Benzoyl chloride → HCID 58869112, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.32 mL, 2.29 mmol, 1.2 eq) was added to a solution of 1-[4-(methoxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]-1,5-naphthyridin-4-amine (0.626 g, 1.91 mmol, 1.0 eq), prepared as described in Parts A-H of Example 1, in dichloromethane (10 mL) and cooled to −8° C. Benzoyl chloride (0.22 mL, 1.91 mmol, 1.0 eq) was added dropwise and the reaction mixture was stirred for 2 hours. The reaction was then diluted with dichloromethane (80 mL) and saturated aqueous sodium bicarbonate (40 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (30 mL). The combined organics were dried over magnesium sulfate, filtered, concentrated, and purified by HPFC (silica gel eluting with 0-25% CMA in chloroform) to afford 0.47 g of a pale yellow substance. The material was dissolved in acetonitrile, sonicated, filtered, and dried under vacuum at 100° C. for 24 hours to afford 0.225 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxybenzamide as off-white needles, mp 125-127° C. Anal. calcd for C24H28N6O2: C, 66.65; H, 6.53; N, 19.43. Found: C, 66.43; H, 6.47; N, 19.60.

Provenance & Evidence