Reaction Steps
Following the procedure as described in Example 1, making variations only as required to use 4-(2-trifluoromethylbenzyl)piperidine (Vice, S. et al J. Org. Chem. 2001, 66, 2487 and references therein) in place of piperidin-4-yl-(2-trifluoromethylphenyl)amine to react with 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide, the title compound was obtained as a white powder in 35% yield. 1H NMR (300 MHz, CDCl3) δ 7.98 (m, 1H), 7.96 (d, J=9.5 Hz, 1H), 7.63 (d, J=8 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 7.33-7.26 (m, 2H), 6.93 (d, J=9.5 Hz, 1H), 4.48 (d, J=13.5 Hz, 2H), 3.51 (q, J=6.5 Hz, 2H), 2.97-2.88 (m, 2H), 2.74 (d, J=6.5 Hz, 2H), 2.03-1.86 (m, 1H), 1.78 (d, J=6.5 Hz, 2H), 1.49 (q, J=6.5 Hz, 2H), 1.41-1.27 (m, 2H), 0.79-0.67 (m, 1H), 0.48-0.37 (m, 2H), 0.10-0.05 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 163.4, 160.0, 144.3, 138.6, 131.7, 131.5, 126.7, 126.4, 126.3, 126.2, 112.0, 45.3, 39.6, 39.4, 37.9, 34.6, 31.7, 8.7, 4.2. MS (ES+) m/z 433.1 (M+1).
