Hydrochloric Acid → N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

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Reaction Steps

A solution of 1-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acid (6) (3.24 g, 6.74 mmol), 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamine (0.95 g, 6.80 mmol), triethylamine (5.70 mL, 40.9 mmol) and propylphosphonic anhydride (T-3-P)(50% in ethyl acetate, 4.85 mL, 8.15 mmol) in dichloromethane (50 mL) was stirred overnight at room temperature. To the reaction 6N HCl (10 mL) was carefully added and was stirred at room temperature for 40 minutes. The solution was basified with saturated sodium bicarbonate and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% MeOH in dichloromethane) to afford N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

Provenance & Evidence