]([C@@H](C1)O)CS(=O)(=O)C1=CC=C(C=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | 1-Methanesulfonyl-4-methylsulfanyl-benzene (3.25 g) was dissolved in THF (50 mL) and cooled to −78° C. prior to the addition of 1.6 M nBuLi (10 mL). After 0.5 h, BF3-Et2O (2.04 mL) was added followed by (±)(1S*,2R*,4S*)-4-(benzyloxy)-1,2-epoxycyclohexane (2.19 g) (Chini et al. J. Org. Chem. 1990, 55, 4265) in THF (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC[C@H]2O[C@H]2C1 | C1CCCCC1 | c1ccccc1.C1CCCCC1.c1ccccc1 | null | C1CCOC1.CCOC(=O)C | -78 | 0.5 | CSc1ccc(S(C)(=O)=O)cc1.c1ccc(CO[C@H]2CC[C@@H]3O[C@@H]3C2)cc1>C1CCOC1.CCOC(=O)C>CSc1ccc(S(=O)(=O)C[C@@H]2CC[C@H](OCc3ccccc3)C[C@H]2O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e6cc379dfa349a28ee987c02c5121ab | C1CC2OC2CO1.CSc1ccc(S(C)(=O)=O)cc1>>CSc1ccc(S(=O)(=O)C[C@@H]2CCOC[C@H]2O)cc1 | O1C2COCCC21.CS(=O)(=O)C1=CC=C(C=C1)SC.[Li]CCCC.[NH4+].[Cl-].B(F)(F)F.CCOCC>>CSC1=CC=C(C=C1)S(=O)(=O)C[C@H]1[C@@H](COCC1)O | [CH:11]12[CH2:12][CH2:13][O:14][CH2:15][CH:16]1[O:17]2.[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH3:10])[cH:18][cH:19]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][C@@H:11]2[CH2:12][CH2:13][O:14][CH2:15][C@H:16]2[OH:17])[cH:18][cH:19]1 | C1CC2OC2CO1.CSc1ccc(S(C)(=O)=O)cc1 | CSc1ccc(S(=O)(=O)C[C@@H]2CCOC[C@H]2O)cc1 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | OtherReaction | 5c86285ae8c712fb10b2856f1c775b687aaa46eb6660d48c8338aff3a4243e43 | 3f6b269d3a99a15a69c35a864bf12ee50f8d35e815861bb36518e2ffe01eeb4e | O=S(=O)(CC1CCOCC1)c1ccccc1 | [#8:1]1-[C:2]-[C:3]-[CH;D3;+0:4]2-[O;H0;D2;+0:5]-[CH;D3;+0:6]-2-[C:7]-1.[CH3;D1;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[O;D1;H0:10]=[#16:9](=[O;D1;H0:11])(-[c:12])-[CH2;D2;+0:8]-[C@@H;D3;+0:4]1-[C:3]-[C:2]-[#8:1]-[C:7]-[C@H;D3;+0:6]-1-[OH;D1;+0:5] | 35.9 | [{"value": 35.9, "product": "CSC1=CC=C(C=C1)S(=O)(=O)C[C@H]1[C@@H](COCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | 1-Methanesulfonyl-4-methylsulfanyl-benzene (4.33 g) was dissolved in THF (50 mL) and cooled to −78° C. prior to the addition of 1.6 M nBuLi (13.4 mL). After 0.5 h, BF3-Et2O (2.7 mL) was added followed (±)3,4-epoxytetrahydropyran (1.2 g) (Tetrahedron 1974, 4013). After an addition 1 h at −78° C., the solution was warmed... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CC2OC2CO1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | null | C1CCOC1.CCOC(=O)C | -78 | 0.5 | C1CC2OC2CO1.CSc1ccc(S(C)(=O)=O)cc1>C1CCOC1.CCOC(=O)C>CSc1ccc(S(=O)(=O)C[C@@H]2CCOC[C@H]2O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93b60822344942a1918edaf6b1b87f2d | CCOC(=O)C#N.O=C1CCC2(CC1)OCCO2>>CCOC(=O)C1CC2(CCC1=O)OCCO2 | CCOC(=O)C.C1COC2(CCC(CC2)=O)O1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C(#N)C(=O)OCC>>C(C)OC(=O)C1CC2(OCCO2)CCC1=O | N#C[C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:6]1[CH2:7][C:8]2([CH2:9][CH2:10][C:11]1=[O:12])[O:13][CH2:14][CH2:15][O:16]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][C:8]2([CH2:9][CH2:10][C:11]1=[O:12])[O:13][CH2:14][CH2:15][O:16]2 | CCOC(=O)C#N.O=C1CCC2(CC1)OCCO2 | CCOC(=O)C1CC2(CCC1=O)OCCO2 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 1a8fe318f105920b5b5c15b644bb0a73f3b0df651aa4c7eefe0a714cb65f980c | ea62efa90ef3cfb13125a23e62e9e1787aa2a0b0ee48c8a61b3326a3bda24134 | O=C1CCC2(CC1)OCCO2 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](-[#8:7])-[C:8]-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[C:12]>>[#8:5]-[C:6](-[#8:7])-[C:8]-[CH;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:10](=[O;D1;H0:11])-[C:12] | null | [] | -78 | CELSIUS | 30 | MINUTE | 1,4-Cyclohexanedione mono-ethylene ketal (25 g) was dissolved in THF and cooled to −78° C. 1.0 M Lithium bis(trimethylsily)amide (160 mL) in THF was added dropwise. After 30 min, ethyl cyanoformate (15.9 mL) was added dropwise. After 60 min, the solution was poured into EtOAc and water containing ice. The organic layer... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Ketone.Ester | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | Other | C1CCOC1.O | -78 | 0.5 | CCOC(=O)C#N.O=C1CCC2(CC1)OCCO2>C1CCOC1.O>CCOC(=O)C1CC2(CCC1=O)OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fdf84e631d54fe4b2045e44440bcbc0 | C=O.CC(C)N[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1>>CC(C)N(C)[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1 | C(C1=CC=CC=C1)OC(N[C@@H]1[C@@H](C[C@@H](CC1)NC(C)C)CS(=O)(=O)C1=CC=C(C=C1)Br)=O.C=O.[BH3-]C#N.[Na+]>>C(C1=CC=CC=C1)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N(C)C(C)C)CS(=O)(=O)C1=CC=C(C=C1)Br)=O | O=[CH2:5].[CH3:1][CH:2]([CH3:3])[NH:4][C@@H:6]1[CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C@H:21]([CH2:22][S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][c:29]([Br:30])[cH:31][cH:32]2)[CH2:33]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH3:5])[C@@H:6]1[CH2:7][CH2:8][C@H:9](... | C=O.CC(C)N[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1 | CC(C)N(C)[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1 | null | null | CO.O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C(N[C@H]1CCCC[C@H]1CS(=O)(=O)c1ccccc1)OCc1ccccc1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[NH;D2;+0:4]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8]>>[C:2]-[C:3](-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8] | 94.4 | [{"value": 94.4, "product": "C(C1=CC=CC=C1)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N(C)C(C)C)CS(=O)(=O)C1=CC=C(C=C1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | The above derivative (118ba) (1.96 g) was dissolved in MeOH (15 ml) prior to the addition of 37% formaldehyde in water (1.41 ml). After 10 min, NaBH3CN (708 mg) was added. After 2 h, the reaction was concentrated. EtOAc was added and the organic layer was washed with H2O, brine, dried, filtered, and concentrated to giv... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | Other | CO.O | null | 0.166667 | C=O.CC(C)N[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1>CO.O>CC(C)N(C)[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](CS(=O)(=O)c2ccc(Br)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07a1586a71a844e8a6e16fd757884448 | CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1>>CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N)CC[C@@H]2NC(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N=[N+]=[N-])CS(=O)(=O)C1=CC=C(C=C1)SC)=O.[H][H]>>C(C)(C)(C)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N)CS(=O)(=O)C1=CC=C(C=C1)SC)=O | [N-]=[N+]=[N:14][C@H:13]1[CH2:12][C@@H:11]([CH2:10][S:7]([c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:27][cH:26]2)(=[O:8])=[O:9])[C@@H:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:16][CH2:15]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][C@@H:11]2[CH2:12][C@H:13]([NH2:14])[C... | CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1 | CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N)CC[C@@H]2NC(=O)OC(C)(C)C)cc1 | null | [Pd].[O-]S(=O)(=O)[O-].[Ba+2] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=S(=O)(CC1CCCCC1)c1ccccc1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 99.9 | [{"value": 99.9, "product": "C(C)(C)(C)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N)CS(=O)(=O)C1=CC=C(C=C1)SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | ±(1S*,2R*,4R*)-[4-Azido-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (from example 55d), (100 mg) was dissolved in MeOH (1 ml) prior to the addition of 5% Pd/BaSO4 (120 mg). A hydrogen balloon was added and the solution was stirred for 1.5 h. The palladium was filtered off and t... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.C1CCCCC1 | Other | [Pd].[O-]S(=O)(=O)[O-].[Ba+2].CO | null | 1.5 | CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1>[Pd].[O-]S(=O)(=O)[O-].[Ba+2].CO>CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N)CC[C@@H]2NC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbcb93dc67a145c3a7c4aba9eb8ad6dc | COS(=O)(=O)OC.CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1>>CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2N(C)C(=O)OC(C)(C)C)cc1 | COS(=O)(=O)OC.C(C)(C)(C)OC(N[C@@H]1[C@@H](C[C@@H](CC1)N=[N+]=[N-])CS(=O)(=O)C1=CC=C(C=C1)SC)=O.C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>C(C)(C)(C)OC(N(C)[C@@H]1[C@@H](C[C@@H](CC1)N=[N+]=[N-])CS(=O)(=O)C1=CC=C(C=C1)SC)=O | COS(=O)(=O)O[CH3:21].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][C@@H:11]2[CH2:12][C@H:13]([N:14]=[N+:15]=[N-:16])[CH2:17][CH2:18][C@@H:19]2[NH:20][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][C@@H:11]2[CH... | COS(=O)(=O)OC.CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1 | CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2N(C)C(=O)OC(C)(C)C)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | DMS Amine methylation | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | O=S(=O)(CC1CCCCC1)c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[C:3](-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]>>[C:2]-[C:3](-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12] | null | [] | -78 | CELSIUS | 20 | MINUTE | ±(1S*,2R*,4R*)-[4-Azido-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester, from Example (55d) (389 mg) was dissolved in THF (3 ml) and cooled to −78° C. prior to the slow addition of a solution of 0.5M KHMDS in THF (2.65 ml). After 20 min, Me2SO4 (0.15 ml) was added. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1ccccc1.C1CCCCC1 | HO- | C1CCOC1 | -78 | 0.333333 | COS(=O)(=O)OC.CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2NC(=O)OC(C)(C)C)cc1>C1CCOC1>CSc1ccc(S(=O)(=O)C[C@@H]2C[C@H](N=[N+]=[N-])CC[C@@H]2N(C)C(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4a2a72cc2724411b370e0075895332a | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O>>Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C.BrC=1C=C(C(=O)O)C=CC1C.S(=O)(Cl)Cl>>BrC=1C=C(C(=O)NC2=C(C=CC=C2)O)C=CC1C | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:17]([Br:18])[cH:16]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[OH:15])[cH:16][c:17]1[Br:18] | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | A mixture of 3-bromo-4-methylbenzoic acid (1.0 g, 4.7 mmol) and thionyl chloride (18 mL) was refluxed for 1 h and then cooled to rt. The excess thionyl chloride was removed in vacuo, the residue was dissolved in THF (10 mL), and was added to a cooled (0° C.) mixture of 2-aminophenol (510 mg, 4.7 mmol) and diisopropylet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O>C1CCOC1>Cc1ccc(C(=O)Nc2ccccc2O)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e394f340d90490fb912d28f8ae83adc | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br>>Cc1ccc(-c2nc3ccccc3o2)cc1Br | BrC=1C=C(C(=O)NC2=C(C=CC=C2)O)C=CC1C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([Br:17])[cH:15]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[Br:17] | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | Cc1ccc(-c2nc3ccccc3o2)cc1Br | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 088185b661aa9468f1c7cc811b018c6406e509618f8bf146f282e07bcdf823de | e4db370caafce196eb62f60d573e0a03e9af17c2927e176eeb3f4f837c389bef | c1ccc(-c2nc3ccccc3o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:7]:[c:5]1:[o;H0;D2;+0:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[n;H0;D2;+0:2]:[c:3]:1:[c:4] | null | [] | null | null | null | null | A mixture of 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide (550 mg, 1.8 mmol), p-toluenesulfonic acid (2.4 g, 12.7 mmol) in toluene (50 mL) was refluxed for 4 h, cooled to rt, and filtered through a Celite pad. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica gel usi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | null | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br>C1(=CC=CC=C1)C>Cc1ccc(-c2nc3ccccc3o2)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-628befcfd14e4cc8a671bfbe61404147 | Cc1ccc(-c2nc3ccccc3o2)cc1Br.O=C1CCC(=O)N1Br>>BrCc1ccc(-c2nc3ccccc3o2)cc1Br | BrC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrC=1C=C(C=CC1CBr)C=1OC2=C(N1)C=CC=C2 | [CH3:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][c:17]1[Br:18].O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][c:17]1[Br:18] | Cc1ccc(-c2nc3ccccc3o2)cc1Br.O=C1CCC(=O)N1Br | BrCc1ccc(-c2nc3ccccc3o2)cc1Br | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole (240 mg, 0.83 mmol), n-bromosuccinimide (180 mg, 0.99 mmol), and benzoyl peroxide (10 mg, 0.041 mmol) in carbon tetrachloride (15 mL) was refluxed for 3 h. The white precipitate was filtered and the filtrate was evaporated to dryness. The resulting solid was purif... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1Br.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>BrCc1ccc(-c2nc3ccccc3o2)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-523f9f484d514ad4a74e2e1e4162434e | BrCc1ccc(-c2nc3ccccc3o2)cc1Br.[C-]#N>>N#CCc1ccc(-c2nc3ccccc3o2)cc1Br | BrC=1C=C(C=CC1CBr)C=1OC2=C(N1)C=CC=C2.[C-]#N.[Na+].O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Br | Br[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[Br:19].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[Br:19] | BrCc1ccc(-c2nc3ccccc3o2)cc1Br.[C-]#N | N#CCc1ccc(-c2nc3ccccc3o2)cc1Br | null | null | CN(C)C=O.O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | A mixture of 2-[3-bromo-4-(bromomethyl)phenyl]-1,3-benzoxazole (156 mg, 0.42 mmol), and sodium cyanide (41 mg, 0.84 mmol) in DMF:H2O (3:1, 16 mL) was stirred at rt for 18 h. Water (50 mL) was added to the reaction mixture and it was extracted with EtOAc (3×). The organics were combined, washed with brine (2×), dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | CN(C)C=O.O | null | 18 | BrCc1ccc(-c2nc3ccccc3o2)cc1Br.[C-]#N>CN(C)C=O.O>N#CCc1ccc(-c2nc3ccccc3o2)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7014225eb7f34ab1bb1c055274cb3365 | COc1ccc(B(O)O)c(OC)c1.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br>>COc1ccc(-c2cc(-c3nc4ccccc4o3)ccc2CC#N)c(OC)c1 | COC1=C(C=CC(=C1)OC)B(O)O.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=C(C=C(C=C2)OC)OC)CC#N | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][c:25]1[O:26][CH3:27].Br[c:7]1[cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[cH:19][cH:20][c:21]1[CH2:22][C:23]#[N:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](-[c:10]3[n:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[o:18]3)[c... | COc1ccc(B(O)O)c(OC)c1.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br | COc1ccc(-c2cc(-c3nc4ccccc4o3)ccc2CC#N)c(OC)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | COCCOC.O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(-c3nc4ccccc4o3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[#8:11]):[c:12]>>[#8:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6]):[c:8]:[c:9] | null | [] | 83 | CELSIUS | null | null | A mixture of 2,4-dimethoxyphenylboronic acid (175 mg, 0.96 mmol), [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile (example 1) (200 mg, 0.64 mmol), dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.032 mmol), triphenylphosphine (17 mg, 0.064 mmol), and potassium carbonate (177 mg, 1.3 mmol) in degassed DME/H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ocnc2c1 | HBr.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O | 83 | null | COc1ccc(B(O)O)c(OC)c1.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O>COc1ccc(-c2cc(-c3nc4ccccc4o3)ccc2CC#N)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99598980dcbc49b2980aba4c026922bd | CB(O)O.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br>>Cc1cc(-c2nc3ccccc3o2)ccc1CC#N | CB(O)O.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)C | OB(O)[CH3:1].Br[c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1[CH2:17][C:18]#[N:19]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1[CH2:17][C:18]#[N:19] | CB(O)O.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br | Cc1cc(-c2nc3ccccc3o2)ccc1CC#N | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | COCCOC.O | C-C Coupling | Suzuki coupling with boronic acids | 39f7c0774f1dd85658d7924179547f5320f630d82338595500ea075e526c2566 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-B(-O)-[CH3;D1;+0:7]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH3;D1;+0:7]):[c:2]:[c:3] | null | [] | 80 | CELSIUS | null | null | A mixture of methane boronic acid (57.6 mg, 0.96 mmol), [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile (example 1) (200 mg, 0.64 mmol), dichlorobis(triphenylphosphine)palladium(II) (22.4 mg, 0.032 mmol), triphenylphosphine (17 mg, 0.064 mmol), and potassium carbonate (177 mg, 1.3 mmol) in degassed DME/H2O (5:1, 12... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1 | HBr.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O | 80 | null | CB(O)O.N#CCc1ccc(-c2nc3ccccc3o2)cc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O>Cc1cc(-c2nc3ccccc3o2)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c9853080e9e4c4981f9fefb9aec9e45 | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O>>Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C.BrC=1C=C(C(=O)O)C=CC1C.S(=O)(Cl)Cl>>BrC=1C=C(C(=O)NC2=C(C=CC=C2)O)C=CC1C | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:17]([Br:18])[cH:16]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[OH:15])[cH:16][c:17]1[Br:18] | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | A mixture of 3-bromo-4-methylbenzoic acid (1.0 g, 4.7 mmol) and thionyl chloride (18 mL) was refluxed for 1 h and then cooled to rt. The excess thionyl chloride was removed int vacuo, the residue was dissolved in THF (10 mL), and it was added to a cooled (0° C.) mixture of 2-aminophenol (507 mg, 4.7 mmol) and diisoprop... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | Cc1ccc(C(=O)O)cc1Br.Nc1ccccc1O>C1CCOC1>Cc1ccc(C(=O)Nc2ccccc2O)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f114aa097314311987a9195a28a0016 | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br>>Cc1ccc(-c2nc3ccccc3o2)cc1Br | BrC=1C=C(C(=O)NC2=C(C=CC=C2)O)C=CC1C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([Br:17])[cH:15]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[Br:17] | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br | Cc1ccc(-c2nc3ccccc3o2)cc1Br | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 088185b661aa9468f1c7cc811b018c6406e509618f8bf146f282e07bcdf823de | e4db370caafce196eb62f60d573e0a03e9af17c2927e176eeb3f4f837c389bef | c1ccc(-c2nc3ccccc3o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:7]:[c:5]1:[o;H0;D2;+0:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[n;H0;D2;+0:2]:[c:3]:1:[c:4] | null | [] | null | null | null | null | A mixture of 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide (554 mg, 1.8 mmol), p-toluenesulfonic acid (2.41 g, 12.7 mmol) and toluene (50 mL) was refluxed for 4 h, cooled to rt, and filtered through a Celite pad. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica gel u... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | null | Cc1ccc(C(=O)Nc2ccccc2O)cc1Br>C1(=CC=CC=C1)C>Cc1ccc(-c2nc3ccccc3o2)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddda68329a1d47baa4ac6fb0eabd16f4 | Cc1ccc(-c2nc3ccccc3o2)cc1Br.N#Cc1cccc(B(O)O)c1>>Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 | C(#N)C=1C=C(C=CC1)B(O)O.BrC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=CC(=CC=C2)C#N)C | Br[c:16]1[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]#[N:23])[cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22... | Cc1ccc(-c2nc3ccccc3o2)cc1Br.N#Cc1cccc(B(O)O)c1 | Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | COCCOC.O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(-c3nc4ccccc4o3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | 80 | CELSIUS | null | null | A mixture of 3-cyano-phenylboronic acid (183 mg, 1.3 mmol), 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole (300 mg, 1.04 mmol), dichlorobis(triphenylphosphine)palladium(II) (36.5 mg, 0.052 mmol), triphenylphosphine (27 mg, 0.104 mmol), and potassium carbonate (287 mg, 2.08 mmol) in degassed DME/H2O (5:1, 18 mL) was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccccc1 | HBr.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O | 80 | null | Cc1ccc(-c2nc3ccccc3o2)cc1Br.N#Cc1cccc(B(O)O)c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC.O>Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5f24134709a4e5289eb9e087aef7de8 | Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1.O=C1CCC(=O)N1Br>>N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1 | O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=CC(=CC=C2)C#N)C.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=CC(=CC=C2)C#N)CBr | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[o:19]3)[cH:20][cH:21][c:22]2[CH3:23])[cH:25]1.O=C1CCC(=O)N1[Br:24]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[o:19]3)[cH:20][c... | Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1.O=C1CCC(=O)N1Br | N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2cccc(-c3nc4ccccc4o3)c2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of 5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile (229 mg, 0.74 mmol), n-bromosuccinimide (145 mg, 0.81 mmol), and benzoyl peroxide (9 mg, 0.037 mmol) in carbon tetrachloride (15 mL) was refluxed for 5 h. The solvent was evaporated to dryness and the crude was purified by flash chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ff639e34c174f3f9b057cc7f2257246 | N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1.[C-]#N>>N#CCc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 | O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=CC(=CC=C2)C#N)CBr.[C-]#N.[Na+].O>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)C2=CC(=CC=C2)C#N)CC#N | Br[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1-[c:19]1[cH:20][cH:2... | N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1.[C-]#N | N#CCc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 | null | null | CN(C)C=O.O.CN(C)C=O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2cccc(-c3nc4ccccc4o3)c2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | A mixture of 5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile (183 mg, 0.47 mmol) and sodium cyanide (46 mg, 0.94 mmol) in DMF:H2O (5:1, 18 mL) and DMF (20 mL) was stirred at rt for 3 h. H2O was added to the reaction mixture and it was extracted with EtOAc (3×). The organics were combined, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1.c1ccccc1 | Br- | CN(C)C=O.O.CN(C)C=O | null | 3 | N#Cc1cccc(-c2cc(-c3nc4ccccc4o3)ccc2CBr)c1.[C-]#N>CN(C)C=O.O.CN(C)C=O>N#CCc1ccc(-c2nc3ccccc3o2)cc1-c1cccc(C#N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9546c37869f440218ad918dc8a6de1f1 | Cc1ccc(C(=O)O)cc1C(F)(F)F.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F | C1(=CC=C(C=C1)S(=O)(=O)O)C.CC1=C(C=C(C(=O)O)C=C1)C(F)(F)F.S(=O)(Cl)Cl.NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C>>CC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C(F)(F)F | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([C:17]([F:18])([F:19])[F:20])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[C:17]([F:18])([F:19])[F:20] | Cc1ccc(C(=O)O)cc1C(F)(F)F.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F | null | null | C1CCOC1.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | 8 | HOUR | A mixture of 4-methyl-3-(trifluoromethyl)benzoic acid (1.0 g, 4.9 mmol) and thionyl chloride (15 mL) was refluxed for 3 h and then stirred at rt overnight. The excess thionyl chloride was removed in vacuo, the residue was dissolved in THF (20 mL), and it was added to a cooled (0° C.) solution of 2-aminophenol (0.53 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.C1(=CC=CC=C1)C | null | 8 | Cc1ccc(C(=O)O)cc1C(F)(F)F.Nc1ccccc1O>C1CCOC1.C1(=CC=CC=C1)C>Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c265964bdeeb4ce9a2b40b477a9f2b81 | Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F.O=C1CCC(=O)N1Br>>FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr | CC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C(F)(F)F.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C(F)(F)F | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH3:20].O=C1CCC(=O)N1[Br:21]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH2:20][Br:21] | Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F.O=C1CCC(=O)N1Br | FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of 2-[4-methyl-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (600 mg, 2.2 mmol), n-bromosuccinimide (579 mg, 3.25 mmol), benzoyl peroxide (26 mg, 0.11 mmol) in carbon tetrachloride (15 mL) was refluxed for 3 h and then cooled to rt. The white precipitate was filtered and the filtrate was concentrated to dryness.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26845d3d550d49b5a8a35ee75d6d3a4d | FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr>>N#CCc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F | BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C(F)(F)F.C(#N)[Si](C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)C(F)(F)F | Br[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr | N#CCc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F | null | null | C(C)#N | Miscellaneous | OtherReaction | 4bbc4849e3d3601d8910de75263b61930fec74d886cf14722416a01754f9091f | b49a6b7ba4a55e705db577d22030a43499e8996164f4ba435ab1a79f9b874e56 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H0:5]#[C:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | To a suspension of 2-[4-(bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (528 mg, 1.5 mmol) and cyanotrimethylsilane (0.30 mL, 2.2 mmol) in acetonitrile (19 mL) was added TBAF (1.0M in THF, 2.2 mL, 2.2 mmol) and the mixture was stirred at rt for 2 h. The solvent was removed in vacuo and the crude was purified b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | C(C)#N | null | 2 | FC(F)(F)c1cc(-c2nc3ccccc3o2)ccc1CBr>C(C)#N>N#CCc1ccc(-c2nc3ccccc3o2)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66860e715ea94b10b846f7aa9de156cf | Nc1ccccc1O.O=C(O)c1ccc(F)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F | C1(=CC=C(C=C1)S(=O)(=O)O)C.FC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].S(=O)(Cl)Cl.NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C>>FC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)[N+](=O)[O-] | [NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15].O=[C:7](O)[c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:18]([F:19])[cH:17][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17][c:18]1[F:19] | Nc1ccccc1O.O=C(O)c1ccc(F)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F | null | null | C1CCOC1.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[o;H0;D2;+0:11]:[c:10]:1:[c:12] | null | [] | null | null | null | null | A mixture of 4-fluoro-3-nitrobenzoic acid (2.1 g, 11.3 mmol) and thionyl chloride (20 mL) was refluxed for 3 h and then cooled to rt. The excess thionyl chloride was removed and the residue dissolved in 10 mL of THF was added to a cooled (0° C.) solution of 2-aminophenol (1.24 g, 11.3 mmol) and diisopropylethylamine (2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.C1(=CC=CC=C1)C | null | null | Nc1ccccc1O.O=C(O)c1ccc(F)c([N+](=O)[O-])c1>C1CCOC1.C1(=CC=CC=C1)C>O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93b94594798b4f44823899c606a2d132 | CC(C)(C)OC(=O)CC#N.O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F>>N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-] | C(C)(C)(C)OC(CC#N)=O.Cl.FC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+].C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)[N+](=O)[O-] | CC(C)(C)OC(=O)[CH2:3][C:2]#[N:1].F[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | CC(C)(C)OC(=O)CC#N.O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F | N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-] | null | null | CS(=O)C.O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | f765507fbb82db4e9301672a9393b9bfb31c98f95bd7103eed2f88ad48f7201f | 48f99921ed16c8d47b04f4220c332af3fff951e27bf725d35a619ab256d5b453 | c1ccc(-c2nc3ccccc3o2)cc1 | C-C(-C)(-C)-O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].F-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[#7;+:8]):[c:9]>>[#7;+:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3]):[c:5]:[c:6] | null | [] | 65 | CELSIUS | null | null | 2-(4-fluoro-3-nitrophenyl)-1,3-benzoxazole (200 mg, 0.77 mmol) was dissolved in DMSO (5 mL) and K2CO3 (267 mg, 1.94 mmol) was added. The resulting yellow mixture was warmed to 65° C. and tert-butylcyanoacetate (137 mg, 0.97 mmol) was added dropwise. The dark red mixture was heated to 65° C. for 30 min, cooled to rt, an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boc | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1 | HF | CS(=O)C.O.C1(=CC=CC=C1)C | 65 | null | CC(C)(C)OC(=O)CC#N.O=[N+]([O-])c1cc(-c2nc3ccccc3o2)ccc1F>CS(=O)C.O.C1(=CC=CC=C1)C>N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7e8b7f610a94a819838d01e0158ca0b | N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-]>>N#CCc1ccc(-c2nc3ccccc3o2)cc1N | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)[N+](=O)[O-]>>NC1=C(C=CC(=C1)C=1OC2=C(N1)C=CC=C2)CC#N | O=[N+:19]([O-])[c:18]1[c:4]([CH2:3][C:2]#[N:1])[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[NH2:19] | N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-] | N#CCc1ccc(-c2nc3ccccc3o2)cc1N | null | [Pd] | CCO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2nc3ccccc3o2)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 | A suspension of [4-(1,3-benzoxazol-2-yl)-2-nitrophenyl]acetonitrile (100 mg, 0.36 mmol) and Pd/C (20 mg) in EtOH/EtOAc (5:1, 60 mL) was hydrogenated (35 psi) over 2d. The resulting reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. The yellow solid obtained was purified by flash ch... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2ocnc2c1 | Other | [Pd].CCO.CCOC(=O)C | null | null | N#CCc1ccc(-c2nc3ccccc3o2)cc1[N+](=O)[O-]>[Pd].CCO.CCOC(=O)C>N#CCc1ccc(-c2nc3ccccc3o2)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdc28b5ce6e24691832732f0a37423ba | Fc1cc(Br)ccc1CBr.[C-]#N>>N#CCc1ccc(Br)cc1F | BrC1=CC(=C(CBr)C=C1)F.[C-]#N.[Na+]>>BrC1=CC(=C(CC#N)C=C1)F | Br[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11] | Fc1cc(Br)ccc1CBr.[C-]#N | N#CCc1ccc(Br)cc1F | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 1 | HOUR | To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 17 mmol). The reaction mixture was stirred at 90° C. for 1 h, cooled to rt and quenched with brine (50 mL). After extraction with EtOAc (3×100 mL), the organic layers were combined, washed with bri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | CN(C)C=O | 90 | 1 | Fc1cc(Br)ccc1CBr.[C-]#N>CN(C)C=O>N#CCc1ccc(Br)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-042cc444894b477f82d1d626a97f37a9 | N#CCc1ccc(Br)cc1F.c1ccc2ocnc2c1>>N#CCc1ccc(-c2nc3ccccc3o2)cc1F | C(CCC)[Li].BrC1=CC(=C(CC#N)C=C1)F.O1C=NC2=C1C=CC=C2.C(CCC)[Li]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)F | Br[c:7]1[cH:6][cH:5][c:4]([CH2:3][C:2]#[N:1])[c:18]([F:19])[cH:17]1.[cH:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[o:16]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[F:19] | N#CCc1ccc(Br)cc1F.c1ccc2ocnc2c1 | N#CCc1ccc(-c2nc3ccccc3o2)cc1F | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Pd].[Cl-].[Cl-].[Zn+2] | C1CCOC1 | C-C Coupling | OtherReaction | e23eb6643b4072441e946357a2e48ae702d599f32b24016f33c67ae4187a67ba | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[#8;a:9]:[cH;D2;+0:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 15 | MINUTE | To a stirred solution of benzoxazole (153 mg, 1.3 mmol) in 5 mL THF at −78° C., was added n-Butyllithium (640 μL, 2.5M in hexanes, 1.6 mmol). The reaction mixture was stirred for 15 min at −78° C. and ZnCl2 (3.9 mL, 1.0M solution in Et2O, 3.9 mmol) was added via a syringe. The reaction was then warmed to 0° C. for 1 h ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Pd].[Cl-].[Cl-].[Zn+2].C1CCOC1 | -78 | 0.25 | N#CCc1ccc(Br)cc1F.c1ccc2ocnc2c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Pd].[Cl-].[Cl-].[Zn+2].C1CCOC1>N#CCc1ccc(-c2nc3ccccc3o2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7fc2c011a3d45d2a266603104d08d7f | Fc1cc(Br)ccc1CBr.[C-]#N>>N#CCc1ccc(Br)cc1F | BrC1=CC(=C(CBr)C=C1)F.[C-]#N.[Na+]>>BrC1=CC(=C(CC#N)C=C1)F | Br[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11] | Fc1cc(Br)ccc1CBr.[C-]#N | N#CCc1ccc(Br)cc1F | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 1 | HOUR | To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The reulting reaction mixture was stirred at 90° C. for 1 h, cooled to rt, quenched with brine (50 mL) and extracted with EtOAc (3×100 mL). The organic layers were combined, washed with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | CN(C)C=O | 90 | 1 | Fc1cc(Br)ccc1CBr.[C-]#N>CN(C)C=O>N#CCc1ccc(Br)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a318cc3736b248789a9b6636f289d356 | Cc1ccc2ncoc2c1.N#CCc1ccc(Br)cc1F>>Cc1ccc2nc(-c3ccc(CC#N)c(F)c3)oc2c1 | CC1=CC2=C(N=CO2)C=C1.C(CCC)[Li].BrC1=CC(=C(CC#N)C=C1)F.C(CCC)[Li].C(=O)(O)[O-].[Na+]>>FC1=C(C=CC(=C1)C=1OC2=C(N1)C=CC(=C2)C)CC#N | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][o:18][c:19]2[cH:20]1.Br[c:8]1[cH:9][cH:10][c:11]([CH2:12][C:13]#[N:14])[c:15]([F:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([CH2:12][C:13]#[N:14])[c:15]([F:16])[cH:17]3)[o:18][c:19]2[cH:20]1 | Cc1ccc2ncoc2c1.N#CCc1ccc(Br)cc1F | Cc1ccc2nc(-c3ccc(CC#N)c(F)c3)oc2c1 | null | [Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1CCOC1 | C-C Coupling | OtherReaction | e23eb6643b4072441e946357a2e48ae702d599f32b24016f33c67ae4187a67ba | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[#8;a:9]:[cH;D2;+0:10]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:2]:[c:3] | null | [] | -78 | CELSIUS | 15 | MINUTE | To a stirred solution of 6-methylbenzoxazole (173 mg, 1.3 mmol) in THF (5 mL) at −78° C., was added n-Butyllithium (640 μL, 2.5M in hexanes, 1.6 mmol). The resulting reaction mixture was stirred for 15 min at −78° C. and ZnCl2 (3.9 mL, 1M in Et2O, 3.9 mmol) was added via a syringe. After warming up the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | HBr | [Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1 | -78 | 0.25 | Cc1ccc2ncoc2c1.N#CCc1ccc(Br)cc1F>[Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1>Cc1ccc2nc(-c3ccc(CC#N)c(F)c3)oc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7bbed90c26a48bca4fae4915f5c924b | Fc1cc(Br)ccc1CBr.[C-]#N>>N#CCc1ccc(Br)cc1F | BrC1=CC(=C(CBr)C=C1)F.[C-]#N.[Na+]>>BrC1=CC(=C(CC#N)C=C1)F | Br[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11] | Fc1cc(Br)ccc1CBr.[C-]#N | N#CCc1ccc(Br)cc1F | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 1 | HOUR | To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The resulting mixture was stirred at 90° C. for 1 h, cooled at rt and quenched with brine (50 mL). After extraction with EtOAc (3×50 mL), the organic layers were combined, washed with b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | CN(C)C=O | 90 | 1 | Fc1cc(Br)ccc1CBr.[C-]#N>CN(C)C=O>N#CCc1ccc(Br)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d1f66853356d467193b9ad4264bc615e | Cc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F>>Cc1ccc2oc(-c3ccc(CC#N)c(F)c3)nc2c1 | BrC1=CC(=C(CC#N)C=C1)F.CC=1C=CC2=C(N=CO2)C1.C(CCC)[Li].C(CCC)[Li]>>FC1=C(C=CC(=C1)C=1OC2=C(N1)C=C(C=C2)C)CC#N | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][cH:7][n:18][c:19]2[cH:20]1.Br[c:8]1[cH:9][cH:10][c:11]([CH2:12][C:13]#[N:14])[c:15]([F:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([CH2:12][C:13]#[N:14])[c:15]([F:16])[cH:17]3)[n:18][c:19]2[cH:20]1 | Cc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F | Cc1ccc2oc(-c3ccc(CC#N)c(F)c3)nc2c1 | null | [Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1CCOC1 | C-C Coupling | OtherReaction | e23eb6643b4072441e946357a2e48ae702d599f32b24016f33c67ae4187a67ba | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[#8;a:9]:[cH;D2;+0:10]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:2]:[c:3] | null | [] | -78 | CELSIUS | 15 | MINUTE | To a stirred solution of 5-methylbenzoxazole (173 mg, 1.3 mmol) in THP (5 mL) at −78° C. was added n-Butyllithium (640 μL, 2.5M in hexanes, 1.6 mmol). The reaction mixture was stirred for 15 min at −78° C. followed by the addition of ZnCl2 (3.9 mL, 1M in Et2O, 3.9 mmol) via a syringe. The reaction mixture was warmed at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | HBr | [Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1 | -78 | 0.25 | Cc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F>[Cl-].[Cl-].[Zn+2].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1>Cc1ccc2oc(-c3ccc(CC#N)c(F)c3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57e9aff840d84b2daacf95eb7f45676b | Fc1cc(Br)ccc1CBr.[C-]#N>>N#CCc1ccc(Br)cc1F | BrC1=CC(=C(CBr)C=C1)F.[C-]#N.[Na+]>>BrC1=CC(=C(CC#N)C=C1)F | Br[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11] | Fc1cc(Br)ccc1CBr.[C-]#N | N#CCc1ccc(Br)cc1F | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 1 | HOUR | To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The reaction was stirred at 90° C. for 1 h, and cooled at rt. After quenching with brine (50 mL) and diluted with EtOAc (100 mL), the EtOAc layer was washed with brine (50 mL), dried (M... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | CN(C)C=O | 90 | 1 | Fc1cc(Br)ccc1CBr.[C-]#N>CN(C)C=O>N#CCc1ccc(Br)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c38c224bdbf645f49b58fc61a53b9b3d | Clc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F>>N#CCc1ccc(-c2nc3cc(Cl)ccc3o2)cc1F | C(CCC)[Li].BrC1=CC(=C(CC#N)C=C1)F.ClC=1C=CC2=C(N=CO2)C1.C(CCC)[Li]>>ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)CC#N)F)C1 | [cH:8]1[n:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]2[o:17]1.Br[c:7]1[cH:6][cH:5][c:4]([CH2:3][C:2]#[N:1])[c:19]([F:20])[cH:18]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]3[o:17]2)[cH:18][c:19]1[F:20] | Clc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F | N#CCc1ccc(-c2nc3cc(Cl)ccc3o2)cc1F | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Cl-].[Zn+2] | C1CCOC1 | C-C Coupling | OtherReaction | e23eb6643b4072441e946357a2e48ae702d599f32b24016f33c67ae4187a67ba | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[#8;a:9]:[cH;D2;+0:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 15 | MINUTE | To a stirred solution of 5-chlorobenzoxazole (200 mg, 1.3 mmol) in 5 mL THF at −78° C., was added n-Butyllithium (640 μL, 2.5M in hexane, 1.6 mmol). The reaction was stirred for 15 min at −78° C. followed by the addition of ZnCl2 (3.9 mL, 1M in Et2O, 3.9 mmol) via a syringe. The reaction was then warmed at 0° C. for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ocnc2c1.c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Cl-].[Zn+2].C1CCOC1 | -78 | 0.25 | Clc1ccc2ocnc2c1.N#CCc1ccc(Br)cc1F>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Cl-].[Zn+2].C1CCOC1>N#CCc1ccc(-c2nc3cc(Cl)ccc3o2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bde3b58972f64cb4a1179033e865bdef | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1O | NC1=C(C=CC=C1)O.C(C)N(CC)CC.OC=1C=C(C(=O)O)C=CC1C.O=S(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([OH:17])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17] | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1O | null | null | C1CCOC1.CCOC(=O)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | 30 | MINUTE | To a 100 mL round-bottom flask with 3-hydroxy-4-methylbenzoic acid (2.5 g, 16.4 mmol), was added dropwise SOCl2 (15 mL). The reaction was refluxed for 30 min and cooled to rt. The excess of SOCl2 was removed in vacuo and the oily acid chloride was dissolved in THF (15 mL). This resulting solution was added dropwise to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.CCOC(=O)C | null | 0.5 | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>C1CCOC1.CCOC(=O)C>Cc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c0144b583b2473bbec649c275f7dd30 | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>N#CCc1ccc(-c2nc3ccccc3o2)cc1O | C(C)(C)(C)[Si](OC=1C=C(C=CC1CBr)C=1OC2=C(N1)C=CC=C2)(C)C.[C-]#N.[Na+]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)O | CC(C)(C)[Si](C)(C)[O:19][c:18]1[c:4]([CH2:3]Br)[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[OH:19] | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | N#CCc1ccc(-c2nc3ccccc3o2)cc1O | null | null | CCOC(=O)C.CN(C)C=O | C-C Coupling | OtherReaction | c744d47eee7c18de54856c89a1449542686c6798698ce42650ae5a80178b708a | b27997093808b32275567415e335e456530981991d4bffd469c23081195b446c | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-[Si](-C)(-C)-C(-C)(-C)-C):[c:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[N;D1;H0:8]#[C;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | 90 | CELSIUS | 8 | HOUR | The mixture of 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole (1.6 g, 3.8 mmol) and sodium cyanide (560 mg, 11.4 mmol) in DMF (10 mL) was stirred at 90° C. overnight. After cooling to rt, the mixture was diluted with EtOAc (100 mL), washed with H2O (2×50 mL), dried (MgSO4), filtered, and co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.TMS ether protective group | Nitrile.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ocnc2c1 | HBr | CCOC(=O)C.CN(C)C=O | 90 | 8 | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>CCOC(=O)C.CN(C)C=O>N#CCc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10019520ef6f48319b08b25838da63f4 | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1O | NC1=C(C=CC=C1)O.C(C)N(CC)CC.OC=1C=C(C(=O)O)C=CC1C.O=S(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([OH:17])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17] | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1O | null | null | C1CCOC1.CCOC(=O)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | null | null | To a 100 mL round-bottom flask with 3-hydroxy-4-methylbenzoic acid (2.5 g, 16.4 mmol), was added SOCl2 (15 mL) dropwise. The reaction was refluxed for 30 min, cooled to rt and the excess of SOCl2 was removed in vacuo. The oily acid chloride was dissolved in THF (15 mL) and the solution was added dropwise to a mixture o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.CCOC(=O)C | null | null | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>C1CCOC1.CCOC(=O)C>Cc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9672a9bf59e345cd9f19654b6ed0dbbb | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.Cc1ccc(-c2nc3ccccc3o2)cc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C | CCOC(=O)C.O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C.C(C)N(CC)CC.[Si](C)(C)(C(C)(C)C)OS(=O)(=O)C(F)(F)F>>C(C)(C)(C)[Si](OC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2)(C)C | O=S(=O)(O[Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])C(F)(F)F.[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[O:17][Si:18]([CH3:19... | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.Cc1ccc(-c2nc3ccccc3o2)cc1O | Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 3e7791d5057fb289e8048b5035f0c3b09f29fa7f60035605ff2d745995f5dccf | 8b52a9ad654b0822222f4a288caf39852066030861639143b3c197de66dd6715 | c1ccc(-c2nc3ccccc3o2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | null | null | A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (0.8 g, 3.5 mmol) and triethylamine (0.6 mL, 4.3 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and TBDMS-OTf (900 mL, 3.9 mmol) was added. The reaction was slowly warmed to rt and EtOAc (200 mL) was added. The mixture was washed with H2O (3×50 mL), dried (MgSO4), filte... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic alcohol.TMS ether protective group | TMS ether protective group | null | null | c1ccccc1.c1ccc2ocnc2c1 | TfOH.HO- | C(Cl)Cl | null | null | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.Cc1ccc(-c2nc3ccccc3o2)cc1O>C(Cl)Cl>Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f439900152384de1b2022bdb92a51c52 | Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C.O=C1CCC(=O)N1Br>>CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr | C(C)(C)(C)[Si](OC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2)(C)C.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(C)(C)(C)[Si](OC=1C=C(C=CC1CBr)C=1OC2=C(N1)C=CC=C2)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c:11](-[c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21][cH:22][c:23]1[CH3:24].O=C1CCC(=O)N1[Br:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c:11](-[c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:... | Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C.O=C1CCC(=O)N1Br | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole (1.46 g, 4.3 mmol) in CCl4 (50 mL) was added NBS (770 mg, 4.3 mmol) and benzoyl peroxide (50 mg). The reaction mixture was refluxed for 6 h, cooled to rt, and CCl4 was removed in vacuo. The residue was dissolved in EtOAc (50 mL), washed with H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-597be74ec6884f958b11150971f674b4 | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>N#CCc1ccc(-c2nc3ccccc3o2)cc1O | C(C)(C)(C)[Si](OC=1C=C(C=CC1CBr)C=1OC2=C(N1)C=CC=C2)(C)C.[C-]#N.[Na+]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)O | CC(C)(C)[Si](C)(C)[O:19][c:18]1[c:4]([CH2:3]Br)[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[OH:19] | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | N#CCc1ccc(-c2nc3ccccc3o2)cc1O | null | null | CCOC(=O)C.CN(C)C=O | C-C Coupling | OtherReaction | c744d47eee7c18de54856c89a1449542686c6798698ce42650ae5a80178b708a | b27997093808b32275567415e335e456530981991d4bffd469c23081195b446c | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-[Si](-C)(-C)-C(-C)(-C)-C):[c:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[N;D1;H0:8]#[C;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | 90 | CELSIUS | 8 | HOUR | A mixture of 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole (1.6 g, 3.8 mmol) and sodium cyanide (560 mg, 11.4 mmol) in DMF (10 mL) was stirred at 90° C. overnight. The reaction was cooled to rt and dissolved in EtOAc (200 mL), washed with H2O (2×50 mL), dried (MgSO4), filtered, and concent... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.TMS ether protective group | Nitrile.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ocnc2c1 | HBr | CCOC(=O)C.CN(C)C=O | 90 | 8 | CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>CCOC(=O)C.CN(C)C=O>N#CCc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a918b239bc5e42d9b18582856ba2fa5e | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1O | NC1=C(C=CC=C1)O.C(C)N(CC)CC.OC=1C=C(C(=O)O)C=CC1C.O=S(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([OH:17])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17] | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1O | null | null | C1CCOC1.CCOC(=O)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | 30 | MINUTE | To a 10 mL round-bottom flask with 3-hydroxy-4-methylbenzoic acid (2.5 g, 16.4 mmol), was added SOCl2 (15 mL) dropwise. The reaction was refluxed for 30 min, cooled to rt. The excess of SOCl2 was removed in vacuo and the oily acid chloride was dissolved in THF (15 mL). The resulting solution was added dropwise to a mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.CCOC(=O)C | null | 0.5 | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>C1CCOC1.CCOC(=O)C>Cc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa5a2b97ad7343c18a3533749cd3c636 | Cc1ccc(-c2nc3ccccc3o2)cc1O>>COCOc1cc(-c2nc3ccccc3o2)ccc1C | O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C.[H-].[Na+].BrCOCBr>>COCOC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | [OH:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH3:20]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH3:20] | Cc1ccc(-c2nc3ccccc3o2)cc1O | COCOc1cc(-c2nc3ccccc3o2)ccc1C | null | null | C1CCOC1 | Functional Group Addition | OtherReaction | ef92e8f4c48a9f40a8d114c6e44306a43d978aa622c66d71bb4c0fbb5451d91c | acfde58648a6ab6bc86adabc05fdd778b477cc582b5f1973b1b51fc7b40eeba7 | c1ccc(-c2nc3ccccc3o2)cc1 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[#8:5]-[C:6]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (200 mg, 0.89 mmol) in THF (6 mL) was cooled to −78° C. under Argon and sodium hydride (24 mg, 1.0 mmol) was added. After 30 min at this temperature, bromomethyl ether (225 mg, 1.8 mmol) was added via syringe. The reaction was warmed to rt for 1 h. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether.Ether | null | null | c1ccccc1.c1ccc2ocnc2c1 | Other | C1CCOC1 | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1O>C1CCOC1>COCOc1cc(-c2nc3ccccc3o2)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fbdb02c28694b2ab3cd6d303a6d36e5 | COCOc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>>COCOc1cc(-c2nc3ccccc3o2)ccc1CBr | COCOC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH3:20].O=C1CCC(=O)N1[Br:21]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH2:20][Br:21] | COCOc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br | COCOc1cc(-c2nc3ccccc3o2)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole (200 mg, 0.74 mmol, 84%), NBS (179 mg, 0.81 mmol), and benzoyl peroxide (50 mg) in CCl4 (10 mL), was refluxed for 12 h. After cooling to rt, CCl4 was removed in vacuo and residue was purified by flash column (silica gel, hexanes:EtOAc 5:1) to afford 2-... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COCOc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COCOc1cc(-c2nc3ccccc3o2)ccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1bb2abbd51504100ae8fddcf2916a41c | COCOc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>COCOc1cc(-c2nc3ccccc3o2)ccc1CC#N | BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OCOC.[C-]#N.[Na+].CCOC(=O)C>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)OCOC | Br[CH2:20][c:19]1[c:5]([O:4][CH2:3][O:2][CH3:1])[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18]1.[C-:21]#[N:22]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1[CH2:20][C:21]#[N:22] | COCOc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | COCOc1cc(-c2nc3ccccc3o2)ccc1CC#N | null | null | CN(C)C=O.O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 2-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole (250 mg, 0.72 mmol) was treated with sodium cyanide (150 mg, 2.2 mmol) in DMF/H2O (15 mL/1.5 mL) at 90° C. for 3 h and EtOAc (150 mL) was added. The EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL), dried (MgSO4), filtered, and concentrated in va... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | CN(C)C=O.O | null | null | COCOc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>CN(C)C=O.O>COCOc1cc(-c2nc3ccccc3o2)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fb7e24f521c44f0ab2773f5aa4bbcbd | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1O | C1(=CC=C(C=C1)S(=O)(=O)O)C.OC=1C=C(C(=O)O)C=CC1C.O=S(Cl)Cl.NC1=C(C=CC=C1)O.C(C)N(CC)CC>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:16]([OH:17])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17] | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1O | null | null | C1CCOC1.CCOC(=O)C.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | 0.5 | HOUR | To a 100 mL round-bottom flask with 3-hydroxy-4-methylbenzoic acid (2.5 g, 16.4 mmol) was added SOCl2 (15 mL) dropwise. This reaction was refluxed for 30 min, cooled to rt and the excess SOCl2 removed in vacuo. The oily acid chloride was dissolved in THF (15 mL) and the solution was added dropwise to a mixture of 2-ami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.CCOC(=O)C.C1(=CC=CC=C1)C | null | 0.5 | Cc1ccc(C(=O)O)cc1O.Nc1ccccc1O>C1CCOC1.CCOC(=O)C.C1(=CC=CC=C1)C>Cc1ccc(-c2nc3ccccc3o2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b17d33ee2364483d9d7165289ffaf585 | CC(C)(C)[Si](C)(C)OCCBr.Cc1ccc(-c2nc3ccccc3o2)cc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1OCCO[Si](C)(C)C(C)(C)C | CCOC(=O)C.[H-].[Na+].O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C2)O)C.BrCCO[Si](C)(C)C(C)(C)C>>[Si](C)(C)(C(C)(C)C)OCCOC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | Br[CH2:18][CH2:19][O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[OH:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]1[O:17][CH2:18][... | CC(C)(C)[Si](C)(C)OCCBr.Cc1ccc(-c2nc3ccccc3o2)cc1O | Cc1ccc(-c2nc3ccccc3o2)cc1OCCO[Si](C)(C)C(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 15 | MINUTE | A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (355 mg, 1.6 mmol) in DMF (10 mL) was cooled to 0° C. and NaH (70 mg, 1.7 mmol) was added slowly. After 15 min, (2-bromoethoxy)(tert-butyl)dimethylsilane (370 μL, 1.7 mmol) was added. The reaction was then elevated to 90° C. for 1 h and EtOAc (100 mL) was added. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ocnc2c1 | HBr | CN(C)C=O | null | 0.25 | CC(C)(C)[Si](C)(C)OCCBr.Cc1ccc(-c2nc3ccccc3o2)cc1O>CN(C)C=O>Cc1ccc(-c2nc3ccccc3o2)cc1OCCO[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6548a23538894aa79436e59d15d367bc | Clc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl | [C-]#N.[Na+].BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)Cl.CN(C)C=O.O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Cl | Br[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[Cl:19].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[Cl:19] | Clc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl | null | null | [Cl-].[Na+].O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A slurry of NaCN (435 mg, 8.9 mmol), 2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole (940 mg, 2.9 mmol), DMF (30 mL) and H2O (30 mL) was stirred at rt for 12 h. The reaction mixture was poured into brine (250 mL) and filtered. The resultant colorless solid was purified by flash chromatography on silica gel (EtOAc:he... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | [Cl-].[Na+].O | null | null | Clc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>[Cl-].[Na+].O>N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f11ad2c55b7f49aca6d002758dd0a103 | BrCCCCBr.N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl>>N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].BrCCCCBr>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCCC2)C#N)Cl | Br[CH2:20][CH2:21][CH2:22][CH2:23]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]1[Cl:19]>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7](-[c:8]3[n:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[o:16]3)[cH:17][c:18]2[Cl:19])[CH2:20][CH2:21][CH2:22][CH2:2... | BrCCCCBr.N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl | N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 90ff2cdd2efc3b7e3d5fddf28ea72ab16385a91dc99fbace2077f543bebdb44a | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | c1ccc2oc(-c3ccc(C4CCCC4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-Br.[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[N;D1;H0:5]#[C:6]-[C;H0;D4;+0:7]1(-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | null | null | 15 | MINUTE | A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (270 mg, 1.0 mmol) and THF (20 mL) was cooled to −78° C. A solution of NaHMDS (3.7 mL, 2.2 mmol, 0.6M solution in PhMe) was added dropwise via syringe to the reaction. After 15 min at −78° C., 1,4-dibromobutane (143 μL, 1.2 mmol) was added dropwise via ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCCC1 | c1ccccc1.c1ccc2ocnc2c1.C1CCCC1 | HBr | C1CCOC1 | null | 0.25 | BrCCCCBr.N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl>C1CCOC1>N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d4b0f70fe88423db019e11bd28d183d | N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1>>N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCCC2)C#N)Cl.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Cl.BrCCCCCBr>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCCCC2)C#N)Cl | [N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7](-[c:8]3[n:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[o:16]3)[cH:17][c:18]2[Cl:19])[CH2:20][CH2:22][CH2:23][CH2:24]1>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7](-[c:8]3[n:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[o:16]3)[cH:17][c:18]2[Cl:19])[CH2:20][CH2:21][CH2:22][CH2:23][... | N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1 | N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 0b44ca91720d79a02cdf7d24f03ae8d8478e1793f3232ee888846945effcbc34 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2oc(-c3ccc(C4CCCCC4)cc3)nc2c1 | [N;D1;H0:1]#[C:2]-[C:3]1(-[c:4])-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1>>[N;D1;H0:1]#[C:2]-[C:3]1(-[c:4])-[C:5]-[C:6]-[CH2;D2;+0:7]-[C:9]-[CH2;D2;+0:8]-1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile, [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (400 mg, 1.5 mmol) and 1,5-dibromopentane (250 μL, 1.8 mmol) reacted to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitri... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCC1 | C1CCCCC1 | c1ccccc1.c1ccc2ocnc2c1.C1CCCCC1 | Other | null | null | null | N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCC1>>N#CC1(c2ccc(-c3nc4ccccc4o3)cc2Cl)CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a8906e3888144a3947ba02112964cb1 | N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>>N#CC(F)c1ccc(-c2nc3ccccc3o2)cc1Cl | C(C)(C)(C)[Li].O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)Cl.C1=CC=C(C=C1)S(=O)(=O)N(F)S(=O)(=O)C2=CC=CC=C2>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)F)Cl | [N:1]#[C:2][CH2:3][c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[o:17]2)[cH:18][c:19]1[Cl:20].O=S(=O)(c1ccccc1)N(S(=O)(=O)c1ccccc1)[F:4]>>[N:1]#[C:2][CH:3]([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[o:17]2)[cH:18][c:19]1[Cl:20] | N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1 | N#CC(F)c1ccc(-c2nc3ccccc3o2)cc1Cl | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 16c5dcf68b4cfdd9dca4002bca5baf3aa7f918125b7bb9f30427118e221d1f28 | f1a9b8761acb2112205a7ea5992183334cc498a6d0cf76b9d9b899ed05d494d1 | c1ccc(-c2nc3ccccc3o2)cc1 | O=S(=O)(-N(-[F;H0;D1;+0:1])-S(=O)(=O)-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[N;D1;H0:2]#[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[F;H0;D1;+0:1]-[CH;D3;+0:4](-[C:3]#[N;D1;H0:2])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (98 mg, 0.36 mmol) and dry THF (5 mL) was cooled to −78° C. A solution of tert-butyllithium (500 μL, 0.80 mmol, 1.7M solution in pentane) was added dropwise via syringe at −78° C. After 1 h, a solution of N-fluorobenzenesulfonimide (113 mg, 0.36 mmol) a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary halide | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1 | null | 1 | N#CCc1ccc(-c2nc3ccccc3o2)cc1Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>C1CCOC1>N#CC(F)c1ccc(-c2nc3ccccc3o2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86e2c3eed48a4101adc2ec27674f9f15 | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O>>COc1cc(C(=O)Nc2ccccc2O)ccc1C | COC=1C=C(C(=O)O)C=CC1C.S(=O)(Cl)Cl.NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C>>OC1=C(C=CC=C1)NC(C1=CC(=C(C=C1)C)OC)=O | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18]([CH3:19])[cH:17][cH:16]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[OH:15])[cH:16][cH:17][c:18]1[CH3:19] | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O | COc1cc(C(=O)Nc2ccccc2O)ccc1C | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 3-Methoxy-4-methyl benzoic acid (1.2 g, 7.2 mmol) and thionyl chloride (10 mL) was heated to reflux conditions under argon until no starting material was observed by TLC. After cooling mixture to rt and concentration in vacuo, the resulting brown oil was dissolved in THF (15 mL) and slowly added to a cooled mixture of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O>C1CCOC1>COc1cc(C(=O)Nc2ccccc2O)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68728a60efc5412a889f57dd78c449dd | COc1cc(C(=O)Nc2ccccc2O)ccc1C>>COc1cc(-c2nc3ccccc3o2)ccc1C | OC1=C(C=CC=C1)NC(C1=CC(=C(C=C1)C)OC)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>COC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([CH3:18])[cH:16][cH:15]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH3:18] | COc1cc(C(=O)Nc2ccccc2O)ccc1C | COc1cc(-c2nc3ccccc3o2)ccc1C | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 088185b661aa9468f1c7cc811b018c6406e509618f8bf146f282e07bcdf823de | e4db370caafce196eb62f60d573e0a03e9af17c2927e176eeb3f4f837c389bef | c1ccc(-c2nc3ccccc3o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:7]:[c:5]1:[o;H0;D2;+0:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[n;H0;D2;+0:2]:[c:3]:1:[c:4] | null | [] | null | null | null | null | 3-Methoxy-4-methyl benzoic acid (1.2 g, 7.2 mmol) and thionyl chloride (10 mL) was heated to reflux conditions under argon until no starting material was observed by TLC. After cooling mixture to rt and concentration in vacuo, the resulting brown oil was dissolved in THF (15 mL) and slowly added to a cooled mixture of ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | null | COc1cc(C(=O)Nc2ccccc2O)ccc1C>C1(=CC=CC=C1)C>COc1cc(-c2nc3ccccc3o2)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a804c7f51ce54084918ff23496b95166 | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>>COc1cc(-c2nc3ccccc3o2)ccc1CBr | COC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.BrN1C(CCC1=O)=O>>BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH3:18].O=C1CCC(=O)N1[Br:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][Br:19] | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br | COc1cc(-c2nc3ccccc3o2)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole (1.0 g, 4.1 mmol), carbon tetrachloride (18 mL), benzoyl peroxide (66 mg, 0.3 mmol) and N-bromosuccinimide (970 mg, 5.4 mmol) was heated to reflux conditions under argon and placed under a UV light. After one hour, no starting material was observed by TLC. After cooling mixt... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | 1 | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COc1cc(-c2nc3ccccc3o2)ccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e21f0f9208d4b068d738415af301ac5 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>COc1cc(-c2nc3ccccc3o2)ccc1CC#N | [C-]#N.[Na+].BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)OC | Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1.[C-:19]#[N:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][C:19]#[N:20] | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | COc1cc(-c2nc3ccccc3o2)ccc1CC#N | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | CN(C=O)C | null | 3 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>CN(C=O)C>COc1cc(-c2nc3ccccc3o2)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-724a3c91a84f48bd9c3cc3b59fcaf0b0 | CCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>CCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)C)OC.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C#N)C=C2)OC.ICC>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)CC)OC | IC[CH3:1].[CH3:2][CH:3]([C:4]#[N:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[cH:19][c:20]1[O:21][CH3:22]>>[CH3:1][CH2:2][CH:3]([C:4]#[N:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[cH:19][c:20]1[O:21][CH3:22] | CCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N | CCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC | null | null | null | C-C Coupling | C-methylation | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(-c2nc3ccccc3o2)cc1 | I-C-[CH3;D1;+0:1].[CH3;D1;+0:2]-[C:3](-[c:4])-[C:5]#[N;D1;H0:6]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3](-[c:4])-[C:5]#[N;D1;H0:6] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]propanenitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (300 mg, 1.1 mmol) was reacted with iodoethane (90 μL, 1.1 mmol) to afford the desired 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]butanenitrile as a yello... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccc2ocnc2c1 | HI | null | null | null | CCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>CCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16d49891de3a4889a573984ceb9536d8 | CCCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>CCCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)C)OC.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C#N)C=C2)OC.ICCC>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)CCC)OC | I[CH2:3][CH2:2][CH3:1].C[CH:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[o:19]2)[cH:20][c:21]1[O:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[o:19]2)[cH:20][c:21]1[O:22][CH3:23] | CCCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N | CCCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC | null | null | null | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(-c2nc3ccccc3o2)cc1 | C-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[c:4](:[c:5]):[c:6].I-[CH2;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[C:8]-[CH2;D2;+0:7]-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]propanenitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (200 mg, 0.75 mmol) was reacted with 1-iodopropane (73 μL, 0.75 mmol) to afford the desired 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]pentanenitrile as a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccc2ocnc2c1 | HI | null | null | null | CCCI.COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>CCCC(C#N)c1ccc(-c2nc3ccccc3o2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aca996cf3f944717aae7a25cfe9fad93 | COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C(C#N)C)OC.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C#N)C=C2)OC.BrCCCBr>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCC2)C#N)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH:18]([C:19]#[N:20])[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[C:18]1([C:19]#[N:20])[CH2:21][CH2:22][CH2:23]1 | COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1 | null | null | null | C-C Coupling | OtherReaction | e5fe4cf750f39ec64297f8ddefcfe6648ddba34129fca901afeeaea9af9f860d | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2oc(-c3ccc(C4CCC4)cc3)nc2c1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[C:3]#[N;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[N;D1;H0:4]#[C:3]-[C;H0;D4;+0:2]1(-[c:5](:[c:6]):[c:7])-[C:8]-[C:9]-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]propanenitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (250 mg, 0.95 mmol) was reacted with 1,3-Dibromopropane (120 μL, 1.1 mmol) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecar... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | C1CCC1 | c1ccccc1.c1ccc2ocnc2c1.C1CCC1 | Other | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1C(C)C#N>>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b79bebf58c34dd69f3bb212bdae195b | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1>>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCC2)C#N)OC.O1C(=NC2=C1C=CC=C2)C2=CC(=C(C#N)C=C2)OC.BrCCCCCBr>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCCCC2)C#N)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[C:18]1([C:19]#[N:20])[CH2:21][CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[C:18]1([C:19]#[N:20])[CH2:21][CH2:22][CH2:23][CH... | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1 | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCCC1 | null | null | null | Miscellaneous | OtherReaction | e12c3bf13d3003ff46295c3c6432594db11ed25b31e35d8b39ba295525f7a154 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2oc(-c3ccc(C4CCCCC4)cc3)nc2c1 | [N;D1;H0:1]#[C:2]-[C:3]1(-[c:4])-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1>>[N;D1;H0:1]#[C:2]-[C:3]1(-[c:4])-[C:5]-[CH2;D2;+0:6]-[C:8]-[C:9]-[CH2;D2;+0:7]-1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for the synthesis of 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclobutanecarbonitrile, 4-(1,3-benzoxazol-2-yl)-2-methoxybenzonitrile (250 mg, 0.95 mmol) was reacted with 1,5-dibromopentane (160 μL, 1.1 mmol) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cycl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCC1 | C1CCCCC1 | c1ccccc1.c1ccc2ocnc2c1.C1CCCCC1 | Other | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCC1>>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f980798fac1b41878444490f8b753fdb | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O>>COc1cc(C(=O)Nc2ccccc2O)ccc1C | COC=1C=C(C(=O)O)C=CC1C.S(=O)(Cl)Cl.NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C>>OC1=C(C=CC=C1)NC(C1=CC(=C(C=C1)C)OC)=O | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18]([CH3:19])[cH:17][cH:16]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[OH:15])[cH:16][cH:17][c:18]1[CH3:19] | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O | COc1cc(C(=O)Nc2ccccc2O)ccc1C | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 3-Methoxy-4-methyl benzoic acid (1.2 g, 7.2 mmol) and thionyl chloride (10 mL) was heated to reflux conditions under argon until no starting material was observed by TLC. After cooling mixture to rt and concentration in vacuo, the resulting brown oil was dissolved in THF (15 mL) and slowly added to a cooled mixture of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | COc1cc(C(=O)O)ccc1C.Nc1ccccc1O>C1CCOC1>COc1cc(C(=O)Nc2ccccc2O)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04560bce4f774e089189eeafb357a37c | COc1cc(C(=O)Nc2ccccc2O)ccc1C>>COc1cc(-c2nc3ccccc3o2)ccc1C | OC1=C(C=CC=C1)NC(C1=CC(=C(C=C1)C)OC)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>COC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2 | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([CH3:18])[cH:16][cH:15]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH3:18] | COc1cc(C(=O)Nc2ccccc2O)ccc1C | COc1cc(-c2nc3ccccc3o2)ccc1C | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 088185b661aa9468f1c7cc811b018c6406e509618f8bf146f282e07bcdf823de | e4db370caafce196eb62f60d573e0a03e9af17c2927e176eeb3f4f837c389bef | c1ccc(-c2nc3ccccc3o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:7]:[c:5]1:[o;H0;D2;+0:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[n;H0;D2;+0:2]:[c:3]:1:[c:4] | null | [] | null | null | null | null | A mixture of N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide (1.5 g, 5.8 mmol), toluene (30 mL), p-toluenesulfonic acid monohydrate (7.6 g, 40 mmol) and molecular sieves was refluxed overnight. After cooling reaction to rt, filtered washing with warm chloroform and concentrated filtrate in vacuo. The resulting brown oi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | null | COc1cc(C(=O)Nc2ccccc2O)ccc1C>C1(=CC=CC=C1)C>COc1cc(-c2nc3ccccc3o2)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b5dc4ac04c6402099cfcfbd4e02fa1a | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>>COc1cc(-c2nc3ccccc3o2)ccc1CBr | COC=1C=C(C=CC1C)C=1OC2=C(N1)C=CC=C2.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.BrN1C(CCC1=O)=O>>BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH3:18].O=C1CCC(=O)N1[Br:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][Br:19] | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br | COc1cc(-c2nc3ccccc3o2)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole (1.0 g, 4.1 mmol), carbon tetrachloride (18 mL), benzoyl peroxide (66 mg, 0.3 mmol) and N-bromosuccinimide (970 mg, 5.4 mmol) was heated to reflux conditions under argon and placed under a UV light. After 1 h, no starting material was observed by TLC. After cooling mixture t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | 1 | COc1cc(-c2nc3ccccc3o2)ccc1C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COc1cc(-c2nc3ccccc3o2)ccc1CBr |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.