3-Hydroxyazetidine → HCID 67064613, compound

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Reaction Steps

A solution of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 151 mmol) and azetidin-3-ol (22 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, 15-40% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (17 mg, 32%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6 H) 4.21 (br. s., 2 H) 4.52-4.89 (m, 3 H) 6.22 (d, J=2.27 Hz, 1 H) 6.74 (s, 1 H) 7.60 (d, J=8.59 Hz, 2 H) 7.91-8.10 (m, 3 H) 10.79 (s, 1 H). ESI-MS: m/z 368.2 (M+H)+.

Provenance & Evidence