(3R)-(+)-3-Acetamidopyrrolidine → (R)-N-(7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

Participants

Reaction Steps

In a 2 mL microwave vial were placed N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 80 mg, 0.24 mmol) and (R)-N-(pyrrolidin-3-yl)acetamide (62 mg, 0.48 mmol). To the sealed vial were then added NMP (2 ml), and the mixture was then heated in the microwave at 100° C. for 15 minutes. After cooling to room temperature, the reaction mixture was filtered by syringe filter and was then directly purified by preparatory HPLC (20-40% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (110 mg, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ=10.84 (s, 1 H), 8.24 (d, J=6.3 Hz, 1 H), 8.01 (d, J=2.3 Hz, 1 H), 8.00-7.95 (m, 2 H), 7.65-7.59 (m, 2 H), 6.90 (s, 1 H), 6.28 (d, J=2.3 Hz, 1 H), 4.41-4.31 (m, 1H), 4.19 (br. s., 1 H), 3.96 (br. s., 2 H), 2.19 (dd, J=5.8, 12.6 Hz, 1 H), 2.01-1.91 (m, 1 H), 1.83 (s, 3 H), 1.46 (s, 6 H); ESI-MS: m/z 423.4 (M+H)+.

Provenance & Evidence