1,4-Dioxane → HCID 69675631, compound

Participants

Reaction Steps

A mixture of tert-butyl 1-(6-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.246 g, 0.547 mmol) in DCM (1.095 mL) and hydrochloric acid, 4M solution in 1,4-dioxane (2.74 mL, 10.95 mmol) was stirred at rt. After 2.5 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 10 N NaOH (1.5 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-(3-methyl-1,2,4-oxadiazol-5-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine as a light yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59-8.64 (1H, m), 8.29 (1H, dd, J=9.3, 5.6 Hz), 7.83-7.92 (2H, m), 7.76 (1H, dd, J=10.0, 2.7 Hz), 7.50 (1H, d, J=7.8 Hz), 7.44 (1H, ddd, J=7.6, 4.9, 1.2 Hz), 4.03 (1H, q, J=6.7 Hz), 2.38 (3H, s), 2.03 (2H, br. s.), 1.24 (3H, d, J=6.5 Hz); LC-MS (ESI) m/z 350.1 [M+H]+. The light yellow syrup was carried on crude without purification for the next step.

Provenance & Evidence