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

Participants

Reaction Steps

Under an N2 atmosphere, ether (5 mL) was added to a solution of (R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (200 mg, 0.47 mmol) in CH2Cl2 (1 mL). A 2.0 M HCl solution in ether (0.236 mL, 0.47 mmol) was added, upon which a precipitate formed. Additional ether was added (5 mL), and the mixture was stirred for 30 minutes. The solid was filtered and dried under vacuum to obtain (R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 14) (160 mg, 80%). 1H NMR (400 MHz, DMSO-d6) δ 8.29-8.24 (m, 2H), 7.82 (s, 1H), 7.75 (d, J=5.5 Hz, 1H), 7.53-7.49 (m, 2H), 7.14 (d, J=8.2 Hz, 1H), 7.06-7.02 (m, 1H), 4.29-3.95 (m, 7H, water in this region), 3.50-3.47 (m, 2H), 3.23 (s, 3H), 2.54 (s, 3H), 2.26-2.23 (m, 1H), 2.08-2.07 (m, 1H) ppm. LC/MS: m/z 423.3 (M+H)+ at 2.22 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence