Acetyl chloride → HCID 178489598, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% dispersion in mineral oil, 0.55 g, 18 mmol) was added to a solution of (S)-6-(2-methoxyphenyl)aminocarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (2.00 g, 7 mmol) in anhydrous N,N-dimethylformamide (70 ml). The reaction mixture was heated to 80° C. for 30 minutes, then allowed to cool to room temperature. Acetyl chloride (1.46 g, 18 mmol) was added to the reaction mixture at 0° C. The reaction mixture was allowed to warm to room temperature, stirred overnight, and brought to pH 8. Water and N,N-dimethylformamide was distilled off under vacuum. The residue was chromatographed on silica gel with a solvent system of ammonium hydroxide/methanol/methylene chloride (1/8/92 v/v) to yield (S)-5-acetyl-6-(2-methoxyphenylaminocarbonyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (free base) (1.13 g, 49%). The free base was converted to the hydrochloric acid salt: m.p.: 159° C.

Provenance & Evidence