Triethylamine → (S)-8-bromo-1-(2-methoxypropyl)-1H-imidazo[4,5-c]quinolin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

Suspend 6-bromo-4-[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylic acid (510 g, 1.5 mol) in dimethylformamide (7.65 L) and add triethylamine (419 mL, 3 mol, 2 eq.) at 70° C. Add diphenylphosphonic azide (390 mL, 1.8 mol., 1.2 eq.) dropwise over 30 minutes. Heat the mixture to 70° C. (internal temperature) for 1 hour. Cool to 10° C. and dilute with water (5 L). Stir the mixture for 1 hour, filter the precipitate, wash it with water (2×1 L) and methyl tert-butyl ether (2×1 L), and then let it dry to give the titled compound as a white solid (445 g, 88%). MS (ESI) m/z (M+H)+ 335.9, 337.9.

Provenance & Evidence