Ammonia → HCID 58318672, compound

Participants

Reaction Steps

A stirred solution of (2R,4R)-1-(tert-butoxycarbonyl)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-2-carboxylic acid (7) (0.13 g, 0.232 mmol) in THF (5 ml) was cooled to −15° C. (acetone/ice). NMM (0.035 g, 0.348 mmol) was added to the solution followed by IBCF (0.041 g, 0.301 mmol). The reaction mixture was held at −15° C. (the formation of the mixed anhydride was monitored by TLC (THF)). After 5-10 minutes, the reaction mixture was treated with aqueous ammonia in THF (0.2 ml) at −15° C. and allowed to warm to room temperature. The reaction mixture was diluted with DCM (20 ml), washed with water (2×2 ml) and concentrated to give tert-butyl (2R,4R)-2-(aminocarbonyl)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-1-carboxylate (8) (0.13 g, 100%) as a pale yellow foam which was used without further purification; Mass Spectrum: (M+H)+ 544.0.

Provenance & Evidence