Acetyl chloride → CPG-52852

Participants

Reaction Steps

A solution of acetyl chloride (0.15 mL, 2 mmol) in ethanol (2 mL) was added to a solution of N-{4-[5-(2-aminophenyl)-4-cyano-2-ethyl-1H-imidazo 1-yl]butyl}methanesulfonamide (0.19 g) in ethanol (4 mL). The mixture was heated at reflux for two hours, allowed to cool to room temperature, and concentrated under reduced pressure. The resulting off-white solid was dissolved in water (2.0 mL) with heating to 60° C. The resulting solution was adjusted to pH 12 with the addition of 10% w/w sodium hydroxide (about 0.2 mL). The mixture was cooled overnight at 5° C. The crystals were collected by filtration, washed with water, and dried under vacuum at 40° C. for two hours to provide N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide as beige crystals, mp 202° C. to 204° C., having a 1H NMR spectrum consistent with an authentic sample.

Provenance & Evidence