HCID 57657244, compound → HCID 57657267, compound

Participants

Reaction Steps

To a stirring solution of 1-[4-amino-7-[3-(1,1-dioxidothiomorpholin-4-yl)-3-oxopropyl]-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (655 mg, 1.34 mmol) in dichloromethane (125 mL), sealed with a septum and purged with nitrogen gas, was added a 1.0 M solution of boron tribromide in dichloromethane (6.6 mL) 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 to a solid. This step was repeated two more times with silica gel (1 tbsp) being added prior to the final concentration. The crude product absorbed on silica was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient; 0-25% CMA over 1200 mL, followed by 25-40% CMA over 1300 mL). The recovered solid was washed with 1% aqueous sodium carbonate and filtered to provide 325 mg of 1-[4-amino-7-[3-(1,1-dioxidothiomorpholin-4-yl)-3-oxopropyl]-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off white semi-solid.

Provenance & Evidence