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

Participants

Reaction Steps

A solution of isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (183 mg, 0.42 mmol) in CH2Cl2 (1.5 mL) was stirred under an N2 atmosphere. A 1.0 M HCl solution in ether (0.42 ml, 0.42 mmol) was added dropwise to this solution. After 10 minutes, 5 mL ether was added, and a precipitate formed which was filtered and dried to obtain isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride (169 mg, 85%). LC/MS: m/z 435.5 (M+H)+at 2.64 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 (d, J=6.8 Hz, 1H), 7.80 (s, 1H), 7.53-7.45 (m, 2H), 7.41-7.38 (m, 1H), 7.12 (d, J=8.2 Hz, 1H), 7.05-7.02 (m, 1H), 4.36-3.85 (m, 5H), 3.77-3.70 (m, 2H), 3.22-3.06 (m, 2H), 2.54 (s, 3H), 2.18-2.13 (m, 1H), 1.87-1.77 (m, 2H), 0.87 (d, J=6.7 Hz, 6H) ppm.

Provenance & Evidence