Acetic Anhydride → HCID 11257222, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.24 mL, 1.69 mmol, 1.2 eq) was added to 1-[4-(methoxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]-1,5-naphthyridin-4-amine (0.46 g, 1.41 mmol, 1.0 eq) in dichloromethane (6 mL) and cooled to 0° C. Acetic anhydride (0.13 mL, 1.41 mmol, 1.0 eq) was added dropwise and the reaction mixture was stirred for 1 hour. The reaction was then diluted with dichloromethane (40 mL) and saturated aqueous sodium bicarbonate (30 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (20 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to afford a yellow solid, which was purified by HPFC (silica gel eluting with 0-25% CMA in chloroform) to afford 0.49 g of a pale yellow substance. The material was dissolved in acetonitrile (10 mL), sonicated for 2 minutes, filtered, and dried under vacuum at 100° C. for 24 hours to afford 0.278 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxyacetamide as off-white needles, mp 155-156° C. Anal. calcd for C19H26N6O2: C, 61.60; H, 7.07; N, 22.69. Found: C, 61.58; H, 7.31; N, 22.64.

Provenance & Evidence