Trifluoroacetic acid → HCID 89735655, compound

Participants

Reaction Steps

To tert-butyl-[(1R,2R)-2-({[4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (3.36 g, 6.39 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL, 130 mmol) and stirred for 16 h at ambient temperature. The reaction was evaporated to dryness, partitioned dichloromethane and saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane 3×. The organic layers were combined, dried with sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (2.46 g, 5.77 mmol). LRMS (APCI) calc'd for (C18H18ClF2N5OS) [M+H]+, 426.1; found 426.0. 1H NMR (CDCl3, 500 MHz) δ 8.74 (s, 1H), 8.48 (s, 1H), 8.25 (s, 1H), 7.91 (s, 1H), 6.98 (d, J=9.3, 1H), 4.46 (d, J=25.3, 1H), 3.34 (m, 1H), 2.57 (s, 3H), 2.18 (m, 1H), 1.67-1.90 (m, 5H).

Provenance & Evidence