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-38a2481c78754a3cb5c7d1ecd2475eae | COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1>>C[C@@H](CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1)C(=O)O | OS(=O)(=O)[O-].[K+].C(C1=CC=CC=C1)N(S(=O)(=O)C[C@@H](C(=O)OC)C)C(C1=CC=CC=C1)C1=CC=CC=C1.[Li+].[OH-].CO>>C(C1=CC=CC=C1)N(S(=O)(=O)C[C@@H](C(=O)O)C)C(C1=CC=CC=C1)C1=CC=CC=C1 | C[O:30][C:28]([C@@H:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:29]>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)... | COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1 | C[C@@H](CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1)C(=O)O | null | null | C1CCOC1.C(C)(=O)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNC(c2ccccc2)c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 80.7 | [{"value": 80.7, "product": "C(C1=CC=CC=C1)N(S(=O)(=O)C[C@@H](C(=O)O)C)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 50 mL round bottom flask equipped with magnetic stir bar was charged with 320 mg of methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate and 120 mg LiOH (4 eq) in 4 mL 50% aq THF. After 5 minutes 2 mL MeOH added to get homogeneous solution, after 1 hour the reaction was partioned between ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C1CCOC1.C(C)(=O)OCC | null | null | COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1>C1CCOC1.C(C)(=O)OCC>C[C@@H](CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e27f850467e44199bcbb1b30c336e84 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | ClCC(=O)CCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1 | O=C(CCl)[CH2:14][Cl:15].O=[C:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:13]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]([OH:13])[CH2:14][Cl:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH... | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | null | null | CO.O1CCCC1 | C-C Coupling | OtherReaction | be975736ea4dc284d6befa072d9777b891132a86c932e209ec3849b788893253 | 1c7c048f8a75ee2977c3642525e5bc0c5f72d9781847729e637668c64f734260 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-C-C(=O)-[CH2;D2;+0:1]-[Cl;D1;H0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5](-[C:6])-[#7:7]-[C:8]=[O;D1;H0:9]>>[C:6]-[C:5](-[#7:7]-[C:8]=[O;D1;H0:9])-[C@H;D3;+0:3](-[O;D1;H1:4])-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 43 | [{"value": 43.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.8, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 75.0 g (0.226 mol) of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone in a mixture of 807 mL of methanol and 807 mL of tetrahydrofuran at −2° C., was added 13.17 g (0.348 mol, 1.54 equiv.) of solid sodium borohydride over one hundred minutes. The solvents were removed under reduced pressure at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Ketone | Primary halide.Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | CO.O1CCCC1 | 60 | null | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>CO.O1CCCC1>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5233044755d24604977768d373a36afd | Cc1ccccc1C(=O)Cl>>NC(=O)c1ccccc1 | C(C)(=O)OCC.C=1(C(=CC=CC1)C(=O)Cl)C.C(C)N(CC)CC>>C(C1=CC=CC=C1)(=O)N | C[c:9]1[c:4]([C:2](Cl)=[O:3])[cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | Cc1ccccc1C(=O)Cl | NC(=O)c1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 78ff435990e953e050e7444d43c9ca53d4ac335b433d123bc0c7b9c47463d8a5 | 488d152322387b3d6492d859888149d6123db859b65cc57f51e0bc93234f4f7b | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6]):[c:7]>>[N;D1;H2:8]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | 337.5 | [{"value": 337.5, "product": "C(C1=CC=CC=C1)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 391 mg (1 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(4-aminophenyl)sulfonyl]amino-1S-(phenylmethyl)propylamine in 3 mL of anhydrous methylene chloride, was added 0.42 mL (3 mmol) of triethylamine, then at room temperature, 0.12 mL (0.9 mmol) of ortho-toluoyl chloride was added. After 15 hours at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Primary amide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(Cl)Cl | null | null | Cc1ccccc1C(=O)Cl>C(Cl)Cl>NC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40de2e1908344d3fa08871d4f95f32e6 | Cc1c(N)cccc1C(=O)O.NC(N)=O>>Cc1c(O)cccc1C(=O)O | N(=O)[O-].[Na+].NC=1C(=C(C(=O)O)C=CC1)C.NC(=O)N.S(O)(O)(=O)=O.N(=O)[O-]>>OC=1C(=C(C(=O)O)C=CC1)C | N[c:3]1[c:2]([CH3:1])[c:8]([C:9](=[O:10])[OH:11])[cH:7][cH:6][cH:5]1.NC(N)=[O:4]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[OH:11] | Cc1c(N)cccc1C(=O)O.NC(N)=O | Cc1c(O)cccc1C(=O)O | null | [Cu-]=O.C1=CC(=C(C=C1NC2=NC(=NC(=N2)N)Cl)NS(=O)(=O)C3=CC4=C5NC(=C4C=C3)NC6=C7C=CC(=CC7=C([N-]6)NC8=C9C=C(C=CC9=C(N8)NC1=C2C=CC(=CC2=C(N5)[N-]1)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Cu+2].O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].[N+](=O)(... | O | Heteroatom Alkylation and Arylation | OtherReaction | f91482c93228799d93382bc41d1e76715a7b04dc6d0a5283c310ecb4d3b98633 | 891ec3b13223a598ccf2a9d11ebe28aad97dbcc6e0037050822ea9d225a1dca7 | c1ccccc1 | N-C(-N)=[O;H0;D1;+0:1].N-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C;D1;H3:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:6]-[c:5](:[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c;H0;D3;+0:2](-[OH;D1;+0:1]):[c:3]:[c:4] | 36 | [{"value": 36.0, "product": "OC=1C(=C(C(=O)O)C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A one-necked 100 mL round-bottomed flask (magnetic stirring) was charged with 1.0 gram (6.6 mM) 3-amino-2-methylbenzoic acid. A warm mixture of 2.3 mL conc. sulfuric acid in 4.3 mL water was added to the flask, the resulting slurry was cooled below 15° C. in an ice bath, and 6.6 grams of ice was added. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cu-]=O.C1=CC(=C(C=C1NC2=NC(=NC(=N2)N)Cl)NS(=O)(=O)C3=CC4=C5NC(=C4C=C3)NC6=C7C=CC(=CC7=C([N-]6)NC8=C9C=C(C=CC9=C(N8)NC1=C2C=CC(=CC2=C(N5)[N-]1)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Cu+2].O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].[N+](=O)(... | null | null | Cc1c(N)cccc1C(=O)O.NC(N)=O>[Cu-]=O.C1=CC(=C(C=C1NC2=NC(=NC(=N2)N)Cl)NS(=O)(=O)C3=CC4=C5NC(=C4C=C3)NC6=C7C=CC(=CC7=C([N-]6)NC8=C9C=C(C=CC9=C(N8)NC1=C2C=CC(=CC2=C(N5)[N-]1)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Cu+2].O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0a4d643b7a549128d1c92d0cabd4388 | Cc1c(O)cccc1C(=O)O>>NC(=O)c1ccccc1 | C(C)(=O)OCC.OC=1C(=C(C(=O)O)C=CC1)C.ON1N=NC2=C1C=CC=C2.C(CCl)Cl>>C(C1=CC=CC=C1)(=O)N | C[c:9]1[c:4]([C:2](O)=[O:3])[cH:5][cH:6][cH:7][c:8]1O>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | Cc1c(O)cccc1C(=O)O | NC(=O)c1ccccc1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 7e5a734297fae3dddc8b341e6a4f963e1a57cd4ae7f346d7fac353fd796e8a2f | ea7c7f06a967f2cbc04d792fa14afdffca1b0df009e58d0ab7cf45d34806d3d4 | c1ccccc1 | C-[c;H0;D3;+0:1]1:[c:2](-[C;H0;D3;+0:3](-O)=[O;D1;H0:4]):[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-O>>[N;D1;H2:9]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:2]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:1]:1 | 183 | [{"value": 183.0, "product": "C(C1=CC=CC=C1)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 175 mg (1.15 mmol) of 3-hydroxy-2-methylbenzoic acid and 203 mg (1.5 mmol) of N-hydroxybenzotriazole in 6 mL of anhydrous N,N-dimethylformamide at 0° C., was added 220 mg (1.15 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 392 mg (1.0 mmol) of 2R-hydroxy-3-[(2-me... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Primary amide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CN(C=O)C | null | 0.333333 | Cc1c(O)cccc1C(=O)O>CN(C=O)C>NC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8275b448dd14a3faa2c16a69cf16fcd | Cc1c(O)cccc1C(=O)O>>NC(=O)c1ccccc1 | C(C)(=O)OCC.OC=1C(=C(C(=O)O)C=CC1)C.ON1N=NC2=C1C=CC=C2.C(CCl)Cl>>C(C1=CC=CC=C1)(=O)N | C[c:9]1[c:4]([C:2](O)=[O:3])[cH:5][cH:6][cH:7][c:8]1O>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | Cc1c(O)cccc1C(=O)O | NC(=O)c1ccccc1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 7e5a734297fae3dddc8b341e6a4f963e1a57cd4ae7f346d7fac353fd796e8a2f | ea7c7f06a967f2cbc04d792fa14afdffca1b0df009e58d0ab7cf45d34806d3d4 | c1ccccc1 | C-[c;H0;D3;+0:1]1:[c:2](-[C;H0;D3;+0:3](-O)=[O;D1;H0:4]):[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-O>>[N;D1;H2:9]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:2]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:1]:1 | 215.8 | [{"value": 215.8, "product": "C(C1=CC=CC=C1)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 134 mg (0.88 mmol) of 3-hydroxy-2-methylbenzoic acid and 155 mg (1.15 mmol) of N-hydroxybenzotriazole in 5 mL of anhydrous N,N-dimethylformamide at 0° C., was added 167 mg (0.88 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 300 mg (1.0 mmol) of 2R-hydroxy-3-[(2-m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Primary amide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CN(C=O)C | null | 0.333333 | Cc1c(O)cccc1C(=O)O>CN(C=O)C>NC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-771a37b166694f87a54ba1bf13c55b3c | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2>>O=S(=O)(Cl)c1ccc2c(c1)OCO2 | O1COC2=C1C=CC=C2.S(=O)(=O)(Cl)Cl>>O1COC2=C1C=CC(=C2)S(=O)(=O)Cl | Cl[S:2](=[O:1])(=[O:3])[Cl:4].[cH:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2 | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2 | O=S(=O)(Cl)c1ccc2c(c1)OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 3fc054f75f198b89d74fcdf05cd9e4e02a6088859e93e9ad89302c849c196bc8 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc2c(c1)OCO2 | Cl-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6]:[c:7]:[c;H0;D3;+0:8](-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:9]:[c:10] | 16.3 | [{"value": 16.3, "product": "O1COC2=C1C=CC(=C2)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | To a solution of 4.25 g of anhydrous N,N-dimethylformamide at 0° C. under nitrogen was added 7.84 g of sulfuryl chloride, whereupon a solid formed. After stirring for 15 minutes, 6.45 g of 1,3-benzodioxole was added, and the mixture heated at 100° C. for 2 hours. The reaction was cooled, poured into ice water, extracte... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | 100 | 0.25 | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2>CN(C=O)C>O=S(=O)(Cl)c1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-679afb7de0c84e5997e01e80c7d10604 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl>>O=S(=O)(Cl)c1ccc2ncsc2c1 | S(=O)(Cl)Cl.S1C=NC2=C1C=C(C=C2)S(=O)(=O)O.CN(C=O)C>>ClS(=O)(=O)C1=CC2=C(N=CS2)C=C1 | O[S:2](=[O:1])(=[O:3])[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][s:11][c:12]2[cH:13]1.O=S(Cl)[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][s:11][c:12]2[cH:13]1 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl | O=S(=O)(Cl)c1ccc2ncsc2c1 | null | null | ClC(C)Cl | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccc2scnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]:[c:8]:[#16;a:9]>>[#16;a:9]:[c:8]:[c:7]:[c:5](-[S;H0;D4;+0:2](-[Cl;H0;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:6] | null | [] | null | null | 1.5 | HOUR | Thionyl chloride (4 mL) was added to a suspension of the benzothiazole-6-sulfonic acid (0.60 g, 2.79 mmol) in dichloroethane (15 mL) and the reaction mixture was heated at reflux and dimethylformamide (5 mL) was added to the reaction mixture to yield a clear solution. After 1.5 hr. at reflux, the solvent was removed in... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccc2scnc2c1 | HCl | ClC(C)Cl | null | 1.5 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl>ClC(C)Cl>O=S(=O)(Cl)c1ccc2ncsc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9a10ec75b564366afe1943f25028665 | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl>>COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 | C(=O)(OC)NC=1NC2=C(N1)C=CC=C2.ClS(=O)(=O)O>>ClS(=O)(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:16][c:17]2[nH:18]1.O=[S:12]([OH:13])(=[O:14])[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][c:17]2[nH:18]1 | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl | COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 | null | null | null | Protection | Aromatic sulfonyl chlorination | 44a9386249fb09c227c1bade83a10e6d0e50059a06b5b8449d6ef54b8e158ff5 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2[nH]cnc2c1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]:1:2>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:13]:2:[c:12]:1 | 78 | [{"value": 78.0, "product": "ClS(=O)(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2-carbomethoxyamino-benzimidazole (5.0 g, 0.026 mole) in chlorosulfonic acid (35.00 mL) was stirred at 0° C. for 30 min. and at room temperature for 3 hr. The resulting dark colored reaction mixture was carefully poured into an ice-water mixture (200 mL) and stirred at room temperature for 30 min. The res... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | null | null | 0.5 | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl>>COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02bfd6ae3cc9411485ab357305a1bce2 | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.c1ccc(CN2CCNCC2)cc1>>C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)N1CCNCC1.CCN(CC)CC.C(C)(=O)OCC.CCCCCC.ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>C(C1=CC=CC=C1)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C | Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:20](=[O:21])[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)(=[O:5])=[O:6].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c... | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.c1ccc(CN2CCNCC2)cc1 | C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(CCS(=O)(=O)N1CCN(Cc2ccccc2)CC1)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | 0 | CELSIUS | 1 | HOUR | A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 2.5 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 25 mL CH2Cl2. The solution was cooled to 0° C. and charged with 1.57 mL (1.0 eq.) 4-benzylpiperazine and 1.26 mL NEt3. The reaction was stirred for 1 hour then concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.c1ccc(CN2CCNCC2)cc1>C(Cl)Cl>C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23f9c4ecd6c3478fab0005d763040104 | C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1>>C[C@](Cc1ccccc1)(CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)O | C(C1=CC=CC=C1)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C.[Li+].[OH-]>>C(C1=CC=CC=C1)[C@](C(=O)O)(CS(=O)(=O)N1CCN(CC1)CC1=CC=CC=C1)C | [CH3:1][C@@H:2]([CH2:10][S:11](=[O:12])(=[O:13])[N:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[O:29][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][C@:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)([CH2:10][S:11](=[O:12])(=[O:13])[N:14]1[CH2:1... | C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1 | C[C@](Cc1ccccc1)(CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 16eb0e22715fadede32e44259800ac2375ae7dbc609f9ec677d59917bae07bec | b51da43dbb7140dac708518f8dbf83c5b067214819134afdb3f427285d08d6f8 | O=S(=O)(CCCc1ccccc1)N1CCN(Cc2ccccc2)CC1 | [#16:1]-[C:2]-[C@H;D3;+0:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#16:1]-[C:2]-[C@;H0;D4;+0:3](-[C;D1;H3:4])(-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | 36.7 | [{"value": 25.0, "product": "C(C1=CC=CC=C1)[C@](C(=O)O)(CS(=O)(=O)N1CCN(CC1)CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "C(C1=CC=CC=C1)[C@](C(=O)O)(CS(=O)(=O)N1CCN(CC1)CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 3.0 g benzyl 3-(4-benzylpiperizin-1-ylsulfonyl)-2(R)-methylpropionate, 1.2 g LiOH (4 eq.) in 20 mL 50% aqueous methanol. After 2 hours HPLC analysis showed no starting material. The reaction was concentrated to half volume and... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | CO | null | 2 | C[C@@H](CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)OCc1ccccc1>CO>C[C@](Cc1ccccc1)(CS(=O)(=O)N1CCN(Cc2ccccc2)CC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b114308753546f9ba44edcd7d8e73f8 | CC(C)CNC[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1.O=S(=O)(Cl)c1ccc2c(c1)OCO2>>CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CN(CC1=CC=CC=C1)[C@H]([C@@H](CNCC(C)C)O)CC1=CC=CC=C1.O1COC2=C1C=CC(=C2)S(=O)(=O)Cl.C(C(=O)O)(=O)O>>O1COC2=C1C=CC(=C2)S(=O)(=O)N(CC(C)C)C[C@H]([C@H](CC2=CC=CC=C2)N(CC2=CC=CC=C2)CC2=CC=CC=C2)O | [CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][C@@H:7]([OH:8])[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[N:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.Cl[S:32](=[O:33])(=[O:34])[c:35]1[cH:36][cH:37][c:38]2[c:39]([cH:40]1)[O:41][CH2:42][O:43]2... | CC(C)CNC[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1.O=S(=O)(Cl)c1ccc2c(c1)OCO2 | CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 | null | null | O.C(C)(=O)OCC.O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(NCC[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)c1ccc2c(c1)OCO2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 105 | [{"value": 105.0, "product": "O1COC2=C1C=CC(=C2)S(=O)(=O)N(CC(C)C)C[C@H]([C@H](CC2=CC=CC=C2)N(CC2=CC=CC=C2)CC2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a 5000 mL, 3-necked flask fitted with a mechanical stirrer was added N-[3(S)-[N,N-bis(phenylmethyl)amino]-2(R)-hydroxy-4-phenylbutyl]-N-isobutylamine.oxalic acid salt (354.7 g, 0.7 mole) and 1,4-dioxane (2000 mL). A solution of potassium carbonate (241.9 g, 1.75 moles) in water (250 mL) was then added. The resultant... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)OCO2 | HCl | O.C(C)(=O)OCC.O1CCOCC1 | null | 2 | CC(C)CNC[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1.O=S(=O)(Cl)c1ccc2c(c1)OCO2>O.C(C)(=O)OCC.O1CCOCC1>CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bef8ec050b714bbf828863d3d57b24dd | CC(C)(C)OC(=O)N1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1 | ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C.C(=O)(OC(C)(C)C)N1CCNCC1.CCN(CC)CC>>C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:20](=[O:21])[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)(=[O:5])=[O:6]>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]... | CC(C)(C)OC(=O)N1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(CCS(=O)(=O)N1CCNCC1)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | 90 | [{"value": 90.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 5.2 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 50 mL CH2Cl2. The flask was cooled to 0° C. and charged with 3.5 g N-Boc-piperazine and 2.9 mL (1.1 eq.) NEt3. The reaction was stirred 30 minutes at 0° C., concentrated i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | CC(C)(C)OC(=O)N1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-086b6567548e4c6f90d72930803a7c36 | C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)O | C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)O)C | c1ccc(C[O:22][C:20]([C@@H:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)=[O:21])cc1>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:1... | C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)O | null | [Pd] | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CNCCN1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 93 | [{"value": 93.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 300 mL Fisher Porter vessel equipped with magnetic stirring bar was charged with 7.2 g benzyl 3-(4-tert-butoxycarbonylpiperizin-1-ylsulfonyl)-2(R)-methylpropionate, 600 mg 10% Pd—C, and 100 mL MeOH. The reaction vessel was charged with 50 psi H2 and stirred for 2 hours at room temperature. The reaction mixture was fi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1C[NH]CC[NH]1 | Other | [Pd].CO | null | 2 | C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCc1ccccc1>[Pd].CO>C[C@@H](CS(=O)(=O)N1CCN(C(=O)OC(C)(C)C)CC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1ae6626684141c2bc4822f377cdc2d6 | COC(=O)[C@@H](N)CCCCN>>NCCCC[C@H](N)C(=O)O | Cl.Cl.COC([C@@H](N)CCCCN)=O>>N[C@@H](CCCCN)C(=O)O | C[O:10][C:8]([C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[NH2:7])=[O:9]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10] | COC(=O)[C@@H](N)CCCCN | NCCCC[C@H](N)C(=O)O | null | null | O.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 110 | CELSIUS | null | null | 2.33 Grams (10 mmol) of L-lysine methyl ester dihydrochloride was dissolved in 5.0 ml of water to prepare a treating agent solution. A cotton cloth (150 mm×170 mm, 4.8 g) was in advance treated to be immersed in 25% aqueous sodium hydroxide solution for an hour at room temperature, washed with water and dried. This tre... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | O.[OH-].[Na+] | 110 | null | COC(=O)[C@@H](N)CCCCN>O.[OH-].[Na+]>NCCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd57e21a6052402ba92034b341776a35 | COC(=O)[C@@H](N)CCCCN>>NCCCC[C@H](N)C(=O)O | Cl.Cl.COC([C@@H](N)CCCCN)=O.[OH-].[Na+]>>N[C@@H](CCCCN)C(=O)O | C[O:10][C:8]([C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[NH2:7])=[O:9]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10] | COC(=O)[C@@H](N)CCCCN | NCCCC[C@H](N)C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 110 | CELSIUS | null | null | 20.88 Grams (90 mmol) of L-lysine methyl ester dihydrochloride was dissolved in 18 ml of methanol, and 45 ml of 2 N aqueous sodium hydroxide solution was added thereto to prepare a treating agent solution. An untreated cotton cloth (480 mm×510 mm, 45 g) was allowed to uniformly absorb the total amount of the above trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | 110 | null | COC(=O)[C@@H](N)CCCCN>CO>NCCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19b3a387dab34adbb5e6b6e4e17962c8 | CCCOC(=O)[C@@H](N)CCCCN>>NCCCC[C@H](N)C(=O)O | Cl.Cl.C(CC)OC([C@@H](N)CCCCN)=O.[OH-].[Na+]>>N[C@@H](CCCCN)C(=O)O | CCC[O:10][C:8]([C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[NH2:7])=[O:9]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10] | CCCOC(=O)[C@@H](N)CCCCN | NCCCC[C@H](N)C(=O)O | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 110 | CELSIUS | null | null | 2.62 Grams (10 mmol) of L-lysine n-propyl ester dihydrochloride was dissolved in 2 ml of methanol, and 5 ml of 2 N aqueous sodium hydroxide solution was added thereto to prepare a treating agent solution. An untreated cotton cloth (160 mm×170 mm, 5.0 g) was allowed to uniformly absorb the total amount of the above trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | 110 | null | CCCOC(=O)[C@@H](N)CCCCN>CO>NCCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffd40b6b4ec94b5291b255c5d7085ef2 | COC(=O)[C@@H](N)CCCCN>>NCCCC[C@H](N)C(=O)O | Cl.Cl.COC([C@@H](N)CCCCN)=O.[OH-].[Na+]>>N[C@@H](CCCCN)C(=O)O | C[O:10][C:8]([C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[NH2:7])=[O:9]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH2:7])[C:8](=[O:9])[OH:10] | COC(=O)[C@@H](N)CCCCN | NCCCC[C@H](N)C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 110 | CELSIUS | null | null | 1.16 Gram (5 mmol) of L-lysine methyl ester dihydrochloride was dissolved in 4.5 ml of methanol, and 2.5 ml of 2 N aqueous sodium hydroxide solution was added thereto to prepare a treating agent solution. An untreated cotton cloth (160 mm×170 mm, 5.0 g) was allowed to uniformly absorb the total amount of the above trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | 110 | null | COC(=O)[C@@H](N)CCCCN>CO>NCCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95c0b4b01a344d0094defd65c6c53294 | COC(=O)[C@@H](N)CCCNC(=N)N>>N=C(N)NCCC[C@H](N)C(=O)O | Cl.Cl.COC([C@@H](N)CCCNC(N)=N)=O.[OH-].[Na+]>>N[C@@H](CCCNC(N)=N)C(=O)O | C[O:12][C:10]([C@H:8]([CH2:7][CH2:6][CH2:5][NH:4][C:2](=[NH:1])[NH2:3])[NH2:9])=[O:11]>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH2:9])[C:10](=[O:11])[OH:12] | COC(=O)[C@@H](N)CCCNC(=N)N | N=C(N)NCCC[C@H](N)C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 110 | CELSIUS | null | null | 1.31 Gram (5 mmol) of L-arginine methyl ester dihydrochloride was dissolved in 4 ml of methanol, and 2.5 ml of 2 N aqueous sodium hydroxide solution was added thereto to prepare a treating agent solution. An untreated cotton cloth (160 mm×170 mm, 5.0 g) was allowed to uniformly absorb the total amount of the above trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | 110 | null | COC(=O)[C@@H](N)CCCNC(=N)N>CO>N=C(N)NCCC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05d081150e494ba1a9034aa8e3bd60ad | CI.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C)c(C)n2)ccn1 | CI.[H-].[Na+].CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.O>>CN1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | I[CH3:10].[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:11]([CH3:12])[n:13]2)[cH:14][cH:15][n:16]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH3:10])[c:11]([CH3:12])[n:13]2)[cH:14][cH:15][n:16]1 | CI.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(C)c(C)n2)ccn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8e073f75e432a7315b707c66eabce47968c081c977c0311c745fc22b6e28fcfe | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | C(#Cc1c[nH]cn1)c1ccncc1 | I-[CH3;D1;+0:1].[C:2]#[C:3]-[c:4]1:[#7;a:5]:[c:6](-[C;D1;H3:7]):[nH;D2;+0:8]:[c:9]:1>>[C:2]#[C:3]-[c:4]1:[#7;a:5]:[c:6](-[C;D1;H3:7]):[n;H0;D3;+0:8](-[CH3;D1;+0:1]):[c:9]:1 | 25 | [{"value": 25.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium hydride (76 mg, 55%, 1.57 mmol) was suspended in 2 mL of dry THF. A solution of 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine (150 mg, 0.76 mmol) in 8 mL of dry THF was added and the reaction mixture was stirred at room temperature for 30 min. A solution of methyliodide (142 mg, 1.00 mmol) in 1 mL of dr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HI | C1CCOC1 | null | 0.5 | CI.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>C1CCOC1>Cc1cc(C#Cc2cn(C)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffc27ed5e3ac42eca87737c19cad4c2d | CC(C)Br.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C(C)C)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.C(C)(C)Br>>C(C)(C)N1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH:10]([CH3:11])[CH3:12].[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH:10]([CH3:11])[CH3:12])[c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1 | CC(C)Br.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(C(C)C)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c371c57fd473e466b8acb15702b4cceb832e90f9eb8d44947b6faa879266a4b0 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[n;H0;D3;+0:10](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:11]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=240.3 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and isopropylbromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HBr | null | null | null | CC(C)Br.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C(C)C)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64e542aaf25a4fba89be3f7bb7cd5aed | CC(C)CBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC(C)C)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.C(C(C)C)Br>>C(C(C)C)N1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH2:10][CH:11]([CH3:12])[CH3:13].[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1 | CC(C)CBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(CC(C)C)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=254.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and isobutylbromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HBr | null | null | null | CC(C)CBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC(C)C)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c01d5a67ec54e1bb487f4e4048478ff | BrCC1CC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC3CC3)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC1CC1>>C1(CC1)CN1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH2:10][CH:11]1[CH2:12][CH2:13]1.[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][CH:11]3[CH2:12][CH2:13]3)[c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1 | BrCC1CC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(CC3CC3)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1cn(CC2CC2)cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]2-[C:3]-[C:4]-2):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=252.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromomethyl-cyclopropane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1.C1CC1 | HBr | null | null | null | BrCC1CC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC3CC3)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bad62e359d54446995609ea47249323a | BrCC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC3CCC3)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC1CCC1>>C1(CCC1)CN1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14]1.[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14]3)[c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1 | BrCC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(CC3CCC3)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1cn(CC2CCC2)cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:3]-[C:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:12]:[c:7](-[C:6]#[C:5]):[#7;a:8]:[c:9]:1-[C;D1;H3:10])-[C:4] | null | [] | null | null | null | null | The title compound, MS: m/e=266.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromomethyl-cyclobutane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1.C1CCC1 | HBr | null | null | null | BrCC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC3CCC3)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-968e7d53e00a490e98435e4b46f07c1f | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.N#CCBr>>Cc1cc(C#Cc2cn(CC#N)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC#N>>CC=1N(C=C(N1)C#CC1=CC(=NC=C1)C)CC#N | [CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1.Br[CH2:10][C:11]#[N:12]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][C:11]#[N:12])[c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1 | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.N#CCBr | Cc1cc(C#Cc2cn(CC#N)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3]):[c:11]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=237.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromoacetonitrile.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HBr | null | null | null | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.N#CCBr>>Cc1cc(C#Cc2cn(CC#N)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4ce5111c707452787e08bc3628bd9f6 | COCCBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>COCCn1cc(C#Cc2ccnc(C)c2)nc1C | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCCOC>>COCCN1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH2:4][CH2:3][O:2][CH3:1].[nH:5]1[cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][n:13][c:14]([CH3:15])[cH:16]2)[n:17][c:18]1[CH3:19]>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][n:13][c:14]([CH3:15])[cH:16]2)[n:17][c:18]1[CH3:19] | COCCBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | COCCn1cc(C#Cc2ccnc(C)c2)nc1C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:11]:[c:6](-[C:5]#[C:4]):[#7;a:7]:[c:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | The title compound, MS: m/e=256.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 2-bromoethyl-methylether.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccncc1 | HBr | null | null | null | COCCBr.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>COCCn1cc(C#Cc2ccnc(C)c2)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0dfd97f4acb491a8e42db7257f82860 | CC(C)CBr.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(C)C | ClC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC(C)C>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC(C)C)C | Br[CH2:16][CH:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][nH:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH2:16][CH:17]([CH3:18])[CH3:19] | CC(C)CBr.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aaed77ecdd7c0a725853ab93c4757e158595aa9f46d9ba0bf760beeb5320d850 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=274.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-chloro-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 1-bromo-2-methylpropane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1 | HBr | null | null | null | CC(C)CBr.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db53373858a944f39a624b8cd39b18f4 | BrCC1CC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CC1 | ClC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC1CC1>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC1CC1)C | Br[CH2:16][CH:17]1[CH2:18][CH2:19]1.[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][nH:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH2:16][CH:17]1[CH2:18][CH2:19]1 | BrCC1CC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aaed77ecdd7c0a725853ab93c4757e158595aa9f46d9ba0bf760beeb5320d850 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1cn(CC2CC2)cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]2-[C:3]-[C:4]-2):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=272.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-chloro-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromomethyl-cyclopropane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1.C1CC1 | HBr | null | null | null | BrCC1CC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7cf513be9187407cafcb4821ea3d0048 | BrCC1CCC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CCC1 | ClC1=NC=CC(=C1)C#CC=1N=C(NC1)C.C1(CCC1)CBr>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC1CCC1)C | Br[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20]1.[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][nH:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20]1 | BrCC1CCC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aaed77ecdd7c0a725853ab93c4757e158595aa9f46d9ba0bf760beeb5320d850 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1cn(CC2CCC2)cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:3]-[C:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:12]:[c:7](-[C:6]#[C:5]):[#7;a:8]:[c:9]:1-[C;D1;H3:10])-[C:4] | null | [] | null | null | null | null | The title compound, MS: m/e=286.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-chloro-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and cydobutyl-methylbromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1.C1CCC1 | HBr | null | null | null | BrCC1CCC1.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC1CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6532b9a829e4ccda2f3f44872e35bdb | BrCCOc1ccccc1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CCOc3ccccc3)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.O(C1=CC=CC=C1)CCBr>>CC1=NC=CC(=C1)C#CC=1N=C(N(C1)CCOC1=CC=CC=C1)C | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:19]([CH3:20])[n:21]2)[cH:22][cH:23][n:24]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][CH2:11][O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]([CH3:20])[n:21]2)[cH:22]... | BrCCOc1ccccc1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(CCOc3ccccc3)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1cn(CCOc2ccccc2)cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:11]:[c:6](-[C:5]#[C:4]):[#7;a:7]:[c:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | The title compound, MS: m/e=318.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 2-phenoxyethyl bromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1.c1ccccc1 | HBr | null | null | null | BrCCOc1ccccc1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CCOc3ccccc3)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b0cafd0ef674192ab8140ab79ece049 | CI.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1C | ClC1=NC=CC(=C1)C#CC=1N=C(NC1)C.CI>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)C)C | I[CH3:16].[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][nH:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH3:16] | CI.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | Cc1nc(C#Cc2ccnc(Cl)c2)cn1C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 729a692410860dfc08595bfe04df8ab01bba19656de1c4809a7144698ae08e36 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | C(#Cc1c[nH]cn1)c1ccncc1 | I-[CH3;D1;+0:1].[C:2]#[C:3]-[c:4]1:[#7;a:5]:[c:6](-[C;D1;H3:7]):[nH;D2;+0:8]:[c:9]:1>>[C:2]#[C:3]-[c:4]1:[#7;a:5]:[c:6](-[C;D1;H3:7]):[n;H0;D3;+0:8](-[CH3;D1;+0:1]):[c:9]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=232.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-chloro-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and methyl iodide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1 | HI | null | null | null | CI.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-775a03628f4f4a1c86c6343eb6cf66fb | CI.Ic1cnc(C2CC2)[nH]1>>Cn1cc(I)nc1C1CC1 | C1(CC1)C=1NC(=CN1)I.IC>>C1(CC1)C=1N(C=C(N1)I)C | I[CH3:1].[n:2]1[cH:3][c:4]([I:5])[nH:6][c:7]1[CH:8]1[CH2:9][CH2:10]1>>[CH3:1][n:2]1[cH:3][c:4]([I:5])[n:6][c:7]1[CH:8]1[CH2:9][CH2:10]1 | CI.Ic1cnc(C2CC2)[nH]1 | Cn1cc(I)nc1C1CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8e073f75e432a7315b707c66eabce47968c081c977c0311c745fc22b6e28fcfe | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1c[nH]c(C2CC2)n1 | I-[CH3;D1;+0:1].[C:2]-[c:3]1:[n;H0;D2;+0:4]:[c:5]:[c:6](-[I;D1;H0:7]):[nH;D2;+0:8]:1>>[C:2]-[c:3]1:[n;H0;D2;+0:8]:[c:6](-[I;D1;H0:7]):[c:5]:[n;H0;D3;+0:4]:1-[CH3;D1;+0:1] | null | [] | null | null | null | null | The title compound, MS: m/e=249.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-cyclopropyl-5-iodo-1H-imidazole (example C) and iodomethane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.C1CC1 | HI | null | null | null | CI.Ic1cnc(C2CC2)[nH]1>>Cn1cc(I)nc1C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddffc2f98c8e4efa92b35cce43d2f25d | CC(C)Br.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1C(C)C | ClC1=NC=CC(=C1)C#CC=1N=C(NC1)C.C(C)(C)Br>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)C(C)C)C | Br[CH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][nH:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH:16]([CH3:17])[CH3:18] | CC(C)Br.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | Cc1nc(C#Cc2ccnc(Cl)c2)cn1C(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1a8503641c3b74bf73ee44d8a17979652497533d1387b119b4e1e5c99da1d650 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[n;H0;D3;+0:10](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:11]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=260.6 (M+H+), was prepared in accordance with the general method of example 1 from 2-chloro-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and isopropylbromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1 | HBr | null | null | null | CC(C)Br.Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbb848fc5c3b459aa02401eec47626b9 | CC(C)Br.Ic1cnc(C2CC2)[nH]1>>CC(C)n1cc(I)nc1C1CC1 | C1(CC1)C=1NC(=CN1)I.C(C)(C)Br>>C1(CC1)C=1N(C=C(N1)I)C(C)C | Br[CH:2]([CH3:1])[CH3:3].[n:4]1[cH:5][c:6]([I:7])[nH:8][c:9]1[CH:10]1[CH2:11][CH2:12]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][c:6]([I:7])[n:8][c:9]1[CH:10]1[CH2:11][CH2:12]1 | CC(C)Br.Ic1cnc(C2CC2)[nH]1 | CC(C)n1cc(I)nc1C1CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c371c57fd473e466b8acb15702b4cceb832e90f9eb8d44947b6faa879266a4b0 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1c[nH]c(C2CC2)n1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[c:5]1:[n;H0;D2;+0:6]:[c:7]:[c:8](-[I;D1;H0:9]):[nH;D2;+0:10]:1>>[C:4]-[c:5]1:[n;H0;D2;+0:10]:[c:8](-[I;D1;H0:9]):[c:7]:[n;H0;D3;+0:6]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | null | null | The title compound, MS: m/e=277.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-cyclopropyl-5-iodo-1H-imidazole (example C) and isopropylbromide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.C1CC1 | HBr | null | null | null | CC(C)Br.Ic1cnc(C2CC2)[nH]1>>CC(C)n1cc(I)nc1C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc6c42da646242948f4458d8f4479984 | CC(C)n1cc(I)nc1C1CC1.Cc1cc(C#C[Si](C)(C)C)ccn1>>Cc1cc(C#Cc2cn(C(C)C)c(C3CC3)n2)ccn1 | CC1=NC=CC(=C1)C#C[Si](C)(C)C.C1(CC1)C=1N(C=C(N1)I)C(C)C>>C1(CC1)C=1N(C=C(N1)C#CC1=CC(=NC=C1)C)C(C)C | I[c:7]1[cH:8][n:9]([CH:10]([CH3:11])[CH3:12])[c:13]([CH:14]2[CH2:15][CH2:16]2)[n:17]1.C[Si](C)(C)[C:6]#[C:5][c:4]1[cH:3][c:2]([CH3:1])[n:20][cH:19][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH:10]([CH3:11])[CH3:12])[c:13]([CH:14]3[CH2:15][CH2:16]3)[n:17]2)[cH:18][cH:19][n:20]1 | CC(C)n1cc(I)nc1C1CC1.Cc1cc(C#C[Si](C)(C)C)ccn1 | Cc1cc(C#Cc2cn(C(C)C)c(C3CC3)n2)ccn1 | null | null | null | C-C Coupling | OtherReaction | 701e77ccf536632aa52beccadbf65b26297ae0694339748e812e0556bc4fd8a1 | 15277fe1c5b030cf73fc449a637bcfbd20022d265ae724c496efffa41f39d2fe | C(#Cc1c[nH]c(C2CC2)n1)c1ccncc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3].I-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6](-[C:7]):[#7;a:8](-[C:9]):[c:10]:1>>[C:9]-[#7;a:8]1:[c:10]:[c;H0;D3;+0:4](-[C;H0;D2;+0:1]#[C:2]-[c:3]):[#7;a:5]:[c:6]:1-[C:7] | null | [] | null | null | null | null | The title compound, MS: m/e=266.3 (M+H+), was prepared in accordance with the general method of example A, step 2 from 2-methyl-4-trimethylsilanylethynyl-pyridine and 2-cyclopropyl-4-iodo-1-isopropyl-1H-imidazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Silyl protective group | Alkyne | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1.C1CC1 | HI | null | null | null | CC(C)n1cc(I)nc1C1CC1.Cc1cc(C#C[Si](C)(C)C)ccn1>>Cc1cc(C#Cc2cn(C(C)C)c(C3CC3)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0776d4ce5d849729060245e1cc1d258 | BrC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C3CCC3)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrC1CCC1>>C1(CCC1)N1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH:10]1[CH2:11][CH2:12][CH2:13]1.[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13]3)[c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1 | BrC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(C3CCC3)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b7580cedc2a849bf2b3c2d0f1306684ca3e8c72c5257b78d7e0700abea46994e | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | C(#Cc1cn(C2CCC2)cn1)c1ccncc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-2):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=252.4 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromocyclobutane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | C1CCC1.c1c[nH]cn1 | c1c[nH]cn1.C1CCC1 | c1ccncc1.c1c[nH]cn1.C1CCC1 | HBr | null | null | null | BrC1CCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C3CCC3)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c846e8a846d445e3af566da439402d4f | BrC1CCCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C3CCCC3)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrC1CCCC1>>C1(CCCC1)N1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | Br[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1 | BrC1CCCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(C3CCCC3)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | cff5da941d2e078c36fbbdf08f04d97719472a4bf67104ccf988186e8c43a7b8 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | C(#Cc1cn(C2CCCC2)cn1)c1ccncc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[C:6]#[C:7]-[c:8]1:[#7;a:9]:[c:10](-[C;D1;H3:11]):[nH;D2;+0:12]:[c:13]:1>>[C:6]#[C:7]-[c:8]1:[#7;a:9]:[c:10](-[C;D1;H3:11]):[n;H0;D3;+0:12](-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]-2):[c:13]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=266.3 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and bromocyclopentane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | C1CCCC1.c1c[nH]cn1 | c1c[nH]cn1.C1CCCC1 | c1ccncc1.c1c[nH]cn1.C1CCCC1 | HBr | null | null | null | BrC1CCCC1.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(C3CCCC3)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ee0bb3ddc264ecaac4ee315d3cd79dd | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr>>Cc1cc(C#Cc2cn(CC(F)F)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC(F)F>>FC(CN1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C)F | [CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1.Br[CH2:10][CH:11]([F:12])[F:13]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][CH:11]([F:12])[F:13])[c:14]([CH3:15])[n:16]2)[cH:17][cH:18][n:19]1 | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr | Cc1cc(C#Cc2cn(CC(F)F)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4].[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[c:12]:1>>[C:5]#[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4]):[c:12]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=262.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 2-bromo-1,1-difluoro ethane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HBr | null | null | null | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr>>Cc1cc(C#Cc2cn(CC(F)F)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1942be038c934a82986d828342141348 | Cc1ncc(I)[nH]1.FC(F)CBr>>Cc1nc(I)cn1CC(F)F | IC1=CN=C(N1)C.BrCC(F)F>>FC(CN1C(=NC(=C1)I)C)F | [CH3:1][c:2]1[nH:3][c:4]([I:5])[cH:6][n:7]1.Br[CH2:8][CH:9]([F:10])[F:11]>>[CH3:1][c:2]1[n:3][c:4]([I:5])[cH:6][n:7]1[CH2:8][CH:9]([F:10])[F:11] | Cc1ncc(I)[nH]1.FC(F)CBr | Cc1nc(I)cn1CC(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aaed77ecdd7c0a725853ab93c4757e158595aa9f46d9ba0bf760beeb5320d850 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4].[C;D1;H3:5]-[c:6]1:[n;H0;D2;+0:7]:[c:8]:[c:9](-[I;D1;H0:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[n;H0;D2;+0:11]:[c:9](-[I;D1;H0:10]):[c:8]:[n;H0;D3;+0:7]:1-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4] | null | [] | null | null | null | null | The title compound, MS: m/e=273.0 (M+H+), was prepared in accordance with the general method of example 1 from 5-iodo-2-methyl-1H-imidazole and 2-bromo-1,1-difluoroethane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1 | HBr | null | null | null | Cc1ncc(I)[nH]1.FC(F)CBr>>Cc1nc(I)cn1CC(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3776236429f4aeb87a7c0b85091fbfc | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)F>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)F | ClC1=NC=CC(=C1)C#C[Si](C)(C)C.FC(CN1C(=NC(=C1)I)C)F>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC(F)F)C | C[Si](C)(C)[C:5]#[C:6][c:7]1[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]1.I[c:4]1[n:3][c:2]([CH3:1])[n:15]([CH2:16][CH:17]([F:18])[F:19])[cH:14]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH2:16][CH:17]([F:18])[F:19] | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)F | Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)F | null | null | null | C-C Coupling | OtherReaction | c53f1e662171168c1ae9dab00befd6689ba0bc4ef93173c74cf0eb36cb584f89 | 15277fe1c5b030cf73fc449a637bcfbd20022d265ae724c496efffa41f39d2fe | C(#Cc1c[nH]cn1)c1ccncc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3].I-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:1>>[C:8]-[#7;a:7]1:[c:9]:[c;H0;D3;+0:4](-[C;H0;D2;+0:1]#[C:2]-[c:3]):[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=282.0 (M+H+), was prepared in accordance with the general method of example A, step 2, from 2-chloro-4-trimethylsilanylethynyl-pyridine and 1-(2,2-difluoro-ethyl)-4-iodo-2-methyl-1H-imidazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Silyl protective group | Alkyne | c1cnc[nH]1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1 | HI | null | null | null | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)F>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-afc8033fd8e945e0bc05e473858ff445 | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr>>Cc1cc(C#Cc2cn(/C=C/F)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.BrCC(F)F>>F/C=C/N1C(=NC(=C1)C#CC1=CC(=NC=C1)C)C | [CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1.F[CH:11]([CH2:10]Br)[F:12]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9](/[CH:10]=[CH:11]/[F:12])[c:13]([CH3:14])[n:15]2)[cH:16][cH:17][n:18]1 | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr | Cc1cc(C#Cc2cn(/C=C/F)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a20ee9717d2123d2c26e5cd8a3bf4802039f199b4b5d8671392faa6d6acff0e7 | f6f272d4596f84f77e1f8751e2d5a2ea7d48666ee2ee6266035940f803cf006d | C(#Cc1c[nH]cn1)c1ccncc1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2](-F)-[F;D1;H0:3].[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[nH;D2;+0:10]:[c:11]:1>>[C:4]#[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;D1;H3:9]):[n;H0;D3;+0:10](/[CH;D2;+0:1]=[CH;D2;+0:2]/[F;D1;H0:3]):[c:11]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=242.3 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 2-bromo-1,1-difluoro ethane as a by-product.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | HF.Br- | null | null | null | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1.FC(F)CBr>>Cc1cc(C#Cc2cn(/C=C/F)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08a2d881db674a16b9f53b7e318f89a5 | CS(=O)(=O)OCC(F)(F)F.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC(F)(F)F)c(C)n2)ccn1 | CC1=NC=CC(=C1)C#CC=1N=C(NC1)C.S(C)(=O)(=O)OCC(F)(F)F>>CC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC(F)(F)F)C | CS(=O)(=O)O[CH2:10][C:11]([F:12])([F:13])[F:14].[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][nH:9][c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][n:9]([CH2:10][C:11]([F:12])([F:13])[F:14])[c:15]([CH3:16])[n:17]2)[cH:18][cH:19][n:20]1 | CS(=O)(=O)OCC(F)(F)F.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | Cc1cc(C#Cc2cn(CC(F)(F)F)c(C)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c442140b096c54ef671e11ca8ca216d6e6322c408fe778838cc14d7f651c7f7d | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | C(#Cc1c[nH]cn1)c1ccncc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[C:6]#[C:7]-[c:8]1:[#7;a:9]:[c:10](-[C;D1;H3:11]):[nH;D2;+0:12]:[c:13]:1>>[C:6]#[C:7]-[c:8]1:[#7;a:9]:[c:10](-[C;D1;H3:11]):[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5]):[c:13]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=280.1 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 2,2,2-trifluoroethyl mesylate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC(F)(F)F.Cc1cc(C#Cc2c[nH]c(C)n2)ccn1>>Cc1cc(C#Cc2cn(CC(F)(F)F)c(C)n2)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78744fdb607348e4bd18f3e963ba1543 | CS(=O)(=O)OCC(F)(F)F.Cc1ncc(I)[nH]1>>Cc1nc(I)cn1CC(F)(F)F | IC1=CN=C(N1)C.S(C)(=O)(=O)OCC(F)(F)F>>IC=1N=C(N(C1)CC(F)(F)F)C | CS(=O)(=O)O[CH2:8][C:9]([F:10])([F:11])[F:12].[CH3:1][c:2]1[nH:3][c:4]([I:5])[cH:6][n:7]1>>[CH3:1][c:2]1[n:3][c:4]([I:5])[cH:6][n:7]1[CH2:8][C:9]([F:10])([F:11])[F:12] | CS(=O)(=O)OCC(F)(F)F.Cc1ncc(I)[nH]1 | Cc1nc(I)cn1CC(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f2ef705d5b14ccab2a095dd763f0e759482bba426a5e129aaf82e6bb7121f29e | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | c1c[nH]cn1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[C;D1;H3:6]-[c:7]1:[n;H0;D2;+0:8]:[c:9]:[c:10](-[I;D1;H0:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[n;H0;D2;+0:12]:[c:10](-[I;D1;H0:11]):[c:9]:[n;H0;D3;+0:8]:1-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5] | null | [] | null | null | null | null | The title compound, MS: m/e=291.0 (M+H+), was prepared in accordance with the general method of example 1 from 5-iodo-2-methyl-1H-imidazole and 2,2,2-trifluoroethyl mesylate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC(F)(F)F.Cc1ncc(I)[nH]1>>Cc1nc(I)cn1CC(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c00e3d49dd94ec4bbdbd013597f9057 | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)(F)F>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)(F)F | ClC1=NC=CC(=C1)C#C[Si](C)(C)C.IC=1N=C(N(C1)CC(F)(F)F)C>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1)CC(F)(F)F)C | C[Si](C)(C)[C:5]#[C:6][c:7]1[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]1.I[c:4]1[n:3][c:2]([CH3:1])[n:15]([CH2:16][C:17]([F:18])([F:19])[F:20])[cH:14]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[cH:14][n:15]1[CH2:16][C:17]([F:18])([F:19])[F:20] | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)(F)F | Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)(F)F | null | null | null | C-C Coupling | OtherReaction | c53f1e662171168c1ae9dab00befd6689ba0bc4ef93173c74cf0eb36cb584f89 | 15277fe1c5b030cf73fc449a637bcfbd20022d265ae724c496efffa41f39d2fe | C(#Cc1c[nH]cn1)c1ccncc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3].I-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:1>>[C:8]-[#7;a:7]1:[c:9]:[c;H0;D3;+0:4](-[C;H0;D2;+0:1]#[C:2]-[c:3]):[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=300.0 (M+H+), was prepared in accordance with the general method of example A, step 2, from 2-chloro-4-trimethylsilanylethynyl-pyridine and 4-iodo-2-methyl-1-(2,2,2-trifluoro-ethyl)-1H-imidazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Silyl protective group | Alkyne | c1cnc[nH]1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccncc1 | HI | null | null | null | C[Si](C)(C)C#Cc1ccnc(Cl)c1.Cc1nc(I)cn1CC(F)(F)F>>Cc1nc(C#Cc2ccnc(Cl)c2)cn1CC(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f135c788388643a69501e1ab66510513 | C#Cc1nc(C)n(C2CC2)c1C.Clc1cc(I)ccn1>>Cc1nc(C#Cc2ccnc(Cl)c2)c(C)n1C1CC1 | C1(CC1)N1C(=NC(=C1C)C#C)C.ClC1=NC=CC(=C1)I>>ClC1=NC=CC(=C1)C#CC=1N=C(N(C1C)C1CC1)C | [CH3:1][c:2]1[n:3][c:4]([C:5]#[CH:6])[c:14]([CH3:15])[n:16]1[CH:17]1[CH2:18][CH2:19]1.I[c:7]1[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]#[C:6][c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]2)[c:14]([CH3:15])[n:16]1[CH:17]1[CH2:18][CH2:19]1 | C#Cc1nc(C)n(C2CC2)c1C.Clc1cc(I)ccn1 | Cc1nc(C#Cc2ccnc(Cl)c2)c(C)n1C1CC1 | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cn(C2CC2)cn1)c1ccncc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[#7;a:8]:[c:9]:[c:10](-[C:11]#[CH;D1;+0:12]):[#7;a:13]>>[#7;a:8]:[c:9]:[c:10](-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1):[#7;a:13] | null | [] | null | null | null | null | The title compound, MS: m/e=272.0 (M+H+), was prepared in accordance with the general method of example A, step 1 from 1-cyclopropyl-4-ethynyl-2,5-dimethyl-1H-imidazole and 2-chloro-4-iodo-pyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1c[nH]cn1.c1ccncc1.C1CC1 | HI | null | null | null | C#Cc1nc(C)n(C2CC2)c1C.Clc1cc(I)ccn1>>Cc1nc(C#Cc2ccnc(Cl)c2)c(C)n1C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c57c50f18db24a3cb9c137f67aa88a92 | C#Cc1nc(C)n(C2CC2)c1C.Cc1cc(I)ccn1>>Cc1cc(C#Cc2nc(C)n(C3CC3)c2C)ccn1 | C1(CC1)N1C(=NC(=C1C)C#C)C.IC1=CC(=NC=C1)C>>C1(CC1)N1C(=NC(=C1C)C#CC1=CC(=NC=C1)C)C | [CH:5]#[C:6][c:7]1[n:8][c:9]([CH3:10])[n:11]([CH:12]2[CH2:13][CH2:14]2)[c:15]1[CH3:16].I[c:4]1[cH:3][c:2]([CH3:1])[n:19][cH:18][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][c:7]2[n:8][c:9]([CH3:10])[n:11]([CH:12]3[CH2:13][CH2:14]3)[c:15]2[CH3:16])[cH:17][cH:18][n:19]1 | C#Cc1nc(C)n(C2CC2)c1C.Cc1cc(I)ccn1 | Cc1cc(C#Cc2nc(C)n(C3CC3)c2C)ccn1 | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cn(C2CC2)cn1)c1ccncc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1.[#7;a:8]:[c:9]:[c:10](-[C:11]#[CH;D1;+0:12]):[#7;a:13]>>[#7;a:8]:[c:9]:[c:10](-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1):[#7;a:13] | null | [] | null | null | null | null | The title compound, MS: m/e=252.1 (M+H+), was prepared in accordance with the general method of example A, step 1 from 1-cyclopropyl-4-ethynyl-2,5-dimethyl-1H-imidazole and 4-iodo-2-methyl-pyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.c1c[nH]cn1.C1CC1 | HI | null | null | null | C#Cc1nc(C)n(C2CC2)c1C.Cc1cc(I)ccn1>>Cc1cc(C#Cc2nc(C)n(C3CC3)c2C)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80181137367c4b76a0553b91aeaf1308 | C#C[Si](C)(C)C.Clc1cc(I)ccn1>>C[Si](C)(C)C#Cc1ccnc(Cl)c1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClC1=NC=CC(=C1)I.C[Si](C)(C)C#C>>ClC1=NC=CC(=C1)C#C[Si](C)(C)C | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].I[c:7]1[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][n:10][c:11]([Cl:12])[cH:13]1 | C#C[Si](C)(C)C.Clc1cc(I)ccn1 | C[Si](C)(C)C#Cc1ccnc(Cl)c1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I | C1CCOC1.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccncc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[C;D1;H3:8]-[#14:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C:12]#[CH;D1;+0:13]>>[C;D1;H3:8]-[#14:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C:12]#[C;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1 | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Chloro-4-iodo-pyridine (10.0 g, 41.8 mmol) was dissolved in 200 mL of dry THF and 17.5 mL of triethyl amine. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (329 mg, 1.25 mmol) and bis(triphenylphosphine)palladium(II)chloride (1.47 g, 2.09 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.C1CCOC1.C(C)N(CC)CC | null | 1 | C#C[Si](C)(C)C.Clc1cc(I)ccn1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.C1CCOC1.C(C)N(CC)CC>C[Si](C)(C)C#Cc1ccnc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a51539e54e6499c8098a02ac20b71d4 | c1c[nH]c(C2CC2)n1>>Ic1cnc(C2CC2)[nH]1 | [OH-].[Na+].C1(CC1)C=1NC=CN1.IC=1N=C(NC1I)C1CC1.S(=O)([O-])[O-].[Na+].[Na+].II>>C1(CC1)C=1NC(=CN1)I | [cH:2]1[cH:3][nH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9]1>>[I:1][c:2]1[cH:3][n:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[nH:9]1 | c1c[nH]c(C2CC2)n1 | Ic1cnc(C2CC2)[nH]1 | null | null | null | Functional Group Addition | Aromatic iodination | 56bbb5847687db5d10da18ddf7c7c8ff306074aa25033533649a9aea6511f147 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1c[nH]c(C2CC2)n1 | [C:1]-[c:2]1:[n;H0;D2;+0:3]:[cH;D2;+0:4]:[c:5]:[nH;D2;+0:6]:1>>[C:1]-[c:2]1:[n;H0;D2;+0:6]:[c:5]:[c;H0;D3;+0:4](-[I;D1;H0:7]):[nH;D2;+0:3]:1 | null | [] | null | null | null | null | The title compound was prepared in accordance with the literature reference of Cliff & Pyne, Synthesis-Stuttgart (7), 681–682(1994) by reacting 2-cyclopropyl-1H-imidazole with iodine in the presence of NaOH. The obtained 4,5-diiodo-2-cyclopropyl-1H-imidazole was then reacted with sodium sulfite to obtain the title comp... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.C1CC1 | Other | null | null | null | c1c[nH]c(C2CC2)n1>>Ic1cnc(C2CC2)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-212504e11fa94b00bf4bfb4a4eca3fe8 | CC1=N/C(=C(/C)N(C)C)C(=O)O1.CCO>>CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C | CN(\C(\C)=C\1/N=C(OC1=O)C)C.C(C)O.[H-].[Na+]>>C(C)OC(/C(=C(\C)/N(C)C)/NC(C)=O)=O | [C:4]1(=[O:5])/[C:6](=[C:11](\[CH3:12])[N:13]([CH3:14])[CH3:15])[N:7]=[C:8]([CH3:9])[O:10]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6]([NH:7][C:8]([CH3:9])=[O:10])=[C:11](\[CH3:12])[N:13]([CH3:14])[CH3:15] | CC1=N/C(=C(/C)N(C)C)C(=O)O1.CCO | CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C | null | null | null | Protection | OtherReaction | 13384887e45228dedceb1ba2bdc4e7b53953181798bf2e31c64aece37ab7fd26 | 3f257f63f9a84fa7d454261c60f7aa76b1865f8669a15800df774e3f8ed893bd | null | [#7:1]/[C:2](-[C;D1;H3:3])=[C:4]1\[N;H0;D2;+0:5]=[C;H0;D3;+0:6](-[C;D1;H3:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[C;D1;H3:11]-[C:12]-[OH;D1;+0:13]>>[#7:1]/[C:2](-[C;D1;H3:3])=[C:4](\[NH;D2;+0:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:13]-[C:12]-[C;D1;H3:11] | null | [] | null | null | null | null | 4-[1-Dimethylamino-eth-(Z)-ylidene]-2-methyl-4H-oxazol-5-one (36.4 g, 216 mmol) was dissolved in ethanol (300 ml) and sodium hydride (0.52 g, 0.022 mmol) was added at room temperature. The dark solution was refluxed for 1 h. The solvent was evaporated and the crude product [MS: m/e=215.5 (M+H+)] was used without any fu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Enamine.Ester.Secondary amide | C1=NCCO1 | null | null | null | null | null | null | CC1=N/C(=C(/C)N(C)C)C(=O)O1.CCO>>CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94af66816df94b35977fe10338796646 | CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C.NC1CC1>>CCOC(=O)/C(NC(C)=O)=C(\C)NC1CC1 | C(C)OC(/C(=C(\C)/N(C)C)/NC(C)=O)=O.C1(CC1)N>>C(C)OC(/C(=C(\C)/NC1CC1)/NC(C)=O)=O | CN(C)/[C:11](=[C:6](/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][C:8]([CH3:9])=[O:10])[CH3:12].[NH2:13][CH:14]1[CH2:15][CH2:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6]([NH:7][C:8]([CH3:9])=[O:10])=[C:11](\[CH3:12])[NH:13][CH:14]1[CH2:15][CH2:16]1 | CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C.NC1CC1 | CCOC(=O)/C(NC(C)=O)=C(\C)NC1CC1 | null | null | O.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | f50f6098817f70d97e0915cb3cba3b66294520a6000d0d990f8842b7864d12a2 | a09a51420020f90d6ea44e3f4a9feb7dbda7b94262453c3c6831412ef36e1efc | C1CC1 | C-N(-C)/[C;H0;D3;+0:1](-[C;D1;H3:2])=[C:3](\[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH2;D1;+0:12]-[C:13]1-[C:14]-[C:15]-1>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])/[C:3](-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])=[C;H0;D3;+0:1](\[C;D1;H3:2])-[NH;D2;+0:12]-[C:13]1-[C:14]-[C:15]-1 | null | [] | null | null | null | null | (Z)-2-Acetylamino-3-dimethylamino-but-2-enoic acid ethyl ester (4.3 g, 20 mmol) and cyclopropylamine (1.14 g, 20 mmol) were stirred at room temperature in acetic acid (40 ml) for 2 hrs. The reaction mixture was diluted slowly with 30 ml of water and evaporated under vacuum at 35° C. Water (30 ml) was added to the resid... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Primary amine | Enamine.Enamine | null | null | C1CC1 | Other | O.C(C)(=O)O | null | null | CCOC(=O)/C(NC(C)=O)=C(\C)N(C)C.NC1CC1>O.C(C)(=O)O>CCOC(=O)/C(NC(C)=O)=C(\C)NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac2fb617a7cc49e7926340e6ef4fdd34 | CCOC(=O)C(NC(C)=O)=C(C)NC1CC1>>CCOC(=O)c1nc(C)n(C2CC2)c1C | S(=O)(=O)([O-])[O-].[NH4+].[NH4+].C(C)OC(C(=C(C)NC1CC1)NC(C)=O)=O.C[Si](N[Si](C)(C)C)(C)C>>C(C)OC(=O)C=1N=C(N(C1C)C1CC1)C | O=[C:8]([NH:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:14]([NH:10][CH:11]1[CH2:12][CH2:13]1)[CH3:15])[CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH3:9])[n:10]([CH:11]2[CH2:12][CH2:13]2)[c:14]1[CH3:15] | CCOC(=O)C(NC(C)=O)=C(C)NC1CC1 | CCOC(=O)c1nc(C)n(C2CC2)c1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6ad4dbba3154377d23cfd4834071a1ea007b94ebdfe246eb7b30f5ace36040b5 | 7cae82b1a0813aa5256e7e48a1c0101eed8d11d7d2b2c8f36c5a671ba39afc85 | c1cn(C2CC2)cn1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])=[C;H0;D3;+0:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[C:12]2-[C:13]-[C:14]-2):[c;H0;D3;+0:9]:1-[C;D1... | 31 | [{"value": 31.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 145 | CELSIUS | null | null | Fine powdered ammonium sulfate (0.13 g, 1 mmol) was added to a suspension of Z)-2-acetylamino-3-cyclopropylamino-but-2-enoic acid ethyl ester (7.0 g, 20 mmol) and hexamethyldisilazane (50 ml, 235 mmol) and refluxed over night at 145° C. The reaction mixture was evaporated and extracted with ethyl acetate and water. The... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ester.Secondary amide | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.C1CC1 | HO- | null | 145 | null | CCOC(=O)C(NC(C)=O)=C(C)NC1CC1>>CCOC(=O)c1nc(C)n(C2CC2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa284e86cc9240c4ba4ba2f67db199c4 | CCOC(=O)c1nc(C)n(C2CC2)c1C>>Cc1nc(CO)c(C)n1C1CC1 | C(C)OC(=O)C=1N=C(N(C1C)C1CC1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C1(CC1)N1C(=NC(=C1C)CO)C | CCO[C:5]([c:4]1[n:3][c:2]([CH3:1])[n:9]([CH:10]2[CH2:11][CH2:12]2)[c:7]1[CH3:8])=[O:6]>>[CH3:1][c:2]1[n:3][c:4]([CH2:5][OH:6])[c:7]([CH3:8])[n:9]1[CH:10]1[CH2:11][CH2:12]1 | CCOC(=O)c1nc(C)n(C2CC2)c1C | Cc1nc(CO)c(C)n1C1CC1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cn(C2CC2)cn1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1-[C;D1;H3:9]>>[C:7]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:8]:1-[C;D1;H3:9] | 104.3 | [{"value": 93.0, "product": "C1(CC1)N1C(=NC(=C1C)CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "C1(CC1)N1C(=NC(=C1C)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.7 g, 3 mmol) was dissolved in 20 mL dry THF and cooled to 0° C. Lithium aluminum hydride (3.4 mL, 1M in THF, 3 mmol) was added dropwise and stirred for 1 h at 0° C. The reaction mixture was quenched with 0.13 ml of water, 0.13 ml of 4N sodium hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cn1.C1CC1 | HO- | C1CCOC1 | 0 | 1 | CCOC(=O)c1nc(C)n(C2CC2)c1C>C1CCOC1>Cc1nc(CO)c(C)n1C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edc697d54b1148c0900b356e7c803263 | Cc1nc(C=O)c(C)n1C1CC1>>C#Cc1nc(C)n(C2CC2)c1C | COP(OC)=O.C1(CC1)N1C(=NC(=C1C)C=O)C.C([O-])([O-])=O.[K+].[K+]>>C1(CC1)N1C(=NC(=C1C)C#C)C | O=[CH:2][c:3]1[n:4][c:5]([CH3:6])[n:7]([CH:8]2[CH2:9][CH2:10]2)[c:11]1[CH3:12]>>[CH:1]#[C:2][c:3]1[n:4][c:5]([CH3:6])[n:7]([CH:8]2[CH2:9][CH2:10]2)[c:11]1[CH3:12] | Cc1nc(C=O)c(C)n1C1CC1 | C#Cc1nc(C)n(C2CC2)c1C | null | null | CO | Miscellaneous | OtherReaction | 43ece31721b9c0b94c3b38429dc87af4ee609b8e9eb8f259c2864b43a0e2659a | 3c4f2599e30dafc74a098cf3d845f2d32e372c3697561f70fd0d41fa9431d448 | c1cn(C2CC2)cn1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5](-[C:6]):[c:7]:1-[C;D1;H3:8]>>[C:6]-[#7;a:5]1:[c:4]:[#7;a:3]:[c:2](-[C;H0;D2;+0:1]#[C;D1;H1:9]):[c:7]:1-[C;D1;H3:8] | 30 | [{"value": 30.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (0.6 g, 3 mmol) was dissolved in 10 mL of methanol. Potassium carbonate (0.74 g, 5 mmol) was added. A solution of 1-Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carbaldehyde (0.42 g, 3 mmol) in 5 ml methanol was added drop wise at room temperature. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Alkyne | null | null | c1c[nH]cn1.C1CC1 | null | CO | null | 8 | Cc1nc(C=O)c(C)n1C1CC1>CO>C#Cc1nc(C)n(C2CC2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30d829900b214d78b3ad1950f83d7458 | COc1ccc(C=O)cn1.Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1>>COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1 | C(#N)[BH3-].[Na+].COC1=CC=C(C=N1)C=O.NC1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1.C(O)([O-])=O.[Na+]>>COC1=CC=C(C=N1)CNC1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1 | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:30][cH:29]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[NH:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[NH... | COc1ccc(C=O)cn1.Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1 | COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1 | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(Nc1ccccc1)c1ccccc1NCc1cccnc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):[c:13] | null | [] | null | null | 16 | HOUR | Sodium cyanoborohydride (8.80 g of 95%, 133 mmol) is added in portions over 30 minutes to a stirred mixture of acetic acid (3.8 mL), 6-methoxy-3-pyridinecarboxaldehyde (Fluka, Buchs, Switzerland; 7.80 g, 57 mmol) and 2-amino-N-(4-bromo-3-trifluoromethylphenyl)-benzamide (step 1.2; 13.65 g, 38 mmol) in methanol (380 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | CO.C(C)(=O)O | null | 16 | COc1ccc(C=O)cn1.Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1>CO.C(C)(=O)O>COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08f8d6788814465f87faa5aa3662b783 | Nc1ccc(Br)c(C(F)(F)F)c1.O=C(Cl)c1ccccc1[N+](=O)[O-]>>O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C(=O)Cl)C=CC=C1.NC=1C=C(C(=CC1)Br)C(F)(F)F.[OH-].[Na+]>>[N+](=O)([O-])C1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1.Cl[C:2](=[O:1])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[N+:21](=[O:22])[O-:2... | Nc1ccc(Br)c(C(F)(F)F)c1.O=C(Cl)c1ccccc1[N+](=O)[O-] | O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-] | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[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 | 30 | MINUTE | A solution of 3-amino-6-bromobenzotrifluoride (Fluka, Buchs, Switzerland; 24.0 g, 100 mmol) in ethyl acetate (240 mL) is added to a stirred aqueous solution of sodium hydroxide (110 mL of 1 M) at room temperature. This stirred solution is then treated dropwise over 30 minutes with a solution of 2-nitrobenzoyl chloride ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 0.5 | Nc1ccc(Br)c(C(F)(F)F)c1.O=C(Cl)c1ccccc1[N+](=O)[O-]>C(C)(=O)OCC>O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa30808a5c6741da93b67d37f1883a74 | O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-]>>Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1 | [N+](=O)([O-])C1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1.[N+](=O)([O-])C1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1.[H][H]>>NC1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-] | Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | A solution of 2-nitro-N-(4-bromo-3-trifluoromethylphenyl)benzamide (intermediate 1a; 32 g, 82 mmol) in methanol (1000 mL) is hydrogenated at atmospheric pressure over Raney nickel (6 g) at 21° C. The calculated amount of hydrogen is taken up after 7 hours. The mixture is filtered and the solvent is evaporated under red... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Ni].CO | null | null | O=C(Nc1ccc(Br)c(C(F)(F)F)c1)c1ccccc1[N+](=O)[O-]>[Ni].CO>Nc1ccccc1C(=O)Nc1ccc(Br)c(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4df73740e5ab472bbaeaa1adeac83fca | CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(F)(F)F>>CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(=O)[nH]c2)cc1C(F)(F)F | COC1=CC=C(C=N1)CNC1=C(C(=O)NC2=CC(=C(C=C2)C#CC)C(F)(F)F)C=CC=C1.C[Si](C)(C)I.CO>>O=C1C=CC(=CN1)CNC1=C(C(=O)NC2=CC(=C(C=C2)C#CC)C(F)(F)F)C=CC=C1 | C[O:23][c:22]1[cH:21][cH:20][c:19]([CH2:18][NH:17][c:16]2[c:11]([C:9]([NH:8][c:7]3[cH:6][cH:5][c:4]([C:3]#[C:2][CH3:1])[c:27]([C:28]([F:29])([F:30])[F:31])[cH:26]3)=[O:10])[cH:12][cH:13][cH:14][cH:15]2)[cH:25][n:24]1>>[CH3:1][C:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16... | CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(F)(F)F | CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(=O)[nH]c2)cc1C(F)(F)F | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | ffbb4288e7102e6f227d930be4a9510dc9e13ff3142954fd43347db64909ca58 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=C(Nc1ccccc1)c1ccccc1NCc1ccc(=O)[nH]c1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1 | null | [] | 60 | CELSIUS | 16 | HOUR | A mixture of 2-[[6-methoxy-3-pyridinyl]methyl]amino-N-[4-(1-propynyl)-3-(trifluoromethyl)-phenyl]benzamide (step 4.1; 1.10 g, 2.5 mmol) and trimethylsilyl iodide (Fluka, Buchs, Switzerland; 1.0 mL, 7.5 mmol) in chloroform (30 mL) is stirred at 60° C. for 16 hours under an argon atmosphere. The cooled mixture is then tr... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1cccnc1 | c1ccccc1.c1ccccc1.c1cccnc1 | Other | C(Cl)(Cl)Cl | 60 | 16 | CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(F)(F)F>C(Cl)(Cl)Cl>CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(=O)[nH]c2)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb3583fec4e14b0cba6036c1e267daa2 | CC#[C][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1>>CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(F)(F)F | COC1=CC=C(C=N1)CNC1=C(C(=O)NC2=CC(=C(C=C2)Br)C(F)(F)F)C=CC=C1.C(CCC)[Sn](C#CC)(CCCC)CCCC.[OH-].[Na+]>>COC1=CC=C(C=N1)CNC1=C(C(=O)NC2=CC(=C(C=C2)C#CC)C(F)(F)F)C=CC=C1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:3]#[C:2][CH3:1].Br[c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([O:23][CH3:24])[n:25][cH:26]2)[cH:27][c:28]1[C:29]([F:30])([F:31])[F:32]>>[CH3:1][C:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c... | CC#[C][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1 | CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(F)(F)F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_other | 686ddce89ee1b82809d138743a9bebfc36a7ed651a8a33084c82d304b7576d29 | 84197a108c0019520f13001872ce55981c95862f930591903269e152b52aac86 | O=C(Nc1ccccc1)c1ccccc1NCc1cccnc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C:11]-[C;D1;H3:12])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:12]-[C:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9] | null | [] | 100 | CELSIUS | null | null | A stirred solution of 2-[[6-methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)-phenyl]benzamide (Reference Example 1; 3.98 g, 8.3 mmol) in dry toluene (200 mL) is purged with argon for 20 minutes at 25° C. Tributyl-1-propynylstannane (4.1 g of 80%, 9.96 mmol) and tetrakis(triphenylphosphine)palladium (0) (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Tin | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccncc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 100 | null | CC#[C][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1ccc(CNc2ccccc2C(=O)Nc2ccc(Br)c(C(F)(F)F)c2)cn1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CC#Cc1ccc(NC(=O)c2ccccc2NCc2ccc(OC)nc2)cc1C(... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2adf7b177715439eb19c5c872418961b | O=Cc1ccc(C=O)cc1>>O=Cc1ccc(CO)cc1 | C1=CC(=CC=C1C=O)C=O.NCC1=NC=CC=C1.[H][H]>>OCC1=CC=C(C=O)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][cH:10]1 | O=Cc1ccc(C=O)cc1 | O=Cc1ccc(CO)cc1 | null | [Pd] | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 78 | [{"value": 78.0, "product": "OCC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "OCC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Terephthaldicarboxaldehyde (30.02 g, 224 mmol), methanol (200 mL), palladium on activated carbon, (10%, 3.02 g) and 2-(aminomethyl)pyridine (2.3 mL, 22 mol, 0.01 mol equiv) were combined in a hydrogenation vessel and the reaction mixture was shaken on a Parr hydrogenator for 2.5 hours at 40 psi of hydrogen. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | [Pd].CO | null | null | O=Cc1ccc(C=O)cc1>[Pd].CO>O=Cc1ccc(CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b440b9cb3e54035b917093b418cdc6b | OC1CCCc2cccnc21>>O=C1CCCc2cccnc21 | OC1CCCC=2C=CC=NC12>>N1=CC=CC=2CCCC(C12)=O | [OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21 | OC1CCCc2cccnc21 | O=C1CCCc2cccnc21 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | b220980a208eb9fed81b429942ce2ac6d169e7e8c5f1ebb0cf2306e7beb5e86a | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCc2cccnc21 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 82 | [{"value": 82.0, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline (13.96 g, 93.6 mmol) in dry CH2Cl2 (400 mL) was added activated manganese dioxide (85% purity, 82.22 g, 804 mmol). The resulting heterogeneous mixture was stirred 18 h, at which point the black slurry was filtered through a cake of celite and washed with CH... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | 18 | OC1CCCc2cccnc21>[O-2].[O-2].[Mn+4].C(Cl)Cl>O=C1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9953a5e7224e4a308613493af7c448a3 | CCOC(=O)c1c(C)cccc1OC>>COc1cccc(C)c1CO | O.[OH-].[Na+].O.COC1=C(C(=O)OCC)C(=CC=C1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>COC1=C(CO)C(=CC=C1)C | CCO[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[CH3:8])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[CH2:10][OH:11] | CCOC(=O)c1c(C)cccc1OC | COc1cccc(C)c1CO | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 99.7 | [{"value": 99.0, "product": "COC1=C(CO)C(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "COC1=C(CO)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 2-methoxy-6-methylbenzoate (1.23 g, 6.33 mmol) in dry diethyl ether (58 mL) was added LiAlH4 (0.467 g, 12.31 mmol) and the resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was treated sequentially with water (0.45 mL), 15% aqueous NaOH (0.45 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | C(C)OCC | null | null | CCOC(=O)c1c(C)cccc1OC>C(C)OCC>COc1cccc(C)c1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ef5756414e1483ebd37c8a4117aa494 | COc1cccc(C)c1CO.O=C1NC(=O)c2ccccc21>>COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O | CS(=O)(=O)Cl.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].COC1=C(CO)C(=CC=C1)C.C(C)N(CC)CC>>COC1=C(CC2=C3C(C(=O)NC3=O)=CC=C2)C(=CC=C1)C | O[CH2:10][c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[CH3:8].[cH:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1[C:17](=[O:18])[NH:19][C:20]2=[O:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1[C:17](=[O:18])[NH:19][C:20]2=[O:21] | COc1cccc(C)c1CO.O=C1NC(=O)c2ccccc21 | COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O | null | null | CCOC(=O)C.CN(C)C=O.O.[Cl-].[Na+].O.C(Cl)Cl | C-C Coupling | OtherReaction | 3312f6196d1a3e1d5e69fdcf3d0c32df574bd87e9e1e2cc8747e78c08d5f7fa9 | 5086858461038ad8c4c4a388cee61b6d9e9118227e969bc00fcc5a7517669191 | O=C1NC(=O)c2c(Cc3ccccc3)cccc21 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1:[cH;D2;+0:12]:[c:13]:[c:14]>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1:[c;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:13]:[c:14] | 66.4 | [{"value": 66.0, "product": "COC1=C(CC2=C3C(C(=O)NC3=O)=CC=C2)C(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "COC1=C(CC2=C3C(C(=O)NC3=O)=CC=C2)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methoxy-6-methylbenzyl alcohol (0.96 g, 6.32 mmol) in CH2Cl2 (35 mL) was added triethylamine (2.00 mL, 14.35 mmol) followed by methanesulfonyl chloride (0.90 mL, 11.63 mmol) and the resultant solution was heated at 40° C. for 45 minutes then cooled to room temperature. The mixture was diluted with CH... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | c1ccccc1.c1ccc2c(c1)CNC2 | HO- | CCOC(=O)C.CN(C)C=O.O.[Cl-].[Na+].O.C(Cl)Cl | null | null | COc1cccc(C)c1CO.O=C1NC(=O)c2ccccc21>CCOC(=O)C.CN(C)C=O.O.[Cl-].[Na+].O.C(Cl)Cl>COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c6876f3a159419d84868a80768d6864 | COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O.O=C1CCC(=O)N1Br>>COc1cccc(CBr)c1Cc1cccc2c1C(=O)NC2=O | BrN1C(CCC1=O)=O.COC1=C(CC2=C3C(C(=O)NC3=O)=CC=C2)C(=CC=C1)C.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=CC=CC(=C1CC1=C2C(C(=O)NC2=O)=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[NH:20][C:21]2=[O:22].O=C1CCC(=O)N1[Br:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][Br:9])[c:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[NH:20][C:21]2=[O:22] | COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O.O=C1CCC(=O)N1Br | COc1cccc(CBr)c1Cc1cccc2c1C(=O)NC2=O | null | null | C(C)OCC | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | O=C1NC(=O)c2c(Cc3ccccc3)cccc21 | 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] | 86.9 | [{"value": 86.0, "product": "BrCC1=CC=CC(=C1CC1=C2C(C(=O)NC2=O)=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "BrCC1=CC=CC(=C1CC1=C2C(C(=O)NC2=O)=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2-methoxy-6-methylbenzyl)phthalimide (0.286 g, 1.02 mmol) in CC4 (25 mL) was added recrystallized N-bromosuccinimide (0.177 g, 0.99 mmol) followed by benzoyl peroxide (28 mg, 0.11 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2c(c1)CNC2 | HO- | C(C)OCC | null | null | COc1cccc(C)c1Cc1cccc2c1C(=O)NC2=O.O=C1CCC(=O)N1Br>C(C)OCC>COc1cccc(CBr)c1Cc1cccc2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98cbae85125a4e74a5cd6403dc05c603 | COC(=O)c1coc(CNC(=O)OC(C)(C)C)n1>>CC(C)(C)OC(=O)NCc1nc(CO)co1 | C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+].COC(=O)C=1N=C(OC1)CNC(=O)OC(C)(C)C.CC(C)C[AlH]CC(C)C>>C(C)(C)(C)OC(NCC=1OC=C(N1)CO)=O | CO[C:13]([c:12]1[n:11][c:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[o:16][cH:15]1)=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[n:11][c:12]([CH2:13][OH:14])[cH:15][o:16]1 | COC(=O)c1coc(CNC(=O)OC(C)(C)C)n1 | CC(C)(C)OC(=O)NCc1nc(CO)co1 | null | null | ClCCl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cocn1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:1 | 28.4 | [{"value": 28.0, "product": "C(C)(C)(C)OC(NCC=1OC=C(N1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.4, "product": "C(C)(C)(C)OC(NCC=1OC=C(N1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | The ester (178 mg, 0.695 mmol) in 0° C. dichloromethane (8 mL) was treated with DIBAL-H (1 M in dichloromethane, 2.08 mL, 2.08 mmol). The mixture was then stirred at 0° C. for 2 hours before being treated with aqueous 5% sodium potassium tartrate (8 mL). The mixture was stirred rapidly for 30 minutes (until the aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cocn1 | Other | ClCCl | 0 | 2 | COC(=O)c1coc(CNC(=O)OC(C)(C)C)n1>ClCCl>CC(C)(C)OC(=O)NCc1nc(CO)co1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88763c2edb2b443a865dc1b2c91ebe21 | C=O.c1ccc(Cn2ccnc2)cc1>>OCc1cnc(CO)n1Cc1ccccc1 | C(C1=CC=CC=C1)N1C=NC=C1.C=O.C(C)(=O)[O-].[Na+]>>OCC=1N(C(=CN1)CO)CC1=CC=CC=C1 | [O:1]=[CH2:2].[cH:3]1[cH:4][n:5][cH:6][n:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[OH:1][CH2:2][c:3]1[cH:4][n:5][c:6]([CH2:7][OH:8])[n:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C=O.c1ccc(Cn2ccnc2)cc1 | OCc1cnc(CO)n1Cc1ccccc1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 942e1926c4eec3bf2d18baf052a35c51db3c2a755c1de0ca5a4f04c59f4cec46 | 699071301e4b420c55fabc7a753b60c76635bc7d4435596b8387e50cc5c1f1a5 | c1ccc(Cn2ccnc2)cc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[#7;a:4]1:[cH;D2;+0:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[C:9]-[O;D1;H1:10] | 24 | [{"value": 24.0, "product": "OCC=1N(C(=CN1)CO)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of S. Zimmerman et al. (S. C. Zimmerman, K. D. Cramer and A. A. Galan J. Org. Chem. 1989, 54, 1256–1264) N-Benzylimidazole (15 g, 95 mmol) was treated with formaldehyde (60 mL of a 37% aqueous solution), to which glacial acetic acid (8 mL) and sodium acetate (10.5 g) were added. The resulting mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol.Primary alcohol | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | C(C)(=O)O | null | null | C=O.c1ccc(Cn2ccnc2)cc1>C(C)(=O)O>OCc1cnc(CO)n1Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed26296c2ba1419eac674707956ad926 | CC(=O)OC(C)=O.OCc1cnc(CO)n1Cc1ccccc1>>CC(=O)OCc1ncc(CO)n1Cc1ccccc1.CC(=O)[O-] | OCC=1N(C(=CN1)CO)CC1=CC=CC=C1.C(C)N(CC)CC.C(C)(=O)OC(C)=O>>CC(=O)[O-].C(C)(=O)OCC=1N(C(=CN1)CO)CC1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[O:23][C:21]([CH3:20])=[O:22].[OH:4][CH2:5][c:6]1[n:7][cH:8][c:9]([CH2:10][OH:11])[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][cH:8][c:9]([CH2:10][OH:11])[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:20][C:21](=[O:22])[O-:2... | CC(=O)OC(C)=O.OCc1cnc(CO)n1Cc1ccccc1 | CC(=O)OCc1ncc(CO)n1Cc1ccccc1.CC(=O)[O-] | null | null | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccc(Cn2ccnc2)cc1 | [#7;a:1]:[c:2](-[C:3]-[OH;D1;+0:4]):[#7;a:5].[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[#7;a:1]:[c:2](-[C:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:7](-[C;D1;H3:6])=[O;D1;H0:8]):[#7;a:5].[C;D1;H3:11]-[C:10](-[O-;H0;D1:9])=[O;D1;H0:12] | null | [] | null | null | 16 | HOUR | To a solution of 2,5-bis-(hydroxymethyl)-N-benzylimidazole (436 mg, 2.0 mmol) in dichloromethane (10 mL) was added triethylamine (0.35 mL, 2.0 mmol) and acetic anhydride (0.19 mL, 2.0 mmol). The mixture was then stirred overnight (16 h) at room temperature. The reaction was then washed with aqueous ammonium chloride an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1c[nH]cn1.c1ccccc1 | null | ClCCl | null | 16 | CC(=O)OC(C)=O.OCc1cnc(CO)n1Cc1ccccc1>ClCCl>CC(=O)OCc1ncc(CO)n1Cc1ccccc1.CC(=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca0cab19f1de48d68d061e1415cf7894 | CCOC(=O)c1ccc(C#N)nc1>>N#Cc1ccc(CO)cn1 | C(C)OC(C1=CN=C(C=C1)C#N)=O.[BH4-].[Na+]>>OCC=1C=NC(=CC1)C#N | CCO[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[n:10][cH:9]1)=[O:8]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][n:10]1 | CCOC(=O)c1ccc(C#N)nc1 | N#Cc1ccc(CO)cn1 | null | null | CO | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 34.4 | [{"value": 34.0, "product": "OCC=1C=NC(=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.4, "product": "OCC=1C=NC(=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of ethyl-6-cyanonicotinate (prepared as per T. Sakamoto, S. Kaneda, S. Nishimura and H. Yamanaka Chem. Pharm. Bull. 1985, 33, 565) (1.58 g, 8.97 mmol) in MeOH (40 mL) was added NaBH4 (1.00 g, 26.4 mmol) and the reaction stirred at room temperature for 8 h. After removal of the solvent, the residue was tak... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | CO | null | 8 | CCOC(=O)c1ccc(C#N)nc1>CO>N#Cc1ccc(CO)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8bd81bc8e07d4d19bf9f7f99862fa9cd | COC(=O)c1ccc(CBr)cc1.[C-]#N>>COC(=O)c1ccc(CC#N)cc1 | BrCC1=CC=C(C(=O)OC)C=C1.[C-]#N.[Na+]>>COC(C1=CC=C(C=C1)CC#N)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12]1.[C-:10]#[N:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][C:10]#[N:11])[cH:12][cH:13]1 | COC(=O)c1ccc(CBr)cc1.[C-]#N | COC(=O)c1ccc(CC#N)cc1 | null | [Br-].C(CCCCCCCCCCCCCCC)[N+](C)(C)C | C1=CC=CC=C1.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] | 60.1 | [{"value": 60.0, "product": "COC(C1=CC=C(C=C1)CC#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.1, "product": "COC(C1=CC=C(C=C1)CC#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of methyl 4-(bromomethyl)benzoate (10.09 g, 44.05 mmol), sodium cyanide (6.42 g, 131 mmol) and cetyltrimethylammonium bromide (1.59 g, 4.36 mmol) in benzene/water (2:1, 187.5 mL) was heated at reflux for 5 h then extracted with CH2Cl2 3×50 mL). The organic extracts were dried (MgSO4), filtered and concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Br- | [Br-].C(CCCCCCCCCCCCCCC)[N+](C)(C)C.C1=CC=CC=C1.O | null | null | COC(=O)c1ccc(CBr)cc1.[C-]#N>[Br-].C(CCCCCCCCCCCCCCC)[N+](C)(C)C.C1=CC=CC=C1.O>COC(=O)c1ccc(CC#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c5eddc74ce24887a0ef1b770b8df69b | CC(C)(C)OC(=O)NCCc1ccc(CO)cc1>>CC(C)(C)OC(=O)NCCc1ccc(C=O)cc1 | C(C)(C)(C)OC(NCCC1=CC=C(C=C1)CO)=O>>C(C)(C)(C)OC(NCCC1=CC=C(C=C1)C=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1 | CC(C)(C)OC(=O)NCCc1ccc(CO)cc1 | CC(C)(C)OC(=O)NCCc1ccc(C=O)cc1 | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 88 | [{"value": 88.0, "product": "C(C)(C)(C)OC(NCCC1=CC=C(C=C1)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 69 | HOUR | To a solution of the alcohol from above (200 mg, 0.796 mmol) in CH2Cl2 (8 mL) was added activated MnO2 (814 mg, 7.96 mmol) and the mixture stirred at room temperature for 69 h. The reaction mixture was filtered through Celite and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O=[Mn]=O.C(Cl)Cl | null | 69 | CC(C)(C)OC(=O)NCCc1ccc(CO)cc1>O=[Mn]=O.C(Cl)Cl>CC(C)(C)OC(=O)NCCc1ccc(C=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93d7d67d5eee4d34a3cabfb59722c5f8 | CC#N.ClCc1ccc(CCl)cc1>>N#CCCc1ccc(CCl)cc1 | ClCC1=CC=C(C=C1)CCl.C(C)#N.C(CCC)[Li]>>ClCC1=CC=C(C=C1)CCC#N | [N:1]#[C:2][CH3:3].Cl[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][Cl:10])[cH:11][cH:12]1>>[N:1]#[C:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][Cl:10])[cH:11][cH:12]1 | CC#N.ClCc1ccc(CCl)cc1 | N#CCCc1ccc(CCl)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6]#[N;D1;H0:7]>>[N;D1;H0:7]#[C:6]-[CH2;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 145.5 | [{"value": 60.0, "product": "ClCC1=CC=C(C=C1)CCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 145.5, "product": "ClCC1=CC=C(C=C1)CCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | Acetonitrile (0.30 mL, 5.7 mmol) was added to a solution of n-butyllithium (2.4 m in hexanes, 1.96 mL, 4.7 mmol) in dry THF (5 mL) at −78° C. and stirred for 45 min. solution of α,α′-dichloro-p-xylene (2.485 g, 14.2 mmol) in dry THF at −78° C. was added to give a yellow, cloudy solution. The mixture was stirred at −78°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HCl | C1CCOC1 | -78 | null | CC#N.ClCc1ccc(CCl)cc1>C1CCOC1>N#CCCc1ccc(CCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ea900c0e78d4c128d01976a5f4b69d7 | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O>>COC(=O)c1cc([N+](=O)[O-])ccc1C | CC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].OS(=O)(=O)O.CO>>COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[CH3:14] | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O | COC(=O)c1cc([N+](=O)[O-])ccc1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 99 | [{"value": 99.0, "product": "COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-5-nitrobenzoic acid (1.51 g, 8.34 mmol) and H2SO4 (catalytic) in MeOH (20 mL) was heated at reflux for 17 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (40 mL), washed with saturated NaHCO3(aq) (30 mL), then dried (MgSO4) and concentrated in vacuo to give yellow crystals (1.6... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O>>COC(=O)c1cc([N+](=O)[O-])ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6d6e34697574e1fafccd9df5eb71cde | COC(=O)c1cc([N+](=O)[O-])ccc1C>>COC(=O)c1cc(N)ccc1C | COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O>>COC(C1=C(C=CC(=C1)N)C)=O | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([CH3:12])[cH:10][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[CH3:12] | COC(=O)c1cc([N+](=O)[O-])ccc1C | COC(=O)c1cc(N)ccc1C | null | [Pd] | CO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.3 | [{"value": 99.0, "product": "COC(C1=C(C=CC(=C1)N)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "COC(C1=C(C=CC(=C1)N)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-5-nitro-benzoic acid methyl ester (1.96 g, 10.0 mmol) in 4:1 MeOH/EtOAc (25 mL) was shaken at room temperature with a suspension of 10% Pd/C (200 mg, 0.19 mmol) under hydrogen atmosphere (35 psi) for 2 h. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO.CCOC(=O)C | null | null | COC(=O)c1cc([N+](=O)[O-])ccc1C>[Pd].CO.CCOC(=O)C>COC(=O)c1cc(N)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1460cafe3e734ae289235f35d72669f6 | CSC#N.Cc1cccc(O)c1>>Cc1ccc(C#N)c(O)c1 | [Al+3].[Cl-].[Cl-].[Cl-].CSC#N.B(Cl)(Cl)Cl.C1=C(C=CC=C1O)C>>OC1=C(C#N)C=CC(=C1)C | CS[C:6]#[N:7].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:8]([OH:9])[cH:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[c:8]([OH:9])[cH:10]1 | CSC#N.Cc1cccc(O)c1 | Cc1ccc(C#N)c(O)c1 | null | null | ClCCCl | C-C Coupling | OtherReaction | 26d0b6325c97a2d4d88061c49486cdd4d0e5ea7b01515b216dd3ddde64c66101 | e50b4e62fc815ead50746f367fd1a71e0b1f306e4a741ea48db98528350e2879 | c1ccccc1 | C-S-[C;H0;D2;+0:1]#[N;D1;H0:2].[O;D1;H1:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[O;D1;H1:3]):[c:5] | 91.1 | [{"value": 91.0, "product": "OC1=C(C#N)C=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "OC1=C(C#N)C=CC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2-Hydroxy-4-methylbenzonitrile was prepared following a modification of the procedure reported by Makoto Adachi and Tsutomu Sugasawa (Synthetic Communications 1990, 20, 71–84.). To a cold (0° C.) solution of BCl3 (1.0 M in heptane, 12.0 mL, 12.0 mmol) in 1,2-dichloroethane was added neat m-cresol (1.00 mL, 9.56 mmol) f... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Monosulfide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | ClCCCl | 80 | null | CSC#N.Cc1cccc(O)c1>ClCCCl>Cc1ccc(C#N)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2baa97bf42c840c6bd37c866ebc46775 | CC(=O)OC(C)=O.Cc1ccc(C#N)c(O)c1>>CC(=O)Oc1cc(C)ccc1C#N | C(C)N(CC)CC.OC1=C(C#N)C=CC(=C1)C.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=C(C=CC(=C1)C)C#N | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][cH:10][c:11]1[C:12]#[N:13] | CC(=O)OC(C)=O.Cc1ccc(C#N)c(O)c1 | CC(=O)Oc1cc(C)ccc1C#N | null | null | C(Cl)Cl | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 97.2 | [{"value": 97.0, "product": "C(C)(=O)OC1=C(C=CC(=C1)C)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "C(C)(=O)OC1=C(C=CC(=C1)C)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-Hydroxy-4-methylbenzonitrile (0.563 g, 4.23 mmol) in CH2Cl2 (21 mL) was added acetic anhydride (0.60 mL, 6.36 mmol) followed by triethylamine (1.20 mL, 8.61 mmol) and the resultant solution was stirred at room temperature for 30 minutes. The mixture was diluted with CH2Cl2 (60 mL), washed with satura... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(=O)OC(C)=O.Cc1ccc(C#N)c(O)c1>C(Cl)Cl>CC(=O)Oc1cc(C)ccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ea7d7bfc1d74fbf8e0b93094079fe04 | CC(=O)Oc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br>>CC(=O)Oc1cc(CBr)ccc1C#N | BrN1C(CCC1=O)=O.C(C)(=O)OC1=C(C=CC(=C1)C)C#N.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(C)(=O)OC1=C(C=CC(=C1)CBr)C#N | [CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([CH3:8])[cH:10][cH:11][c:12]1[C:13]#[N:14].O=C1CCC(=O)N1[Br:9]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11][c:12]1[C:13]#[N:14] | CC(=O)Oc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br | CC(=O)Oc1cc(CBr)ccc1C#N | null | null | C(Cl)(Cl)(Cl)Cl.C(C)OCC | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | 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] | 30 | [{"value": 30.0, "product": "C(C)(=O)OC1=C(C=CC(=C1)CBr)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.7, "product": "C(C)(=O)OC1=C(C=CC(=C1)CBr)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2-cyano-5-methyl-phenyl) acetate (0.72 g, 4.11 mmol) in CCl4 (10 mL) was added recrystallized N-bromosuccinimide (0.767 g, 4.31 mmol) followed by benzoyl peroxide (56 mg, 0.23 mmol). The resultant mixture was heated to reflux for 2.5 hours then cooled to room temperature. The mixture was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl.C(C)OCC | null | null | CC(=O)Oc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl.C(C)OCC>CC(=O)Oc1cc(CBr)ccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc4168f35ad440549ee8108f3a2b6374 | CC(=O)Oc1cc(CBr)ccc1C#N.CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21>>NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1O | C(C)(=O)OC1=C(C=CC(=C1)CBr)C#N.C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C(C)(C)N(C(C)C)CC>>NCC1=C(C=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)O | CC(=O)[O:31][c:30]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([CH2:7]Br)[cH:29]1.CC(C)(C)OC(=O)[n:18]1[c:10]([CH2:9][NH:8][CH:19]2[CH2:20][CH2:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][n:27][c:28]32)[n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH2:9][c:10]2[n:11][c:12]3[... | CC(=O)Oc1cc(CBr)ccc1C#N.CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1O | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | a365214ae3304aad35e12f2893548a41d066ad941590504caa87bbbb3a18727b | 3162faeb7a1d6ae2d75182e20164ac2d3ef32bb8492a04e611f89d9c81892db9 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[O;H0;D2;+0:5]-C(-C)=O):[c:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9]:[c:10]:1.C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:11]1:[c:12](-[C:13]-[NH;D2;+0:14]-[C:15](-[C:16])-[c:17]:[#7;a:18]):[#7;a:19]:[c:20](:[c:21]):[c:22]:1:[c:23]>>[#7;a:18]:[c:17]-[C:15](-[N;H0;D3;+0:14](-[C:13]-[c:12]1:[#7;a:... | 68.4 | [{"value": 51.0, "product": "NCC1=C(C=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "NCC1=C(C=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.375 g, 0.99 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.00 mmol) followed by a solution of (5-bromomethyl-2-cyano-phenyl) acetate (0.318 g, 1.25 mmol) in CH3CN (5 mL). The resultant ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Nitrile.Secondary amine.Boc | Aromatic alcohol.Primary amine.Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HBr | CC#N | null | null | CC(=O)Oc1cc(CBr)ccc1C#N.CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21>CC#N>NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db2fd0075fa6482e8c3b42e6ac372ca6 | COS(=O)(=O)OC.Cc1ccc(C#N)c(O)c1>>COc1cc(C)ccc1C#N | S(=O)(=O)(OC)OC.OC1=C(C#N)C=CC(=C1)C.O.[OH-].[Li+]>>COC1=C(C#N)C=CC(=C1)C | COS(=O)(=O)O[CH3:1].[OH:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[C:10]#[N:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[C:10]#[N:11] | COS(=O)(=O)OC.Cc1ccc(C#N)c(O)c1 | COc1cc(C)ccc1C#N | null | null | C1CCOC1.C(C)OCC | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90 | [{"value": 90.0, "product": "COC1=C(C#N)C=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "COC1=C(C#N)C=CC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-Hydroxy-4-methylbenzonitrile (0.46 g, 3.46 mmol) in THF (17 mL) was added lithium hydroxide monohydrate (0.292 g, 6.95 mmol) followed by dimethyl sulfate (0.50 mL, 5.28 mmol). The resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was diluted with diethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | C1CCOC1.C(C)OCC | null | null | COS(=O)(=O)OC.Cc1ccc(C#N)c(O)c1>C1CCOC1.C(C)OCC>COc1cc(C)ccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99fb53d680b64d348c12f770dc6887ea | COc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br>>COc1cc(CBr)ccc1C#N | COC1=C(C#N)C=CC(=C1)C.BrN1C(CCC1=O)=O>>BrCC1=CC(=C(C#N)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:8][cH:9][c:10]1[C:11]#[N:12].O=C1CCC(=O)N1[Br:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][Br:7])[cH:8][cH:9][c:10]1[C:11]#[N:12] | COc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br | COc1cc(CBr)ccc1C#N | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl.C(C)OCC | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | 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] | 68.3 | [{"value": 68.0, "product": "BrCC1=CC(=C(C#N)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "BrCC1=CC(=C(C#N)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methoxy-4-methylbenzonitrile (0.438 g, 2.98 mmol) in CCl4 (6 mL) was added recrystallized N-bromosuccinimide (0.544 g, 3.05 mmol) followed by benzoyl peroxide (47 mg, 0.19 mmol). The resultant mixture was heated to reflux for 45 minutes then cooled to room temperature. The mixture was diluted with di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl.C(C)OCC | null | null | COc1cc(C)ccc1C#N.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl.C(C)OCC>COc1cc(CBr)ccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-774d4e5daa204a3195728880496ffb61 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COc1cc(CBr)ccc1C#N>>COc1cc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)ccc1CN | BrCC1=CC(=C(C#N)C=C1)OC.C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C(C)(C)N(C(C)C)CC>>NCC1=C(C=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1)OC | CC(C)(C)OC(=O)[n:17]1[c:9]([CH2:8][NH:7][CH:18]2[CH2:19][CH2:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][n:26][c:27]32)[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21.Br[CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:30]([C:31]#[N:32])[cH:29][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][N:7]([CH2:8][c:9]2[n:10][c:11]3[cH:12][... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COc1cc(CBr)ccc1C#N | COc1cc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)ccc1CN | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | bea76215d74a0e7f89d73d95d31d77ccc966681eedcfaa92a7adcb5a0166cad3 | ab7d6c06cd5c025f2d753f07706188aa0265353c776d5a983b46946698525bfa | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]:[c:9]:1.C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:10]1:[c:11](:[c:12]):[c:13](:[c:14]):[#7;a:15]:[c:16]:1-[C:17]-[NH;D2;+0:18]-[C:19](-[C:20])-[c:21]:[#7;a:22]>>[#7;a:22]:[c:21]-[C:19](-[N;H0;D3;+0:18](-[C:17]-[c:16]1:[#7;a:15]:[c:13](:[c:14]):[c:11]... | 68.8 | [{"value": 56.0, "product": "NCC1=C(C=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.8, "product": "NCC1=C(C=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.386 g, 1.02 mmol) in CH3CN (10 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.00 mmol) followed by of 4-(bromomethyl)-2-methoxybenzonitrile (0.363 g, 1.60 mmol). The resultant mixture was heated to 60° C... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Nitrile.Secondary amine.Boc | Primary amine.Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HBr | CC#N | null | null | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COc1cc(CBr)ccc1C#N>CC#N>COc1cc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)ccc1CN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84ad598adf5a425ab72a5d36c32f40d4 | COC(=O)c1cc(C#N)ccc1CN(Cc1nc2ccccc2n1C(=O)OC(C)(C)C)C1CCCc2cccnc21>>COC(=O)c1cc(CN)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(C=C(C=C2)C#N)C(=O)OC.CO>>COC(C1=C(C=CC(=C1)CN)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O | CC(C)(C)OC(=O)[n:24]1[c:16]([CH2:15][N:14]([CH2:13][c:12]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]2)[CH:25]2[CH2:26][CH2:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][n:33][c:34]32)[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][NH2:9])[cH:10... | COC(=O)c1cc(C#N)ccc1CN(Cc1nc2ccccc2n1C(=O)OC(C)(C)C)C1CCCc2cccnc21 | COC(=O)c1cc(CN)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | null | [Ni] | N | Reduction | OtherReaction | 05b594f309e96f2fadfb42b0f7af1410d1400d062c71c657cb6248d978f69186 | a4666bc19ab169a23e3bd7c8888f526de2342415202d9023ecb448f440a89d43 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:1]:1.[NH2;D1;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13] | 71 | [{"value": 71.0, "product": "COC(C1=C(C=CC(=C1)CN)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "COC(C1=C(C=CC(=C1)CN)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-{[(4-cyano-2-methoxycarbonyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester (710 mg, 1.29 mmol) in saturated NH3(g)/MeOH (25 mL) was shaken at room temperature with a suspension of Raney® nickel (1.2 g) under hydrogen atmosphere (50 psi) for 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile.Boc | Primary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | [Ni].N | null | null | COC(=O)c1cc(C#N)ccc1CN(Cc1nc2ccccc2n1C(=O)OC(C)(C)C)C1CCCc2cccnc21>[Ni].N>COC(=O)c1cc(CN)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cf1a118bd624400a5dfbc0d32a82514 | COC(=O)c1ccc(CBr)cc1.Cc1ccc(S(=O)(=O)C#N)cc1>>COC(=O)c1ccc(CBr)c(C#N)c1 | BrCCBr.S(=O)(=O)(C1=CC=C(C)C=C1)C#N.COC(C1=CC=C(C=C1)CBr)=O>>COC(C1=CC(=C(C=C1)CBr)C#N)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][cH:14]1.Cc1ccc(S(=O)(=O)[C:12]#[N:13])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[c:11]([C:12]#[N:13])[cH:14]1 | COC(=O)c1ccc(CBr)cc1.Cc1ccc(S(=O)(=O)C#N)cc1 | COC(=O)c1ccc(CBr)c(C#N)c1 | null | [Zn].Cl[Si](C)(C)C | C1CCOC1 | C-C Coupling | OtherReaction | e29a35124fa47bc3ffeb0ef54be75863c97f87521fbf1c88b815028ee35da91e | e46c12615177276839b321a85599b052f95421e22fae791b6280ebffda0acb3c | c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-[C;H0;D2;+0:1]#[N;D1;H0:2]):c:c:1.[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[C:10]):[c:11]>>[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[c;H0;D3;+0:8](-[C;H0;D2;+0:1]#[N;D1;H0:2]):[c:9](-[C:10]):[c:11] | 44.6 | [{"value": 44.6, "product": "COC(C1=CC(=C(C=C1)CBr)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 10 | MINUTE | A suspension of zinc dust (792 mg, 12.12 mmol) and 1,2-dibromoethane (44 μL, 0.51 mmol) in THF (3 mL) was stirred at 70° C. for 10 minutes. The mixture was cooled to room temperature and chlorotrimethylsilane (45 μL, 0.36 mmol) was added. The mixture was cooled to 0° C. and a solution of methyl-4(bromomethyl)benzoate (... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Nitrile | Nitrile | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | TsOH.HO- | [Zn].Cl[Si](C)(C)C.C1CCOC1 | 70 | 0.166667 | COC(=O)c1ccc(CBr)cc1.Cc1ccc(S(=O)(=O)C#N)cc1>[Zn].Cl[Si](C)(C)C.C1CCOC1>COC(=O)c1ccc(CBr)c(C#N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e314cf9f68045ed83a0ce26b3cd1414 | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21>>N=C(N)NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(C=CC=C2)CN.C(C)(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)N1N=CC=C1.C([O-])([O-])=O.[K+].[K+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(CNC(=N)N)C=CC=C2 | CC(C)(C)OC(=O)[N:1]=[C:2](n1cccn1)[NH:3]C(=O)OC(C)(C)C.[NH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH2:12][N:13]([CH2:14][c:15]1[n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1)[CH:24]1[CH2:25][CH2:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][n:32][c:33]21>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][c:6]1[cH:7][cH:... | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | N=C(N)NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | null | null | C1CCOC1.[NH4+].[Cl-] | Heteroatom Alkylation and Arylation | OtherReaction | 0ac40e88831de40da91859e2f8501f8ccdba04b72a2bb842e65c2ccb421f3f22 | deff2335f9b9dec7bedc93cfff41fd024a04685bc319ecdeb4446903a4c0abca | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:3]-C(=O)-O-C(-C)(-C)-C)-n1:c:c:c:n:1.[NH2;D1;+0:4]-[C:5]-[c:6]>>[NH2;D1;+0:3]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[NH;D2;+0:4]-[C:5]-[c:6] | 92.8 | [{"value": 64.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(CNC(=N)N)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(CNC(=N)N)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (1H-Benzimidazol-2-ylmethyl)-(2-Aminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (see AMD9720) (50 mg, 0.125 mmol) in THF (5 mL) was added added N,N′-di-t-butoxycarbonyl-pyrazole-1-carboxamidine (60 mg, 0.187 mmol) and potassium carbonate (35 mg, 0.25 mmol) and the mixture stirred overnight... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Primary amine.Boc.Boc | Primary amine.Secondary amine | c1cn[nH]c1 | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | C1CCOC1.[NH4+].[Cl-] | null | 8 | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21>C1CCOC1.[NH4+].[Cl-]>N=C(N)NCc1ccccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4a7391387e441a4bad470593fc16605 | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>CC(C)(C)OC(=O)N=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)NC(=O)OC(C)(C)C | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)N1N=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)NC(NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=NC(=O)OC(C)(C)C | c1cnn([C:9](=[N:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[NH:40][C:41](=[O:42])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])c1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][N:17]([CH2:18][c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[nH:27]2)[CH:28]2[CH2:29][CH2:30][CH2:31][c:32]3[cH:33][cH:34][cH... | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CC(C)(C)OC(=O)N=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)NC(=O)OC(C)(C)C | null | null | C1CCOC1.[NH4+].[Cl-] | Heteroatom Alkylation and Arylation | OtherReaction | fc40081018b37da8451450064d8784be1219df3f09b9877dca11163275b8a8c2 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]=[C;H0;D3;+0:9](-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])-n1:c:c:c:n:1.[NH2;D1;+0:18]-[C:19]-[c:20]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]=[C;H0;D3;+0:... | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)NC(NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=NC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(C)(C)(C)OC(=O)NC(NCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=NC(=O)OC(C)(C)C", "details": "CALCULATEDPE... | null | null | 16 | HOUR | To a solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (397 mg, 1.0 mmol) in THF (10 mL) was added N,N′-di-t-butoxycarbonyl-pyrazole-1-carboxamidine (370 mg, 1.2 mmol) and potassium carbonate (207 mg, 1.5 mmol) and the mixture stirred at room temperature for 16 h.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1cn[nH]c1 | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C1CCOC1.[NH4+].[Cl-] | null | 16 | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)n1cccn1.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1.[NH4+].[Cl-]>CC(C)(C)OC(=O)N=C(NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f311fc80c113400083d5a3966db9b7c5 | CN(C)C#N.c1cn[nH]c1>>CN(C)C(=N)n1cccn1 | N1N=CC=C1.CN(C#N)C.Cl>>Cl.CN(C(=N)N1N=CC=C1)C | [CH3:1][N:2]([CH3:3])[C:4]#[N:5].[nH:6]1[cH:7][cH:8][cH:9][n:10]1>>[CH3:1][N:2]([CH3:3])[C:4](=[NH:5])[n:6]1[cH:7][cH:8][cH:9][n:10]1 | CN(C)C#N.c1cn[nH]c1 | CN(C)C(=N)n1cccn1 | null | null | O1CCOCC1.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | ba27ee2f0dfaad7f78d2dd2ccfb506b0cfe177b7163fb2af3eca210eff0c2390 | 9a7f188066dd5c094af690d634d1af31abc9c4cf66623fee532625d39064836a | c1cn[nH]c1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1.[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[C;H0;D2;+0:9]#[N;H0;D1;+0:10]>>[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[n;H0;D3;+0:5]1:[#7;a:1]:[c:2]:[c:3]:[c:4]:1 | 78 | [{"value": 78.0, "product": "Cl.CN(C(=N)N1N=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "Cl.CN(C(=N)N1N=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of pyrazole (1.01 g, 14.8 mmol) and dimethylcyanamide (1.20 mL, 14.8 mmol) in 1,4-dioxane (15 mL) was added HCl (4.0 N in 1,4-dioxane, 3.8 mL, 15.2 mmol) and the resultant mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and diluted with dry ether (15 mL) to pr... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1 | null | O1CCOCC1.CCOCC | null | null | CN(C)C#N.c1cn[nH]c1>O1CCOCC1.CCOCC>CN(C)C(=N)n1cccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8753c4924bb442778d438b5dc7c0fe64 | BrCc1ccccc1.NC(=S)c1ccccc1>>Br.N=C(SCc1ccccc1)c1ccccc1 | C(C1=CC=CC=C1)(=S)N.C(C1=CC=CC=C1)Br>>Br.C(C1=CC=CC=C1)SC(C1=CC=CC=C1)=N | [Br:1][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:2][C:3](=[S:4])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[BrH:1].[NH:2]=[C:3]([S:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrCc1ccccc1.NC(=S)c1ccccc1 | Br.N=C(SCc1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Protection | OtherReaction | ddda3e1e92d7f1fa1319a29d3c73d5659af49e3919539dd5106dabaa650d0b90 | f6443ba6d4b21f38fdeff3a3f6fb7b4e653a82aa26dae817e1a62477b0d72142 | N=C(SCc1ccccc1)c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[BrH;D0;+0:1].[NH;D1;+0:6]=[C;H0;D3;+0:7](-[S;H0;D2;+0:8]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])-[c:9](:[c:10]):[c:11] | 85 | [{"value": 85.0, "product": "Br.C(C1=CC=CC=C1)SC(C1=CC=CC=C1)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "Br.C(C1=CC=CC=C1)SC(C1=CC=CC=C1)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of thiobenzamide (0.307 g, 2.24 mmol) in CH2Cl2 (11 mL) was added benzyl bromide (0.26 mL, 2.19 mmol) and the resultant solution was heated to reflux for 2 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The resultant yellow solid was dried under vacuum to provide S-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thioamide | Monosulfide | null | null | c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | BrCc1ccccc1.NC(=S)c1ccccc1>C(Cl)Cl>Br.N=C(SCc1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f232c8b7f054fe783728d26df89483d | BrCc1ccccc1.CC(N)=S>>Br.CC(=N)SCc1ccccc1 | CCOCC.C(C)(=S)N.C(C1=CC=CC=C1)Br>>Br.C(C1=CC=CC=C1)SC(C)=N | [Br:1][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[CH3:2][C:3]([NH2:4])=[S:5]>>[BrH:1].[CH3:2][C:3](=[NH:4])[S:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | BrCc1ccccc1.CC(N)=S | Br.CC(=N)SCc1ccccc1 | null | null | C(Cl)(Cl)Cl | Protection | OtherReaction | ddda3e1e92d7f1fa1319a29d3c73d5659af49e3919539dd5106dabaa650d0b90 | f6443ba6d4b21f38fdeff3a3f6fb7b4e653a82aa26dae817e1a62477b0d72142 | c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]>>[BrH;D0;+0:1].[C;D1;H3:6]-[C;H0;D3;+0:7](=[NH;D1;+0:8])-[S;H0;D2;+0:9]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "Br.C(C1=CC=CC=C1)SC(C)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "Br.C(C1=CC=CC=C1)SC(C)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of thioacetamide (0.478 g, 6.36 mmol) in CHCl3 (16 mL) was added benzyl bromide (0.76 mL, 6.39 mmol) and the resultant solution was heated to reflux for 2 hours. The mixture was cooled to room temperature. Ether (50 mL) was added and the mixture was cooled in an ice-water bath to precipitate a white solid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thioamide | Monosulfide | null | null | c1ccccc1 | null | C(Cl)(Cl)Cl | null | null | BrCc1ccccc1.CC(N)=S>C(Cl)(Cl)Cl>Br.CC(=N)SCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5953b38797a94f048008796da7f74c46 | O=Cc1ccc(-c2ccccn2)cc1>>OCc1ccc(C2CCCCN2)cc1 | N1=C(C=CC=C1)C1=CC=C(C=O)C=C1>>OCC1=CC=C(C=C1)C1NCCCC1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[cH:13][cH:14]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][NH:12]2)[cH:13][cH:14]1 | O=Cc1ccc(-c2ccccn2)cc1 | OCc1ccc(C2CCCCN2)cc1 | null | O=[Pt]=O | CCO.Cl | Reduction | OtherReaction | 2aad61a5aeb2eb004b8423a898426a83aa4264feb4027e1e8935eddc2a218d68 | 77dff2be9cc883d679b523f1cf99d8978c98f82435310f81b1528a2a97430dd9 | c1ccc(C2CCCCN2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[n;H0;D2;+0:12]:2):[c:13]:[c:14]:1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH;D3;+0:7]2-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[NH;D2;+0:12]-2):... | 90.7 | [{"value": 90.7, "product": "OCC1=CC=C(C=C1)C1NCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | To a solution of 4-pyridin-2-yl-benzaldehyde (1.036 g, 5.65 mmol) in EtOH (95%, 3.1 mL) and conc. HCl (0.48 mL) in a Parr hydrogenation flask was added PtO2 (57 mg, 0.251 mmol) and the mixture hydrogenated at 50 psi H2 for 40 h. The mixture was filtered through celite, the cake washed with MeOH and the solvent was remo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol.Secondary amine | c1ccncc1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | null | O=[Pt]=O.CCO.Cl | null | 40 | O=Cc1ccc(-c2ccccn2)cc1>O=[Pt]=O.CCO.Cl>OCc1ccc(C2CCCCN2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16bde70fcd064c18a0e2fb70f4c85ac0 | C1CCNCC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCCC2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.N1CCCCC1.C(#N)[BH3-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCCC2 | [NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1.O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:26][c:27]2[n:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[nH:35]2)[cH:25][cH:24]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:... | C1CCNCC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCCC2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCCC2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | 30 | [{"value": 30.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Using General Procedure A: To a stirred solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (AMD9882) (144 mg, 0.36 mmol) in dry MeOH (5 mL) was added piperidine (0.040 mL, 0.40 mmol) and sodium cyanoborohydride (44 mg, 0.70 mmol) and the mixture stirred for 5 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1cnc2c(c1)CCCC2.c1ccccc1.C1CC[NH]CC1.c1ccc2[nH]cnc2c1 | Other | CO | null | 5 | C1CCNCC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCCC2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e96c583bbdf40ccb5d85ce6a07bda75 | CN.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | [BH4-].[Na+].N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.CN>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[nH:19]2)[CH:20]2[CH2:21][CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][n:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[n:12][c:13]3[cH:14][cH:... | CN.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59.9 | [{"value": 59.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.9, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Using General Procedure B: To a solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (AMD9882) (120 mg, 0.30 mmol) in MeOH (2 mL) was added methylamine (2.0 M solution in methanol, 1 mL, 2.00 mmol) and the resultant solution was stirred at room temperature for 5 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | CO | null | 0.5 | CN.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-214ef05a35294d9a86a8c36032007d91 | C1CNCCN1.CCOC(=O)C(F)(F)F>>O=C(N1CCNCC1)C(F)(F)F | N1CCNCC1.C(C)OC(C(F)(F)F)=O>>FC(C(=O)N1CCNCC1)(F)F | [NH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1.CCO[C:2](=[O:1])[C:9]([F:10])([F:11])[F:12]>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[C:9]([F:10])([F:11])[F:12] | C1CNCCN1.CCOC(=O)C(F)(F)F | O=C(N1CCNCC1)C(F)(F)F | null | null | CO | Acylation | Aminolysis of esters | 28fa86b96af5740128c30d4dea8abf89e5ff48bf24970582cfb131225bda0ca7 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | C1CNCCN1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | 58 | [{"value": 58.0, "product": "FC(C(=O)N1CCNCC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.8, "product": "FC(C(=O)N1CCNCC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of piperazine (1.444 g, 16.8 mmol) in MeOH (10 mL) was added trifluroacetic acid ethyl ester (2.0 mL, 16.8 mmol) and the mixture stirred at room temperature overnight. The reaction was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH, 9:1) to afford the desired mono-protected ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CNCCN1 | C1C[NH]CCN1 | C1C[NH]CCN1 | HO- | CO | null | 8 | C1CNCCN1.CCOC(=O)C(F)(F)F>CO>O=C(N1CCNCC1)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32ee4c940d754b23bf862be162c61ba9 | C=CCBr.O=C(N1CCNCC1)C(F)(F)F>>C=CCN1CCNCC1 | FC(C(=O)N1CCNCC1)(F)F.C(C=C)Br.C([O-])([O-])=O.[K+].[K+]>>C(C=C)N1CCNCC1 | Br[CH2:3][CH:2]=[CH2:1].O=C(C(F)(F)F)[N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1>>[CH2:1]=[CH:2][CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1 | C=CCBr.O=C(N1CCNCC1)C(F)(F)F | C=CCN1CCNCC1 | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | ab086d5e3c9be9295011a3cdd44ab44a85e667b73e838917a997c19964e1e466 | c61803908e898915e337f8475a84de182862bc4be9906a546dbfa5cb06720508 | C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[C:8]-[C:9]-1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[C:8]-[C:9]-1 | 155.1 | [{"value": 155.1, "product": "C(C=C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone (515 mg, 2.83 mmol) in dry CH3CN (6 mL) was added allyl bromide (0.32 mL, 3.7 mmol) and powdered potassium carbonate (0.78 g, 5.65 mmol) and the mixture stirred overnight. The reaction was concentrated under reduced pressure, diluted with CH2Cl2 (30 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Primary halide.Tertiary amide | Tertiary amine.Allyl | C1C[NH]CCN1 | C1C[NH]CCN1 | C1C[NH]CCN1 | Br- | CC#N | null | 8 | C=CCBr.O=C(N1CCNCC1)C(F)(F)F>CC#N>C=CCN1CCNCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc9e474d8b844c12ad0aa6bd3324f2d5 | CNC.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>CN(C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.CNC.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN(C)C | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]2)[CH:21]2[CH2:22][CH2:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][n:29][c:30]32)[cH:31][cH:32]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]2[n:13][c... | CNC.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CN(C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 43 | [{"value": 43.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.3, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure B: Reaction of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (AMD9882) (157 mg, 0.40 mmol) and dimethylamine (2.0 M in THF, 0.4 mL, 0.80 mmol) with NaBH(OAc)3 (0.179 g, 0.84 mmol) in CH2Cl2 (4 mL) overnight followed by purification of the crude m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | C(Cl)Cl | null | null | CNC.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C(Cl)Cl>CN(C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46852be027304803a1cc633363f06368 | CC(C)(C)OC(=O)NCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>NCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)(C)OC(NCC=O)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(CNCCN)C=C2 | CC(C)(C)OC(=O)[NH:1][CH2:2][CH:3]=O.[NH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([CH2:12][c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[nH:21]2)[CH:22]2[CH2:23][CH2:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][n:30][c:31]32)[cH:32][cH:33]1>>[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][... | CC(C)(C)OC(=O)NCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | NCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d2298fd8d9cb9280e0697a929831ef6823a33d0c9289091f842a1097865a18e6 | f266d2bed6d4f6d9aedca71eb0ac4dfa9f766f2a63837e311e77461e5dc0fc9c | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[CH;D2;+0:3]=O.[NH2;D1;+0:4]-[C:5]-[c:6]>>[NH2;D1;+0:1]-[C:2]-[CH2;D2;+0:3]-[NH;D2;+0:4]-[C:5]-[c:6] | 17 | [{"value": 17.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(CNCCN)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (250 mg, 0.629 mmol) and (2-oxo-ethyl)-carbamic acid tert-butyl ester (100 mg, 0.628 mmol) in THF (6.3 mL) was added NaBH(OAc)3 (173 mg, 0.816 mmol) and the mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | C1CCOC1 | null | 22 | CC(C)(C)OC(=O)NCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1>NCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae80fdd148ec4aacaabb2cf0591340b1 | CCCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>CCCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(CCC)=O>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CNCCCC | O=[CH:4][CH2:3][CH2:2][CH3:1].[NH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][N:12]([CH2:13][c:14]2[n:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[nH:22]2)[CH:23]2[CH2:24][CH2:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][n:31][c:32]32)[cH:33][cH:34]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:1... | CCCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | CCCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | 20 | HOUR | A solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (165 mg, 0.415 mmol) and butyraldehyde (50 mg, 0.69 mmol) in MeOH (4 mL) was heated at reflux for 30 minutes. The solution was allowed to cool to room temperature, 1.0% Pd/C (20 mg, 0.019 mmol) was added, and the... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | Other | [Pd].CO | null | 20 | CCCC=O.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>[Pd].CO>CCCCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8deeeb89dda443bc86cf0dc19ec0e570 | C=CCBr.CCN(C(C)C)C(C)C.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>C=CCN(CC=C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C(C=C)Br.N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)N(C(C)C)CC>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN(CC=C)CC=C | Br[CH2:3][CH:2]=[CH2:1].CC(C)N([CH:5](C)C)[CH2:6][CH3:7].[NH2:4][CH2:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][N:14]([CH2:15][c:16]2[n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[nH:24]2)[CH:25]2[CH2:26][CH2:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][n:33][c:34]32)[cH:35][cH:36]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[C... | C=CCBr.CCN(C(C)C)C(C)C.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C=CCN(CC=C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9adbf456ebd513e8ac58ccf51c66ae8f8eed399eee5ab7a5baf63cca6af0f413 | d24e6b0f80e3fccea3ed086f635ca47e223e1a58307b6b46a31c18238f7eead2 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].C-C(-C)-N(-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH;D3;+0:6](-C)-C.[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:8]-[c:9])-[CH2;D2;+0:6]-[CH;D2;+0:4]=[CH2;D1;+0:5] | 56.6 | [{"value": 56.6, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN(CC=C)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (156 mg, 0.39 mmol) in CH2Cl2 (4 mL) was added N,N-diisopropylethylamine (65 μL, 0.37 mmol). Allyl bromide (35 μL, 0.40 mmol) was added dropwise and the resultant mixture stirred at room temperature for 3 days... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine.Tertiary amine.Allyl | Tertiary amine.Allyl.Allyl | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HBr | C(Cl)Cl | null | null | C=CCBr.CCN(C(C)C)C(C)C.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C(Cl)Cl>C=CCN(CC=C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73213d6191a84b5a8196e33486f8db14 | C=CCBr.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>C=CCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.C(C)(C)N(C(C)C)CC.C(C=C)Br>>C(C=C)NCC1=CC=C(CN(C2CCCC=3C=CC=NC23)CC2=NC3=C(N2)C=CC=C3)C=C1 | Br[CH2:3][CH:2]=[CH2:1].[NH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([CH2:12][c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[nH:21]2)[CH:22]2[CH2:23][CH2:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][n:30][c:31]32)[cH:32][cH:33]1>>[CH2:1]=[CH:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([CH2:1... | C=CCBr.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C=CCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | dc54b39728c20d1e14e24fa825ca1b425643f9ce98835dcbd69717ccd1b96e2d | 78766a0004b98aba3e32292d7dad3399dbbd2742bcae1f4a68422c47b1ae1d13 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | To a solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.39 mmol) in CH2Cl2 (˜0.4 mL) was added N,N-diisopropylethylamine (90 μL, 0.52 mmol). Allyl bromide (35 μL, 0.40 mmol) was dissolved in CH2Cl2 (˜9.6 mL) and added to the amine mixture at a rate of 5.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine.Allyl | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HBr | C(Cl)Cl | null | null | C=CCBr.NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C(Cl)Cl>C=CCNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-411c738f6b344128b6b29e27670d6a84 | C1CCNC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCC2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.N1CCCC1.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCC2 | [NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1.O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:25][c:26]2[n:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]3[nH:34]2)[cH:24][cH:23]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:1... | C1CCNC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCC2)cc1)Cc1nc2ccccc2[nH]1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCC2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | 98.4 | [{"value": 96.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.4, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Using General Procedure B: To a stirred solution of 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (150 mg, 0.37 mmol), pyrrolidine (30 μL, 0.36 mmol) and AcOH (20 μL, 0.37 mmol) in THF (4 mL) was added NaBH(OAc)3 (235 mg, 1.11 mmol) and the mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1cnc2c(c1)CCCC2.c1ccccc1.C1CC[NH]C1.c1ccc2[nH]cnc2c1 | Other | C1CCOC1 | null | 1.5 | C1CCNC1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>C1CCOC1>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCCC2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3093032516746d0b011d6d4903b35f5 | C1COCCN1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCOCC2)cc1)Cc1nc2ccccc2[nH]1 | N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=O)C=C2.N1CCOCC1.C(#N)[BH3-].[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCOCC2 | [NH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1.O=[CH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][N:11]([CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[CH2:26][c:27]2[n:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[nH:35]2)[cH:25][cH:24]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10... | C1COCCN1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCOCC2)cc1)Cc1nc2ccccc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCOCC2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1):[c:4] | 7 | [{"value": 7.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.8, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=C2)CN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Using General Procedure A: To a stirred solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (0.285 g, 0.72 mmol) in dry MeOH (5 mL) was added morpholine (0.068 mL, 0.78 mmol) and sodium cyanoborohydride (0.107 g, 1.7 mmol) and the mixture stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1cnc2c(c1)CCCC2.c1ccccc1.C1COCC[NH]1.c1ccc2[nH]cnc2c1 | Other | CO | null | 24 | C1COCCN1.O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1>CO>c1cnc2c(c1)CCCC2N(Cc1ccc(CN2CCOCC2)cc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ae33e70ed0a4b709b1d6590d317a032 | NCc1ccccc1N.O=C1CCCc2cccnc21>>Nc1ccccc1CNC1CCCc2cccnc21 | NC1=C(CN)C=CC=C1.N1=CC=CC=2CCCC(C12)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1=CC=CC=2CCCC(C12)NCC1=C(C=CC=C1)N | [NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9].O=[C:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18][c:19]21>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18][c:19]21 | NCc1ccccc1N.O=C1CCCc2cccnc21 | Nc1ccccc1CNC1CCCc2cccnc21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 8a78537bd4beb037f975f95605700fd9f4fd57c27fb34d55c5286ac9db07202f | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNC2CCCc3cccnc32)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10])-[c:4](:[c:5]):[#7;a:6]:[c:7] | 53.1 | [{"value": 52.0, "product": "N1=CC=CC=2CCCC(C12)NCC1=C(C=CC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "N1=CC=CC=2CCCC(C12)NCC1=C(C=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | Using General Procedure B: To a solution of 2-aminobenzylamine (0.36 g, 2.9 mmol) and 6,7-dihydro-5H-quinolin-8-one (0.43 g, 2.9 mmol) in CH2Cl2 (15 mL) was added NaBH(OAc)3 (0.92 g, 4.4 mmol) and the mixture stirred at room temperature for 64 h. Purification of the crude material by column chromatography on silica gel... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1ccccc1.c1cnc2c(c1)CCCC2 | Other | C(Cl)Cl | null | 64 | NCc1ccccc1N.O=C1CCCc2cccnc21>C(Cl)Cl>Nc1ccccc1CNC1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3bccefe8a7947608797d443fe4904be | CCOC(=O)c1c(C)cccc1O.COS(=O)(=O)OC>>CCOC(=O)c1c(C)cccc1OC | S(=O)(=O)(OC)OC.CC=1C=CC=C(C1C(=O)OCC)O.O.[OH-].[Li+]>>COC1=C(C(=O)OCC)C(=CC=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][cH:10][cH:11][c:12]1[OH:13].COS(=O)(=O)O[CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14] | CCOC(=O)c1c(C)cccc1O.COS(=O)(=O)OC | CCOC(=O)c1c(C)cccc1OC | null | null | C1CCOC1.C(C)OCC | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1]):[c:8] | 91 | [{"value": 91.0, "product": "COC1=C(C(=O)OCC)C(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "COC1=C(C(=O)OCC)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 6-methylsalicylate (1.27 g, 6.97 mmol) in THF (35 mL) was added lithium hydroxide monohydrate (0.594 g, 14.2 mmol) followed by dimethyl sulfate (1.00 mL, 10.6 mmol). The resultant mixture was heated to reflux for 1 hour then cooled to room temperature. The mixture was diluted with diethyl ether (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | C1CCOC1.C(C)OCC | null | null | CCOC(=O)c1c(C)cccc1O.COS(=O)(=O)OC>C1CCOC1.C(C)OCC>CCOC(=O)c1c(C)cccc1OC |
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