Cyclopropaneacetic acid → 2-Cyclopropyl-1-{4-[6-fluoro-2-phenoxymethyl-3-(4-trifluoromethoxy-benzyl)-3H-benzoimidazol-5-yl]-piperazin-1-yl}-ethanone

HRID 507224

반응식

HRID 507224 반응식
[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.[F:8][C:9]1[C:37]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:36][C:12]2[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][C:11]=2[CH:10]=1>ClCCl>[CH:1]1([CH2:4][C:5]([N:41]2[CH2:42][CH2:43][N:38]([C:37]3[C:9]([F:8])=[CH:10][C:11]4[N:15]=[C:14]([CH2:16][O:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:13]([CH2:24][C:25]5[CH:26]=[CH:27][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:29][CH:30]=5)[C:12]=4[CH:36]=3)[CH2:39][CH2:40]2)=[O:7])[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 138440Cyclopropaneacetic acidHCID 684671025-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole

생성물 1

HCID 684635972-Cyclopropyl-1-{4-[6-fluoro-2-phenoxymethyl-3-(4-trifluoromethoxy-benzyl)-3H-benzoimidazol-5-yl]-piperazin-1-yl}-ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

0.020 ml of cyclopropyl-acetic acid (0.2 mmol) and 40 mg of 1,1-carbonyldiimidazole (0.24 mmol) were refluxed in 4 ml dichloromethane under nitrogen for 40 minutes. 100 mg 5-Fluoro-2-phenoxymethyl-6-piperazin-1-yl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole (0.2 mmol) were added and the resulting mixture refluxed for additional 26 h. The reaction mixture was then diluted with dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 129 mg yellow solid. This residue was purified by column chromatography (24 g silicagel, dichloromethane/methanol 24:1) leading to 77 mg light yellow solid (63%). MS (ISP) 583.3 (M+H)+.

후처리

  1. temperaturethe resulting mixture refluxed for additional 26 h
  2. washwashed with water, saturated sodium bicarbonate and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis residue was purified by column chromatography (24 g silicagel, dichloromethane/methanol 24:1)

출처 및 근거

ORD 기록
ord-71cc8eb6381e4697b4c8b3c0345d8b33
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786128B2

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