original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
744,462 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([CH2:14][OH:15])[CH:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([CH:14]=[O:15])[CH:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:1... | Cc1c(CO)cc(-c2ccc(S(C)(=O)=O)cc2)n1-c1ccc(F)cc1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Example 49(i), but using 1-(4-fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl) pyrrole (prepared as described in Example 47) and manganese dioxide as starting materials, the title compound was obtained as a white powder (yield 98%), melting at 167-169°... | Cc1c(C=O)cc(-c2ccc(S(C)(=O)=O)cc2)n1-c1ccc(F)cc1 | null | null | null |
1,696,541 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:27])=[C:6]([C@:8]2([CH3:26])[CH2:12]OS(=O)(=O)[N:9]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[CH:7]=1.CN(C)C(N(C)C)=N.[SH:36][CH2:37][C:38]#[N:39]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:27])=[C:6]([C@:8]([NH:9][CH2:15][C:16]2[CH:21]=[CH:20]... | COc1ccc(CN2[C@](C)(c3cc(Br)ccc3F)COS2(=O)=O)c(OC)c1 | N#CCS | null | CN(C)C(=N)N(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 23 | 16 | To a solution of (R)-4-(5-Bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide (5.1 g, 11.1 mmol, Eq: 1.00) and 1,1,3,3-tetramethylguanidine (1.91 g, 2.09 ml, 16.6 mmol, Eq: 1.5) in DMF (77.3 ml) was added at 23° C. 2-mercaptoacetonitrile (1.22 g, 16.6 mmol, Eq: 1.5) dropwise. The... | COc1ccc(CN[C@@](C)(CSCC#N)c2cc(Br)ccc2F)c(OC)c1 | null | 98.2 | null |
383,191 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]([OH:20])[CH2:16][N:17]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]([OH:20])[CH2:16][NH2:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | [N-]=[N+]=NCC(O)COCCCCCCc1ccccc1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A procedure similar to that described in Preparation 13 was repeated, except that 4.5 g of 3-(6-phenylhexyloxy)-2-hydroxypropylazide (prepared as described in Preparation 62), 1.23 g of lithium aluminum hydride and 150 ml of anhydrous tetrahydrofuran were used, to give 3.14 g of the title compound as a pale yellow oil ... | NCC(O)COCCCCCCc1ccccc1 | null | 77 | null |
1,232,197 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:22][C:11]3=[N:12][C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([I:16])[CH:15]=[C:10]3[C:9]=2[C:23]([NH:25][CH3:26])=[O:24])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38].CN(C=O)C>O>[CH3:26][NH:25][C:23]([C:9]1[C:10]2[C:11](=[N:12][C... | C=CCCCBr | CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(NS(C)(=O)=O)c(I)cc12 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 150 | 0.25 | A mixture of 2-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (440 mg), Cs2CO3 (322 mg, 1.1 eq.), 5-bromopent-1-ene (402 mg, 3 eq.) and dry DMF (4.5 ml) was stirred in a microwave reactor at 150° C. for 15 min and cooled to rt. Water was added and the mixture was extracted with ... | C=CCCCN(c1nc2oc(-c3ccc(F)cc3)c(C(=O)NC)c2cc1I)S(C)(=O)=O | null | 49.9 | null |
1,410,062 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[OH:28].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH3:36]>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]... | CCI | COC(=O)c1cccc(Cn2c(-c3ccccc3)cc3cc(O)c(Cl)cc32)n1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (100 mg) in N,N-dimethylformamide (1 mL) were added, potassium carbonate (70.4 mg) and ethyl iodide (0.031 mL) and the mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with water and extra... | CCOc1cc2cc(-c3ccccc3)n(Cc3cccc(C(=O)OC)n3)c2cc1Cl | null | null | null |
1,228,371 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Li]CCCC.[CH2:14]([C@H:18]1[CH2:22][O:21][CH:20]([C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[NH:19]1)[CH:15]([CH3:17])[CH3:16].[Cl-].[NH4+]>C1COCC1>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([C@H:20]([NH:19][C@@H:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:22][OH:21])[C:23]([F... | CC(C)C[C@H]1COC(C(F)(F)C(F)(F)F)N1 | Brc1ccccc1Br | null | [Cl-] | [Li]CCCC | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a −78° C. solution of dibromobenzene (9.85 g, 41.8 mmol) in 100 mL of THF was added nBuLi (16.5 mL of 2.5M hexanes solution, 41.2 mmol) giving a thick suspension. After stirring 10 min, a solution of (4S)-4-isobutyl-2-(pentafluoroethyl)-1,3-oxazolidine (3.3 g, 13 mmol) in 3 mL THF was added giving a dark brown solut... | CC(C)C[C@@H](CO)N[C@@H](c1ccc(Br)cc1)C(F)(F)C(F)(F)F | null | null | null |
5,907 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11](=[O:17])[C:12]([O:14]CC)=[O:13])#[N:2].[OH-].[Na+:19]>O>[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11](=[O:17])[C:12]([O-:14])=[O:13])#[N:2].[Na+:19] | CCOC(=O)C(=O)Nc1sc(C)c(C)c1C#N | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | Approximately 0.756 g. (0.003 mole) of the purified ethyl (3-cyano-4,5-dimethylthiophen-2-yl)oxamate is suspended in 20 ml. of water and hydrolyzed by the addition of 32 ml. of 0.1N NaOH in a dropwise manner during about twenty minutes. The hydrolysis mixture is stirred for an additional twenty minutes at room temperat... | Cc1sc(NC(=O)C(=O)[O-])c(C#N)c1C | null | null | null |
928,645 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1 | CC(C)(C)OC(=O)N1CCC(CC2CCN(C3CCC3)CC2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 1,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate (may be prepared as described in Description 5) (5.7 g) was stirred in a solution of HCl-Dioxane (100 ml, 4M) for 1 h. The solvent was evaporated and the resultant yellow solid was dissolved in saturated potassium carbonate (25 ml). The so... | C1CC(N2CCC(CC3CCNCC3)CC2)C1 | null | null | null |
852,353 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19](O)=[O:20])=[CH:13][CH:12]=2)=[N:6][CH:5]=1.[CH2:31]([N:33](CC)[CH2:34]C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CNC>C(Cl)Cl... | COC(=O)c1ccc(Oc2ccc(CC(NC(=O)OC(C)(C)C)C(=O)O)cc2)nc1 | CCN(CC)CC | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | CNC | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | null | The compound 17 (2.2 g, 5.28 mmol) was dissolved in CH2Cl2 and stirred at room temperature under an atmosphere of argon. Triethylamine (0.883 mL, 6.33 mmol) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 2.5 g, 5.80 mmol) were added and the reaction mixture was stirred for 15 ... | COC(=O)c1ccc(Oc2ccc(CC(NC(=O)OC(C)(C)C)C(=O)N(C)C)cc2)nc1 | null | 55.5 | null |
1,289,028 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18]([C:22]1[N:23]=[N:24][C:25](Cl)=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:30][CH:29]=1)[CH2:19][CH2:20][CH3:21]>C1COCC1>[C:... | CCCCc1nnc(Cl)cc1-c1ccc(OC2CCCCC2)cc1 | CC(C)(C)OC(=O)N[C@H]1CC[C@H](O)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 50 | 0.25 | A stirred solution of trans-(4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (1.0 mmol) in anhydrous THF at 0° C. may be treated with sodium hydride (60% dispersion in mineral oil) (1.3 mmol). After stirring for 15 min the reaction mixture is allowed to come to room temperature. To the alkoxide solution is added 3... | CCCCc1nnc(O[C@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1-c1ccc(OC2CCCCC2)cc1 | null | null | null |
455,134 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:11])[S:2]1.[OH-].[Na+]>CO>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:11])[S:2]1 | COC(=O)CCCNC(=O)CCCCC1CCSS1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | The reaction was effected as described in Example 49, but using 0.65 g of methyl 4-[5-(1,2-dithiolan-3yl)pentanoylamino]butanoate (prepared as described in Example 73), 13 ml of methanol and a 1N aqueous solution of sodium hydroxide. The solvent was removed from the reaction mixture by distillation under reduced pressu... | O=C(O)CCCNC(=O)CCCCC1CCSS1 | null | 45.2 | null |
726,603 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([P:8](=[O:13])([O:11]C)[O:9]C)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1.CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([P:8](=[O:9])([OH:13])[OH:11])=[O:7])=[CH:4][CH:3]=1 | COP(=O)(OC)C(=O)c1ccc(Cl)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | null | null | To a solution of dimethyl p-chlorobenzoylphosphonate (1 mmol) in dry dioxane (5 ml), BrMe3Si (3 mmol) was added dropwise under magnetic stirring, in nitrogen atmosphere at room temperature. After 5 h the solvent was removed under vacuum and the brown residue was dissolved in MeOH at 0° C. The solvent was evaporated and... | O=C(c1ccc(Cl)cc1)P(=O)(O)O | null | 76 | null |
1,189,958 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [S:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[N+:13]([O-])([OH:15])=[O:14]>C(OC(=O)C)(=O)C.C(O)(=O)C>[N+:13]([C:11]1[CH:10]=[CH:9][C:3]2[C:4]([C:6]([OH:8])=[O:7])=[CH:5][S:1][C:2]=2[CH:12]=1)([O-:15])=[O:14] | O=C(O)c1csc2ccccc12 | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 1.5 | 2 g benzo[b]thiophene-3-carboxylic acid are dissolved in 11 ml acetic anhydride and cooled to 0° C. A solution of 4.4 ml concentrated nitric acid in 10 ml acetic acid is added dropwise, while not allowing the temperature to rise above 5° C. Then the mixture is stirred for 1.5 hours and then combined with 200 ml ice wat... | O=C(O)c1csc2cc([N+](=O)[O-])ccc12 | null | 66 | null |
1,336,827 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[N:3]=1.O.[OH-].[Li+].Br[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:3... | CCc1nc(N)nc(N)c1O | CCOC(=O)CCCOc1ccccc1OCCCBr | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | 2,4-Diamino-6-ethyl-5-hydroxypyrimidine (0.4625 g, 3 mmol) was added to a stirred solution of lithium hydroxide monohydrate (0.4406 g, 10.5 mmol) in DMF (4 mL) and the reaction mixture was stirred at 25° C. for 1 hour. A solution of ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate (1.0357 g, 3 mmol) in DMF (1 mL) was added... | CCc1nc(N)nc(N)c1OCCCOc1ccccc1OCCCC(=O)O | null | 59 | null |
1,307,787 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([Li])CCC.[C:15]([N:22]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CCOCC>[OH:27][C:24]1([C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH2:25][CH2:26][N:22]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:... | CC(C)(C)OC(=O)N1CCC(=O)C1 | COc1ccc(Br)cn1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | -78 | 0.17 | 5-bromo-2-methoxypyridine (324 μL, 2.50 mmol) was added dropwise to a stirred suspension of n-butyllithium (1.72 mL of a 1.6 M hexanes solution, 2.75 mmol) in ether (10.0 mL) at −78° C. After 10 min, a solution of N-Boc-3-pyrrolidinone (463 mg, 2.50 mmol) in ether (2.00 mL) was added dropwise, and the reaction mixture ... | COc1ccc(C2(O)CCN(C(=O)OC(C)(C)C)C2)cn1 | null | null | null |
756,874 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | Cl.Cl.[NH2:3][C:4]1[C:8]([NH2:9])=[CH:7][S:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[CH3:19][C:20]1[C:21]([N:25]=[C:26]=[S:27])=[CH:22][S:23][CH:24]=1>O1CCCC1>[NH2:3][C:4]1[C:8]([NH:9][C:26]([NH:25][C:21]2[C:20]([CH3:19])=[CH:24][S:23][CH:22]=2)=[S:27])=[CH:7][S:6][CH:5]=1 | Nc1cscc1N | Cc1cscc1N=C=S | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of 1.87 g of 3,4-diaminothiophene dihydrochloride, 60 ml of anhydrous tetrahydrofuran (THF) and 2.58 g of N-ethyl-N,N-diisopropylamine was stirred at room temperature for 30 minutes and then admixed with 1.5 g of 4-methyl-3-thienyl isothiocyanate. After stirring over approx. 18 hours, the solvent was distille... | Cc1cscc1NC(=S)Nc1cscc1N | null | null | null |
1,545,102 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | COC[O:4][C@@H:5]1[CH2:28][C@@H:9]2[C:10](=[O:27])[O:11][C:12]3[C@@H:13]4[CH2:20][CH2:19][C@H:18]([C@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[C@@:14]4([CH3:26])[CH2:15][CH2:16][C:17]=3[C@@:8]2([CH3:29])[CH2:7][CH2:6]1.CC1C=CC(S(O)(=O)=O)=CC=1.[Cl-].[NH4+]>C(O)(C)(C)C>[OH:4][C@@H:5]1[CH2:28][C@@H:9]2[C:10](=[O:27])[O:11][C... | COCO[C@H]1CC[C@]2(C)C3=C(OC(=O)[C@H]2C1)[C@@H]1CC[C@H]([C@H](C)COC)[C@@]1(C)CC3 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 105 | 4 | Compound 67 (581.6 mg, 1.431 mmol) obtained in Example 63 was dissolved in tert-butanol (48 mL), and pyrimidium p-toluenesulfonate (3.6 g; 14 mmol) was added thereto, followed by stirring at 105° C. for 4 hours. The reaction mixture was cooled to 0° C., a saturated aqueous ammonium chloride solution was added, followed... | COC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@@H]1C(=O)O3 | null | 28.9 | null |
510,624 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([OH:16])[O:7][CH:6]=1)=[O:4].FB(F)F.[CH2:21](OCC)C.C(=O)(O)[O-].[Na+]>CO>[OH:15][CH2:14][C:13]1[C@@H:9]2[C@@H:10]([C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][O:7][CH:8]2[O:16][CH3:21])[CH2:11][CH:12]=1 | CCOCC | COC(=O)C1=CO[C@@H](O)[C@@H]2C(CO)=CC[C@H]12 | null | FB(F)F | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 3 | Genipin (5 g, 22.1 mmol) was dissolved with 250 ml of methanol and catalytic amount of trifluoroboron diethylether was added, and stirred for 3 hours, then saturated sodium bicarbonate solution was added to finish the reaction. Under reduce pressure, methanol was removed and extracted with ethylacetate, and dried, filt... | COC(=O)C1=COC(OC)[C@@H]2C(CO)=CC[C@H]12 | null | null | null |
1,243,837 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([C:21](O)=[O:22])[CH:20]=1)[NH:17][CH:16]([C:24]1[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=1)[C:15]([CH3:40])([CH3:39])[CH2:14]2.C(N1C=CN=C1)(N1... | CN(C)c1ccc(-c2cccc(C3Nc4c(cc(Cl)cc4C(=O)O)CC3(C)C)c2)cc1 | NS(=O)(=O)C1CC1 | null | O=C(n1ccnc1)n1ccnc1 | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a suspension of 60% sodium hydride (91 mg, 2.2 mmol) in N,N-dimethylformamide (1.5 mL) was added cyclopropanesulfonamide (280 mg, 2.3 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 6-chloro-2-(4′-dimethylamino-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-c... | CN(C)c1ccc(-c2cccc(C3Nc4c(cc(Cl)cc4C(=O)NS(=O)(=O)C4CC4)CC3(C)C)c2)cc1 | null | 39.6 | null |
217,812 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]=1[C:18]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH3:26])[N:25]=1)=[O:19]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:26][C:24]1[N:25]=[C:21]([NH:20][C:18]([C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][... | Cc1csc(NC(=O)C2=C(O)c3ccccc3N(c3ccccc3)C2)n1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 9.0 g of 1,2-dihydro-4-hydroxy-N-(4-methyl-2-thiazolyl)-1-phenyl-3-quinolinecarboxamide in 250 ml of hot toluene was treated with 36.0 g of activated manganese dioxide and stirred for two hours at ambient temperature. The slurry was filtered and evaporated. Recrystallization of the residue from chloroform... | Cc1csc(NC(=O)c2cn(-c3ccccc3)c3ccccc3c2=O)n1 | null | 67 | null |
1,199,431 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C(O[C@H](C)[C:10]([NH:12][C@H:13]1[CH2:17][C@@H:16]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21]([N:42]2[CH2:46][CH2:45][C@@H:44]([NH:47][C:48]([NH:50][C:51]4[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=4)=[O:49])[CH2:43]2)=[N:22][C:23]=3[NH:27][CH2:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[... | C[C@@H](OCc1ccccc1)C(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(N4CC[C@@H](NC(=O)Nc5cccnc5)C4)nc32)[C@H](O)[C@@H]1O | C[C@@H](OCc1ccccc1)C(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(N4CC[C@@H](N)C4)nc32)[C@H](O)[C@@H]1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared analogously to (R)-2-benzyloxy-N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 181, step 5), by substituting N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-et... | O=C(CCO)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(N4CC[C@@H](NC(=O)Nc5cccnc5)C4)nc32)[C@H](O)[C@@H]1O | null | null | null |
179,210 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:8][CH:9]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[OH:8][CH:9]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14] | CCCCCC(O)c1cccc(CBr)c1 | Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | For compounds in which X is --NR2 --(CHR1)n --, the corresponding amino starting compounds are employed to form the desired amino compound. Thus, aniline is condensed with 3-(1-hydroxyhexyl)benzylbromide to form 2-[3-(1-hydroxyhexyl)benzylamino]benzene. Alternatively, benzyl bromide is condensed with 3-(1-hydroxyhexyl)... | CCCCCC(O)c1cccc(CNc2ccccc2)c1 | null | null | null |
70,671 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[C:23]([O:25][CH3:26])=[O:24].O>C(Cl)Cl>[C:5]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH2:14][CH:15]([C:23]([O:25][CH3:26])=[O:24])[CH2:16]2)(=[O:12])[C:6... | COC(=O)C1Cc2ccccc2C1 | O=C(Cl)c1ccccc1 | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | In a 250 cm3 reaction vessel fitted with a stirrer, a cooler, a dropping funnel and a thermometer, is placed 23.2 g (0.173 mole) of anhydrous aluminum chloride in suspension in 40 ml of methylene chloride. 35.3 g (0.252 mole) of benzoyl chloride dissolved in 40 cm3 of methylene chloride is then slowly added at ambient ... | COC(=O)C1Cc2ccc(C(=O)c3ccccc3)cc2C1 | null | null | null |
1,225,854 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)=[CH:11][C:10]([C:23]([O:25]CC)=[O:24])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)=[CH:11][... | CCOC(=O)c1cc(-c2ccc(OC)c(OC)c2)n(-c2cccc(Cl)c2)n1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 500 mg (1.29 mmol) of ethyl 1-(3-chlorophenyl)-5-(3,4-dimethoxy-phenyl)-1H-pyrazole-3-carboxylate from example 17A and 725.2 mg (12.9 mmol) of potassium hydroxide, 434.1 mg (1.2 mmol, 94% yield of theory) are obtained as crystals according to the method described in example 7A. | COc1ccc(-c2cc(C(=O)O)nn2-c2cccc(Cl)c2)cc1OC | null | 94 | null |
1,602,064 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]3[CH:18]=[CH:19][C:20]([NH:22][C:14]=3[CH:13]=2)=[O:21])[CH2:5][CH2:4][N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[Cl:30])[CH2:2]1.CC(C)([O-])C.[K+].CC1CCCO1.Cl[C:44]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[O:45... | CCCCCCOC(=O)Cl | O=c1ccc2ccc(OCCCCN3CCN(c4cccc(Cl)c4Cl)CC3)cc2[nH]1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC1CCCO1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of dehydro-aripiprazole (1.5 g, 3.4 mmol), potassium tert-butoxide (0.75 g, 6.7 mmol) and 2-methyltetrahydrofuran (30 mL) at 0° C. was added hexyl chloroformate (1.32 mL, 8.1 mmol). The reaction mixture was stirred for 2 h, allowed to self warm to room temperature and stirred for a further 4 h. The reactio... | CCCCCCOC(=O)Oc1ccc2ccc(OCCCCN3CCN(c4cccc(Cl)c4Cl)CC3)cc2n1 | null | null | null |
1,105,427 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Br[C:7]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:17]>ClCCl>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:7]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([NH:5][CH2:4][CH:1]3[C... | O=C1Nc2cc(Cl)ccc2C1(Br)Cc1cccc(Cl)c1 | NCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of cyclopropanemethylamine (142 mg, 2.0 mmol) in dichloromethane (20 mL) was added rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (0.37 g, 0.99 mmol). After the mixture was stirred at room temperature for 1 h, another portion of dichloromethane (20 mL) was added. The mixture was washed w... | O=C1Nc2cc(Cl)ccc2C1(Cc1cccc(Cl)c1)NCC1CC1 | null | 95.1 | null |
490,161 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]([O:14][CH3:15])[O:9][CH:10]([O:12][CH3:13])[CH:11]=2)=[CH:3][CH:2]=1>CCO.CCOC(C)=O.[Pd]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:2]=[CH:3][C:4]([CH:7]2[CH2:11][CH:10]([O:12][CH3:13])[O:9][CH:8]2[O:14][CH3:15])=[CH:5][... | COC1C=C(c2ccc(-c3ccccc3)cc2)C(OC)O1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 1.75 | A mixture of 3-biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran (1.00 g, 3.55 mmol) and 5% Pd/C (300 mg) in EtOH:EtOAc (1:2) was stirred under H2 atmosphere for 1.75 hours. The catalyst was filtered onto Celite. The filtrate was concentrated to provide 0.97 g (97%) of a diastereomeric mixture of 3-biphenyl-4-yl-2,5-dimetho... | COC1CC(c2ccc(-c3ccccc3)cc2)C(OC)O1 | null | 96.1 | null |
789,174 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | C([O:3][C:4](=[O:36])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[N:18]([CH:33]([F:35])[F:34])[N:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)[CH:21]=3)[CH:13]=2)[CH:8]=[CH:7]1)C.[Li+].[OH-]>>[F:35][CH:33]([F:34])[N:18]1[C:17]([CH2:16][O:15][C:12... | CCOC(=O)Cn1ccc2ccc(OCc3cc(-c4ccc(OC(F)(F)F)cc4)nn3C(F)F)cc21 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 1 f], {6-[2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester was treated with LiOH to obtain {6-[2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid as colorless crystals. | O=C(O)Cn1ccc2ccc(OCc3cc(-c4ccc(OC(F)(F)F)cc4)nn3C(F)F)cc21 | null | null | null |
1,540,295 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[O:25][N:24]=[C:23]([CH2:26]OS(C)(=O)=O)[CH:22]=1>CC#N.O>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:26][C:23]2[CH:22]=[C:21]([CH3:20])[O:25][N:24]=2)[CH2:12][CH2:13]1)=[O:2])([... | CC(C)(C)OC(=O)N1CCNCC1 | Cc1cc(COS(C)(=O)=O)no1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | null | null | To a solution of N-BOC-piperazine (300 mg) in MeCN (5 mL) was added potassium carbonate (289 mg) followed by methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl ester (369 mg). The reaction mixture was heated to reflux for 24 h. After cooling the reaction mixture was diluted with water, extracted into ethyl acetate, drie... | Cc1cc(CN2CCN(C(=O)OC(C)(C)C)CC2)no1 | null | 89.1 | null |
107,387 | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | null | 1983-01-01T00:08:00 | true | Cl.[CH2:2]([O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)=[O:6])[CH3:3].[Sn].C(=O)=O>C(O)C>[CH2:2]([O:4][C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:17])[CH:13]=2)[NH:8]1)=[O:6])[CH3:3] | CCOC(=O)c1cc2cc(OC)ccc2[nH]1 | null | null | Cl | O=C=O | [Sn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 1 | A three neck 3-liter round bottom flask equipped with a mechanical stirrer, water condenser, and a gas inlet tube was charged with 500 ml. of absolute ethanol and chilled in a dry ice-acetone bath. Dry hydrogen chloride gas was added at a rapid rate for 0.5 hours. Fifty grams of 5-methoxyindole-2-carboxylic acid ethyl ... | CCOC(=O)C1Cc2cc(OC)ccc2N1 | null | null | null |
1,265,619 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Na].C(O)C.[CH:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:10][CH2:11][C:12](OCC)=[O:13]>C(OCC)C>[Cl:10][CH:11]([CH:12]=[O:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6] | CCOC(=O)CCl | CCOC=O | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCO | null | null | null | null | null | null | null | null | null | 25 | 4 | To a flask was added sodium (4.45 g, 194 mmol) and ethanol (56.5 mL, 968 mmol) and the mixture was stirred at room temperature for 4 hours until all of the metal had dissolved. Diethyl ether (100 mL) was added, followed by the slow addition of a solution of ethyl formate (17.20 mL, 213 mmol) and ethyl chloroacetate (22... | CCOC(=O)C(Cl)C=O | null | 14 | null |
578,400 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | C(O)=O.[NH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])=[O:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1.C([Si]([O:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH:60]2[CH2:62][O:61]2)=[CH:54... | CC(C)(C)[Si](Oc1ccc(OCC2CO2)cc1)(c1ccccc1)c1ccccc1 | NCC1CCN(S(=O)(=O)c2ccc(NC(=O)NCc3cc(F)ccc3F)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N′-(2,5-difluorobenzyl)urea formate (0.433 g, 1.00 mmol) was reacted with t-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.404 g, 1.00 mmol) according to example 37 to give the title compound (0.084 g, 0.13 mmol). | O=C(NCc1cc(F)ccc1F)Nc1ccc(S(=O)(=O)N2CCC(CNC[C@H](O)COc3ccc(O)cc3)CC2)cc1 | null | 13 | null |
1,152,151 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[Li]CCCC.[C:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C1COCC1>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH2:24][C:23]([OH:26])([CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:22][CH2:21]1)=[O:14])([CH3:19])(... | Cc1ccccn1 | CC(C)(C)OC(=O)N1CCC(=O)CC1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Amine preparation: To a solution of 2-picoline (333 mg) in dry THF (5 mL) at −78° C. was added nBuLi (2.5M solution in hexanes, 1.50 mL). The reaction mixture was warmed to room temperature over 30 min and then cooled to −78° C. 1-BOC-4-piperidone (713 mg) was then added, and the reaction mixture was raised to 0° C. ov... | CC(C)(C)OC(=O)N1CCC(O)(Cc2ccccn2)CC1 | null | 27.7 | null |
1,376,669 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][CH:2]([CH3:13])[C:3]([O:5][CH2:6][O:7][C:8](SCC)=[O:9])=[O:4].S(Cl)([Cl:17])(=O)=O>>[CH3:1][CH:2]([CH3:13])[C:3]([O:5][CH2:6][O:7][C:8]([Cl:17])=[O:9])=[O:4] | O=S(=O)(Cl)Cl | CCSC(=O)OCOC(=O)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.33 | The compound (400 mg) obtained in Step 2 of this Example was cooled to −30° C. Sulfuryl chloride (159 μL) was added thereto, and the mixture was stirred at the same temperature for 20 minutes. The mixture was in turn stirred for 20 minutes in an ice bath and further at room temperature for 1 hour. The solvent was disti... | CC(C)C(=O)OCOC(=O)Cl | null | null | null |
1,273,883 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C[O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5].O>C(O)C>[Cl:13][C:11]1[CH:12]=[C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:15])=[O:2])[CH:8]=[C:9]([Cl:14])[CH:10]=1 | COC(=O)C(C)(C)c1cc(Cl)cc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | To a solution of 9.0 g (36 mmol) 2-(3,5-dichloro-phenyl)-2-methyl-propionic acid methyl ester in 40 ml ethanol 40 ml 2 N sodium hydroxide solution was added. After stirring for 4 hrs at RT 150 ml water was added and the solution washed twice with 200 ml Et2O. The aqueous phase was acidified with 25% hydrochloric acid s... | CC(C)(C(=O)O)c1cc(Cl)cc(Cl)c1 | null | 98.9 | null |
1,095,882 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | C[O:2][P:3]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[O:4][CH3:5].[C:12]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[CH2:19]Cl)([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:5][O:4][P:3]([CH2:19][C:18]1[CH:17]=[C:16]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:23]([OH:24])=... | COP(OC)C1CCCCC1 | CC(C)(C)c1cc(CCl)cc(C(C)(C)C)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 10.47 grams (59 mmol) of dimethylcyclohexylphosphonite with 15.14 grams (59 mmol) of 3,5-di-tert-butyl-4-hydroxybenzyl chloride (CAS REG # 955-01-1) in 45 mL of toluene is refluxed for 2 hours and is cooled. The resultant precipitated crystals are collected by filtration, washed with toluene, then hexane a... | COP(=O)(Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)C1CCCCC1 | null | 51.2 | null |
17,576 | ord_dataset-d625331704b34593871e69cd09a5cd83 | null | 1976-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:27])[C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[N:19]1[C:23]([CH3:24])=[N:22][N:21]=[C:20]1[CH2:25]O.P(Br)(Br)[Br:29]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:27])[C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:... | BrP(Br)Br | Cc1nnc(CO)n1-c1ccc(C(F)(F)F)cc1C(=O)c1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | In the manner given in Example 5, 2'-chloro-5-(trifluoromethyl)-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenone is treated with phosphorus tribromide in chloroform to give 2'-chloro-5-(trifluoromethyl)-2-[3-(bromomethyl)-5-methyl-4H-1,2,4-triazol-4-yl] -benzophenone. | Cc1nnc(CBr)n1-c1ccc(C(F)(F)F)cc1C(=O)c1ccccc1Cl | null | null | null |
706,142 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[S:17][C:18]([C:22]([OH:24])=O)=[C:19]([CH3:21])[N:20]=3)[CH:14]=2)[C:9](=[O:25])[N:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:7]=1[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:2][CH2:3][CH3:4].Cl.C[N:41](C)CCCN=C=N.[NH4+].ON1C2C=... | CN(C)CCCN=C=N | CCCCOc1c(CNC(=O)OC(C)(C)C)n(CC(C)C)c(=O)c2ccc(-c3nc(C)c(C(=O)O)s3)cc12 | null | Cl | On1nnc2ccccc21 | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-(4-butoxy-3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl)-4-methyl-1,3-thiazole-5-carboxylic acid (0.60 g, 1.1 mmol), 1-ethyl,-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.42 g, 2.2 mmol) and 1-hydroxybenzotriazole ammonium salt (0.33 g, 2.2 mmol) in N,N-di... | CCCCOc1c(CNC(=O)OC(C)(C)C)n(CC(C)C)c(=O)c2ccc(-c3nc(C)c(C(N)=O)s3)cc12 | null | 97.2 | null |
797,171 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:15]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=2[C:17]#[N:18])[CH2:12][CH2:... | N#Cc1c(F)cccc1Cl | CC(C)(C)OC(=O)N1CCNCC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CS(C)=O | null | null | null | null | null | null | null | null | null | 80 | 48 | To a solution of N-Boc-piperazine (2.02 g, 11.0 mmol) in DMSO (20 mL) was added 2-fluoro-6-chlorobenzonitrile (1.55 g, 10 mmol) and potassium carbonate (1.52 g, 11 mmol). The mixture was stirred at 80° C. for about 48 hours. The mixture was cooled to r.t. and diluted with diethyl ether (200 mL). The solution was washed... | CC(C)(C)OC(=O)N1CCN(c2cccc(Cl)c2C#N)CC1 | null | 77.7 | null |
293,414 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[CH:12]1([C:15](=[N:17]O)[NH2:16])[CH2:14][CH2:13]1>C(O)C>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]1[O:6][N:17]=[C:15]([CH:12]2[CH2:14][CH2:13]2)[N:16]=1 | NC(=NO)C1CC1 | COC(=O)c1ccccc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 2-amino-benzoate (6 g, 40 mmol) and cyclopropylcarboxamid oxime (5 g, 50 mmol) was refluxed for 10 h in dry ethanol containing 0.25 g sodium and 2 g molecular sieves. The mixture was filtered while hot, and cooled precipitating 2.8 g of the desired product as white needles. Upon additionof water to the flitrate,... | Nc1ccccc1-c1nc(C2CC2)no1 | null | null | null |
1,044,040 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | C([C@H:3]([S:7]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[N:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]3[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[CH:30]=3)=[O:28])[CH:21]=2)[CH:17]=1)=[O:11])=[O:8])[C:4]([O-])=[O:5])C.[CH3:42][NH:43][CH2:44][... | CNCCO | CC[C@@H](C(=O)[O-])S(=O)(=NC(=O)c1cncc(C#Cc2cccc(NC(=O)c3cc(C)nn3C)c2)c1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to that described in Example 534, (S)-Ethyl[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate and 2-methylaminoethanol were reacted to give the title compound. | Cc1cc(C(=O)Nc2cccc(C#Cc3cncc(C(=O)N=[S@](=O)(CC(=O)N(C)CCO)c4ccccc4)c3)c2)n(C)n1 | null | null | null |
467,754 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:26][CH3:27])=[C:17]3[N:22]([CH:23]=2)[CH:21]=[C:20]([O:24][CH3:25])[CH:19]=[CH:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([C:34]([O:36][CH3:37])=[O:35])#[C:29][C:30]([O:32][CH3:33])=[O:31]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([... | COC(=O)C#CC(=O)OC | CCc1c(-c2ccc(OCc3ccccc3)cc2)cn2cc(OC)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The general synthetic pathway outlined in example 23, step 1-5, have been applied to proper starting materials in the preparation of 2-(4-benzyloxyphenyl)-1-ethyl-6-methoxyindolizine, which was reacted with dimethyl acetylene dicarboxylate by the general synthetic principle outlined in example 23, step 6, to afford dim... | CCc1c(-c2ccc(OCc3ccccc3)cc2)c2c(C(=O)OC)c(C(=O)OC)c3c(OC)ccc1n32 | null | 80 | null |
168,733 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [Cl:1][C:2]1[C:3]([NH:9][C:10](=[O:18])OC2C=CC=CC=2)=[CH:4][N:5]=[N:6][C:7]=1[Cl:8].[CH3:19][CH:20]([NH2:22])[CH3:21]>O1CCCC1>[Cl:1][C:2]1[C:3]([NH:9][C:10]([NH:22][CH:20]([CH3:21])[CH3:19])=[O:18])=[CH:4][N:5]=[N:6][C:7]=1[Cl:8] | O=C(Nc1cnnc(Cl)c1Cl)Oc1ccccc1 | CC(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A stirred solution of 1.0 gram (0.004 mole) of phenyl N-(5,6-dichloro-4-pyridazinyl)carbamate and 0.27 gram (0.005 mole) of 1-methylethylamine in tetrahydrofuran is heated under reflux for 18 hours. The reaction mixture is filtered and the filtrate concentrated under reduced pressure to a residue. The residue is purifi... | CC(C)NC(=O)Nc1cnnc(Cl)c1Cl | null | 10 | null |
1,649,759 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:39]=[CH:40][N:41]=3)[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([C:23]([NH:25][C:26]4[CH:38]=[CH:37][C:29]([C:30]([O:32]C(C)(C)C)=[O:31])=[CH:28][CH:27]=4)=[O:24])[CH2:19]3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]... | COc1ccc(Nc2cc(N3CCC(C(=O)Nc4ccc(C(=O)OC(C)(C)C)cc4)C3)nn3ccnc23)nc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxamido)benzoate (200 mg, 0.36 mmol) and TFA (2 mL) in dichloromethane (2 mL) was stirred at room temperature for 2 h. The residue was concentrated in vacuo. The crude product was purified by prep-HPLC (Gemini... | COc1ccc(Nc2cc(N3CCC(C(=O)Nc4ccc(C(=O)O)cc4)C3)nn3ccnc23)nc1OC | null | 3.3 | null |
825,066 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [SH:1][C:2]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6](=[O:12])[N:5]([CH3:13])[C:4](=[O:14])[CH:3]=1.Br[CH:16]([CH3:23])[C:17](=O)[C:18]([O:20][CH3:21])=[O:19]>C([O-])(=O)C.[Na+].O.C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:13][N:5]1[C:4](=[O:14])[C:3]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([CH3:23])[S:1][C:2]=2[N:7]([CH2:... | CC(C)Cn1c(S)cc(=O)n(C)c1=O | COC(=O)C(=O)C(C)Br | null | Cl[Ti](Cl)(Cl)Cl | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 0 | null | 6-Mercapto-3-methyl-1-(isobutyl)-pyrimidine-2,4(1H,3H)-dione (50 g) was dissolved in a solution of sodium acetate (95.6 g) in water (1.5 L), and methyl 3-bromo-2-oxo-butanoate (44.6 g) was added dropwise with stirring. After stirring 1 h at room temperature the mixture was extracted into ethyl acetate. The organic solu... | COC(=O)c1c(C)sc2c1c(=O)n(C)c(=O)n2CC(C)C | null | 59.2 | null |
1,333,685 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH:1]1([NH:4][C:5]([C:7]2([CH3:21])[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([CH3:20])[C:11]([CH3:19])=[C:12]([OH:18])[C:13]=3[CH3:17])[O:8]2)=[O:6])[CH2:3][CH2:2]1.[O:22]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>>[CH:1]1([NH:4][C:5](=[O:6])[C:... | Cc1c(C)c2c(c(C)c1O)CCC(C)(C(=O)NC1CC1)O2 | O=[N+]([O-])[O-] | null | [Ce+4] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Oxidation as described in protocol B, using 100 mg (0.346 mmol) of N-cyclopropyl-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide and 417 mg CAN (0.762 mmol) yielded 40 mg of N-cyclopropyl-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow oil. | CC1=C(C)C(=O)C(CCC(C)(O)C(=O)NC2CC2)=C(C)C1=O | null | 37.9 | null |
1,218,938 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]([C:19]1[NH:20][CH:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[CH:16]([C:19]1[N:20]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH:21]=[... | CC(C)c1ncc[nH]1 | CCOC(=O)c1ccc(F)c([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC#N | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 4-fluoro-3-nitrobenzoate 4.26 g, 2-isopropylimidazole 2.20 g, N,N-diisopropylethylamine 5.2 mL and acetonitrile 40 mL was heated under reflux for 24 hours. After distilling the solvent off, water was added to the residue and extracted with ethyl acetate. The organic layer was washed with brine, dried... | CCOC(=O)c1ccc(-n2ccnc2C(C)C)c([N+](=O)[O-])c1 | null | 81.7 | null |
83,273 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | C[O:2][C:3](=O)[CH2:4][N:5]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]1[Cl:11].[NH3:13]>CCOCC>[Cl:11][C:6]1[N:5]([CH2:4][C:3]([NH2:13])=[O:2])[C:9]([Cl:10])=[CH:8][CH:7]=1 | N | COC(=O)Cn1c(Cl)ccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl(2,5-dichloro-1H-pyrrol-1-yl)acetate (0.5 g), in ether (3 cm3), and concentrated aqueous ammonia solution (3 cm3) was stirred at room temperature overnight in a stoppered flask. The precipitated crystalline product was collected by filtration and washed with ether to give 0.07 g of title compound. Th... | NC(=O)Cn1c(Cl)ccc1Cl | null | null | null |
10,850 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[CH:6]2.[Mg].[C:20](=[O:22])=[O:21].[Cl-].[NH4+]>C(OCC)C>[C:13]1([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][C:20]([OH:22])=[O:21])[CH:4]=3)[N:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:1... | BrCc1ccc2nc(-c3ccccc3)ccc2c1 | O=C=O | null | [Cl-] | [Mg] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | The Grignard compound is prepared in the customary manner from 5 g of 6-bromomethyl-2-phenyl-quinoline and magnesium in 30 ml of diethyl ether. It is added to a solution of solid carbon dioxide in 100 ml of diethyl ether. At the same time a further quantity of solid carbon dioxide is added in portions to the reaction s... | O=C(O)Cc1ccc2nc(-c3ccccc3)ccc2c1 | null | null | null |
1,695,242 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][NH2:10].[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:18]=[C:19]([C:21](OCC)=[O:22])[N:20]=2)[CH:17]=1>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:18]=[C:19]([C:21]([NH:10][CH2:9][C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])=[O:22])[N:20]=2)[CH:17]=1 | CCOC(=O)c1cn2cc(Br)ccc2n1 | NCc1c(F)cccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by essentially following the same procedures described for Intermediate I, using (2,6-difluorophenyl)methanamine and ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate as starting materials. | O=C(NCc1c(F)cccc1F)c1cn2cc(Br)ccc2n1 | null | null | null |
617,454 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[CH:11]=[CH:12]/[C:13]1[N:18]=[C:17](O)[CH:16]=[C:15]([CH3:20])[N:14]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:17]1[CH:16]=[C:15]([CH3:20])[N:14]=[C:13]([CH:12]=[CH:11][C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[N:18]=1 | COc1ccc(/C=C/c2nc(C)cc(O)n2)c(OC)c1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 12c), by heating (E)-2-[2-(2,4-dimethoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (0.33 g, 1.22 mmol) in POCl3 (2.24 ml, 24.5 mmol) at 130° C. for 4.5 h there was obtained 4-chloro-2-[2-(2,4-dimethoxy-phenyl)-vinyl]-6-methyl-pyrimidine (0.21 g, 60%) as a light yellow solid. EI mass spectrum, m/e: 29... | COc1ccc(C=Cc2nc(C)cc(Cl)n2)c(OC)c1 | null | 59.2 | null |
1,735,794 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][N:15]=[CH:16]3)=[CH:11][CH:10]=2)O1.[NH2:20][C:21]1[C:30]2[C:25](=[C:26](Br)[C:27]([CH3:31])=[CH:28][CH:29]=2)[N:24]=[N:23][C:22]=1[C:33]([NH2:35])=[O:34]>>[NH2:20][C:21]1[C:30]2[C:25](=[C:26]([C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][N:15]=[CH:16]4)=[CH:11]... | Cc1ccc2c(N)c(C(N)=O)nnc2c1Br | CC1(C)OB(c2ccc3ccncc3c2)OC1(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to EXAMPLE 1 using 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (500 MHz, CD3OD) δ ppm 2.30-2.36 (m, 3 H), 7.72-7.79 (m, 2 H), 7.94 (d, J=5.86 Hz, 1 H), 8.07-8.14 (m, 2 H), 8.22-8.31 (m, 1 H), ... | Cc1ccc2c(N)c(C(N)=O)nnc2c1-c1ccc2ccncc2c1 | null | null | null |
80,246 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[OH-].[Na+].[CH2:20](O)[CH3:21]>>[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:20][CH3:21])=[O:4] | CCCCCCCCC(N)C(=O)O | CCO | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | 2 | 2-Aminodecanoic acid (J. Am. Chem. Soc., 1946, 68, 450) (16.0 g) was added in portions to a cooled (-10° C.) mixture of absolute ethanol (70 ml) and thionyl chloride (6 ml) with stirring. The resulting solution was set aside for 2 hours, at room temperature, refluxed for 1 hour, cooled, poured into ice-water, and the p... | CCCCCCCCC(N)C(=O)OCC | null | 75 | null |
16,328 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:27])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([CH2:20]O)=[N:18][N:17]=[C:16]1[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25].[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N... | CN(C)CCc1nnc(CO)n1-c1ccccc1C(=O)c1ccccc1Cl | O=C1NC(=O)c2ccccc21 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | In the manner given in Example 1B, 2'-chloro-2-[3-[2-(dimethylamino)ethyl]-5-(hydroxymethyl)-4H-1,2,4-triazol-4-yl]benzophenone in tetrahydrofuran is treated with phthalimide, triphenylphosphine and diethylazodicarboxylate to give 2'-chloro-2-[3-[2-(dimethylamino)-ethyl]-5-(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benz... | CN(C)CCc1nnc(CN2C(=O)c3ccccc3C2=O)n1-c1ccccc1C(=O)c1ccccc1Cl | null | null | null |
1,660,465 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]([F:19])([CH3:18])[CH2:3][O:4][C:5]1[C:6]([CH3:17])=[CH:7][C:8]([C:11](N(OC)C)=[O:12])=[N:9][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[F:19][C:2]([F:1])([CH3:18])[CH2:3][O:4][C:5]1[C:6]([CH3:17])=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1 | CON(C)C(=O)c1cc(C)c(OCC(C)(F)F)cn1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared in >99% yield (1.01 g, pale orange solid) from 5-(2,2-difluoropropoxy)-N-methoxy-N,4-dimethylpicolinamide (1.25 g, 4.57 mmol, Step-4) and lithium aluminum hydride (87 mg, 2.3 mmol) in a similar manner to Step-2 of Amine-3. | Cc1cc(C=O)ncc1OCC(C)(F)F | null | 99 | null |
1,579,337 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl.[CH3:2][C:3]1[N:4]=[CH:5][O:6][C:7]=1[CH2:8][N:9]1[C:14]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:17][C:13]=2[C:12](=[O:24])[N:11]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:10]1=[O:31].[CH2:32]([O:34][C:35]1[C:44]([O:45][CH3:46])=[CH:43][C:42]2[C:41]([C:47]3[CH:55]=[CH:54][C:50]([C:... | CCOc1cc2c(cc1OC)C(c1ccc(C(=O)O)cc1)=N[C@@H]1CCSC[C@H]21 | Cc1ncoc1Cn1c(=O)n(C2CCNCC2)c(=O)c2sc(-c3ccccc3)cc21 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | 1-[(4-Methyl-1,3-oxazol-5-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (253 mg; compound B94) is reacted with 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (207 mg; compound C10) and HATU (257 mg) in DCM (7 ml) in... | CCOc1cc2c(cc1OC)C(c1ccc(C(=O)N3CCC(n4c(=O)c5sc(-c6ccccc6)cc5n(Cc5ocnc5C)c4=O)CC3)cc1)=N[C@@H]1CCSC[C@H]21 | null | null | null |
674,616 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1[CH:17]=O>N1CCCCC1.C(O)C>[CH3:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1[CH:17]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10] | Cc1cc[nH]c1C=O | O=C1Cc2ccccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCNCC1 | null | null | null | null | null | null | null | null | null | 90 | 3 | A reaction mixture of 133.0 mg of oxindole, 130.9 mg of the 3-methylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90° C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 150.9 mg (67%) of the title compound as a yellow solid. | Cc1cc[nH]c1C=C1C(=O)Nc2ccccc21 | null | 67.4 | null |
1,726,388 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2].Cl.Cl.[CH3:27][C@H:28]1[CH2:33][NH:32][CH2:31][CH2:30][N:29]1[CH2:34][CH2:35][CH3:36]>>[OH:14][C:13]1[N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([N:32]3... | Cc1cc(C#N)ccc1-c1cnn(-c2ccc(C(=O)O)cn2)c1O | CCCN1CCNC[C@@H]1C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and (S)-2-methyl-1-propylpiperazine dihydrochloride. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.86 (t, J=7.32 Hz, 3H) 0.90-1.15 (m, 3H) 1.35-1.56 (m, 2H) 2.31-2.41 (m, 2H) 2.43 (s, 3H) ... | CCCN1CCN(C(=O)c2ccc(-n3ncc(-c4ccc(C#N)cc4C)c3O)nc2)C[C@@H]1C | null | null | null |
1,577,981 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[N:20]=[C:19]([CH3:21])[NH:18][N:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:28][C:29]1[CH:34]=[C:33]([CH2:35]Cl)[CH:32]=[CH:31][N:30]=1>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]=[C:14]([C:16]3[N:2... | Cc1nc(-c2nc(-c3ccc(C(C)(C)C)cc3)no2)n[nH]1 | ClCc1ccnc(Cl)c1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 0.08 | 3-(4-(tert-Butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole (140 mg, 0.495 mmol) was placed in DMF (10 mL) and Cs2CO3 (193 mg, 0.594 mmol) was added. The reaction was stirred for 5 min and 2-chloro-4-(chloromethyl)pyridine (96 mg, 0.594 mmol) was added. The reaction was stirred at 45° C. overnight and ... | Cc1nc(-c2nc(-c3ccc(C(C)(C)C)cc3)no2)nn1Cc1ccnc(Cl)c1 | null | 44.5 | null |
151,143 | ord_dataset-772de90433b44abbbacf9b316b845c31 | null | 1986-01-01T00:12:00 | true | N12CCCN=C1CCCCC2.Cl[C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[C:14]=1[NH:25][C:26](=[O:29])[CH2:27][CH3:28].[CH3:30][O:31][CH2:32][CH2:33][OH:34]>>[C:26]([NH:25][C:14]1[C:15](=[O:24])[C:16]2[C:21]([C:22](=[O:23])[C:13]=1[O:34][CH2:33][CH2:32][O:31][CH3:30])=[CH:20][CH:19]=[CH:1... | CCC(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O | COCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | 0 | 8 | 15.2 g (0.1 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 50 ml of ethylene glycol monomethyl ether are added to a suspension of 26.35 g (0.1 mol) of 3-chloro-2-propionylamino-1,4-naphthoquinone in 100 ml of ethylene glycol monomethyl ether, and the mixture is stored at room temperature overnight. After cooling to 0° C... | CCC(=O)NC1=C(OCCOC)C(=O)c2ccccc2C1=O | null | null | null |
1,698,338 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([N:16]2[CH2:27][CH2:26][C:19]3([C:23](=[O:24])[N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)[C:9]=1[Cl:28])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[C:12]([CH:11]=[C:10]([N:16]2[CH2:27][CH2:26][C:19]3([C:23](=[O:24])[N:22]([CH3:25])[CH2:... | CN1CCC2(CCN(c3cc(C#N)cc(NC(=O)OC(C)(C)C)c3Cl)CC2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | tert-butyl-(2-chloro-5-cyano-3-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl)carbamate (336 mg, 0.802 mmol) in DCM (3 mL) was treated with TFA (1.174 mL, 15.24 mmol) at room temperature for 2 h. Solvent was evaporated and the residue was redissolved in DCM and concentrated again. The reaction mixture was diluted... | CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O | null | 70 | null |
1,344,251 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [O:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C>>[O:11]=[C:6]1[C:3]2[CH:4]=[CH:5][O:1][C:2]=2[CH2:10][CH2:9][CH2:8][CH:7]1[C:16]([O:15][CH3:14])=[O:17] | O=C1CCCCc2occc21 | COC(=O)OC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5,6,7,8-Tetrahydro-cyclohepta[b]furan-4-one (J. Chem. Soc., Perkin Trans. 1, 1980, 2081-2083) (0.1 g, 0.7 mmol) in dimethylcarbonate (2 mL) was treated with a 60% dispersion of sodium hydride (0.06 g, 0.15 mmol) as described in Example 1A to yield the title product. NMR in CDCl3 indicates a 70:30 mixture of keto and en... | COC(=O)C1CCCc2occc2C1=O | null | null | null |
1,089,141 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][NH2:11]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[N:11]/[CH3:10])[CH:7]=[CH:8][CH:9]=1 | O=Cc1cccc(Cl)c1 | CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 3-chloro-benzoaldehyde (Aldrich, 97%) (4.21 g, 30.0 mmol) and methyl amine (2.0 M in THF, Aldrich, 22.5 mL, 45.0 mmol) in CH2Cl2 (50 mL) was stirred at rt overnight. The reaction mixture was concentrated and the residue was dried under reduced pressure to afford [[1-(3-chloro-phenyl)-meth-(E)-ylidene]-meth... | C/N=C/c1cccc(Cl)c1 | null | 99.8 | null |
1,261,378 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=O.Cl.[NH2:17][OH:18]>C(O)C.O>[Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[N:17][OH:18] | NO | CC(C)(C)Sc1c(C=O)ccc(I)c1Br | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-bromo-2-tert-butylsulfanyl-4-iodo-benzaldehyde (1.5 g, 3.8 mmol) and hydroxylamine hydrochloride in ethanol (20 mL) and water (4 mL) was heated to reflux for 2 h. The reaction mixture was cooled and concentrated. The residue was treated with water (40 mL) and then saturated aqueous sodium bicarbonate sol... | CC(C)(C)Sc1c(C=NO)ccc(I)c1Br | null | 70 | null |
833,760 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | C(#N)C.Br[C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]([O:30][CH3:31])=[CH:20][C:13]=3[N:14]([CH3:19])[C:15](=[O:18])[CH2:16][N:17]=2)[CH:8]=[CH:9][CH:10]=1.[C:32]1(C#C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu](I)I.Cl[Pd]C... | C#Cc1ccccc1 | COc1cc2c(cc1-c1ccccc1)C(c1cccc(Br)c1)=NCC(=O)N2C | null | Cl[Pd]Cl | I[Cu]I | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 50 | 16 | To 10 mL of degazed acetonitrile, 5-(3-bromo-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one Example 62 (200 mg, 0.46 mmol), phenylacetylene (715 μL, 2.30 mmol), copper iodide (15 mg, 0.08 mmol), triphenylphosphine (30 mg, 0.11 mmol), PdCl2 (10 mg, 0.06 mmol) and triethylamine (0.9 mL) were ... | CCCCC#Cc1cccc(C2=NCC(=O)N(C)c3cc(OC)c(-c4ccccc4)cc32)c1 | null | 90 | null |
808,166 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [Si:1]([O:8][CH2:9][C@@H:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:11](N(OC)C)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[C... | CON(C)C(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)OC(C)(C)C | Br[Mg]c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 1 | (R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-1 (methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (22) (2.2 g, 6.0 mmol, 1.0 equiv.) was added to a 250 mL RBF followed by THF (60 mL). The mixture was cooled to 0° C. via an ice bath and a 1.0 M solution of PhMgBr in THF (18.0 mL, 18.0 mmol, 3.0 equiv.) was added over 8 m... | CC(C)(C)OC(=O)N[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)c1ccccc1 | null | 89 | null |
282,524 | ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07 | null | 1993-01-01T00:12:00 | true | [CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[Cl:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Cl)[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOCC>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:22][C:18]1[CH:19]=[CH:20][C... | COC(=O)CCc1ccccc1O | ClCc1cccc(CCl)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOCC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1.8 g (10 mmol) of 2-hydroxybenzenepropanoic acid methyl ester, 14 g (80 mmol) of α,α'-dichloro-m-xylene, 4.25 g (30.8 mmol) of anhydrous, granular potassium carbonate, and 70 mL of acetonitrile was stirred and refluxed for 4 hr. After being cooled, the resulting mixture was diluted with 200 mL of ether an... | COC(=O)CCc1ccccc1OCc1cccc(CCl)c1 | null | 54.6 | null |
655,786 | ord_dataset-f5d908a6dcb44353a706166b5e9f7f88 | null | 2004-01-01T00:12:00 | true | C([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([Cl:14])=[CH:13][C:8]=2[C:7]=1[Cl:15])=[O:5])C.Cl>>[Cl:14][C:12]1[S:11][C:9]2[NH:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([Cl:15])[C:8]=2[CH:13]=1 | CCOC(=O)c1[nH]c2sc(Cl)cc2c1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | 2,4-Dichloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester was hydrolyzed according to Procedure E (reflux for 12 h before allowing to cool to room temperature; acidification with concentrated HCl; no purification). | O=C(O)c1[nH]c2sc(Cl)cc2c1Cl | null | null | null |
1,510,957 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [N+:1]([C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][CH:10]=1)=[O:7])([O-])=O.O.O.[Sn](Cl)Cl>CCO>[NH2:1][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[S:1... | Cc1ccc2nc(-c3ccc(NC(=O)c4ccccc4[N+](=O)[O-])cc3)sc2c1 | null | null | Cl[Sn]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | Prepared as described in the Nitro Reduction section using 2-nitro-N-[4-(6-methylbenzothiazol-2-yl)-phenyl]-benzamide (0.5 g, 1.28 mmol) and tin (II) chloride dihydrate (1.45 g, 6.42 mmol) in EtOH (50 ml) to give the title compound (0.063 g, 14%) as a tan needles after recrystallisation from EtOH. | Cc1ccc2nc(-c3ccc(NC(=O)c4ccccc4N)cc3)sc2c1 | null | 13.7 | null |
671,942 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [H-].[Na+].[CH:3]1([CH2:9][CH2:10][CH2:11][C@@H:12]([C:21]2[O:25][N:24]=[C:23]([CH2:26][OH:27])[N:22]=2)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:29][C:30]([NH2:32])=[O:31]>O1CCCC1.C(OCC)(=O)C>[NH2:32][C:30](=[O:31])[CH2:29][O:27][CH2:26][C:23]1[N:22]=[C... | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)c1nc(CO)no1 | NC(=O)CBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A suspension of sodium hydride 60% suspension in mineral oil (51 mg, 1.28 mmol) in anhydrous tetrahydrofuran (3 ml) was cooled to 0° C. and treated with a solution of tert-butyl (3R)-6-cyclohexyl-3-[3-(hydroxymethyl)-1,2,4-oxadiazol-5-yl]hexanoate (Preparation 85) (105 mg, 0.30 mmol) in anhydrous tetrahydrofuran (3 ml)... | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)c1nc(COCC(N)=O)no1 | null | 268.6 | null |
394,159 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH2:1]([C:3]1[C:8]([CH2:9][Cl:10])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[C:8]([CH2:9][Cl:10])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:19])[CH3:2] | O=C(OO)c1cccc(Cl)c1 | CCc1ncccc1CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | 2 | The 2-ethyl-3-chloromethylpyridine (2.4 g, 15.4 mmol) was dissolved in CHCl3 (100 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 4.2 g) was added in small portions. The reaction was stirred for 2 hours. The reaction was extracted twice with saturated aqueous sodium bicarbonate (100 mL). The or... | CCc1c(CCl)ccc[n+]1[O-] | null | null | null |
189,187 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22]C(O)=O)[CH:9]=2)=[CH:4][CH:3]=1.CC[N:28](CC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH... | COc1ccc(-n2nc(CCC(=O)O)cc2-c2ccc(Cl)cc2)cc1 | CCN(CC)CC | null | [N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of the acid 12 (1.0 g, 2.8 mM) in benzene (25 ml) was added Et3N (0.39 ml, 2.8 mM) and diphenylphosphoryl azide (0.60 ml, 2.8 mM). After stirring overnight at room temperature, the reaction mixture was heated to 70° C. for 1.5 hours, cooled and concentrated in vacuo. Dioxane (2 ml), followed by a solution... | COc1ccc(-n2nc(CCN)cc2-c2ccc(Cl)cc2)cc1 | null | null | null |
1,086,730 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14]>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14] | COC(=O)c1ccc(CO)cc1NC(C)=O | null | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 50 | 18 | To a suspension of 2-acetylamino-4-hydroxymethyl-benzoic acid methyl ester (1.7 g, 7.62 mmol) in DCM (40 mL) was added MnO2 (1.32 g, 2 equiv) and the resulting mixture was stirred at 50° C. for 18 h. MnO2 (0.66 g, 1 equiv) was added and the mixture was stirred at 50° C. for 2 h. The mixture was cooled down, filtered th... | COC(=O)c1ccc(C=O)cc1NC(C)=O | null | 68.2 | null |
1,166,327 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[N:8]=1)=O.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31]N>>[CH3:23][S:20]([C:16]1[CH:15]=[C:14]([N:9]2[CH:10]=[CH:11][C:12](=[O:13])[C:7]([C:5]3[N:31]([C:26]4[CH... | NNc1ccccn1 | CN(C)/C=C/C(=O)c1nn(-c2cccc(S(C)(=O)=O)c2)ccc1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Reaction of 3-((E)-3-dimethylamino-acryloyl)-1-(3-methansulfonyl-phenyl)-1H-pyridazin-4-one (A-7) and pyridin-2-yl-hydrazine according to example 43 gave the desired product. MS: M=393.9 (M+H)+ | CS(=O)(=O)c1cccc(-n2ccc(=O)c(-c3ccnn3-c3ccccn3)n2)c1 | null | null | null |
1,451,279 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:10].[Na+]>S(=O)(=O)(O)O>[C:2]1([CH2:1][C:8]([NH2:9])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | N#CCc1ccccc1 | [OH-] | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 8 | Benzyl cyanide (5 g, 42.7 mmol) was added slowly to concentrated sulfuric acid (20 ml) cooled by water-ice bath. The solution was stirred overnight. The reaction mixture was poured into ice water and neutralized with 20% NaOH. The aqueous phase was extracted by ethyl acetate (3×15 mL). The combined organic layers were ... | NC(=O)Cc1ccccc1 | null | 78 | null |
820,592 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [NH2:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[CH2:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[CH3:23]C(C)(C)C(C(OC(C(=O)C(C)(C)C)=O)=O)=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:19]([O:20][CH2:21][CH3:23])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C... | C=C1CC[C@H]2[C@@H]3CCc4cc(N)c(OC)cc4[C@H]3CC[C@]12C | CC(C)(C)C(=O)C(=O)OC(=O)C(=O)C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 0.67 | Representative preparation of 3-formamide estrane derivatives: Preparation of 3-formamide-17-methylene-2-methoxyestra-1,3,5(10)-triene (Compound #88): 3-Amino-17-methylene-2-methoxyestra-1,3,5(10)-triene (293 mg, 0.99 mmol) was dissolved in chloroform (1 mL) and trimethylacetyl formic anhydride (170 mg, 1.30 mmol, prep... | C=C1CC[C@H]2[C@@H]3CCc4cc(N)c(OCC)cc4[C@H]3CC[C@]12C | null | 42.1 | null |
1,573,399 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=O)[C:9]=3[N:8]=2)=[CH:3][CH:2]=1.N1C=CN=C1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][... | NC(=O)c1cccc2[nH]c(-c3ccc(-c4ccccc4)cc3)nc12 | null | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | -30 | 4 | To the solution of 2-biphenyl-4-yl-1H-benzoimidazole-4-carboxylic acid amide (0.24 g, 0.76 mmol) in pyridine (10 mL) was added imidazole (0.11 g, 1.53 mmol). The reaction mixture was cooled to −30° C. and phosphorous oxy chloride (0.3 mL, 3.1 mmol) was added drop wise. The reaction mixture was then stirred at −10° C. f... | N#Cc1cccc2[nH]c(-c3ccc(-c4ccccc4)cc3)nc12 | null | null | null |
755,456 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)O)[C:5]1=[O:24])(=[O:3])[CH3:2].C(Cl)(Cl)(Cl)[Cl:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)... | ClC(Cl)(Cl)Cl | CC(=O)c1ccc2c(c1)C(=C(O)c1cnccn1)C(=O)N2C(C)=O | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 1.2 g (3.7 mmol) 1,5-diacetyl-3-[pyrazin-2-yl-hydroxy-methylidene]-2-indolinone (Ex. V.23) are dissolved in 50 ml dioxane and refluxed with 2 ml carbon tetrachloride and 2 g triphenylphosphine for 5 h. Then the mixture is left to cool and evaporated down. The residue is chromatographed through a silica gel column with ... | CC(=O)c1ccc2c(c1)C(=C(Cl)c1cnccn1)C(=O)N2C(C)=O | null | null | null |
1,615,454 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Cl.[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[NH2:15])[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11].CCCP(=O)=O.[N:29]1[CH:30]=[CH:31][N:32]2[CH:37]=[C:36]([C:38](O)=[O:39])[CH:35]=[CH:34][C:33]=12.CCN(C(C)C)C(C)C>CCOC(C)=O>[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:16]2[C:... | O=C(O)c1ccc2nccn2c1 | N[C@@H](c1ccc(OC(F)(F)F)c(F)c1)c1ncccc1F | null | CCCP(=O)=O | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of (S)-(3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methanamine hydrochloride (81 mg, 0.238 mmol, Intermediate 6) and EtOAc (3 mL) was added 50% propylphosphonic anhydride in EtOAc (0.28 mL, 0.470 mmol), imidazo[1,2-a]pyridine-6-carboxylic acid (47 mg, 0.290 mmol) and DIPEA (0.12 mL, 0.689 m... | O=C(N[C@@H](c1ccc(OC(F)(F)F)c(F)c1)c1ncccc1F)c1ccc2nccn2c1 | null | null | null |
804,662 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH:14]([S:17]([N:20]1[C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[NH2:32])(=[O:19])=[O:18])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH:14]([S:17]([N:20]1[C:24]2[CH:25]=[C:26]([C:2]3[N:6]([C:7]4[... | Cc1cc(Br)n(-c2ccccc2)n1 | CC(C)S(=O)(=O)n1c(N)nc2ccc(B(O)O)cc21 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOC | null | null | null | null | null | null | null | null | null | 100 | 2 | To a solution of 5-(bromo)-3-(methyl)-1-(phenyl)-pyrazole (264 mg, 1.11 mmol) in 6 mL DME add 1-isopropylsulfonyl-2-amino-benzimidazole-6-boronic acid (694 mg, 2.45 mmol). Add sodium carbonate (354 mg, 3.34 mmol) dissolved in 0.5 mL of water and trans-dichlorobis(triphenylphosphine) palladium (II) (234 mg, 0.33 mmol). ... | Cc1cc(-c2ccc3nc(N)n(S(=O)(=O)C(C)C)c3c2)n(-c2ccccc2)n1 | null | 45.8 | null |
1,334,878 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3S(C3C=CC(C)=CC=3)(=O)=O)=[C:15]([C:32]3[O:33][C:34]([CH2:37]Cl)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.[OH-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[C:7]([NH:8][S:9... | C1COCCN1 | Cc1ccc(S(=O)(=O)n2ncc3c(-c4nnc(CCl)o4)cc(-c4cnc(Cl)c(NS(C)(=O)=O)c4)cc32)cc1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 90 | 2 | N-(2-Chloro-5-{4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-[(4-methylphenyl)sulfonyl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (30 mg, 0.051 mmol) and morpholine (1 ml, 11.48 mmol) were placed a vial and heated in a microwave at 90° C. for 15 mins. The morpholine was blown off under a stream of nitrogen and the ... | CS(=O)(=O)Nc1cc(-c2cc(-c3nnc(CN4CCOCC4)o3)c3cn[nH]c3c2)cnc1Cl | null | 20 | null |
1,712,497 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:23])=[CH:8][C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:23])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3] | C=CCON1C(=O)N2C[C@H]1C(C)=C[C@H]2CO[Si](C)(C)C(C)(C)C | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 13, 1.76 g, 5.20 mmol) in THF (20 mL) at 0° C. was added tetrabutylammonium fluoride (1M in THF) (6.76 mL, 6.76 mmol). Stirred at 0° C. for 1 hour. The reaction mixture was concentra... | C=CCON1C(=O)N2C[C@H]1C(C)=C[C@H]2CO | null | 91.8 | null |
1,566,397 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[F:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[C:31]([F:38])[N:30]=1>>[F:28][C:29]1[CH:34]=[C:33]([C:2]2[N:3]=[C:4]([N:22]3[CH2:... | OB(O)c1cc(F)nc(F)c1 | CS(=O)(=O)N1CCN(Cc2cc3nc(Cl)nc(N4CCOCC4)c3s2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidine was reacted with 2,6-difluoropyridine-4-boronic acid in General Procedure A. Purification on silica yielded 2-(2,6-difluoro-pyridin-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine. | CS(=O)(=O)N1CCN(Cc2cc3nc(-c4cc(F)nc(F)c4)nc(N4CCOCC4)c3s2)CC1 | null | null | null |
1,687,634 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [F:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:11]=2)=[C:6]([CH3:25])[C:5]([OH:26])=[CH:4][CH:3]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:26])=[C:6]([CH3:25])[C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([C:1... | Cc1cc(C(=O)Nc2c(F)ccc(O)c2C)cc(-c2cccc(F)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide (394 mg, 1.11 mmol, 1.0 eq) in THF (15 mL) under N2 was added a solution of BH3 (1M in THF, 6.7 mL, 6.7 mmol, 6.0 eq) dropwise The reaction mixture was heated at 60° C. overnight. After cooling, the reaction was quenched by ad... | Cc1cc(CNc2c(F)ccc(O)c2C)cc(-c2cccc(F)c2)c1 | null | 86 | null |
1,367,015 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH3:1][C:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH2:5][CH2:6][N:7]1[C@H:12]2[CH2:13][CH2:14][C@@H:8]1[CH2:9][CH:10]([N:15]1[C:19]([CH:20]([CH3:22])[CH3:21])=[N:18][N:17]=[C:16]1[CH3:23])[CH2:11]2)[CH2:3][NH2:4].C(N(C(C)C)CC)(C)C.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(... | Cc1nnc(C(C)C)n1C1C[C@H]2CC[C@@H](C1)N2CCC(C)(CN)c1ccccc1 | O=S(=O)(Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of intermediate 24 (158 mg, 0.4 mmol) in CH2Cl2 (4 mL) was added diisopropylethylamine (0.175 mL, 1.0 mmol) followed by phenylsulfonyl chloride (0.065 mL, 0.5 mmol) and the solution stirred at room temperature under nitrogen atmosphere for 18 h. The reaction was concentrated in vacuo and purified by silic... | Cc1nnc(C(C)C)n1C1C[C@H]2CC[C@@H](C1)N2CCC(C)(CNS(=O)(=O)c1ccccc1)c1ccccc1 | null | 70 | null |
1,218,158 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [OH:1][CH2:2][CH2:3][C:4]1([OH:7])[CH2:6][CH2:5]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:1][CH2:2][CH2:3][C:4]1([OH:7])[CH2:6][CH2:5]1)(=[O:18])=[O:17] | OCCC1(O)CC1 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | -10 | 0.5 | A mixture of 1-(2-hydroxyethyl)cyclopropanol (86 mg, 0.843 mmol) and triethylamine (136 mg, 1.35 mmol, Shantou Xilong chemical factory) in 10 mL of dichloromethane was stirred at −10° C. for 30 min. Methanesulfonyl chloride (106 mg, 0.927 mmol, Shanghai Haiqu chemical Ltd.) was then added via a syringe. The reaction wa... | CS(=O)(=O)OCCC1(O)CC1 | null | null | null |
663,917 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | C(OC([NH:11][C:12]1[CH:13]=[C:14]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:15]=[CH:16][C:17]=1[C:18]([O:20]C(C)(C)C)=[O:19])=O)C1C=CC=CC=1.[OH:29][C:30]1[CH:31]=[C:32]([NH:46][C:47](OC2C=CC=CC=2)=[O:48])[C:33](=[CH:44][CH:45]=1)[C:34](OCC1C=CC=CC=1)=[O:35]>>[OH:29][C:30]1[CH:31]=[C:32]2[C:33]([C:34](=[O:35])[N:28]([S:25]([... | O=C(Nc1cc(O)ccc1C(=O)OCc1ccccc1)Oc1ccccc1 | CC(C)(C)OC(=O)c1ccc(S(N)(=O)=O)cc1NC(=O)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 620 mg (1.53 mmol) of 3-benzyloxycarbonylamino-4-t-butoxycarbonylbenzenesulfonamide and 550 mg (1.51 mmol) of benzyl 4-hydroxy-2-N-phenoxycarbonylanthranilate were treated in the same way as in Example 17 to obtain 25 mg (yield 4%: 4 steps) of the above-identified compound. Properties: colorless crystal, Melting point:... | Nc1cc(S(=O)(=O)n2c(=O)[nH]c3cc(O)ccc3c2=O)ccc1C(=O)O | null | 4 | null |
755,215 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:34]1([CH2:40][CH2:41]O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:41][CH2:40][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36... | OCCC1CCCCC1 | Clc1nccc(Nc2ccccc2)n1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 2-Chloro-4-anilinopyrimidine (Reference Example A-9, 700 mg, 3.4 mmol) was dissolved in DCM (70 ml), triphenyl phosphine (1.07 g, 4.1 mmol) and 2-cyclohexyl ethanol (0.57 ml, 4.1 mmol) were added followed by dropwise addition of DEAD (0.646 ml, 4.1 mmol). After 1 hour additional triphenyl phosphine (0.5 g, 2 mmol), 2-c... | Clc1nccc(N(CCC2CCCCC2)c2ccccc2)n1 | null | 34.3 | null |
132,176 | ord_dataset-232d09663ed349c2a1fb1f05d411eae0 | null | 1985-01-01T00:07:00 | true | [Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]([O-:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].[OH-].[K+].C(O)C>O>[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11] | O=C([O-])COc1cc2ccsc2c(Cl)c1Cl | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of 7.5 g of ethyl[(6,7-dichlorobenzo[b]thien-5-yl oxy]acetate, 15 g of potassium hydroxide pellets, 125 ml of ethanol and 125 ml of water is refluxed for 1 hour. Ethanol is removed under reduced pressure at 60° and the aqueous suspension is acidified with conc hydrochloric acid. The slurry is stirred at room ... | O=C(O)COc1cc2ccsc2c(Cl)c1Cl | null | null | null |
1,387,835 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:33])=[N:13][C:14]2[N:15]([N:23]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[CH:25]=2)[C:16]=1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:33])=[N:13][C:14... | COC(=O)[C@@H](OC(C)(C)C)c1c(C)nc2cc(-c3cccc(Cl)c3)nn2c1C1CCCCC1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-cyclohexyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.048 g, 0.102 mmol) and 1M NaOH (1.021 ml, 1.021 mmol) in MeOH (5 mL) was heated at reflux for h. Then, cooled, neutralized with 1M HCl (0.8 mL), concentrated and the residue was taken up in Et2O ... | Cc1nc2cc(-c3cccc(Cl)c3)nn2c(C2CCCCC2)c1[C@H](OC(C)(C)C)C(=O)O | null | 90.2 | null |
1,443,079 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])=[O:4].[Br:25]N1C(=O)CCC1=O>>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:25])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21... | COC(=O)c1ncc2c(Oc3ccccc3OC)cccc2c1O | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized from 4-hydroxy-8-(2-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester and N-bromosuccinimide in analogy to example 19e; MS-(+)-ion: M+1, 79Br/81Br=404.3 and 406.3. | COC(=O)c1nc(Br)c2c(Oc3ccccc3OC)cccc2c1O | null | null | null |
826,028 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | Cl.Cl.[F:3][C:4]([F:9])([CH2:7][NH2:8])[CH2:5][NH2:6].Cl.[NH2:11][C:12](N)=N.C[O-].[Na+]>>[F:3][C:4]1([F:9])[CH2:7][NH:8][C:12]([NH2:11])=[N:6][CH2:5]1 | NCC(F)(F)CN | N=C(N)N | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 150 | null | A mixture of 2.95 g (16.12 mmol) of 2,2-difluoro-1,3-propandiamine dihydrochloride (Tetrahedron (1994) 50(29), 8617-8632), 1.54 g (16.12 mmol) of guanidine hydrochloride and 2.19 g (32.23 mmol) of sodium methylate was heated at 150° C. during 18 h. The cooled mixture was used as such in the subsequent step. | NC1=NCC(F)(F)CN1 | null | null | null |
488,100 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [F:1][CH:2]1[CH2:15][C:14]2[CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:6][CH:7]=2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][C:12]([O:1... | CCCCCCOc1ccc2c(c1)CC(F)c1cc(OCCCCCC)ccc1-2 | null | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | From 9-fluoro-2,7-dihexyloxy-9,10-dihydrophenanthrene by dehydrogenation with DDQ in toluene. | CCCCCCOc1ccc2c(c1)cc(F)c1cc(OCCCCCC)ccc12 | null | null | null |
751,459 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | Cl.[CH2:2]([C:6]1[N:7]([NH2:19])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:3][CH2:4][CH3:5].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(C)C>[CH:20](=[N:19][N:7]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:6]1[CH2:2][CH2:... | O=Cc1ccccc1 | CCCCc1nc2cnc3ccccc3c2n1N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-butyl-1H-imidazo[4,5-c]quinolin-1-amine hydrochloride (503 mg, 1.82 mmol) in 10 mL of isopropanol was treated with benzaldehyde (220 μL, 2.17 mmol) and 200 mg of DOWEX W50-X1 acid resin. The reaction mixture was heated to reflux overnight. The reaction mixture was filtered, and the filtrate was treated ... | CCCCc1nc2cnc3ccccc3c2n1N=Cc1ccccc1 | null | 96.2 | null |
1,386,315 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [C:1]([O:5][C:6]([NH:8][C:9]([C:21]([O:23]CC)=[O:22])([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>P([O-])([O-])([O-])=O.C(#N)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([C:21]([OH:23])=[O:22])[CH2:15][C:16]([O:18][CH2:1... | CCOC(=O)CC(NC(=O)OC(C)(C)C)(C(=O)OCC)C(=O)OCC | null | null | O=P([O-])([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 30 | 4 | 1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019] was dissolved in a 0.1 mol/L phosphate buffer adjusted to pH 7.5 (90 mL), and the solution was added with a solution of diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate (1.0 g) dissolved in acetonitrile ... | CCOC(=O)C[C@@](NC(=O)OC(C)(C)C)(C(=O)O)C(=O)OCC | null | 108.4 | null |
1,410,604 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]>C(Cl)(Cl)Cl>[Cl:24][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH:19]=[O:20])=[O:15])=[CH:11][... | O=C(NCCCO)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 6 | To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-N-(3-hydroxypropyl)-4-nitrothiophene-2-carboxamide (800 mg, 1.2 mmol) in chloroform (15 mL) was added Dessmartin reagent (611 mg, 1.4 mmol) at 0° C. The resulting reaction mixture was warmed up to ambient temperature and stirred at this temperature for 6 hours. After ... | O=CCCNC(=O)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1 | null | 88.2 | null |
972,975 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [OH:1][CH2:2][C@H:3]([CH3:31])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:30]=[CH:29][NH:28][N:27]=2)=[O:24])[CH:22]=1)[O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1.O>[OH:1][CH2:2][C@H:3]([CH3:31])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][... | CCOC(=O)c1ccc(Oc2cc(O[C@@H](C)CO)cc(C(=O)Nc3cc[nH]n3)c2)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of ethyl 4-{3-[(1S)-2-hydroxy-1-methylethoxy]-5-[(1H-pyrazol-3-ylamino)carbonyl]phenoxy}benzoate (175 mg, 0.4 mmol) in THF (5 mL) and water (1 mL) was treated with 1N sodium hydroxide solution (3 mL) and the reaction stirred at RT for 16 hours. On completion, the solvent was removed in vacuo and 1N citric ac... | C[C@@H](CO)Oc1cc(Oc2ccc(C(=O)O)cc2)cc(C(=O)Nc2cc[nH]n2)c1 | null | 86.8 | null |
1,223,071 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:11][C:12]1[C:13]([F:37])=[C:14]([CH2:19][NH:20][C:21]([C:23]2[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[N:25][C:24]=2[Cl:36])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].N(OC(C)(C)C)=O>C(#N)C.CCOC(C)=O>[Cl:36][C:24]1[N:25]=[C... | C[Si](C)(C)CCOCn1cnc(Cl)c1C(=O)NCc1ccc(Cl)c(Oc2cc(C#N)c(F)cc2N)c1F | null | null | CC(C)(C)ON=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of N-({3-[(2-amino-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (110 mg, 0.194 mmol) in Acetonitrile (8 ml) was added tert butyl nitrite (0.046 ml, 0.387 mmol) and the reaction mixture was stirred at RT for 1 hour.... | C[Si](C)(C)CCOCn1cnc(Cl)c1C(=O)NCc1ccc(Cl)c(Oc2ccc(F)c(C#N)c2)c1F | null | 45.9 | null |
1,682,502 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([C:4]1([C:7]2[CH:38]=[CH:37][CH:36]=[CH:35][C:8]=2[CH2:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([NH:27]C(=O)OC(C)(C)C)[CH3:26])=[CH:21][CH:20]=3)[N:12]=2)[CH2:6][CH2:5]1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][CH:25]([C:22]1[CH:21]=[CH:20][C:19]([NH... | CC(NC(=O)OC(C)(C)C)c1ccc(Nc2ncc(Cl)c(CCc3ccccc3C3(C(N)=O)CC3)n2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of tert-butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate 24 (0.012 g, 0.022 mmol) in DCM (1 mL) was added trifluoroacetic acid (0.5 mL). The mixture was stirred at ambient temperature for 2 hours before the volatiles were removed in vacuo. The crude... | CC(N)c1ccc(Nc2ncc(Cl)c(CCc3ccccc3C3(C(N)=O)CC3)n2)cc1 | null | 93.8 | null |
1,671,354 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([CH:3]([OH:33])[CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]4)[C:7]=3[C:6]1=2)#[N:2].N1C=CN=C1.[C:39]([Si:43](Cl)([CH3:45])[CH3:44])([CH3:42])([CH3:41])[CH3... | CN(C(=O)OC(C)(C)C)C1CCC(Oc2ncnc3sc4c(c23)[C@@H](CC(O)C#N)CC4)CC1 | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 20 | 2 | Reference: For the preparation of the starting material compound 48.1, please refer to the experimental procedure for the synthesis of compound I-57. Into a 50-mL round-bottom flask, a solution of tert-butyl N-(4-[[(3R)-3-(2-cyano-2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-y... | CN(C(=O)OC(C)(C)C)C1CCC(Oc2ncnc3sc4c(c23)[C@@H](CC(C#N)O[Si](C)(C)C(C)(C)C)CC4)CC1 | null | 93.3 | null |
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