Hydrochloric Acid → HCID 72703417, compound

Participants

Reaction Conditions

Reaction Steps

Potassium cyanate (11.9 mg, 0.147 mmol) and HCl (138 μL, 0.138 mmol) was added to the 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidin-4-ol (50.0 mg, 0.092 mmol) in THF (383 μL) and water (1.15 mL) and heated to 50° C. for 4 hours. The reaction mixture was cooled to room temperature and neutralize with aqueous 10% NH4OH. The resulting precipitate was collected by filtration to yield 4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidine-1-carboxamide. MS APCI calc'd for C23H24F3N6O2 [M+H]+ 473. found 473. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.82 (d, J=5.2 Hz, 1H), 8.68 (dd, J=2.4 Hz, 6.3 Hz, 2H), 8.02 (s, 1H), 7.97 (s, 1H), 7.56 (s, 1H), 7.25 (d, J=10.2 Hz, 1H), 7.22 (s, 1H), 5.92 (s, 2H), 3.85 (d, J=16.4 Hz, 2H), 3.09 (t, J=14.5 Hz, 2H), 2.36 (s, 3H), 1.88 (t, J=15.9 Hz, 2H), 1.63 (d, J=14.3 Hz, 2H).

Provenance & Evidence