Hydrochloric Acid → HCID 66876268, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.371 g, 1.00 mmol) (from Example 1, Step 5) and phenyl 6-cyanopyridin-3-ylcarbamate (0.286 g, 1.00 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-amino-6-cyanopyridine) in DMSO (2.5 mL) was treated with diisopropylethylamine (0.155 g, 1.2 mmol) and was heated to 50° C. After 3 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulfate, filtered and concentrated to form a residue. The residue was purified by silica gel chromatography (10% of the 1N NH3 in MeOH, in dichloromethane) to provide an oil upon concentration of the pure fractions. This oil was dissolved in 20 mL of diethyl ether and treated with 1 mL of 1N HCl in diethyl ether. The resulting solid was collected by filtration to provide the title compound (270 mg, 56%). MS (APCI 10V) AP+ 480.20; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (t, J=5.46 Hz, 2H) 2.46 (t, J=5.46 Hz, 2H+DMSO) 3.49 (t, J=5.46 Hz, 2H) 3.56 (t, J=5.46 Hz, 2H) 6.39 (s, 1H) 7.03 (m, 2H) 7.12 (d, J=7.80 Hz, 1H) 7.21 (d, J=8.80 Hz, 1H) 7.4 (dd, J=8.5 Hz, 1 Hz, 1H) 7.84 (d, J=8.75 Hz, 1H) 8.10 (dd, J=8.57 Hz, 2.2 Hz, 1H) 8.20 (dd, J=9.24 Hz, 3 Hz, 1H) 8.55 (s, 1H) 8.8 (d, J=2.3 Hz, 1H) 9.29 (s, 1H).

Provenance & Evidence