5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one → 2-(5-Amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36275

反応式

HRID 36275 の反応式
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[CH:30][C:29]=3[S:36](=[O:48])(=[O:47])[NH:37][C:38](=[O:46])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:45])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[Cl:19])[N:9]=1)[CH2:2][CH2:3][CH3:4]>[Pt]=O.C(OCC)(=O)C>[NH2:16][C:14]1[CH:13]=[CH:12][C:11]([Cl:19])=[C:10]([N:8]2[C:7](=[O:20])[N:6]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[CH:30][C:29]=4[S:36](=[O:47])(=[O:48])[NH:37][C:38](=[O:46])[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[Cl:45])=[CH:26][CH:27]=3)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]2)[CH:15]=1

参加物

4

反応物 1

HCID 199394375-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 199394622-(5-Amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one収率 63%

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 135 mg (0.191 mmole) of 5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C), 10 mg of platinum oxide, and 2 mL of ethyl acetate was stirred under an atmosphere of hydrogen (balloon) for 1 day and then then filtered through Celite. The crude product was chromatographed on a column of silica gel (gradient elution with 0.5-4% MeOH in CH2Cl2) to give 81 mg (63%) of the title compound; homogeneous by TLC in 9:1CH2Cl2 --MeOH; m/e 678 (M+1)+.

後処理

  1. filtrationfiltered through Celite
  2. customThe crude product was chromatographed on a column of silica gel (gradient elution with 0.5-4% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-5802bf49e165435391bbeac50bb50e2a
出典データセット
uspto-grants-1995_05
特許番号
US05411980

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