(2R)-2-(Methoxymethyl)pyrrolidine → HCID 67064477, 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 (R)-2-(methoxymethyl)pyrrolidine (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, 20-45% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a orange solid (44 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6 H) 1.90-2.18 (m, 4 H) 3.24 (s, 3 H) 3.37 (dd, J=9.47, 7.20 Hz, 1 H) 3.54 (dd, J=9.73, 3.66 Hz, 1 H) 3.68-3.79 (m, 1 H) 3.83-3.98 (m, 1 H) 5.25 (br. s., 1 H) 6.28 (d, J=2.27 Hz, 1 H) 7.06 (s, 1 H) 7.61 (d, J=8.59 Hz, 2 H) 7.98 (d, J=8.59 Hz, 2 H) 8.04 (d, J=2.02 Hz, 1 H) 10.81 (s, 1 H). ESI-MS: m/z 410.3 (M+H)+.

Provenance & Evidence