1,4-Dioxane → 1-(6-Fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine

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Reaction Steps

A mixture of tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.252 g, 0.561 mmol) in DCM (1.121 mL) and hydrochloric acid, 4M solution in 1,4-dioxane (2.80 mL, 11.21 mmol) was stirred at rt. After 24 h, the mixture was partitioned between DCM (50 mL) and water (50 mL). The acidic aq mixture was washed with DCM (30 mL×2) to remove organic impurities. The aq layer was basified to ˜pH 13 with 10N NaOH (1 mL) and extracted with DCM (50 mL×3). The combined organic layers were washed with water (100 mL×1), dried over MgSO4, filtered, and concentrated in vacuo to give 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60-8.65 (1H, m), 8.24-8.31 (1H, m), 7.80-7.91 (3H, m), 7.41-7.49 (2H, m), 4.03 (1H, q, J=6.6 Hz), 2.34 (3H, s), 2.03 (2H, br. s.), 1.24 (3H, d, J=6.7 Hz); LC-MS (ESI) m/z 350.0 [M+H]+. The solid was carried on crude without further purification.

Provenance & Evidence