3,3-Dimethylpiperidine → HCID 67064740, compound

Participants

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 3,3-dimethylpiperidine (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, 40-65% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (33 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99 (s, 6 H) 1.45 (s, 6 H) 1.50 (t, J=6.06 Hz, 2 H) 1.80 (br. s., 2 H) 3.51 (s, 2 H) 3.65 (t, J=5.05 Hz, 2 H) 6.33 (d, J=2.02 Hz, 1 H) 7.39 (s, 1 H) 7.60 (d, J=8.34 Hz, 2 H) 8.00 (d, J=8.34 Hz, 2 H) 8.08 (d, J=2.02 Hz, 1 H) 10.85 (s, 1 H). ESI-MS: m/z 408.3 (M+H)+.

Provenance & Evidence