Hydrochloric Acid → HCID 86706869, compound

Participants

Reaction Steps

4.0 M Hydrogen chloride in dioxane (36 mL, 140 mmol) was added to a solution of tert-butyl 4-{[4-(hydroxymethyl)-6-(trifluoromethyl)pyridin-2-yl]amino}piperidine-1-carboxylate (2.7 g, 7.2 mmol, from Step 3) in 1,4-dioxane (18 mL). After stirring for 30 minutes, the mixture was then basified to pH 12-13 by the addition of 1.0 N NaOH. The product was extracted with DCM (6×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford the product as a white powder (1.64 g, 83%). 1H NMR (400 MHz, d6-DMSO) δ 6.94 (d, J=7.6 Hz, 1H), 6.77 (s, 1H), 6.67 (s, 1H), 5.39 (t, J=5.8 Hz, 1H), 4.42 (d, J=5.5 Hz, 2H), 3.76-3.60 (m, 1H), 2.92 (dt, J=12.4, 3.3 Hz, 2H), 2.57-2.43 (m, 2H), 1.87-1.77 (m, 2H), 1.25 (qd, J=11.8, 3.8 Hz, 2H). 19F NMR (376 MHz, d6-DMSO) δ −67.68 (s).

Provenance & Evidence