Hydrochloric Acid → HCID 58869084, compound

Participants

Reaction Steps

A solution of 4N hydrochloric acid in dioxane (2.5 mL, 10.2 mmol, 20 eq) was added to a solution of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate (250 mg, 0.51 mmol), prepared as described in Parts A-F of Example 14, and stirred for 1 hour at ambient temperature. Methanol (2 mL) was added to the reaction mixture, which was stirred overnight. The reaction mixture was concentrated under reduced pressure and the material was concentrated from methanol and chloroform and dried. The material was suspended in dichloromethane (5 mL) and triethylamine (0.71 mL, 5.1 mmol) and cooled to −5° C. Phenyl isocyanate (0.056 mL, 0.51 mmol) was added dropwise and the reaction mixture was slowly allowed to warm to ambient temperature. After two hours, the reaction mixture was diluted with dichloromethane (10 mL) and saturated aqueous sodium bicarbonate (5 mL) and stirred vigorously and the phases were separated. The aqueous layer was extracted with dichloromethane (2×10 mL) and the combined organics were washed with saturated aqueous sodium bicarbonate (10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to produce a white solid. The material was purified by HPFC (eluting with 5-30% CMA in chloroform), recrystallized from acetonitrile, triturated with ethyl acetate and dried at 80° C. under high vacuum to afford 60 mg of 1-[4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridine-1-yl)butyl]-1-hydroxy-3-phenyl-urea as a white powder, mp 159.0-160.5° C. Anal. Calcd for C22H30N6O2 C, 64.37; H, 7.37; N, 20.47. Found: C, 64.01; H, 7.20; N, 20.27.

Provenance & Evidence