Diisopropylethylamine → N-pyridin-3-yl-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide Phenyl pyridin-3-ylcarbamate

Beteiligte Stoffe

Reaktionsschritte

2-(3-Piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (800 mg, 2.16 mmol, from Step 5), phenyl pyridin-3-ylcarbamate (508 mg, 2.37 mmol) and diisopropylethylamine (0.75 mL, 4.52 mmol) were combined in acetonitrile (10 mL) and stirred at room temperature. After 16 hours, the reaction was concentrated forming a residue and the residue was partitioned between EtOAc and water. The organic layer was separated, washed with 5% NaOH (aq), dried over anhydrous sodium sulfate, filtered and concentrated. Treatment of the residue with hot isopropyl ether and purified from isopropyl ether/methanol provided the title compound as a white solid (574 mg). MS (APCI 10V) AP+ 455.3, 376.2, 335.2, AP− 453.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.46 (td, J=5.86, 0.97 Hz, 2H) 2.58 (td, J=5.82, 1.16 Hz, 2H) 3.51-3.60 (m, 2H) 3.61-3.70 (m, 2H) 6.46 (s, 1H) 6.98-7.07 (m, 2H) 7.09-7.19 (m, 2H) 7.34 (ddd, J=8.41, 4.81, 0.65 Hz, 1H) 7.40 (td, J=7.69, 0.74 Hz, 1H) 7.91 (ddd, J=8.38, 2.58, 1.44 Hz, 1H) 8.08 (ddd, J=8.73, 2.61, 0.55 Hz, 1H) 8.16 (dd, J=4.84, 1.06 Hz, 1H) 8.43 (td, J=1.74, 0.91 Hz, 1H) 8.58 (d, J=1.88 Hz, 1H).

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