A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol), 4-(phenylthio)piperidine hydrochloride (128 mg, 0.50 mmol), and N,N-diisopropylethylamine (116 mg, 0.90 mmol) in DMF (1.0 mL) was stirred at 100° C. for 2 h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (55-55% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (82.0 mg, 65%). 1H NMR (DMSO-d6) δ: 10.83 (s, 1H), 7.99 (d, J=8.6 Hz, 2H), 7.60 (d, J=8.3 Hz, 2H), 7.47 (d, 2H), 7.33-7.42 (m, 3H), 7.26-7.33 (m, 1H), 6.15 (s, 1H), 4.33 (d, J=12.6 Hz, 2H), 3.27 (t, J=10.9 Hz, 2H), 2.37 (s, 3H), 2.03-2.18 (m, 2H), 1.63-1.79 (m, 2H), 1.46 (s, 6H); ESI-MS: m/z 502.3 (M+H)+.
