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

Participants

Reaction Steps

Under an N2 atmosphere, anhydrous ether (12 mL) was added to a solution of (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (306 mg, 0.73 mmol). A 2.0 M HCl solution in ether (0.365 mL, 0.73 mmol) was added over a period of 45 seconds, upon which a precipitate formed. The reaction was stirred for 10 additional minutes, before the solid was obtained by vacuum filtration and dried under high vacuum to give (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 5) (300 mg, 90%). 1H NMR (400 MHz, acetic acid-d4) δ 8.28 (d, J=8.3 Hz, 1H), 8.20 (m, 1H), 7.75 (s, 1H), 7.53 (m, 2H), 7.08 (m, 2H), 4.00 (m, 7H), 2.54 (s, 3H), 2.27 (m, 1H), 2.01 (m, 1H), 1.82 (m, 1H), 0.87 (d, J=6.5 Hz, 6H) ppm. LC/MS: m/z 421.0 (M+H)+ at 2.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence