HCID 57657232, compound → HCID 57657234, compound

Participants

Reaction Steps

A solution of N-{3-[4-amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propyl}methanesulfonamide (630 mg, 1.45 mmol) in dichloromethane (125 mL) was sealed with a septum and purged with nitrogen gas. A 1.0 M solution of boron tribromide in dichloromethane (7.3 mL) was added via syringe. The resulting mixture was stirred for 18 hours. Methanol (50 mL) was added and the solution was concentrated under reduced pressure. The resulting solid was dissolved in a 2.0 M solution of ammonia in methanol (75 mL) and then concentrated under reduced pressure. This step was repeated two more times with silica gel (1 tbsp) being added prior to final concentration. The crude product absorbed on silica was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with CMA:chloroform gradient; 0-25% CMA over 1200 mL, followed by 25-40% CMA over 1900 mL). The solid product was washed with water, filtered, and dried to provide 325 mg of N-{3-[4-amino-2-(hydroxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propyl}methanesulfonamide as a white solid, mp 202-205° C.

Provenance & Evidence