2,6-Dimethylmorpholine → HCID 67064243, 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, 0.151 mmol) and 2,6-dimethylmorpholine (35 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, 35-65% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (41 mg, 66%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (d, J=6.06 Hz, 6H) 1.46 (s, 6H) 2.68 (t, J=11.24 Hz, 2H) 3.80-3.91 (m, 2H) 4.38 (d, J=11.62 Hz, 2H) 6.37 (d, J=2.27 Hz, 1H) 7.40 (s, 1H) 7.60 (d, J=8.34 Hz, 2H) 8.00 (d, J=8.59 Hz, 2H) 8.10 (d, J=2.27 Hz, 1H) 10.91 (s, 1H). ESI-MS: m/z 410.3 (M+H)+.

Provenance & Evidence