Pyrrolidine, 3-fluoro- → HCID 67064572, 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-fluoropyrrolidine (27 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, 25-50% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (31 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6 H) 2.02-2.45 (m, 2 H) 3.86-4.02 (m, 1 H) 4.05-4.47 (m, 3 H) 5.35-5.64 (m, 1 H) 6.26 (s, 1 H) 7.01 (br. s., 1 H) 7.60 (d, J=8.34 Hz, 2 H) 7.88-8.10 (m, 3 H) 10.80 (br. s., 1 H). ESI-MS: m/z 384.2 (M+H)+.

Provenance & Evidence