Hydrochloric Acid → propyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride

Participants

Reaction Steps

A solution of propyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (232 mg, 0.552 mmol) in CH2Cl2 (2 mL) was stirred under an N2 atmosphere. A 2.0 M HCl solution in ether (0.276 mL, 0.552 mmol) was added dropwise to this solution. After 10 minutes, ether (8 mL) was added until a precipitate formed, which was filtered and dried to obtain propyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride (223 mg, 88%). LC/MS: m/z 421 (M+H)+ at 2.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.31 (d, J=8.7 Hz, 1H), 8.24 (dd, J=7.9, 1.4 Hz, 1H), 7.82 (s, 1H), 7.54-7.49 (m, 2H), 7.41-7.37 (m, 1H), 7.14 (d, J=8.1 Hz, 1H), 7.06-7.02 (m, 1H), 4.29-3.78 (m, 7H), 3.24-3.08 (m, 2H), 2.54 (s, 3H), 2.18-2.12 (m, 1H), 1.84-1.79 (m, 1H), 1.59-1.50 (m, 2H), 0.87 (t, J=7.4 Hz, 3H) ppm.

Provenance & Evidence