Benzyl Bromide → 2-amino-1-benzyl-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 1367854

반응식

HRID 1367854 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

참가 물질

4

반응물 2

HCID 7498Benzyl BromideHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylate2회

생성물 1

HCID 669403202-amino-1-benzyl-1H-benzoimidazole-4-carboxylic acid methyl ester수율 55%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 0.1 g (0.52 mmol) of 2-amino-1H-benzoimidazole-4-carboxylic acid methyl ester (intermediate A) in DMSO (1 mL) was added 0.089 g (0.52 mmol) of benzyl bromide, the reaction mixture was stirred at room temperature for 3 h. The conversion was monitored by LCMS. After usual work up, the residue was purified by column chromatography eluting with DCM/methanol (v/v=10:1) to afford 0.08 g (55%) of 2-amino-1-benzyl-1H-benzoimidazole-4-carboxylic acid methyl ester. LCMS: 281 (M+1)+; 1H NMR (DMSO-d6, 400 MHz): δ 7.49 (dd, 1H), 7.29 (t, 2H), 7.25 (m, 2H), 7.16 (m, 2H), 7.05 (bs, 2H), 6.85 (t, 1H), 5.28 (s, 2H), 3.79 (s, 3H) ppm.

후처리

  1. customAfter usual work up, the residue was purified by column chromatography
  2. washeluting with DCM/methanol (v/v=10:1)

출처 및 근거

ORD 기록
ord-a68b4c00973242178ed78c489211d322
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893267B2

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