(R)-3-Pyrrolidinol → HCID 67064056, compound

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A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2F, 52 mg, 0.151 mmol) and (R)-pyrrolidin-3-ol (53 mg, 0.603 mmol) in DMF (0.5 mL) was stirred at 100° C. for 3 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 (25-25% MeCN/H2O+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (21.1 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6 H), 1.91-2.12 (m, 2 H), 2.34 (s, 3 H), 3.82-4.13 (m, 5 H), 4.44 (br. s., 1 H), 6.16 (s, 1 H), 6.71 (s, 1 H), 7.63 (d, J=8.59 Hz, 2 H), 7.98 (d, J=8.34 Hz, 2 H), 10.95 (s, 1 H); ESI-MS: m/z 396.2 (M+H)+.

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