Trimethylsilyl isocyanate → HCID 58869094, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsilyl isocyanate (0.250 mL, 1.85 mmol) was added dropwise to a solution of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-O-methyl-hydroxylamine in dichloromethane (10 mL) cooled to −16° C. The reaction temperature was cooled to −20° C. over 10 minutes. After stirring for 1.5 hours, the reaction was warmed to 0° C. and stirred for an additional hour. A drop of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.250 mL, 1.85 mmol) was added to the reaction mixture and stirred for 3 days. The reaction mixture was diluted with dichloromethane (50 mL) and saturated aqueous sodium bicarbonate and stirred for 30 minutes. The layers were separated, and the organic layer was dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.82 g of 1-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-methoxyurea as off-white crystals, mp 179-181° C. MS (APCI) m/z 371 (M+H+); Anal. calcd for C19H26N6O2: C, 61.36; H, 7.09; N, 22.60. Found: C, 61.08; H, 7.41; N, 22.69.

Provenance & Evidence