[Synthesis]
Step F4: Under dry conditions, 3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid (0.092 g, 0.302 mmol) and 1-(3-methylcyclopentyl)-2-piperazinone (0.060 g, 0.274 mmol) were dissolved in DMF (3.07 mL). Subsequently, HATU (0.115 g, 0.302 mmol) and DIPEA (0.120 mL, 0.686 mmol) were added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc and water. The organic phase was separated and washed sequentially with 5% LiCl aqueous solution (3 times), saturated NaHCO3 aqueous solution (3/4 v/v), brine, then dried with anhydrous MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (elution gradient: 0-2% MeOH/DCM) to afford the title compound (0.101 g, 79% yield) as a white solid.1H NMR (400 MHz, chloroform-d) δ ppm: 7.37-7.48 (m, 1H), 7.06 (br.s., 1H), 4.87-5.21 (m, 1H) , 4.42-4.51 (m, 1H), 4.34 (s, 1H), 3.90-4.12 (m, 2H), 3.43 (d, J = 5.66 Hz, 2H), 1.79-2.19 (m, 5H), 1.46-1.56 (m, 1H), 1.10-1.32 (m, 4H), 1.04 (ddd, J = 12.58, 6.44, 2.24 H 6.44, 2.24 Hz, 3H), 0.87 (d, J = 5.27 Hz, 2H). ES-LCMS m/z: 469.3 (M + 1). |