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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
603,317 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16]2)(=[O:12])=[O:11].[OH:23][C@@H:24]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[C:31]([CH3:38])=[C:32]([CH:36]=O)[NH:33][C:34]=2[CH3:35])[CH2:25]1>C(O)C.N1CCCCC1>[Cl:8][C:4]1[CH:5]=[... | Cc1[nH]c(C=O)c(C)c1CN1CC[C@@H](O)C1 | O=C1Cc2cc(S(=O)(=O)Cc3c(Cl)cccc3Cl)ccc2N1 | 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 | null | null | 5-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one was condensed with 4-((R)-3-hydroxy-pyrrolidin-1-ylmethyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde in ethanol and piperidine to give the titled compound as a yellow solid. | Cc1[nH]c(/C=C2\C(=O)Nc3ccc(S(=O)(=O)Cc4c(Cl)cccc4Cl)cc32)c(C)c1CN1CC[C@@H](O)C1 | null | null | null |
891,804 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:19][CH2:18][C:15]([C:20](ON3C4C=CC=CC=4N=N3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:43]1([NH2:46])[CH2:45][CH2:44]1>>[CH2:1]([O:8][C:9]([... | N#C[C@@H]1C[C@H](F)CN1C(=O)CN(C(=O)OCc1ccccc1)C12CCC(C(=O)On3nnc4ccccc43)(CC1)CC2 | NC1CC1 | 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 similar manner to Example 4, (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and cyclopropylamine (8.0 μL) were used to obtain (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(N-cyclopropylamino)carbonylbicyclo[2.2.2]oct-1-yl... | N#C[C@@H]1C[C@H](F)CN1C(=O)CN(C(=O)OCc1ccccc1)C12CCC(C(=O)NC3CC3)(CC1)CC2 | null | null | null |
330,575 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | N[C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:4][N:3]=1.C(=O)(O)O.[NH2:28][C:29]([NH2:31])=[NH:30].O>CN(C)C(=O)C>[NH2:30][C:29]1[N:31]=[C:8]([NH2:9])[C:7]2[C:2](=[N:3][CH:4]=[C:5]([C:10]3[CH:15]=[C:14]([C:16]([F:19])([F... | N=C(N)N | N#Cc1nc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cnc1N | null | O=C(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | null | Under a nitrogen atmosphere, a stirred solution of 1.0 gram (0.003 mole) of 2-amino-3-cyano-5-[3,5-di(trifluoromethyl)phenyl]pyrazine and 1.3 grams (0.007 mole) of guanidine carbonate in 10 mL of N,N-dimethylacetamide is heated at about 150° C. for 40 hours. After this time, the reaction mixture is poured into 50 mL of... | Nc1nc(N)c2nc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cnc2n1 | null | null | null |
706,426 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:23])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17](Cl)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2].[F:24][C:25]([F:39])([F:38])[O:26][C:27]1[CH:28]=[C:29]([C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[K+].[K+].[F-].[K+]... | CCOCCCNC(=O)C(CC(C)C)Nc1cc(Cl)nc(Cl)n1 | FC(F)(F)Oc1cccc(-c2c[nH]cn2)c1 | null | O=C([O-])[O-] | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 2-(2,6-dichloro-pyrimidin-4-ylamino)-4-methylpentanoic acid (3-ethoxypropyl)amide (1.5 gram), 4-(3-trifluoromethoxyphenyl)-1H-imidazole (0.99 gram), K2CO3 (1.7 gram) and KF (0.24 gram) in dimethylsulfoxide (40 ml) was heated to 100° C. for 17 hours. The solution was cooled to room temperature, taken up in... | CCOCCCNC(=O)C(CC(C)C)Nc1cc(Cl)nc(-n2cnc(-c3cccc(OC(F)(F)F)c3)c2)n1 | null | 122.2 | null |
817,266 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24](O)=[O:25])[CH2:19][CH2:18]3)=[O:16])[N:13]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=... | O=C(O)CN1CCN(C(=O)Cc2csc(NC(=O)c3ccc(Cl)cc3)n2)CC1 | CN1CCNCC1 | 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 | 22.3 Using general procedure A, (4-{2-[2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetic acid was coupled with 1-methyl piperazine to give 4-chloro-N-[4-(2-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-piperazin-1-yl}-2-oxo-ethyl)-thiazol-2-yl]-benzamide. White solid. MS 505.3 ([M+H]+) | CN1CCN(C(=O)CN2CCN(C(=O)Cc3csc(NC(=O)c4ccc(Cl)cc4)n3)CC2)CC1 | null | null | null |
609,845 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [CH:1]1([NH:5][C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25][CH3:26])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:30]I>CN(C)C=O.Cl>[CH:1]1([N:5]([CH3:30])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[C... | COCc1cc(Cl)c(Oc2ccc(OC)c(C(=O)NC3CCC3)c2)c(Cl)c1 | CI | null | Cl | [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 | 0 | 0.5 | To a solution of the title compound of Step E (170 mg, 0.41 mmol) in dimethylformamide (4 ml) at 0° C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 41 mg, 1 mmol). The resulting slurry mixture was stirred at 0° C. for about 30 minutes and gradually became a brownish-yellow solution. To this s... | COCc1cc(Cl)c(Oc2ccc(OC)c(C(=O)N(C)C3CCC3)c2)c(Cl)c1 | null | 89.1 | null |
261,440 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH:10]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[C:3]2[NH:8][C:9]3[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]=3[C:4]=2[CH:5]=[CH:6][CH:7]=1 | O=C1C=C(Nc2ccccc2F)CCN1 | null | null | [Pd+2] | CC(=O)[O-] | 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 | null | Cupric acetate (2.71 g) was added to a stirred solution of 4-[(2-fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone (1.4 g) and palladium (II) acetate (280 mg) in dry DMF (28 ml) under nitrogen. The mixture was heated at 130° for 1.5 h and the solvent was removed in vacuo. The residue was treated with hot methanol (50 ml... | O=C1NCCc2[nH]c3c(F)cccc3c21 | null | 155.8 | null |
1,373,042 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1.[OH-].[NH4+:14]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:14])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1 | Cn1cc(Br)c2c(Cl)ncnc21 | [NH4+] | null | [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 | 100 | 48 | A suspension of 5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g, 69.0 mmol) in ammonium hydroxide (150 mL, 3852 mmol) was stirred for 2 days at 100° C. in a sealed vessel. The reaction was allowed to cool to room temperature and filtered. The collected solid was washed with Et2O to afford the product 5-brom... | Cn1cc(Br)c2c(N)ncnc21 | null | 79.8 | null |
852,466 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]([OH:6])(=[O:5])[C:2]#[C:3][CH3:4].[CH:7]1[C:19]2[CH:18]([CH2:20]O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:6][CH2:20][CH:18]1[C:19]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:1... | CC#CC(=O)O | OCC1c2ccccc2-c2ccccc21 | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccccn1 | Cc1ccc(S(=O)(=O)O)cc1 | 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 | 0 | 0.25 | First, 9-fluorenylmethyl 2-butynoate was prepared. A mixture of 2-butynoic acid (11.6 g, 138 mmol), 9-fluorenemethanol (35.2 g, 179 mmol), dimethylamino-pyridine-p-toluenesulfonic acid salt (16.3 g, 55 mmol), and anhydrous dichloromethane (210 mL) was cooled to 0° C. under nitrogen, and 1,3-dicyclohexylcarbodiimide (34... | CC#CC(=O)OCC1c2ccccc2-c2ccccc21 | null | 55.3 | null |
146,068 | ord_dataset-4731a430f0af464b83e8b5b145cd2c77 | null | 1986-01-01T00:07:00 | true | [F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl.[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1)([O-:29])=[O:28].C(N(CC)CC)C>CN(C)C=O>[N+:27]([C:30]1[CH:37]=[CH:36]... | O=[N+]([O-])c1ccc(CBr)cc1 | CC1CCc2c(N3CCNCC3)c(F)cc3c(=O)c(C(=O)O)cn1c23 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 10 | A mixture of 9-fluoro-6,7-dihydro-5-methyl-8-(1-piperazinyl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid (Compound [III]), hydrochloride (1.1 g), p-nitrobenzyl bromide (Compound [IV]) (1.87 g) and triethylamine (1.46 g) in N,N-dimethylformamide (50 ml) was heated with stirring at 80°-90° C. for 10 hr. After evap... | CC1CCc2c(N3CCN(Cc4ccc([N+](=O)[O-])cc4)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23 | null | 60 | null |
792,159 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][C:13]([CH3:15])=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:16][C:17]1[CH:18]=[C:19]2[C:24](=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:16][C:17]1[CH:18]=[C:19]2[C... | COc1cccc2c(CC(C)=O)coc12 | Cc1cc(N2CCNCC2)c2ncccc2c1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 6-methyl-8-{4-[2-(7-methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline was prepared by generally following the procedure outlined in example 35, step 2, starting from the 1-(7-methoxy-1-benzofuran-3-yl)acetone (204 mg, 1 mmol) and 6-methyl-8-piperazino quinoline (227.0 mg, 1 mmol) in 1,2-dichloroethane (... | COc1cccc2c(CC(C)N3CCN(c4cc(C)cc5cccnc45)CC3)coc12 | null | null | null |
465,011 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[NH:16][C:15]([CH3:17])=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[CH:19]1([CH2:22]Br)[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][N:16]2[C:12]([C:10](=[O:11])[CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:13][C:14]([CH3:18])=[C:15]2[CH3:17])[... | Cc1cc(C(=O)CCc2ccc(F)cc2)[nH]c1C | BrCC1CC1 | 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 as a pale yellow oil in 64.8% yield in a similar procedure to that described in Referential Example 97 by using 5-[3-(4-fluorophenyl)propionyl]-2,3-dimethylpyrrole and cyclopropylmethyl bromide. | Cc1cc(C(=O)CCc2ccc(F)cc2)n(CC2CC2)c1C | null | 64.8 | null |
163,757 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)=[O:4].[CH3:13][O:14][C:15]1[CH:23]=[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:20][C:16]=1[C:17](O)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]=[C:17]([C:16]3[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:... | COC(=O)c1ccc(N)c(N)c1 | COc1cc(NS(C)(=O)=O)ccc1C(=O)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 | Prepared analogously to Example 14 from 4-methoxycarbonyl-1,2-phenylenediamine and 2-methoxy-4-methanesulfonylamino-benzoic acid. | COC(=O)c1ccc2nc(-c3ccc(NS(C)(=O)=O)cc3OC)[nH]c2c1 | null | null | null |
1,011,650 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.Br[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1>>[F:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[O:26][CH2:25][CH2:24]... | Fc1cccc(OCCCBr)c1 | CC(C)(C)OC(=O)N1CCC(c2ccc(O)cc2)C(O)C1 | 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 | Analogously to Method I, 0.750 g of tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate and 0.723 g of 1-(3-bromopropoxy)-3-fluorobenzene are reacted. The title compound is obtained as a slightly yellowish oil. Rf=0.30 (1:2 EtOAc-heptane); Rt=5.29. | CC(C)(C)OC(=O)N1CCC(c2ccc(OCCCOc3cccc(F)c3)cc2)C(O)C1 | null | null | null |
1,670,583 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][CH:8]=2)[N:3]=1.[C:13]([NH2:16])(=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>O>[C:13]([NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][CH:8]=2)[N:3]=1)(=[O:15])[CH3:14] | Cc1ccc2ccc(Cl)nc2c1 | CC(N)=O | null | O=C([O-])[O-] | [K+] | 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 | 230 | null | Chloride 19a (0.300 g, 1.69 mmol) was diluted with molten anhydrous acetamide (8 g, 135 mmol) and K2CO3 (1.17 g, 8.45 mmol) was added. The mixture was heated in a sand bath, at reflux (˜230° C.) for 17 h. The mixture was cooled, poured into H2O (120 mL) and extracted with EtOAc (4×30 mL). The organic layers were washed... | CC(=O)Nc1ccc2ccc(C)cc2n1 | null | 78.3 | null |
1,461,725 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:4]=[C:3]1[CH2:15][C:16]([O-:18])=O.[Na+].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[N:20]1([C:16](=[O:18])[CH2:15][C:3]2[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([... | c1ccc2c(c1)CCN2 | Cn1c(CC(=O)[O-])nc(N2CCOCC2)cc1=O | null | CCN=C=NCCCN(C)C | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 80 | null | The product is prepared according to the procedure described in example 5, using 200 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 1 of example 68, 174 mg of 2,3-dihydro-1H-indole, and 185 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mix... | Cn1c(CC(=O)N2CCc3ccccc32)nc(N2CCOCC2)cc1=O | null | 20.2 | null |
1,750,352 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH:1]1[CH2:4][CH2:3][CH2:2]1.Cl[C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][N:20]=2)[C:16]#[N:17])[CH:9]=[C:8]([C:21]2([C:27]#[N:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:7]=1>>[N:1]1([C:6]2[N:11]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][N:20]=3)[C:16]#[N:17])[CH:9]=[C:8]([C:21]3([... | C1CNC1 | N#Cc1ccnc(Nc2cc(C3(C#N)CCOCC3)cc(Cl)n2)c1 | 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 azetidine with 2-((6-chloro-4-(4-cyanotetrahydro-2H-pyran-4-yl)pyridin-2-yl)amino)isonicotinonitrile (50.0 mg, 0.147 mmol) following procedure of Method A afforded the target compound as a colorless solid (8.9 mg, 17%); 1H NMR (400 MHz, DMSO) δ 9.95 (br s, 1H), 8.48 (s, 1H), 8.42 (d, J=5.0 Hz, 1H), 7.23 (dd... | N#Cc1ccnc(Nc2cc(C3(C#N)CCOCC3)cc(N3CCC3)n2)c1 | null | 17 | null |
890,992 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21... | O=C(c1ccc2c(c1)OCCO2)c1c[nH]c2ccccc2c1=O | FC(F)(F)c1cccc(CBr)c1 | 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 | Experimental conditions analogous to those described for Step 3 of Example 1, from 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one 70.7 mg (0.296 mmol) and 71.1 mg (0.296 mmol) of 1-Bromomethyl-3-trifluoromethyl-benzene, to give 21 mg of desired compound. LCMS (M+H)+: 466. | O=C(c1ccc2c(c1)OCCO2)c1cn(Cc2cccc(C(F)(F)F)c2)c2ccccc2c1=O | null | 15.2 | null |
1,712,061 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:29][CH:28]=1)[C:10]([NH:12][C@@H:13]([CH:23]([CH3:25])[CH3:24])[CH2:14][O:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[NH2:33][C:30]1[CH:31]=... | CCOC(=O)CCOC[C@@H](NC(=O)[C@@H](Cc1ccc(NC(=O)OCC2c3ccccc3-c3ccccc32)cc1)NC(=O)OC(C)(C)C)C(C)C | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 1 | 355.0 mg (0.52 mmol) of ethyl 3-((S)-2-{(R)-2-tert-butoxycarbonylamino-3-[4-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]propionylamino}-3-methylbutoxy)propionate were dissolved in a mixture of 9 ml of THF and 3 ml of MeOH. 1.29 ml (1.29 mmol) of an aqueous 1M LiOH solution were added, and the resulting reaction mixture... | CC(C)[C@@H](COCCC(=O)O)NC(=O)[C@@H](Cc1ccc(N)cc1)NC(=O)OC(C)(C)C | null | null | null |
1,770,688 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11]C)=[O:10])=[C:5]([CH3:17])[CH:4]=[N:3]1.[Li+].[OH-]>CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([OH:11])=[O:10])=[C:5]([CH3:17])[CH:4]=[N:3]1 | COC(=O)c1ccccc1-c1c(C)cnn1C | null | null | [Li+] | [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 | 50 | null | To a solution of the title compound of Step A (680 mg, 2.95 mmol) in MeOH (15 mL) was added 4 M LiOH (4 mL). The mixture was heated at 50° C. overnight. MeOH was removed and HCl added until pH=2. White solids precipitated from the reaction mixture and the precipitate was filtered, washed with EtOAc and collected to giv... | Cc1cnn(C)c1-c1ccccc1C(=O)O | null | null | null |
1,219,088 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15]C)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19](#[N:21])[CH3:20].Cl>C1(C)C=CC=CC=1>[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13](=[O:15])[CH2:20][C:19]#[N:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1 | CC#N | COC(=O)C(C)(C)COCc1ccccc1 | null | Cl | [H-] | [Na+] | 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 | 1 | To a suspension of sodium hydride (1.62 g of a 60% w/w dispersion in mineral oil, 40.5 mmol) in toluene (20 mL) at reflux was added a solution of methyl 3-(benzyloxy)-2,2-dimethylpropanoate [Eur. J. Org. Chem., 2007 (6) 934-942] (6.00 g, 27.0 mmol) and acetonitrile (2.12 ml, 40.5 mmol) in toluene, dropwise over 1 hr. T... | CC(C)(COCc1ccccc1)C(=O)CC#N | null | 120.1 | null |
1,648,483 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH2:1]([C:3]1[N:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23](C(F)(F)F)[CH:22]=3)[CH2:17][CH2:16]2)[C:11](=[O:31])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[CH3:32][O:33]C1C=CC=CC=1N1CCNCC1>>[CH2:1]([C:3]1[N:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:2... | COc1ccccc1N1CCNCC1 | CCc1nc2ccccc2c(=O)n1CCN1CCN(c2cccc(C(F)(F)F)c2)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 | This compound was prepared in compliance with the procedure described in 7d, using 1-(2-methoxyphenyl)piperazine instead of 1-(3-(trifluoromethyl)phenyl)piperazine. | CCc1nc2ccccc2c(=O)n1CCN1CCN(c2ccccc2OC)CC1 | null | null | null |
155,426 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23](O)=[O:24])=[C:10]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].B>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([... | CCOC(=O)C1=C(COCC(=O)O)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | null | B | 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 | was prepared by the method described in Example 1 using 2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}acetic acid (see Preparation 5 of European patent application publication No. 0100189) and borane as the starting materials. | CCOC(=O)C1=C(COCCO)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | null | null |
472,993 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | C(OC(=O)[NH:7][C@@H:8]([C:16](=[O:19])[NH:17][CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.[ClH:21].O1CCOCC1>>[ClH:21].[NH2:7][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]([NH:17][CH3:18])=[O:19] | CNC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C | 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 | 25 | 1 | (R)-(1-Methylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (722 mg, 2.6 mmol) was dissolved in 4M HCl-dioxane (10 mL) at 0° C. The mixture was stirred for 1 hour at 25° C., concentrated and the residue triturated with ether. Yield, 517 mg, 93%. | CNC(=O)[C@H](N)Cc1ccccc1 | null | null | null |
517,121 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([CH3:32])=[CH:26][C:27](=[O:31])[O:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]... | Cc1cc(=O)oc2cc(N)ccc12 | CCOc1cc2ncc(C#N)c(Cl)c2cc1OCC | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | 100 | null | A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 330 mg (1.88 mM) of 7-Amino-4-methyl-coumarin in 15 ml of 2-methoxyethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml... | CCOc1cc2ncc(C#N)c(Nc3ccc4c(C)cc(=O)oc4c3)c2cc1OCC | null | 71.8 | null |
1,315,218 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25].O>N1C=CC=CC=1>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:24]([C:20]2... | Nc1cc(NC(=O)c2c(Cl)cccc2Cl)ccn1 | O=C(Cl)c1cccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 0 | 0.33 | N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (240 mg, 0.86 mmol) was dissolved in pyridine (10 mL). The mixture was stirred at 0° C. for 20 min. and then thiophene-2-carbonyl chloride (113 mg, 0.77 mmol) was added dropwise. The mixture was warmed to 23° C. and stirred under nitrogen overnight. The next day, water (1 m... | O=C(Nc1cc(NC(=O)c2c(Cl)cccc2Cl)ccn1)c1cccs1 | null | 24 | null |
1,625,544 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[C:11]([F:27])[CH:10]=1)#[N:2].[CH3:28][O:29][CH2:30][CH:31]([NH:33][C:34]1[NH:38][C:37]([CH3:39])=[N:36][N:35]=1)[CH3:32]>>[F:27][C:11]1[CH:10]=[C:9]([C:4]2[C:3]([C:1]#[N:2])=... | COCC(C)Nc1nnc(C)[nH]1 | CCCC(=O)C(Cc1ccc(-c2ccccc2C#N)cc1F)C(=O)OCC | 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 | 250 | 0.33 | A mixture of ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (1 g) and N-(2-methoxy-1-methylethyl)-5-methyl-4H-1,2,4-triazol-3-amine (0.25 g) was stirred at 250° C. for 20 min under microwave irradiation. The obtained reaction mixture was purified by silica gel column chromatography to give the title co... | CCCc1c(Cc2ccc(-c3ccccc3C#N)cc2F)c(=O)n(C(C)COC)c2nc(C)nn12 | null | 40.3 | null |
1,414,098 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.[OH:13][CH2:14][C:15]([CH3:19])([CH2:17]O)[CH3:16].C(OCC)(OCC)OCC>CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:7]([CH:8]2[O:13][CH2:14][C:15]([CH3:19])([CH3:17])[CH2:16][O:9]2)=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1 | CC(C)(CO)CO | COc1ccc(Br)c(C=O)c1O | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(OCC)OCC | null | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 6-bromo-2-hydroxy-3-methoxy-benzaldehyde (2.31 g, 10.0 mmol), neopentyl glycol (1.14 g, 11.0 mmol), TsOH (9.5 mg) and triethyl orthoformate (1.93 g, 13.0 mmol) were heated at 110° C. for 30 min and then partitioned between NaHCO3 (300 mL) solution and EtOAc (200 mL). The aqueous layer was extracted with Et... | COc1ccc(Br)c(C2OCC(C)(C)CO2)c1O | null | 99.9 | null |
679,369 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [CH3:1][S:2]([C:5]1[CH:6]=[C:7]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:4])=[O:3].[CH2:19](Br)[CH:20]=[CH2:21]>>[CH2:21]([N:16]1[CH2:15][CH2:14][N:13]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=2)[CH2:18][CH2:17]1)[CH:20]=[CH2:19] | COc1ccc(N2CCNCC2)cc1S(C)(=O)=O | C=CCBr | 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 | Beginning with 1-(3-Methanesulfonyl-4-methoxy-phenyl)-piperazine and allylbromide, the title compound was recovered by the procedure described in Example 2: MS m/z (rel. intensity, 70 eV)) 310 (M+, 91), 214 (73), 96 (86), 69 (80), 56 (bp). | C=CCN1CCN(c2ccc(OC)c(S(C)(=O)=O)c2)CC1 | null | null | null |
1,502,088 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].F[C:9](F)(F)[C:10](O)=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:47]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38](=[O:46])[CH2:39][C@@H:40]1[CH2:45][CH2:44][CH2:43][NH:42][C... | O=C(C[C@@H]1CCCNC1)Nc1ccc2cc1CCc1cccc(c1)Nc1ncc(Cl)c(n1)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)Cl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | The desired compound was prepared according to the procedure of Example D94 using N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-2-[(3S)-piperidin-3-yl]acetamide bis(trifluoroacetate) and acetyl chloride as the starting materials in 67% yield. LCMS f... | CC(=O)N1CCC[C@@H](CC(=O)Nc2ccc3cc2CCc2cccc(c2)Nc2ncc(Cl)c(n2)N3)C1 | null | 67 | null |
1,601,848 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]1([CH3:23])[C@@H:5]([C:6]([O:8]C(C)(C)C)=[O:7])[CH2:4][C@H:3]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl.O1CCOCC1>C(OCC)(=O)C>[CH2:16]([O:15][C:13]([C@@H:3]1[CH2:4][C@H:5]([C:6]([OH:8])=[O:7])[C:2]1([CH3:23])[CH3:1])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 | CC(C)(C)OC(=O)[C@H]1C[C@@H](C(=O)OCc2ccccc2)C1(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 12 | To a solution of (1R,3S)-1-benzyl 3-tert-butyl 2,2-dimethylcyclobutane-1,3-dicarboxylate (step 3, 1.0 g) dioxane-HCl (10 ml) was added at about 0° C. under nitrogen atmosphere. The reaction mixture was stirred for about 12 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixt... | CC1(C)[C@@H](C(=O)O)C[C@H]1C(=O)OCc1ccccc1 | null | 97.1 | null |
755,960 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [NH2:1][CH:2]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3]1.CCN(C(C)C)C(C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[C:29](Cl)=[N:30][C:31]([S:34][CH3:35])=[N:32][CH:33]=2)=[O:27])=[CH:21][CH:20]=1>CO>[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[C:29]([NH:1][CH:2]3[CH2:6][CH2:5][S:4](=[O:8])(=... | CSc1ncc(C(=O)Nc2ccc(F)cc2)c(Cl)n1 | NC1CCS(=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 | CO | null | null | null | null | null | null | null | null | null | 0 | 16 | To a suspension of 3-amino-1,1-dioxotetrahydrothiophene (345 mg, 2.01 mmol) in methanol (5 mL) was added DIPEA (350 μL) followed by 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (200 mg, 0.67 mmol). The mixture was allowed to stir for 16 h. The resulting mixture was poured into ice-water a... | CSc1ncc(C(=O)Nc2ccc(F)cc2)c(NC2CCS(=O)(=O)C2)n1 | null | 55.2 | null |
191,182 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | [C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CO[CH:11]([CH3:15])[C:12](=O)[CH3:13]>C1(C)C=CC=CC=1>[CH3:15][C:11]1[O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=2[C:12]=1[CH3:13] | Oc1cccc(O)c1 | COC(C)C(C)=O | 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 | 90 | 10 | A mixture of 1.9 g of resorcinol, 1.8 g of 3-methoxy-2-butanone, 0.2 g of Amberlyst-15 and 2 ml of toluene was stirred at 90° C. for 10 hours. After cooling, the catalyst was separated, and the filtrate was concentrated. The residue was purified by column chromatography to give 1.7 g of 2,3-dimethyl-6-hydroxybenzofuran... | Cc1oc2cc(O)ccc2c1C | null | 60.7 | null |
1,460,433 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[CH3:14][O:15][C:16]1[CH:22]=[C:21]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[CH:20]=[CH:19][C:17]=1[NH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:14][O:15][C:16]1[CH:22]=[C:21]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[CH:20]=[CH:19][C:17]=... | COc1cc(-n2cncn2)ccc1N | CNc1nc(Cl)ncc1C(F)(F)F | null | Cc1ccc(S(=O)(=O)O)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 | 100 | null | A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (80 mg, 0.38 mmol), 2-methoxy-4-(1H-1,2,4-triazol-1-yl)aniline (72 mg, 0.38 mmol) and p-toluene sulphonic acid (72 mg, 0.38 mmol) in dioxane (2 mL) was heated at 100° C. for 1 h. The mixture was cooled and filtered. The solid was partitioned between di... | CNc1nc(Nc2ccc(-n3cncn3)cc2OC)ncc1C(F)(F)F | null | 24.9 | null |
1,655,471 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]2)#[N:2].Cl.[NH2:20][OH:21].CCN(C(C)C)C(C)C>CCO>[OH:21][NH:20][C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]2)=[NH:2... | NO | CC(C)(C)OC(=O)N1Cc2ccc(C#N)cc2C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CCO | null | null | null | null | null | null | null | null | null | null | null | A product of Step C (0.22 g; 0.904 mmol), HCl×NH2OH (0.16 g; 2.3 mmol) and DIPEA (0.48 ml; 5 mmol) in anhydrous EtOH (3.5 ml) was refluxed for 2 h under N2. The solvents were removed under reduced pressure and the residue was diluted to 30 ml with EtOAc, washed with H2O (2×5 ml), brine, dried over anhydrous MgSO4, filt... | CC(C)(C)OC(=O)N1Cc2ccc(C(=N)NO)cc2C1 | null | 99.7 | null |
1,047,715 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[N:21]1(N)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CS(C)=O>[N:21]1([C:2]2[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=4[CH:9]=3)[... | NN1CCCCC1 | CC(=O)Nc1nc2ccc(-c3ccnc(Cl)n3)cc2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 80 | 0.33 | A mixture of N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.100 g, 0.3 mmol) and piperidin-1-amine (0.03 g, 0.3 mmol) in DMSO (0.03 g, 0.3 mmol) was heated under microwave (CEM) at 80° C. and 130 W (Powermax® off) for 20 min. Then, the mixture was diluted with 1 ml of DMSO and purified by HPLC (5-50% CH... | CC(=O)Nc1nc2ccc(-c3ccnc(N4CCCCC4)n3)cc2s1 | null | 18.9 | null |
1,754,713 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[N+:15]([O-])=O.[H][H]>CCOC(C)=O.CCO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([NH2:15])=[CH:5][CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:8]=1 | [H][H] | COc1nc(N2CCOCC2)ccc1[N+](=O)[O-] | 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 | 25 | 2 | To a solution of 4-(6-methoxy-5-nitropyridin-2-yl)morpholine (Preparation 81, 280 mg, 1.170 mmol) in EtOAc/EtOH (1:1, 10 ml) was added palladium on charcoal (10%, 100 mg). The flask was charged with hydrogen and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered through ... | COc1nc(N2CCOCC2)ccc1N | null | 100.1 | null |
100,844 | ord_dataset-d06b137b66b3478fb6a0d41a5efd32f8 | null | 1982-01-01T00:12:00 | true | [C:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12][CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15])([OH:3])=O.N#N>C(OC(=O)C)(=O)C.C(N(CC)CC)C>[CH2:10]([C:8]1[CH:7]=[CH:6][C:5]2[S:12][C:13]3([C:1](=[O:3])[C:4]=2[CH:9]=1)[CH2:18][CH2:17][O:16][C:14]3=[O:15])[CH3:11] | CCc1ccc(SC2CCOC2=O)c(C(=O)O)c1 | null | null | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of α-[(2-carboxy-4-ethylphenyl)thio]-γ-butyrolactone (1.0 g) in acetic anhydride (30 ml) and triethylamine (6 ml) was heated at 130° C. for 30 minutes under a stream of N2 gas with stirring. The mixture was evaporated in vacuo. The resulting residue was submitted to column chromatography on silica gel (20 g) ... | CCc1ccc2c(c1)C(=O)C1(CCOC1=O)S2 | null | null | null |
934,038 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [N:1]1([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:22]=[C:19]([CH:20]=O)[C:18]([OH:23])=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([OH:23])=[C:19]([CH:22]=1)[CH2:20][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:2][... | O=c1cc(N2CCNCC2)nc[nH]1 | O=Cc1cc(Cl)ccc1O | 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 | 6-[4-(5-Chloro-2-hydroxy-benzyl)-piperazin-1-yl]-3H -pyrimidin-4-one was prepared using Procedure B from 6-piperazin-1-yl-3H-pyrimidin-4-one (Intermediate 4) and 5-chlorosalicylaldehyde (available from Aldrich). 1H NMR (400 MHz, CDCl3) δ 2.60-2.64 (m, 4H), 3.58-3.65 (m, 4H), 3.70 (s, 2H), 5.40 (s, 1H), 6.76-6.78 (m, 1H... | O=c1cc(N2CCN(Cc3cc(Cl)ccc3O)CC2)nc[nH]1 | null | null | null |
1,759,630 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[N:16][N:17]([CH:19]4[CH2:22][O:21][CH2:20]4)[CH:18]=3)=[CH:11][CH:12]=2)[N:7]([C:23](Cl)=[O:24])[CH2:6][C@@H:5]1[CH3:26])(=[O:3])[CH3:2].[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=1.N1C=CC=CC=1>ClCCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=... | Oc1cccnc1 | CC(=O)N1c2ccc(-c3cnn(C4COC4)c3)cc2N(C(=O)Cl)C[C@@H]1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 50 | 6 | A solution of (S)-4-acetyl-3-methyl-7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinoxaline-1(2H)-carbonyl chloride (0.050 g, 0.13 mmol) in 1,2-dichloroethane (1 mL) was added dropwise to a 50° C. solution of pyridine-3-ol (0.053 g, 0.26 mmol) and pyridine (1 mL) in 1,2-dichloroethane (20 mL). The resulting solution... | CC(=O)N1c2ccc(-c3cnn(C4COC4)c3)cc2N(C(=O)Oc2cccnc2)C[C@@H]1C | null | 0 | null |
1,299,856 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | Br[C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:11]([OH:17])([C:13](F)(F)F)=[O:12]>>[S:9]1[C:10]2[C:2]([CH2:13][C:11]([OH:17])=[O:12])=[CH:3][CH:4]=[CH:5][C:6]=2[N:7]=[CH:8]1 | O=C(O)C(F)(F)F | Brc1cccc2ncsc12 | 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 (20 mg) was prepared from 7-bromobenzo[d]thiazole according to protocol P. LCMS (0.05% TFA): [M+1]+ 194.1. 1H-NMR (CDCl3, 400 MHz): δ9.05 (s, 1H), 8.10 (d, 1H, J=6.8 Hz), 7.53 (m, 1H), 7.39 (d, 1H, J=6.8 Hz), 3.96 (s, 2H). | O=C(O)Cc1cccc2ncsc12 | null | null | null |
1,730,265 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].C([O-])(O)=O.[Na+].[CH:14]1([O:20][C:21](N2C=CC=CC2=O)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O.C1COCC1>[CH:14]1([O:20][C:21]([NH:1][C@H:2]([C@@H:3]([OH:4])[CH3:5])[C:6]([OH:8])=[O:7])=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1 | O=C(OC1CCCCC1)n1ccccc1=O | C[C@H](O)[C@@H](N)C(=O)O | null | O=C([O-])O | [Na+] | 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 | null | null | To a stirred mixture of D-threonine (0.150 g, 1.25 mmol) and NaHCO3 (0.158 g, 1.89 mmol) in H2O (3.5 mL), the crude mixture containing cyclohexyl-2-pyridyl-carbonate and cyclohexyl-2-oxopyridine 1-carboxylate (0.418 g, 1.89 mmol) in THF (3.5 mL) was added. After 15 h at rt the crude mixture was rotary evaporated to rem... | C[C@H](O)[C@@H](NC(=O)OC1CCCCC1)C(=O)O | null | 97.9 | null |
427,830 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([NH:21][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:1... | CCCCCCCC(=O)N[C@H]1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C | null | null | BrB(Br)Br | 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 | 0 | 2.5 | To a solution comprising about 1.3 g of compound 9a (m=6) in 50 ml of CH2Cl2 was added 7.0 ml of boron tribromide (BBr3, 1M solution in CH2Cl2) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 2.5 h and quenched by adding about 30 ml of 1N HCl. The organic layer was separated and the aq... | CCCCCCCC(=O)N[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C | null | 87.6 | null |
1,213,559 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]([F:15])([F:14])[C:3]1[NH:12][C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.P(Cl)(Cl)([Cl:18])=O>CN(C=O)C>[Cl:18][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[N:12]=1 | O=P(Cl)(Cl)Cl | O=c1[nH]c(C(F)(F)F)nc2ccccc12 | null | null | 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 | null | null | To a mixture of 2-(trifluoromethyl)quinazolin-4(3H)-one (12 g) and phosphorous oxychloride (100 ml) was added DMF (0.5 ml) and the mixture was refluxed under nitrogen for 16 h. The excess phosphorous oxychloride was distilled off and the residue was diluted with ethyl acetate (200 ml). The ethyl acetate layer was washe... | FC(F)(F)c1nc(Cl)c2ccccc2n1 | null | 61 | null |
1,390,098 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:17]#[N:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1>[Ni].N.CO>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([CH2:17][NH2:18])[CH:3]=1 | Cc1cc(C#N)c2cnn(C3CCCCO3)c2c1 | null | null | [Ni] | N | 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 | 25 | 2 | To a solution of 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (120 mg, 0.5 mmol) in a solution of NH3/MeOH (7 N, 10 mL) was added Raney nickel (50 mg). The mixture was stirred under hydrogen at RT for 2 hours. It was filtered with Celite, and the filtrate was concentrated in vacuo to afford (6-methy... | Cc1cc(CN)c2cnn(C3CCCCO3)c2c1 | null | 97.8 | null |
94,712 | ord_dataset-6f715747ea754945a2f0af4a8482c7d2 | null | 1982-01-01T00:06:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][C:12]1[N:17]=[CH:16][C:15]([CH2:18]Br)=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:16][N:17]=1 | O=[N+]([O-])c1ccc(O)cc1 | Clc1ccc(CBr)cn1 | 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 substituted aniline compounds of formula (I) wherein W is oxygen can be prepared by the reaction of nitrophenol with a substituted pyridylalkyl halide to obtain the corresponding substituted nitrobenzene which is reduced to the desired substituted aniline of formula (I). For example, the reaction of 4-nitrophenol a... | O=[N+]([O-])c1ccc(OCc2ccc(Cl)nc2)cc1 | null | null | null |
651,607 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | C[O:2][C:3](=O)[CH2:4][N:5]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[CH:23][C:22]([C:32]([F:35])([F:34])[F:33])=[N:21]2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:6][C:7](OC)=[O:8].[BH4-].[Na+]>CO>[OH:8][CH2:7][CH2:6][N:5]([CH2:4][CH2:3][OH:2])[S:11]([C:14... | COC(=O)CN(CC(=O)OC)S(=O)(=O)c1ccc(-n2nc(C(F)(F)F)cc2-c2ccc(C)cc2)cc1 | null | null | [BH4-] | [Na+] | 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 | 2 | To a solution of methyl N-(2-methoxy-2-oxoethyl)-N-({4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}sulfonyl)glycinate prepared as in example 2.A. (0.330 g, 0.628 mmol) in anhydrous methanol (50 mL), was added NaBH4 (0.4 g, 10.6 mmol) and the mixture was allowed to stand at room temperature for 2 hour... | Cc1ccc(-c2cc(C(F)(F)F)nn2-c2ccc(S(=O)(=O)N(CCO)CCO)cc2)cc1 | null | 97 | null |
688,580 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([SH:15])=[N:6][C:5]=2[N:16]=1.Cl[CH2:18][C:19]1[N:20]=[C:21]([NH:24][C:25](=[O:27])[CH3:26])[S:22][CH:23]=1>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([S:15][CH2:18][C:19]3[N:20]=[C:21]([NH:24][C:... | C[C@H](CO)Nc1nc(S)nc2nc(N)sc12 | CC(=O)Nc1nc(CCl)cs1 | 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 titled compound was prepared from the product of example 4, step (b), and N-[4-(chloromethyl)-2-thiazolyl]-acetamide, using the method of example 4, step (c) | CC(=O)Nc1nc(CSc2nc(N[C@H](C)CO)c3sc(N)nc3n2)cs1 | null | null | null |
110,937 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[I-:25].[Na+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([CH2:13][I:25])[CH2:10][O:9]2)=[CH:4][CH:3]=1 | Cc1ccc(S(=O)(=O)OC[C@@H]2CO[C@@H](c3ccc(F)cc3)C2)cc1 | [I-] | null | [Na+] | 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 mixture of 9.2 g of trans-2-(4-fluorophenyl)-4-(tosyloxymethyl)tetrahydrofuran and 12.6 g of sodium iodide in 130 ml of acetone is heated under reflux for 6 hours. The solvent is then distilled off under reduced pressure, and the residue is extracted with ether. The extract is washed with water and dried over magnesi... | Fc1ccc([C@H]2C[C@H](CI)CO2)cc1 | null | null | null |
1,325,913 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13].O>C(O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:13][CH3:12])[CH:7]=1 | CN | O=[N+]([O-])c1ccc(Br)cc1Br | 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 | 80 | 3 | To a solution of 2,4-dibromo-1-nitro-benzene (2.0 g, 7.14 mmol) in ethanol (50 mL) was added a 40% aqueous solution of methylamine (50 mL). The reaction mixture was stirred at 80° C. in a closed vessel for 3 h, then cooled to 0° C. Water was added and the precipitate was filtered, washed with water, and dried in vacuo ... | CNc1cc(Br)ccc1[N+](=O)[O-] | null | 76 | null |
486,846 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1>C(N)(C)C>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([NH:4][CH:3]([CH3:12])[CH3:2])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])... | O=[N+]([O-])c1cc(-c2ncc(C(F)(F)F)cc2Cl)ccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)N | null | null | null | null | null | null | null | null | null | null | null | null | 44.0 g of 3-chloro-2-(4-fluoro-3-nitrophenyl)-5-trifluoromethylpyridine in 250 ml of isopropylamine were stirred at 23° C. for six hours. The reaction mixture was then concentrated. The residue was stirred with 100 ml of water, after which the residual solid portion was separated off, washed with water and dried in a v... | CC(C)Nc1ccc(-c2ncc(C(F)(F)F)cc2Cl)cc1[N+](=O)[O-] | null | null | null |
468,221 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=2[O:2]1.[H-].[Na+].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]I)[CH3:17]>CN(C)C=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][CH:10]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[C:11](=[O:13])[CH3:12])... | CCOC(CI)OCC | CC(=O)Cc1ccc2c(c1)OCO2 | null | [H-] | [Na+] | 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 | null | To 11.7 g of 3,4-methylenedioxyphenylacetone in 100 ml of dimethylformamide, 2.76 g of 60% oily sodium hydride was added under cooling with ice with stirring, and after stirring at the same temperature for 30 minutes, 20.9 g of iodoacetaldehyde diethyl acetal in 20 ml of dimethylformamide was added. The reaction soluti... | CCOC(CC(C(C)=O)c1ccc2c(c1)OCO2)OCC | null | 94.7 | null |
261,527 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:... | CCCCc1cc(C(=O)OCC)nn1Cc1ccc(-c2ccccc2C#N)cc1 | [N-]=[N+]=[N-] | null | [Cl-] | [NH4+] | [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 | null | 72 | To a solution of ethyl 5-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]pyrazole-3-carboxylate (730 mg) in dimethylformamide (10 ml) were added sodium azide (1.3 g) and ammonium chloride (1.07 g) and the mixture was stirred at 110°-115° C. for 72 hours. Insoluble materials were filtered off, and the filtrate was concentrated t... | CCCCc1cc(C(=O)OCC)nn1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | 57.9 | null |
1,676,726 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=S)[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37][CH2:38][CH2:39][C:40]([NH:42][NH2:43])=O>CC1C... | CC(C)(C)OC(=O)NC1(c2ccc(-c3nc4c(cc3-c3ccccc3)NC(=S)CO4)cc2)CCC1 | COCCC(=O)NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccc(C)cc1 | null | null | null | null | null | null | null | null | null | null | 150 | null | A suspension of tert-butyl(1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (100 mg, 0.205 mmol) and 3-methoxypropanehydrazide (48 mg, 0.410 mmol) in p-xylene (2 ml) was heated to 150° C. for 15 minutes under microwave irradiation. The resulting reaction mixture was conce... | COCCc1nnc2n1-c1cc(-c3ccccc3)c(-c3ccc(C4(NC(=O)OC(C)(C)C)CCC4)cc3)nc1OC2 | null | 29.1 | null |
1,628,021 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C1([O:7][C:8](=O)[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:26]4[C:25](=[O:27])[N:24]([CH:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH2:23][C:22]([CH3:35])([CH3:34])[O:21][C:20]=4[N:19]=[C:18]([N:36]4[CH2:42][CH:41]5[O:43][CH:38]([CH2:39][CH2:40]5)[CH2:37]4)[N:17]=3)=[CH:12][CH:11]=2)C=CC=CC=1.[CH3:45][N:46]1[CH:5... | CC1(C)CN(C2CCOCC2)C(=O)c2c(nc(N3CC4CCC(C3)O4)nc2-c2ccc(NC(=O)Oc3ccccc3)cc2)O1 | Cn1ccc(N)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 100 | null | 50 mg (83.4 μmol) of {4-[8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-6-(tetrahydropyran-4-yl)-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}carbamic acid phenyl ester are placed in a microwave reactor and 25 mg (26 μmol) of 1-methyl-1H-pyrazol-3-ylamine are added. 1 ml of DMF and 2 ml o... | Cn1ccc(NC(=O)Nc2ccc(-c3nc(N4CC5CCC(C4)O5)nc4c3C(=O)N(C3CCOCC3)CC(C)(C)O4)cc2)n1 | null | null | null |
977,691 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH3:1][C:2]1([CH3:21])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[O:20])[NH:3]1.[Br:22][C:23]1[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:24]=1[CH2:25]Br>>[Br:22][C:23]1[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:24]=1[CH2:25][N:3]1[C:2](... | Clc1cc(Cl)c(Br)c(CBr)c1 | CC1(C)NC(=O)N(c2ccc(C#N)c(C(F)(F)F)c2)C1=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 | Compound 38.2 was prepared as described for example 6.2, by reacting compound 1.1 with 2-bromo-3,5-dichlorobenzyl bromide. 4-[3-(2-Bromo-3,5-dichlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile was obtained in a yield of 55%. 1H NMR: 8.35, d, 1H, 8.25, s, 1H, 8.1, d, 1H, 7.7, s, 1H, 7.... | CC1(C)C(=O)N(c2ccc(C#N)c(C(F)(F)F)c2)C(=O)N1Cc1cc(Cl)cc(Cl)c1Br | null | 55 | null |
1,247,046 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[CH3:21])[C:10](=[O:22])[CH2:9]1)=O)(C)(C)C.[ClH:23].C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:23].[CH3:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1=[O:22] | Cc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2=O)c(C)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 3 | To a mixture of 3-oxopiperazine-1-carboxylic acid tert-butyl ester (5 g), 1-bromo-2,4-dimethylbenzene (3.4 mL), potassium carbonate (10.6 g) and copper (I) iodide (952 mg) were added toluene (25 mL) and N,N′-dimethylethylenediamine (1.1 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the r... | Cc1ccc(N2CCNCC2=O)c(C)c1 | null | null | null |
838,211 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [CH:1]1([CH2:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=3)[C:8](=O)[NH:7][N:6]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:6][N:7]=1 | O=P(Cl)(Cl)Cl | COc1ccc2c(CC3CC3)n[nH]c(=O)c2c1 | 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 | This compound is obtained according to the procedure described in 1.3. by reacting 4-cyclopropylmethyl-7-methoxy-2H-phthalazin-1-one with phosphoryl chloride. | COc1ccc2c(CC3CC3)nnc(Cl)c2c1 | null | null | null |
440,717 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])C(O)=O.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12] | COc1cc(C(=O)O)cc(Cl)c1OC | 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 | null | null | null | null | null | null | null | null | null | null | null | null | from 2-chloro-N-(3-methoxyphenyl)-4-pyrimidineamine (0.50 g, 2.13 mmol) [see Example 92] and 3-chloro-4,5-dimethoxyaniline (0.40 g, 2.13 mmol) to give the title compound (0.55 g) as a white soid m.p. 204-205°. δH (d6DMSO) 11.19 (1H, br s),10.85 (1H, brs), 8.00 (1H, d, J 7.1 Hz), 7.23 (4H, m), 7.12 (1H, d, J 4.4 Hz), 6.... | COc1cc([N+](=O)[O-])cc(Cl)c1OC | null | null | null |
1,411,939 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:31])/[C:5](/[C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18])=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:... | CCOC(=O)/C(=C\c1cccc(C(F)(F)F)c1)C(=O)C1CCC(c2ccccc2)CC1 | null | null | [Pd] | 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 | 2 | A mixture of (Z)-2-(4-phenylcyclohexanecarbonyl)-3-(3-trifluoromethylphenyl)-acrylic acid ethyl ester (10) (12.3 g, 28.6 mmol) and 10% Pd on carbon (2.5 g, 20% by weight) in denatured ethanol (250 mL) was stirred under a hydrogen atmosphere for 2 hr. The solids were removed by filtration through celite and washed with ... | CCOC(=O)C(Cc1cccc(C(F)(F)F)c1)C(=O)C1CCC(c2ccccc2)CC1 | null | 69.5 | null |
1,570,594 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | P(Cl)(Cl)(Cl)=[O:2].[CH3:6][N:7]1[C:12]2[C:13]([CH3:16])=[CH:14][NH:15][C:11]=2[C:10](=[O:17])[N:9]([CH3:18])[C:8]1=[O:19]>CN(C)C=O>[CH3:6][N:7]1[C:12]2[C:13]([CH:16]=[O:2])=[CH:14][NH:15][C:11]=2[C:10](=[O:17])[N:9]([CH3:18])[C:8]1=[O:19] | O=P(Cl)(Cl)Cl | Cc1c[nH]c2c(=O)n(C)c(=O)n(C)c12 | null | null | 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 | null | 2 | At a temperature of 5-10° C., phosphorous oxychloride (1.84 ml, 20.087 mmol) was mixed with N,N-dimethylformamide (2 mL). Then a solution of Intermediate 1 (600 mg, 3.348 mmol) in N,N-dimethylformamide (3 mL) was added while stirring. The reaction mixture was held for 2 h at 95° C., cooled and poured onto ice (10 g). T... | Cn1c(=O)c2[nH]cc(C=O)c2n(C)c1=O | null | 43.2 | null |
1,563,441 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [NH:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=1)[NH2:2].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=O)[CH2:19][C:20](OCC)=[O:21]>>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:19]=[C:20]([OH:21])[N:1]([C:3]2[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=2)[N:2]=1 | CCOC(=O)CC(=O)c1ccccc1Cl | N#Cc1ccnc(NN)c1 | 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 75% yield from 2-hydrazinylpyridine-4-carbonitrile (PREPARATION 2) and ethyl 3-(2-chlorophenyl)-3-oxopropanoate according to the procedure for the preparation of Example 3, part A. [M+H] Calc'd for C15H9ClN4O 297; Found, 297. | N#Cc1ccnc(-n2nc(-c3ccccc3Cl)cc2O)c1 | null | 75 | null |
1,591,930 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH3:31])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[C:13]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:12]=3)[O:8][C:7](=[O:29])[C:6]=2[CH:30]=1.[CH3:32][NH2:33].C(OCC)C>O1CCCC1>[Cl:1][C:2]1[CH:30]=[C:6]([C:7]([NH:33][CH3:32])=[O:29])[C:5]([... | CN | Cc1cc(Cl)cc2c(=O)oc(-c3cc(OCC(F)(F)F)nn3-c3ncccc3Cl)nc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 0.75 | To a suspension of the 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (i.e. precipitate product of Step E) (3.53 g, 7.5 mmol) in tetrahydrofuran (15 mL), methylamine (2.0 M solution in THF, 11 mL, 22 mmol) was added dropwise, and the resulting solution w... | CNC(=O)c1cc(Cl)cc(C)c1NC(=O)c1cc(OCC(F)(F)F)nn1-c1ncccc1Cl | null | 21.8 | null |
240,956 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | C1(C[N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][CH2:17][CH2:18][O:19][CH3:20])[CH2:10][CH2:9]2)C=CC=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:20][O:19][CH2:18][CH2:17][O:16][C:15](=[O:21])[NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1 | COCCOC(=O)NC1CCN(Cc2ccccc2)CC1 | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 6 | 2-Methoxyethyl (1-phenylmethyl-4-piperidyl)carbamate (9.6 g), prepared according to Preparation 3, was dissolved in ethyl acetate (100 mL). Palladium hydroxide (10% on carbon, 1 g) was added, and the mixture was stirred under hydrogen (1 bar) for 6 hours. The catalyst was removed by filtration, and the solvent evaporat... | COCCOC(=O)NC1CCNCC1 | null | 97.9 | null |
1,267,895 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]=O)[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[NH:25]1[CH2:28][CH:27]([N:29]2[CH2:34][CH2:33][NH:32][C:31](=[O:35])[CH2:30]2)[CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CN(C=O)C>[Cl:1][C:... | O=C1CN(C2CNC2)CCN1 | O=Cc1nc2c(N3CCOCC3)nc(Cl)nc2n1C1CCCCO1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 0.17 | A mixture of 2-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde (1.06 g, 3.01 mmol) and 4-azetidin-3-ylpiperazin-2-one (560 mg, 3.61 mmol) in DCE (60 mL) and DMF (20 mL) was allowed to stir at r.t. for 10 min before the addition of 4 Å powdered molecular sieves (3.0 g) followed by sodium triace... | O=C1CN(C2CN(Cc3nc4c(N5CCOCC5)nc(Cl)nc4n3C3CCCCO3)C2)CCN1 | null | 67.5 | null |
1,153,968 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34]([OH:36])=[O:35])=[O:29])[CH2:24][CH:23]1[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[... | C[C@H](c1cccc2ccccc12)N(CC1CCN(C(=O)Oc2cccc(C(=O)O)c2)CC1c1cccc(F)c1)C(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 88 mg of 3-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]carbonyl}oxy)benzoic acid in 2.0 mL of ethyl acetate was added 1.00 mL of a 4 M hydrogen chloride/ethyl acetate solution at room temperature, followed by stirring for 2 hours. The resulting p... | C[C@@H](NCC1CCN(C(=O)Oc2cccc(C(=O)O)c2)CC1c1cccc(F)c1)c1cccc2ccccc12 | null | null | null |
418,759 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [I-:1].[Na+].I.Cl[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1>CC(C)=O>[I:1][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1 | O=C(O)c1ccc(Cl)nc1 | [I-] | null | I | [Na+] | 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 | 25 | 0.08 | To 27.97 g (186.6 mmol) of sodium iodide cooled to -78° C. was added 121.77 g (71.6 ml, 952.0 mmol) of hydriodic acid (in 57 wt % aqueous solution). The reaction mixture was allowed to warm slightly with stirring for 5 minutes and then 30.00 g (190.4 mmol) of 6-chloronicotinic acid was added. The resulting mixture was ... | O=C(O)c1ccc(I)nc1 | null | null | null |
1,486,902 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[N:12][N:11]3[C:23]=2[C:24]2[CH:29]=[CH:28][N:27]=[C:26](F)[CH:25]=2)=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[C... | CN1CCN(c2ccc3nc(-c4ccc(F)cc4)c(-c4ccnc(F)c4)n3n2)CC1 | CNC | null | null | null | 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 | 150 | null | 0.10 g (0.25 mmol) of 2-(4-fluorophenyl)-3-(2-fluoropyrid-4-yl)-6-(4-methylpiperazin-1-yl)imidazo[1,2-b]pyridazine and 10 mL of dimethylamine are introduced into an autoclave. The mixture is heated at 150° C. overnight and then cooled and poured into water. The product is extracted with chloroform, and the organic phas... | CN1CCN(c2ccc3nc(-c4ccc(F)cc4)c(-c4ccnc(N(C)C)c4)n3n2)CC1 | null | null | null |
728,788 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12.CCCCCC.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12 | O=P(Cl)(Cl)Cl | N#Cc1cnc2c(oc3ccccc32)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 2.10 g (11.0 mmol) of 4-hydroxybenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile in 15 mL of phosphorous oxychloride is heated at reflux temperature for 1.5 hours, then cooled to room temperature. Hexane is added and the solid is collected by filtration, dissolved in ethyl acetate and washed with cold 1 N NaOH.... | N#Cc1cnc2c(oc3ccccc32)c1Cl | null | 65 | null |
777,806 | ord_dataset-bf316bf78f4f45d4b275959c08104b7c | null | 2007-01-01T00:06:00 | true | CS([Cl:5])(=O)=O.[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=1)[CH:7]=[CH2:8].C(N(CC)CC)C>ClCCl>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Cl:5])=[CH:12][CH:11]=1)[CH:7]=[CH2:8] | CS(=O)(=O)Cl | C=CCOc1ccc(CO)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | 7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at r.t. overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried o... | C=CCOc1ccc(CCl)cc1 | null | null | null |
822,131 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.O>[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][... | O=C(OCc1ccccc1)N1CCNCC1 | CC(C)(C)OC(=O)NC(C)(C)C(=O)O | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | 8 | To a solution of 2-(tert-butoxycarbonylamino)-2-methylpropionic acid (10 g) in tetrahydrofuran (20 mL) were added 1-(benzyloxycarbonyl)piperazine (16.3 g), 1-hydroxybenzotriazole (8.02 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (11.4 g), and the mixture was stirred at room temperature overnight.... | CC(C)(C)OC(=O)NC(C)(C)C(=O)N1CCN(C(=O)OCc2ccccc2)CC1 | null | 67.7 | null |
70,187 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([CH2:12][CH:13]2[NH:19][C:18](=O)[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19]2)=[CH:10][CH:9]=1 | O=C1CCCCC(Cc2ccc(Cl)cc2)N1 | 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 | 0 | null | Add 0.5 g of lithium aluminum hydride to a solution of 2.8 g 7-(4-chlorobenzyl)-perhydroazepin -2-one in 30 ml of tetrahydrofurane. Boil the mixture under reflux for 16 hours, cool it and then carefully treat it with ice-water. After extraction with diethyl ether, dry the extract over sodium sulfate concentrate the oil... | Clc1ccc(CC2CCCCCN2)cc1 | null | 68.3 | null |
750,590 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[NH:13][CH:12]=2)=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[N:6]=[C:5]1[NH2:25])[CH:2]=[CH2:3].[C:26](=O)([O-])[O-].[K+].[K+].IC>CS(C)=O>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH3:26])[CH:12... | O=C([O-])[O-] | C=CCn1c(N)nc(-c2cccc(F)c2)c(-c2ccc(=O)[nH]c2)c1=O | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CS(C)=O | null | null | null | null | null | null | null | null | null | 50 | 16 | To a solution of 3-allyl-2-amino-6-(3-fluorophenyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)-3,4-dihydro-4-pyrimidinone in dimethyl sulfoxide were added potassium carbonate (2 equivalents) and iodomethane (4 equivalents), followed by stirring at 50° C. for 16 hours. After filtering off the insoluble matters, the filtrate was ... | C=CCn1c(N)nc(-c2cccc(F)c2)c(-c2ccc(=O)n(C)c2)c1=O | null | null | null |
1,421,191 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH3:1][NH:2][CH2:3][CH2:4][OH:5].CO[C:8]([C:10]1[C:14]([NH:15][C:16]([C:18]2[C:23]([NH:24][C:25]3[CH:26]=[N:27][CH:28]=[N:29][CH:30]=3)=[CH:22][CH:21]=[C:20]([CH:31]3[CH2:33][CH2:32]3)[N:19]=2)=[O:17])=[CH:13][N:12]([CH3:34])[N:11]=1)=[O:9]>>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:8]([C:10]1[C:14]([NH:15][C:16]([C:18]2[C... | COC(=O)c1nn(C)cc1NC(=O)c1nc(C2CC2)ccc1Nc1cncnc1 | CNCCO | 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 | According to the general method described in step 5 of example 27, reaction of 2-methylamino-ethanol with 4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester provided the title compound (13%) as amorphous yellow solid. | CN(CCO)C(=O)c1nn(C)cc1NC(=O)c1nc(C2CC2)ccc1Nc1cncnc1 | null | 13 | null |
1,632,110 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([OH:11])[CH:3]=1.O[CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:1... | C[C@@H](CO)NC(=O)OC(C)(C)C | O=[N+]([O-])c1cnc(O)cc1Cl | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 4-chloro-5-nitropyridin-2-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.51 g) and triphenylphosphine (2.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.52 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixt... | C[C@@H](COc1cc(Cl)c([N+](=O)[O-])cn1)NC(=O)OC(C)(C)C | null | 45.2 | null |
422,939 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | F[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][NH2:12].C(Cl)Cl>C(O)CO>[CH3:2][C:3]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:12][N:11]=1 | NN | O=C(CF)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | OCCO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirring solution of 36.2 g (0.26 mol) of 2-Fluoroacetophenone in 120 mL of ethylene glycol is added 8.6 mL (0.27 mol, 1.05 equiv.) of hydrazine. The resulting solution is stirred 2 h at RT and then heated at 165° C. for 40 h. The solution is cooled to RT, poured into CH2Cl2 (200 mL) and extracted with H2O (2×200 ... | Cc1n[nH]c2ccccc12 | null | 75.7 | null |
1,294,340 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11](=[O:26])[NH:12][C:13]1[C:14]([CH3:25])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)[CH3:9].[CH2:27]([O:29][C:30](=[O:49])[C:31]([CH3:48])([C:33]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=1)[CH3:32])[CH3:28]>>[CH2:... | CCOC(=O)C(C)(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | Cc1noc(-c2ccc(Br)cc2)c1NC(=O)O[C@H](C)c1ccccc1F | 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 | Following the procedure described in Example 36, Step 6, [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester and 2-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid ethyl ester were reacted to provide 2-(4′-{4-[(R)-1-(2-Fluoro-phenyl)-ethoxycarbo... | CCOC(=O)C(C)(C)c1ccc(-c2ccc(-c3onc(C)c3NC(=O)O[C@H](C)c3ccccc3F)cc2)cc1 | null | null | null |
790,641 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11](Cl)[N:10]=1.[Cl:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([OH:34])[CH:33]=1>>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:9]([C:3]3[CH:4]=[CH:5][C:6]... | Oc1cncc(Cl)c1 | COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)nc1Cl | 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 | Using the procedure described in Example 84, methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-chloro-nicotinate Example 83 was reacted with 3-chloro-5-hydroxypyridine to afford the title compound: m/e=521 (M+3); Rt=4.65 min | COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)nc1Oc1cncc(Cl)c1 | null | null | null |
138,903 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | [Cl:1][CH:2]=[C:3]1[C:7]([CH2:9][CH3:10])([CH3:8])[CH2:6][CH2:5][O:4]1.[ClH:11]>>[Cl:1][CH2:2][C:3](=[O:4])[C:7]([CH2:9][CH3:10])([CH3:8])[CH2:6][CH2:5][Cl:11] | CCC1(C)CCOC1=CCl | 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 | 2 | 64 g (0.4 mole) of 2-chloromethylene-3-ethyl-3-methyl-tetrahydrofuran are saturated with hydrogen chloride gas at 10° to 20° C., while cooling with ice. After the mixture has been left to stand at room temperature for 2 hours, excess hydrogen chloride is stripped off and the residue is distilled. 60 g (81% of theory) o... | CCC(C)(CCCl)C(=O)CCl | null | 81 | null |
389,881 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | S(=O)(=O)(O)O.[CH3:6]O.[C:8]([OH:17])(=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH3:6][O:16][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14] | CO | CC(C)CCCCC(=O)O | null | O=S(=O)(O)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 | 2 g concentrated sulfuric acid were added to a solution of 32 g (1 mol) methanol and 144 g (1 mol) "isooctanoic acid" (isomeric mixture from Ruhrchemie A. G. Oberhausen) in 200 ml toluene and heated to boiling with hater separation until the equimolar amount of water separates (about 2 hours). After cooling it was wash... | COC(=O)CCCCC(C)C | null | 95 | null |
1,626,462 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH:34]=[C:35]([S:41]([CH3:44])(=[O:43])=[O:42])[C:36]([O:38]CC)=O)=[CH:29][CH:28]=1>>[Br:26][C:27]1[CH:28]=[C:29]2[C:30](=[CH:31][CH:32]=1)[N:33]=[CH:34][C:35]([S:41]([CH3:44])(=[O:42])=[O:43])=[C:36]2[OH:38] | CCOC(=O)C(=CNc1ccc(Br)cc1)S(C)(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | c1ccc(-c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To Dowtherm at 250° C. was added ethyl 3-(4-bromophenylamino)-2-(methylsulfonyl)acrylate (1.08 g, 3.10 mmol) portionwise and the reaction mixture was stirred for 2 h. The reaction mixture was cooled to room temperature, diluted with hexanes and the resulting precipitate was filtered to afford the desired product (573 m... | CS(=O)(=O)c1cnc2ccc(Br)cc2c1O | null | 61.2 | null |
391,607 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | [C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(N)[CH2:23][NH2:24]>CN(C=O)C.O>[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12]([C:23]#[N:24])[CH:11]=[CH:10][C:9]=1[OH:15]... | CC(C)(C)O/N=C(\c1ccccn1)c1cc(Br)ccc1O | NCCN | null | null | null | 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 | 25 | 0.5 | (Z)-2-(5-bromo-2-hydroxybenzoyl)pyridine O-t-butyloxime (12.7 g) was dissolved in DMF (100 ml). To the solution was added cuprous cyanide (4.64 g), and the mixture was heated, under argon atmosphere, for 3 hours under reflux. To the reaction mixture was added a solution of ethylenediamine (30 ml) in water (20 ml). The ... | CC(C)(C)O/N=C(\c1ccccn1)c1cc(C#N)ccc1O | null | null | null |
525,035 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]2[C:11]=1/[C:12](=[CH:23]/[C:24]1[NH:25][CH:26]=[CH:27][C:28]=1[O:29][CH3:30])/[C:13](=[O:22])[NH:14]2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P... | COc1cc[nH]c1/C=C1\C(=O)Nc2ccc([N+](=O)[O-])c(Br)c21 | C#Cc1cccnc1 | null | [Cu]I | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | Using Method D above, 3-ethynyl pyridine (0.14 g, 1.38 mmol) (see Example 64) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (0.2 g, 0.55 mmol) (Starting Material 3) using (Ph3P)4Pd (31.8 mg) (Aldrich) and CuI (5.3 mg) (Aldrich) as catalyst in DMF (6 mL) and Et3N... | COc1cc[nH]c1/C=C1\C(=O)Nc2ccc([N+](=O)[O-])c(C#Cc3cccnc3)c21 | null | null | null |
1,142,483 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH3:11][C:12]1([CH3:25])[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15][C:14]([CH3:24])([CH3:23])[O:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:16]2[CH2:15][C:14]([CH3:24])([CH3:23])[O:13][C:12]([CH3:25])([CH3:11])[CH2:17]2)=... | CC1(C)CC(OS(C)(=O)=O)CC(C)(C)O1 | O=Cc1cc(Cl)ccc1O | 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 | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to the method described in example 4a, 5-chlorosalicylaldehyde (4.6 g, 30 mmol) (Aldrich) reacted with methanesulfonic acid 2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl ester (8 g, 34 mmol) and K2CO3 in N,N-dimethylformamide to give 5-chloro-2-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yloxy)-benzaldehyde... | CC1(C)CC(Oc2ccc(Cl)cc2C=O)CC(C)(C)O1 | null | null | null |
1,272,094 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:12]1[S:25][C:15]2[C:16]3[CH:24]=[N:23][CH:22]=[CH:21][C:17]=3[O:18][CH2:19][CH2:20][C:14]=2[CH:13]=1)=[N:10][NH2:11].[CH2:26](OC(OCC)OCC)C>>[S:25]1[C:15]2[C:16]3[CH:24]=[N:23][CH:22]=[CH:21][C:17]=3[O:18][CH2:19][CH2:20][C:14]=2[CH:13]=[C:12]1[C:9]1[N:8]([C:3]... | NN=C(Nc1ccccc1Cl)c1cc2c(s1)-c1cnccc1OCC2 | CCOC(OCC)OCC | 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 | 85 | null | A mixture of N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine-2-carbohydrazonamide (44 mg, 0.12 mmol) and 3 ml of triethylorthoformate was heated at 85° C. for 4 hours. The mixture was concentrated in vacuum and triturated with diethylether. The precipitate was collected, washed with diethylether and pur... | Clc1ccccc1-n1cnnc1-c1cc2c(s1)-c1cnccc1OCC2 | null | 38 | null |
359,342 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(O)C>CS(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH:25]... | c1cc(OC[C@@H]2CO2)c2cc[nH]c2c1 | Clc1ccc2[nH]cc(C3CCNCC3)c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 5-chloro-3-(piperidin-4-yl)-1H-indole using ethanol as the reaction solvent. Yield 0.380 g (42%) as a yellowish foam. mp 109°-114° C. (dec) FDMS m/e=423 (M+ of free base). α[D]589 =+6.5 (c... | O[C@H](COc1cccc2[nH]ccc12)CN1CCC(c2c[nH]c3ccc(Cl)cc23)CC1 | null | null | null |
409,358 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [CH3:1][N:2]([O:7][CH3:8])[C:3](=[O:6])[CH2:4]Br.[C:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][N:2]([O:7][CH3:8])[C:3](=[O:6])[CH2:4][O:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:9](=[O:11])[CH3:10])=[CH:18][CH:17]=1 | CON(C)C(=O)CBr | CC(=O)Nc1ccc(O)cc1 | null | O=C([O-])[O-] | [Cs+] | 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 | null | null | This bromoacetamide was dissolved in acetonitrile and to the solution were added 10.75 gm (71.15 mMol) 4-acetamidophenol followed by 23.10 gm (71.1 mMol) cesium carbonate. The reaction mixture was heated at reflux for 3 hours and then concentrated under reduced pressure. The residue was partitioned between dichlorometh... | CON(C)C(=O)COc1ccc(NC(C)=O)cc1 | null | 74 | null |
166,688 | ord_dataset-5c25f386f4664070a72d578feacedf86 | null | 1987-01-01T00:12:00 | true | [F:1][CH2:2][C:3]([CH3:13])([CH3:12])[C:4](=[O:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[OH-].[K+].[CH3:16]I.[ClH:18]>CS(C)=O.O>[ClH:18].[F:1][CH2:2][C:3]([CH3:13])([CH3:12])[C:4](=[O:11])[CH:5]([N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)[CH3:16] | CI | CC(C)(CF)C(=O)Cn1cncn1 | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 24 | 37.2 g (0.2 mol) of 1-fluoro-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one were dissolved in 200 ml of dimethylsulphoxide, 11.2 g (0.2 mol) of potassium hydroxide, dissolved in 24 ml of water, were added and 28.4 g (0.2 mol) of methyl iodide were added dropwise at 20° C., whilst cooling. The reaction mixture was subs... | CC(C(=O)C(C)(C)CF)n1cncn1 | null | 71.7 | null |
496,927 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[OH:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([OH:3])=[O:2].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:27]([O:2][C:1]([C:4]1[C... | BrCc1ccccc1 | CC(C)(C)OC(=O)C(Cc1ccccc1C(=O)O)C(O)C1CCCCC1 | 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 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of t-butyl 2-(2-carboxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionate (200 mg) in dimethylformamide (2 ml) were added benzyl bromide (100 mg) and potassium carbonate (270 mg) successively. After being stirred for 30 minutes the mixture was filtered and the filtrate was evaporated under reduced pressure. T... | CC(C)(C)OC(=O)C(Cc1ccccc1C(=O)OCc1ccccc1)C(O)C1CCCCC1 | null | 43.2 | null |
274,978 | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | null | 1993-01-01T00:09:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[N:15]1([C:21]2[CH:30]=[CH:29][C:24]3[O:25][CH2:26][CH2:27][O:28][C:23]=3[CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(#N)C>[N:6]1([CH2:5][CH2:4][CH2:3][CH2:2][N:18]2[CH2:19][CH2:20][N:15]([C:21]3[CH:30]=[CH:29][C:24]4[... | c1cc2c(cc1N1CCNCC1)OCCO2 | BrCCCCn1cnc2ccccc21 | null | null | 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 | null | null | Analogously to Example 1, reaction of 1-(4-bromobutyl)benzimidazole with 6-piperazino-1,4-benzodioxane ("A") in 200 ml of acetonitrile gives 6-[4-(4-(benzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane, m.p. 247-248°. | c1ccc2c(c1)ncn2CCCCN1CCN(c2ccc3c(c2)OCCO3)CC1 | null | null | null |
557,759 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][C:30]=1[OH:31])[O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:25]([O-])=O)=[C:13]([N:15]([CH2:23]C)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:25][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]2[CH:28]=[CH:29][C:30]([OH:31])=[C:5]([C:1](... | CCN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(O)c(C(C)(C)C)c2)ccc1[N+](=O)[O-] | null | null | [Pd] | null | 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 | In a similar manner to that described in Reference Example 7, a reaction was carried out using t-butyl N-[5-(3-t-butyl-4-hydroxyphenoxy)-2-nitrophenyl]-N-ethylcarbamate (1.29 g), palladium on carbon (10%, 0.16 g) and methanol (40 ml) and the reaction mixture was purified to give the title compound (1.11 g). | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(O)c(C(C)(C)C)c2)ccc1N | null | 95.8 | null |
1,067,321 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][OH:17])[CH:11]=[CH:12][C:13]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][O:17][S:28]([CH3:27])(=[O:30])=[O:29])[CH... | CS(=O)(=O)Cl | CC(C)(C)[SiH2]OC(C)(C)c1cc(CCO)ccc1Cl | 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 | 0 | 1 | To a sol. of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethanol (2.00 g, 6.65 mmol) in CH2Cl2 (66 mL) at 0° C. were added dropwise Et3N (1.02 mL, 7.31 mmol) and methanesulfonyl chloride (0.57 mL, 7.3 mmol). The reaction was stirred at 0° C. for 1 h, and was diluted with CH2Cl2 (40 mL). The resulting m... | CC(C)(C)[SiH2]OC(C)(C)c1cc(CCOS(C)(=O)=O)ccc1Cl | null | 101.2 | null |
464,331 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [C:1]1([CH2:7][CH:8]=[CH:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([SH:23])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].N1CCCCC1>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23][CH:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][C:10]([OH:12])=[O:11])[CH:18]=[CH:19][... | COc1ccc(S)cc1OC | O=C(O)C=CCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 4-phenylbut-2-enoic acid (2 g, 12.33 mmol) prepared as in Example 6, Step B, 3,4-dimethoxybenzenethiol (2.1 mL, 14.79 mmol, 1.2 eq), and piperidine (0.4 mL (3.7 mmol, 0.3 eq) is heated at 110° C. in a bomb for 18 hours. The reaction is partitioned between ethyl ether and 1 N HCl. The organic layer is dried... | COc1ccc(SC(CC(=O)O)Cc2ccccc2)cc1OC | null | null | null |
1,610,657 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[N:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1.[C:16](Cl)(=[O:18])[CH3:17].CO>C(Cl)Cl>[CH3:5][O:6][C:7]1[N:15]=[C:14]2[NH:13][CH:12]=[C:11]([C:16](=[O:18])[CH3:17])[C:10]2=[CH:9][CH:8]=1 | COc1ccc2cc[nH]c2n1 | CC(=O)Cl | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a suspension of AlCl3 (1.37 g, 10.3 mmol) in CH2Cl2 (40 mL) was added 6-methoxy-7-azaindole (315 mg, 2.07 mmol) and the mixture was stirred at RT for 30 min under nitrogen. Acetyl chloride (736 μL, 10.3 mmol) was added dropwise and the resulting mixture stirred at RT overnight. MeOH (8 mL) was added cautiously to qu... | COc1ccc2c(C(C)=O)c[nH]c2n1 | null | null | null |
1,034,101 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [Br:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])OC[C:9]=2[CH:16]=1)=[O:4].B.C1C[O:21][CH2:20]C1>C1COCC1>[Br:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:14])([CH3:15])[CH2:20][O:21][C:9]=2[CH:16]=1)[OH:4] | C1CCOC1 | CC1(C)OCc2cc(C(=O)CBr)ccc2O1 | null | B | 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 | 0.5 | To the product of step (c) (10 g, 35.1 mmol) in 100 mL of THF was added the solid catalyst of Preparation 13, step (c)(1) (0.97 g, 3.5 mmol). The solution was cooled to between −20° C. and −10° C. and BH3-THF (35 mL, 35 mmol) diluted with 50 mL THF was added dropwise via a dropping funnel. After the addition was comple... | CC1(C)COc2cc([C@@H](O)CBr)ccc2O1 | null | null | null |
1,275,233 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:20])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.[CH3:21][C:22]1[O:26][CH:25]=[N:24][C:23]=1[C:27](O)=[O:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([NH:20][C:27]([C:23]3[N:24]=[CH:25][O:26][C:22]=3[CH3:21])=[O:28])[... | Nc1cnc(OCC(F)(F)F)c(-c2ccc(Cl)cc2)c1 | Cc1ocnc1C(=O)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 | The title compound was synthesized in analogy to Example 1, using 5-(4-chloro-phenyl)-6-(2,2, 2-trifluoro-ethoxy)-pyridin-3-ylamine and 5-methyl-4-oxazolecarboxylic acid as starting materials, MS (LC/MS): 412.2 (M+H). | Cc1ocnc1C(=O)Nc1cnc(OCC(F)(F)F)c(-c2ccc(Cl)cc2)c1 | null | null | null |
988,749 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][Cl:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1 | ClCCBr | CC(=O)c1ccc(O)cc1 | null | O=C([O-])[O-] | [K+] | 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 | To a solution of 4′-hydroxyacetophenone (101 g, 0.74 mole) in acetone (800 mL) was added 1-bromo-2-chloroethane (638 g, 4.45 mole) followed by K2CO3 (307 g, 2.22 mole). The reaction was heated to reflux for 48 h then filtered. The K2CO3 was washed with acetone (1 L) and the filtrate was evaporated. The residue was then... | CC(=O)c1ccc(OCCCl)cc1 | null | 99.3 | null |
1,077,205 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=O)[O:25]C2C=CC=CC=2)=[C:19]([Cl:33])[CH:18]=1)(=[O:3])[NH2:2].[CH:34]1([NH2:37])[CH2:36][CH2:35]1.O>CN(C)C=O>[Cl:33][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[NH:23][C:24]([NH:37... | COc1cc2nccc(Oc3ccc(NC(=O)Oc4ccccc4)c(Cl)c3)c2cc1C(N)=O | NC1CC1 | null | null | null | 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 | 25 | 8 | To a solution of phenyl N-(4-(6-carbamoyl-7-methoxy-4-quinolyl)oxy-2-chlorophenyl)carbamate (described in WO02/32872; 17.5 g, 37.7 mmol) dissolved in N,N-dimethylformamide (350 mL), was added cyclopropylamine (6.53 mL, 94.25 mmol) under nitrogen atmosphere, and the mixture were stirred at room temperature overnight. Th... | COc1cc2nccc(Oc3ccc(NC(=O)NC4CC4)c(Cl)c3)c2cc1C(N)=O | null | 80.2 | null |
1,518,261 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [OH:1][C:2]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:7][CH2:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][CH2:3]1.FC(F)(F)S(O[C:33]1[C:34]([CH3:62])([CH3:61])[C@H:35]2[C@:48]([CH3:51])([CH2:49][CH:50]=1)[C@@H:47]1[C@:38]([CH3:60])([C@@:39]3([CH3:59])[C@H:44]([CH2:45][CH2:46]1)[C@H:43]1[C@... | CC1(C)OB(C2=CCC(O)(C(=O)OCc3ccccc3)CC2)OC1(C)C | C=C(C)[C@@H]1CC[C@]2(N)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(OS(=O)(=O)C(F)(F)F)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 85 | null | A flask containing benzyl 1-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate (0.113 g, 0.221 mmol) and (1R,3aS,5aR,5bR,7aR,11aR,11bR,13 aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-... | C=C(C)[C@@H]1CC[C@]2(N)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(C6=CCC(O)(C(=O)OCc7ccccc7)CC6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12 | null | 56.5 | null |
735,345 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>N1C=CC=CC=1.O>[CH2:13]([O:12][C:10](=[O:11])[C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])[CH3:14] | Nc1ccccc1 | CCOC(=O)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 25 | 48 | Aniline (3.4 g, 37 mmol) was dissolved in pyridine (50 mL), then ethyl chloroxoacetate (5.0 g, 37 mmol) was added to the resulting solution dropwise. The resulting mixture was stirred at room temperature for 48 hours, then diluted with water and extracted twice with EtOAc. The combined organic extracts were washed with... | CCOC(=O)C(=O)Nc1ccccc1 | null | 81.1 | null |
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