Dimethyl Sulfoxide → N-(6-methoxypyridazin-3-yl)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide

関与物質

反応条件

反応手順

A solution of 2-(3-piperidin-4-ylidene-methyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.371 g, 1.00 mmol) (from Example 1, Step 5) and phenyl 6-methoxypyridazin-3-ylcarbamate (0.215 g, 1.00 mmol, from Step 1) in DMSO (2.5 mL) was treated with diisopropylethylamine (0.155 g, 1.2 mmol) and heated to 60° 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 layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The residue was crystallized in a 1:1 mix of hexanes and ethyl ether to afford the title compound (365 mg, 75%) as white crystals. MS (APCI 10V) AP+ 486.19; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (t, J=5.46 Hz, 2H) 2.44 (t, J=5.46 Hz, 2H+DMSO) 3.48 (t, J=5.46 Hz, 2H) 3.55 (t, J=5.46 Hz, 2H) 3.93 (s, 3H) 6.37 (s, 1H) 7.02-7.04 (m, 2H) 7.11 (d, J=9.37 Hz, 2H) 7.21 (d, J=8.79 Hz, 1H) 7.39 (t, J=8.77 Hz, 1H) 7.86 (d, J=9.57 Hz, 1H) 8.19 (dd, J=8.59 Hz, 2.54 Hz, 1H) 8.54 (s, 1H) 9.60 (s, 1H).

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