Trifluoroacetic acid → HCID 58404779, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}azetidine-1-carboxylate (24 mg, 0.059 mmol) in dichloromethane (0.5 ml), was added trifluoroacetic acid (0.50 ml, 6.49 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 30 mins. The reaction was diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate. The organic layer was separated, and the aqueous layer was back extracted two times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient) to afford 1-[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-2-[1-(trifluoroacetyl)azetidin-3-yl]ethanone. 1H NMR (500 MHz, CDCl3) δ 8.35 (s, 1H), 8.32 (s, 1H), 7.77 (s, 1H), 7.67 (s, 1H), 6.81 (s, 1H), 4.68 (app t, 1H), 4.39 (app t, 1H), 4.10-4.16 (m, 1H), 4.06 (s, 3H), 3.98 (s, 3H), 3.85-3.91 (m, 1H), 3.36-3.53 (m, 2H), 3.23-3.33 (m, 1H). LRMS (ESI) calculated for C19H19F3N5O3 [M+H]+, 422.1; found 422.0.

Provenance & Evidence