Hydrochloric Acid → HCID 69672515, compound

Participants

Reaction Steps

tert-Butyl 4-{[4-(aminocarbonyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.20 g, 0.41 mmol, from Step B) was dissolved in 1,4-dioxane (3.0 mL, 38 mmol) and treated with 4.0M hydrogen chloride in dioxane (2.4 mL, 9.8 mmol). After 2.5 hours, the mixture was treated with ammonium hydroxide to achieve pH 11, and 15 mL of acetonitrile was added. The mixture was filtered and purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) to afford product (72 mg, 60%). 1H NMR (400 MHz, dmso) δ 8.35 (s, 1H), 7.91 (s, 1H), 7.76 (d, J=1.2 Hz, 1H), 7.49 (s, 1H), 5.05 (tt, J=8.9, 4.1 Hz, 1H), 2.95 (dt, J=12.6, 4.2 Hz, 2H), 2.57 (ddd, J=12.7, 10.0, 2.9 Hz, 2H), 2.01-1.87 (m, 2H), 1.60-1.41 (m, 2H); 19F NMR (376 MHz, dmso) δ−67.49 (s); LCMS (M+H)+: 290.1.

Provenance & Evidence