2,1-Benzoxazol-3-amine → N-2,1-benzisoxazol-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 benzo[c]isoxazol-3-ylcarbamate (113 mg, 0.40 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-amino-2,1-benzisoxazole) were combined to provide the title compound (168 mg). MS (APCI 10V) AP+ 495.2, 376.2, 335.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.56 (dt, J=50.88, 5.69 Hz, 4H) 3.66 (dt, J=37.31, 5.71 Hz, 4H) 6.48 (s, 1H) 6.98-7.07 (m, 2H) 7.13 (ddd, J=8.75, 0.68, 0.56 Hz, 1H) 7.16 (d, J=7.77 Hz, 1H) 7.30 (ddd, J=8.05, 6.80, 1.16 Hz, 1H) 7.41 (t, J=7.99 Hz, 1H) 7.49-7.66 (m, 2H) 7.85 (dt, J=8.13, 1.03 Hz, 1H) 8.09 (ddd, J=8.72, 2.67, 0.38 Hz, 1H) 8.43 (td, J=1.82, 0.93 Hz, 1H).

Provenance & Evidence