Benzenesulfonyl chloride → HCID 58967533, compound

Participants

Reaction Conditions

Reaction Steps

1-[2-Ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyrrolidin-2-one (0.38 g) was dissolved in chloroform (10 mL). 3-Chloroperoxybenzoic acid (60% pure, 0.37 g) was added in one portion and the mixture was allowed to stir for 16 hours. Ammonium hydroxide (10 mL) was added and the biphasic mixture was cooled to 2° C. with an ice/water bath. Benzenesulfonyl chloride (0.22 mL) was added and the reaction was stirred for 3 hours. The layers were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered and concentrated under reduced pressure. The residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 99:1 to 73:27. Fractions containing product were combined and concentrated under reduced pressure. The residue was recrystallized from acetonitrile to afford 0.14 g of 1-[4-amino-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyrrolidin-2-one as a white solid, mp 165-167° C.

Provenance & Evidence