Trifluoroacetic acid → Methyl-3-(5-{[(1R,6R)-6-amino-2,2-difluorocyclohexyl]carbamoyl}-2-methylthiophen-3-yl)pyrazolo[1,5-a]pyrimidine-6-carboxylate

Participants

Reaction Steps

tert-Butyl{(1R,2R)-3,3-difluoro-2-[({5-methyl-4-[6-(trimethoxymethyl)pyrazolo[1,5-a]pyrimidin-3-yl]thiophen-2-yl}carbonyl)amino]cyclohexyl}carbamate (45 mg, 0.076 mmol) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (275 μL, 3.55 mmol) added. The reaction mixture was stirred at room temperature for 1 h, neutralized with saturated sodium bicarbonate (aq) and extracted 3× with dichloromethane. The organic layers were combined and dried with sodium sulfate, concentrated and purified by column chromatography (0-10% MeOH/DCM) to afford the title compound (quantitative yield). LRMS (APCI) calc'd for (C20H21F2N5O3S) [M+H]+, 450.1; found 450.1. 1H NMR (CDCl3, 500 MHz) δ 9.33 (s, 1H), 9.03 (s, 1H), 8.40 (s, 1H), 7.93 (s, 1H), 6.98 (d, J=8.1, 1H), 4.45 (d, J=25.3, 1H), 4.01 (s, 3H), 3.34 (s, 1H), 2.60 (s, 3H), 2.18 (s, 1H), 1.70-1.90 (s, 5H).

Provenance & Evidence