Acetyl chloride → HCID 15984032, compound

Participants

Reaction Steps

Acetyl chloride (150 μL, 1.1 equivalents (eq)) was added to N-{2-[4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (750 mg, 1 eq) in a mixture of triethylamine (401 μL, 1.5 eq) and N,N-dimethylformamide (DMF) (5 mL) and the resulting solution was stirred at ambient temperature. After 2 hours acetic anhydride (1 mL) was added. The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica gel eluted with a gradient of 0-10% methanol in dichloromethane containing 1% ammonium hydroxide) to provide 278 mg of N-(2-ethoxymethyl-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-4-yl)acetamide as a white powder, mp 75-76° C. Anal. calcd for C20H27N5O4S.0.40H2O: C, 54.50; H, 6.36; N, 15.89. Found: C, 54.70; H, 6.10; N, 15.58.

Provenance & Evidence