Benzimidazole → 2-(1H-benzimidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 1991225

反応式

HRID 1991225 の反応式
CC(C)([O-])C.[K+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1.Br[CH2:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)=[O:19]>>[N:7]1([CH2:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=2)=[O:19])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1

参加物

4

反応物 3

HCID 5798BenzimidazoleHCID 23171522-bromo-N-[3-(trifluoromethyl)phenyl]acetamideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 7448412-(1H-benzimidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide収率 27%

実験手順

A solution of potassium tert-butoxide (1.7 mL of 1 M solution in THF, 1.7 mmol,) was added to a solution of 1H-benzoimidazole (165 mg, 1.4 mmol) in anhydrous TBF (3 mL). The reaction mixture was stirred for 20 min at ambient temperature. 2-Bromo-N-(3-trifluoromethyl-phenyl)-acetamide (Example 92 part A) was added (261 mg, 0.93 mmol) and the mixture was stirred at 55° C. for subsequent 24 h. The crude product was purified on a preparative HPLC (XTerra C8 column 19×300 mm, 0.1 M aqueous NH4Ac/CH3CN). The pooled fractions were lyophilized to afford 81 mg (27%) of the title compound. Calculated for C16H12F3N3O m/z: 319.29, found 320.0 [M+H]+. 1H NMR (400 MeOH) δ ppm 5.2 (s, 2H), 7.3 (m, 2H), 7.4 (d, J=7.6 Hz, 1H), 7.5 (m, 2H), 7.7 (d,J=7.1 Hz, 1H), 7.8 (d, J=8.6 Hz, 1H), 8.0 (s, 1H), 8.2 (s, 1H).

後処理

  1. stirringthe mixture was stirred at 55° C. for subsequent 24 h
  2. customThe crude product was purified on a preparative HPLC (XTerra C8 column 19×300 mm, 0.1 M aqueous NH4Ac/CH3CN)

出典と根拠

ORDレコード
ord-110f99951c78407bb9d7bc1f01e3d192
出典データセット
uspto-grants-2010_01
特許番号
US07645784B2

関連ノート

読み込み中…