Phenyl isocyanate → HCID 58869069, compound

Participants

Reaction Conditions

Reaction Steps

The preparation of 4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl O-methylhydroxylamine is described in Parts A-H of Example 1. Triethylamine (0.23 mL, 1.64 mmol) was added to a solution of 4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl O-methylhydroxylamine (0.45 g, 1.37 mmol) in dichloromethane (10 mL) cooled to −10° C. Phenyl isocyanate (0.15 mL, 1.37 mmol) was added to the reaction mixture and it was allowed to warm to 0° C. over 1 hour. The reaction mixture was diluted with dichloromethane (50 mL) and saturated sodium bicarbonate (40 mL) and the phases were separated. The aqueous layer was extracted with dichloromethane (30 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a yellow material. The material was purified by HPFC (0-25% CMA in chloroform) and recrystallized from acetonitrile to afford an off-white solid. The solid was dried at 100° C. under high vacuum to afford 0.388 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxy-N′-phenylurea as an off-white powder, mp 155-156° C. Anal. calcd for C24H29N7O2: C, 64.41; H, 6.53; N, 21.91. Found: C, 64.20; H, 6.64; N, 21.93.

Provenance & Evidence