Reaction Steps
To a mixture of 4-aminobenzylpiperidine (0.460 g, 2.42 mmol), 6-chloropyridazine-3-carboxylic acid pentylamide (0.500 g, 2.20 mmol) and tetrabutylammonium bromide (0.071 g, 10 mole %) in DMF (5 mL) was added 1,8-diazabicyclo[5,4,0]undec-7-ene (0.66 mL, 4.40 mmol). The brown reaction mixture was heated at 80° C. for 24 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water, dried over Na2SO4, filtered, and concentrated. The crude material was subjected to column chromatography to afford the title compound as a brown solid in 27% yield (0.238 g). 1H NMR (300 MHz, CDCl3) δ 7.92 (d, J=9.3 Hz, 1H), 7.87 (t, J=5.7 Hz, 1H), 7.31-7.20 (m, 6H), 6.65 (d, J=9.3 Hz, 1H), 4.91 (d, J=7.5 Hz, 1H), 3.91 (m, 1H), 3.51 (s, 2H), 3.42 (q, J=7.2 Hz, 2H), 2.86 (m, 2H), 2.21-2.06 (m, 4H), 1.64-1.54 (m, 4H), 1.37-1.28 (m, 4H), 0.91-0.85 (m, 3H). 13C NMR (75 MHz, CDCl3) δ 163.3, 159.1, 145.2, 138.3, 129.1, 128.3, 127.1, 126.8, 113.7, 63.1, 52.2, 48.8, 39.4, 32.2, 29.3, 29.1, 22.4, 14.0. MS (ES+) m/z 380 (M+1).
