Reaction Steps
To a solution of compound 132 (120 mg, 0.304 mmol) in diethyl ether (3.0 mL) was added methanesulfonic acid (0.0394 mL, 0.608 mmol) in diethyl ether (1.0 mL) at room temperature. After stirring for 30 min, the resulting solid was filtered, washed with diethyl ether, and dried in vacuo at room temperature, to give 2-[2-((S)-3-Dimethylamino-pyrrolidin-1-yl)-pyridin-3-yl]-5-ethyl-7-methoxy-4H-benz[d][1,3]oxazin-4-one methanesulfonate monohydrate (141 mg) as a white solid. Mp 43-49° C. [α]D25-205 (c 0.34, MeOH). 1H NMR (DMSO-d6, 400 MHz): δ 1.21 (3H, t, J=7.3 Hz), 2.07-2.12 (1H, m), 2.31-2.35 (1H, m), 2.33 (6H, s), 2.79 (3H, d, J=4.9 Hz), 2.82 (3H, d, J=4.3 Hz), 3.07-3.15 (2H, m), 3.48 (2H, dd, J=8.6, 5.5 Hz), 3.68-3.80 (2H, m), 3.89-3.96 (1H, m), 3.91 (3H, s), 6.27 (1H, brs), 6.91 (1H, dd, J=7.9, 4.9 Hz), 7.01 (1H, d, J=2.4 Hz), 7.03 (1H, d, J=2.4 Hz), 8.05 (1H, dd, J=7.9, 1.8 Hz), 8.32 (1H, dd, J=4.9, 1.8 Hz), 9.77 (1H, brs). Anal. C, 47.64%; H, 6.01%, N, 9.21%. Calcd for C22H26N4O3.2CH3SO3H.H2O, C, 47.67%; H, 6.00%; N, 9.27%.
