4-Toluenesulfonyl chloride → HCID 57657260, compound

Participants

Reaction Steps

To a stirring solution of crude 1-{3-[2-(2-methoxyethyl)-8-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one, (0.85 g) in dichloromethane (75 mL) was added 3-chloroperoxybenzoic acid (60% pure, 500 mg, 1.91 mmol). After 18 hours concentrated ammonium hydroxide (50 mL) was added and the reaction was vigorously stirred for 10 minutes. p-Toluenesulfonyl chloride (690 mg, 3.60 mmol) was added in one portion and the mixture was stirred for one hour. The fractions were separated and aqueous fraction was extracted with chloroform (3×50 mL). The combined organic fractions were concentrated under reduced pressure. Purification by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-30% CMA in chloroform) followed by recrystallization from acetonitrile provided 75 mg of 1-{3-[4-amino-2-(2-methoxyethyl)-8-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as a pale yellow solid, mp 168-170° C.

Provenance & Evidence