Hydrochloric Acid → (R)-neopentyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride

Participants

Reaction Steps

To a solution of (R)-neopentyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (343 mg, 0.79 mmol) in CH2Cl2 (3 mL) was added a 2.0 M solution of HCl in ether (0.395 mL, 0.79 mmol). After the addition of ether (12 mL), a precipitate formed, and the mixture was stirred for 30 minutes. The solid was filtered and dried under vacuum to give (R)-neopentyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 9) (325 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (t, J=8.5 Hz, 2H), 7.75 (s, 1H), 7.61 (d, J=5.4 Hz, 1H), 7.51-7.47 (m, 2H), 7.09-7.01 (m, 2H), 4.29 (d, J=4.8 Hz, 2H), 4.14-3.82 (m, 3H), 3.72-3.62 (m, 2H, broad due to water), 2.53 (s, 3H), 2.25 (d, J=5.7 Hz, 1H), 2.08 (d, J=5.3 Hz, 1H), 0.89 (s, 9H) ppm. LC/MS: m/z 435.5 (M+H)+ at 2.66 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence