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

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 2,5-dimethylpiperazine (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, 15-40% (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 1.30 (d, J=6.57 Hz, 3 H) 1.36 (d, J=6.82 Hz, 3 H) 1.46 (s, 6 H) 3.17 (d, J=5.81 Hz, 1 H) 3.60 (dd, J=13.14, 5.31 Hz, 2 H) 3.73 (br. s., 1 H) 3.93 (dd, J=13.14, 2.78 Hz, 1 H) 4.62 (d, J=4.55 Hz, 1 H) 6.44 (d, J=2.27 Hz, 1 H) 7.51 (s, 1 H) 7.61 (d, J=8.59 Hz, 2 H) 8.00 (d, J=8.34 Hz, 2 H) 8.13 (d, J=2.27 Hz, 1 H) 8.94 (br. s., 1 H) 9.04 (br. s., 1 H) 11.04 (s, 1 H). ESI-MS: m/z 409.3 (M+H)+.

Provenance & Evidence