A 2.0 M solution of HCl in ether (0.15 mL) was added to solution of (R)-2-methoxyethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (130 mg, 0.3 mmol) in CH2Cl2 (2 mL) and ether (10 mL). After addition of ether (10 mL), a precipitate formed which was filtered and dried. The material was dissolved in MeOH and dried under reduced pressure to give (R)-2-methoxyethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 1) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.76 (d, J=5.5 Hz, 1H), 7.67 (s, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.47 (m, 1H), 6.99 (d, J=8.3 Hz, 1H), 6.87 (t, J=9.0 Hz, 1H), 4.29 (m, 3H), 3.77-3.36 (m, 5H), 3.23 (s, 3H), 3.06 (m, 1H), 2.56 (s, 3H), 2.23 (s, 1H), 2.06 (s, 1H) ppm. LC/MS: m/z 441.3 (M+H)+ at 2.11 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
