Trifluoroacetic acid → HCID 58318651, compound

Participants

Reaction Steps

TFA (15 ml) was added over a period of 5 minutes to a stirred solution of tert-butyl (2S,4S)-2-(aminocarbonyl)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-1-carboxylate (4) (5 g, 9.16 mmol) in DCM (15 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour after which time, the reaction was complete. The reaction mixture was concentrated to dryness, azeotroped twice with toluene and the residue was purified by flash chromatography (silica gel, DCM-NH3/MeOH 5%) to give (2S,4S)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-2-carboxamide (5) (3.1 g, 76%) as a white solid: 1H NMR Spectrum: (DMSO d6) 1.72-1.89 (m, 2H), 1.91 (m, 1H), 2.03 (m, 1H), 2.78 (m, 1H), 2.92 (m, 1H), 3.47 (m, 1H), 3.95 (s, 3H), 4.84 (m, 1H), 7.06 (s, 1H), 7.27 (s, 1H), 7.30 (m, 2H), 7.49-7.55 (m, 2H), 7.84 (s, 1H), 8.37 (s, 1H), 9.56 (s, 1H), Mass Spectrum: (M+H)+ 446.1.

Provenance & Evidence