(3S)-(-)-3-(Dimethylamino)pyrrolidine → HCID 67064229, 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 (S)-N,N-dimethylpyrrolidin-3-amine (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, 10-35% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (60 mg, 97%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6 H) 2.20-2.37 (m, 1 H) 2.61-2.71 (m, 1 H) 2.90 (d, J=3.79 Hz, 6 H) 3.79-3.91 (m, 1 H) 4.02-4.19 (m, 2 H) 4.35 (d, J=6.57 Hz, 2 H) 6.26 (d, J=2.27 Hz, 1 H) 7.15 (s, 1 H) 7.60 (d, J=8.59 Hz, 2 H) 7.99 (d, J=8.59 Hz, 2 H) 8.04 (d, J=2.02 Hz, 1 H) 9.87 (br. s., 1 H) 10.77 (s, 1 H). ESI-MS: m/z 409.3 (M+H)+.

Provenance & Evidence