Sodium Hydroxide → HCID 58318667, compound

Participants

Reaction Steps

2N NaOH (1.3 ml, 2.66 mmol) was added to a solution of methyl (2S,4R)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)-1-methylpiperidine-2-carboxylate (14) (0.252 g, 0.53 mmol) in THF (5 ml) and methanol (1 ml). The reaction mixture was stirred overnight at room temperature and evaporated to dryness. The residues were dissolved in water (10 ml) and the solution acidified to pH6 with 2N HCl. The resulting solids were collected by filtration, washed with water (5 ml) followed by diethylether (5 ml) and dried under vacuum to give (2S,4R)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)-1-methylpiperidine-2-carboxylic acid (15) as a cream solid (145 mg, 59%): 1H NMR Spectrum: (DMSO-d6) δ1.72-1.90 (2H, m), 2.20-2.31 (1H, m), 2.40-2.55 (1H+DMSO, m), 2.66 (3H, s), 2.84-2.94 (1H, m), 3.10-4.10 (2H, m), 3.95 (3H, s), 4.56-4.60 (1H, m), 7.18-7.25 (2H, m), 7.48-7.55 (2H, m), 8.05 (1H, s), 8.40 (1H, s); Mass Spectrum: (M+H)+ 461.

Provenance & Evidence