Cyclopropanecarboxylic acid → N-(2-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)ethyl)cyclopropanecarboxamide

Participants

Reaction Steps

Dichloromethane (1 mL) and N,N-diisopropylethylamine (0.087 mL, 0.50 mmol) were added to a vial containing cyclopropanecarboxylic acid (17.2 mg, 0.2 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.025 g, 0.15 mmol). The reaction mixture was stirred for 10 minutes and N-(3-(1-(2-amino ethyl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine hydrochloride (38 mg, 0.10 mmol) was added. The reaction mixture was stirred for two hours and then concentrated under reduced pressure. The residue was purified by reverse phase chromatography (acetonitrile/water with 0.1% TFA modifier) to afford N-(2-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)ethyl)cyclopropanecarboxamide. MS ESI calc'd. for C21H23F2N6O [M+H]+ 413. found 413. 1H NMR (600 MHz, DMSO): δ 9.78 (s, 1H), 8.64 (d, J=4.9 Hz, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.77 (s, 1H), 7.76 (s, 1H), 7.29 (s, 1H), 7.01 (d, J=4.9 Hz, 1H), 7.00 (s, 1H), 6.80 (t, J=54.5 Hz, 1H), 4.13 (t, J=6.2 Hz, 2H), 3.44 (q, J=6.0 Hz, 2H), 2.25 (s, 3H), 1.47-1.45 (m, 1H), 0.61-0.59 (m, 4H).

Provenance & Evidence