Dimethylformamide → HCID 57937599、化合物

HRID 1435136ノート

反応式

HRID 1435136 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11]1[CH:12]=[C:13]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29](O)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[S:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:9].C(N(C(C)C)CC)(C)C.[C:41]([NH:44][NH2:45])(=[O:43])[CH3:42].CN(C=O)C>C(Cl)Cl.O>[C:41]([NH:44][NH:45][C:29]([C:27]1[CH:26]=[CH:25][C:24]2[N:20]([C:13]3[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:10][C@@H:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH3:9])[CH:12]=3)[CH:21]=[N:22][C:23]=2[CH:28]=1)=[O:30])(=[O:43])[CH3:42]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 685699691-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid2 回

生成物 1

HCID 57937599HCID 57937599、化合物収率 91.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A 20.0 mL flask was charged with 150 mg (0.329 mmol) of 1-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid (Intermediate 34, 0.120 mL, 0.658 mmol) of diisopropyl ethylamine, 24.4 mg (0.329 mmol) of acethydrazide and 2.00 ml of DMF. Next, 125 mg (0.329 mmol) of O-(7-Aza benzotriazole-1-yl)-N,N,N′,N′ tetramethyluranium hexafluoro phosphate was added and the reaction mixture stirred at rt for 30 min. 10 mL of water and 30 mL of DCM was added and the organic layer separated. The organic layer was adsorbed onto silica gel and chromatographed to give 154 mg (91% yield) of a tan solid. MS (APCI): 513 [M+H]+.

後処理

  1. customthe organic layer separated
  2. customchromatographed

出典と根拠

ORDレコード
ord-252524b17ac3428a9a2e177da461c5a4
出典データセット
uspto-grants-2009_11
特許番号
US07615643B2

反応ノート

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