5-Amino-2-methylpyridine → N-(6-methylpyridin-3-yl)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide

Participants

Reaction Steps

Following the procedure in Example 1, Step 6, 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (150 mg, 0.40 mmol, from Example 1, Step 5) and phenyl 6-methylpyridin-3-ylcarbamate (92 mg, 0.40 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-amino-6-methylpyridine, 3B Medical Systems, Inc.) were used to provide the title compound (184 mg). MS (APCI 10V) AP+ 469.3, AP− 467.2, 448.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.41-2.44 (m, 2H) 2.46 (s, 3H) 2.58 (td, J=5.80, 0.83 Hz, 2H) 3.51-3.57 (m, 2H) 3.60-3.67 (m, 2H) 6.45 (s, 1H) 6.97-7.05 (m, 2H) 7.09-7.17 (m, 2H) 7.20 (d, J=8.50 Hz, 1H) 7.40 (td, J=7.70, 0.78 Hz, 1H) 7.77 (dd, J=8.37, 2.52 Hz, 1H) 8.08 (ddd, J=8.71, 2.56, 0.50 Hz, 1H) 8.42 (d, J=0.54 Hz, 1H) 8.43 (s, 1H).

Provenance & Evidence