N-methyl-2-pyrrolidone → Diisopropylethylamine

Participants

Reaction Steps

In a 2 ml microwave vial was placed N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(2-hydroxypropan-2-yl)nicotinamide (11C, 75 mg, 0.217 mmol) and 1-(piperidin-4-yl)urea, HCl salt (39 mg, 0.22 mmol). To the sealed vial was then added NMP (1 ml) and then N,N-diisopropylethylamine (0.079 ml, 0.46 mmol) to give a deep blue solution. The mixture was then heated in the microwave at 100° C. for 10 minutes. After cooling to room temperature, the crude product mixture was purified by preparatory HPLC (20-40% MeCN/H2O gradient+0.01% TFA). Lyophilization of the collected fractions gave the titled product (47 mg, 48% yield) as an off white powder. 1H NMR (DMSO-d6) δ: 11.13 (s, 1H), 9.07 (dd, J=2.4, 0.9 Hz, 1H), 8.38 (dd, J=8.3, 2.3 Hz, 1H), 7.80 (d, J=8.3 Hz, 1H), 7.33 (s, 1H), 6.17 (d, J=0.5 Hz, 1H), 6.06-6.15 (m, 1H), 4.31 (d, J=12.6 Hz, 2H), 3.69 (br. s., 1H), 3.22 (t, J=10.9 Hz, 2H), 2.38 (s, 3H), 1.90-1.99 (m, 2H), 1.51 (br. s., 2H), 1.47 (s, 7H); ESI-MS: m/z 453.3 (M+H)+.

Provenance & Evidence