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

HRID 967811Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-285b0dd33ba04319ab5b2bce40b71266
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956050B2

Reaction notes

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