Water → N-(Pyridin-3-yl)-4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl pyridin-3-ylcarbamate (120 mg, 0.562 mmol) in DMSO (5 mL) was added 2-(3-(1-(piperidin-4-ylidene)ethyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate (260 mg, 0.516 mmol), followed by triethylamine (0.16 mL, 1.12 mmol). The reaction was stirred at 60° C. overnight. Water was added and the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH/CH2Cl2) to give the title compound (161 mg, 61% yield) as a clear oil which formed a foam under high vacuum. MS (APCI 10V) AP+ 469.18; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.99 (s, 3H) 2.31 (t, 2H) 2.50 (t, 2H) 3.40 (t, 2H) 3.61 (t, 2H) 6.63 (br. s., 1H) 6.89 (t, 1H) 6.97-7.04 (m, 3H) 7.17-7.22 (m, 1H) 7.37 (t, 1H) 7.89 (dd, 1H) 7.96 (dd, 1H) 8.23 (dd, 1H) 8.41 (dd, 2H).

Provenance & Evidence