tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-7-fluoro-3-oxo-4-(thiophen-2-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate → 6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(thiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

Participants

Reaction Steps

A solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-7-fluoro-3-oxo-4-(thiophen-2-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (30 mg, 0.055 mmol) in TFA/DCM (1:1, 10 mL) was stirred at RT for 2 h. The solvent was removed and the resulting crude material was reconstituted in MeOH/DCM (20 mL) and purified via preparative HPLC. The collected fractions were combined and stripped to dryness via rotary evaporation to yield the title compound (16 mg, 85%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.79 (d, J=9.76 Hz, 1 H), 2.12 (qd, J=12.94, 5.13 Hz, 1 H), 3.56-3.68 (m, 1 H), 3.75 (d, J=11.72 Hz, 1 H), 3.89 (br s, 1 H), 4.02 (d, J=11.72 Hz, 2 H), 4.28-4.37 (m, 1 H), 4.38-4.49 (m, 2 H), 7.10-7.20 (m, 1 H), 7.28 (d, J=4.88 Hz, 1 H), 7.59-7.70 (m, 1 H), 7.93 (br s, 2 H), 8.52 (s, 1 H), 9.02 (dd, J=3.91, 0.98 Hz, 1 H). [M+H] calc'd for C16H17FN4O2S, 349; found, 349.

Provenance & Evidence