Diisopropylethylamine → HCID 67064268, compound

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, 437 mg, 1.3 mmol) and (R)-N-methylpiperidine-3-carboxamide, trifluoroacetate salt (585 mg, 2.2 mmol). To the sealed vial were then added NMP (6 ml) and diisopropylethylamine (0.67 ml, 3.85 mmol), 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 (25-50% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (510 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ=10.96 (br. s., 1 H), 8.11 (br. s., 1 H), 8.00 (d, J=8.1 Hz, 3 H), 7.61 (d, J=8.1 Hz, 2 H), 7.35 (s, 1 H), 6.39 (br. s., 1 H), 4.48-4.25 (m, 2 H), 3.29 (t, J=11.1 Hz, 1 H), 3.08 (br. s., 1 H), 2.61 (s, 3 H), 2.60 (m, 1 H), 2.08 (s, 1 H), 1.94 (br. s., 1 H), 1.83 (br. s., 1 H), 1.73 (br. s., 2 H), 1.46 (s, 6 H); ESI-MS: m/z 437.4 (M+H)+.

Provenance & Evidence