p-Toluenesulfonyl isocyanate → 2-[4-(2-Amino-5-methyl-4-phenyl-1H-imidazol-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 967811

반응식

HRID 967811 반응식
[NH2:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=2)[C:4]([CH3:13])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:23]1([CH3:35])[CH:28]=[CH:27][C:26]([S:29]([N:32]=[C:33]=[O:34])(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:35][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:33](=[O:34])[O:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([N:3]3[C:4]([CH3:13])=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:6]=[C:2]3[NH2:1])=[CH:19][CH:18]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 222913562-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol

생성물 1

HCID 865903002-[4-(2-Amino-5-methyl-4-phenyl-1H-imidazol-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate수율 4.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol (100 mg, 0.34 mmol) and p-toluenesulfonylisocyanate (67 mg, 0.34 mmol) in dichloromethane (5 mL) was stirred at 0° C. for 10 min. It was washed with water and organic phase was dried over Na2SO4. After removal of solvent, the residue was purified by TLC with dichloromethane/methanol (10:1) to afford 8 mg (4.8%) of the title compound as white solids: MS (ESI) m/z 491 [M+H]+, 489 [M−H]−, 1H-NMR (CDCl3) δ 2.27 (s, 3H), 2.87 (2H, t, J=5.9 Hz), 3.50 (3H, s), 4.24 (2H, t, J=5.7 Hz), 7.56-7.15 (11H, m), 7.83-7.80 (2H, m).

후처리

  1. washIt was washed with water and organic phase
  2. dry with materialwas dried over Na2SO4
  3. customAfter removal of solvent
  4. customthe residue was purified by TLC with dichloromethane/methanol (10:1)

출처 및 근거

ORD 기록
ord-285b0dd33ba04319ab5b2bce40b71266
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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