Trifluoroacetic acid → HCID 66970364, compound

Participants

Reaction Steps

To a solution of compound 132 (120 mg, 0.304 mmol) in diethyl ether (2.0 mL) was added trifluoroacetic acid (0.0215 mL, 0.289 mmol) 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 trifluoroacetate (112 mg) as a pale yellow solid. Mp 117-119° C. [α]D25-258 (c 0.56, MeOH). 1H NMR (DMSO-d6, 400 MHz): δ 1.21 (3H, t, J=7.3 Hz), 2.02-2.12 (1H, m), 2.28-2.36 (1H, m), 2.79 (6H, s), 3.08-3.17 (2H, m), 3.47 (1H, dd, J=8.0, 5.5 Hz), 3.67-3.79 (2H, m), 3.86-3.91 (1H, m), 3.91 (3H, s), 6.90 (1H, dd, J=7.9, 4.3 Hz), 7.00 (1H, d, J=2.4 Hz), 7.02 (1H, d, J=2.4 Hz), 8.03 (1H, dd, J=7.4, 1.8 Hz), 8.33 (1H, dd, J=4.3, 1.8 Hz), 9.85 (1H, s). Anal. C, 56.05%; H, 5.21%; N, 10.91%. Calcd for C22H26N4O3.CF3CO2H, C, 56.69%; H, 5.35%; N, 11.02%.

Provenance & Evidence