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

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A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 0.151 mmol) and 4-methoxypiperidine (27 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, 5-95% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (16 mg, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6 H) 1.59-1.75 (m, 2 H) 1.98-2.12 (m, 2 H) 3.31 (s, 3 H) 3.41-3.58 (m, 3 H) 3.97-4.15 (m, 2 H) 6.35 (d, J=2.27 Hz, 1 H) 7.40 (s, 1 H) 7.60 (m, J=8.34 Hz, 2 H) 7.99 (m, J=8.59 Hz, 2 H) 8.08 (d, J=2.27 Hz, 1 H) 10.88 (s, 1 H). ESI-MS: m/z 410.3 (M+H)+.

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