Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

A solution of tert-butyl (3R,4R)-4-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(5-methylthiophen-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (31 mg, 0.051 mmol) in TFA (10 mL) was heated to 80° C. for 1 h. After the solvent was removed, the residue was dissolved in MeOH and DCM (8 mL) and was purified via preparative HPLC eluting with water (0.05% TFA) and ACN (15-30% gradient, 0.035% TFA). The collected fractions were combined and the solvent was stripped to dryness via rotary evaporation to give the title compound as a TFA salt (13.5 mg, 74%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.78 (d, J=13.18 Hz, 1 H), 2.03-2.18 (m, 1 H), 2.46 (s, 3 H), 3.17 (d, J=4.88 Hz, 1 H), 3.55-3.65 (m, 1 H), 3.75 (d, J=13.18 Hz, 1 H), 3.85 (br s, 1 H), 3.96-4.06 (m, 2 H), 4.41 (d, J=7.81 Hz, 2 H), 6.84 (d, J=2.44 Hz, 1 H), 7.22 (d, J=4.88 Hz, 1 H), 7.92 (br s, 2 H), 8.47 (s, 1 H), 8.83 (d, J=3.42 Hz, 1 H). [M+H] calc'd for C17H19FN4O2S, 363; found, 363.

Provenance & Evidence