N-methyl-2-pyrrolidone → HCID 67064708, compound

Participants

Reaction Steps

In a 2 mL microwave vial was placed N-(7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2J, 100 mg, 0.27 mmol) and 4-hydroxypiperidine (55.0 mg, 0.54 mmol). To the sealed vial was then added NMP (2 ml) and the mixture was then heated in the microwave at 120° C. for 15 minutes. After cooling to room temperature, DMF (1 ml) was added. The crude product mixture was filtered by syringe filter and purified by preparatory HPLC (20-40% ACN/water, TFA mode). Lyophilization of the collected fractions gave the titled compound product (30 mg, 26% yield) as an off-white powder. 1H NMR (400 MHz, DMSO-d6) δ=10.78 (s, 1 H), 7.98 (d, J=8.6 Hz, 2 H), 7.59 (d, J=8.6 Hz, 2 H), 7.34 (s, 1 H), 6.02 (s, 1 H), 5.18 (s, 1 H), 4.84 (d, J=4.3 Hz, 1 H), 4.12 (d, J=12.6 Hz, 2 H), 3.79 (dd, J=4.2, 8.5 Hz, 1 H), 3.41-3.36 (m, 1 H), 2.11-2.00 (m, 1 H), 1.91 (br. s., 2 H), 1.65-1.51 (m, 2 H), 1.45 (s, 6 H), 1.04-0.94 (m, 2 H), 0.88-0.75 (m, 2 H); ESI-MS: m/z 436.3 (M+H)+.

Provenance & Evidence