1-Piperazinecarboxaldehyde → N-(7-(4-formylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

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A solution of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 0.151 mmol) and piperazine-1-carbaldehyde (34 mg, 0.302 mmol) in NMP (0.950 mL) was stirred at 85° C. overnight. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC, 20-45% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (35 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6 H) 3.59-3.82 (m, 8 H) 6.39 (d, J=2.02 Hz, 1 H) 7.43 (s, 1 H) 7.60 (d, J=8.59 Hz, 2 H) 8.00 (d, J=8.34 Hz, 2 H) 8.08-8.15 (m, 2 H) 10.94 (s, 1 H). ESI-MS: m/z 409.2 (M+H)+.

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