Trifluoroacetic acid → HCID 24968962, compound

Participants

Reaction Steps

tert-Butyl{[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate (31.0 mg, 0.0570 mmol) was dissolved in DCM (0.803 mL) and trifluoroacetic acid (0.803 mL, 10.4 mmol) was added. The solution was stirred at rt for 15 min before being concentrated in vacuo. The residue was taken up in MeOH (5.00 mL), treated with solid sodium bicarbonate (300 mg) and stirred for 10 min. Filtration and silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (7.20 mg, 58%). 1H NMR (400 MHz, CD3OD, δ): 8.17 (s, 1H), 7.27-7.14 (m, 5H), 6.64 (d, J=3.5 Hz, 1H), 5.86 (t, J=7.5 Hz, 1H), 5.49-5.42 (m, 1H), 4.51-4.48 (m, 1H), 4.38 (dd, J=7.5, 9.8 Hz, 1H), 4.21 (dd, J=7.3, 9.8 Hz, 1H), 3.10-3.03 (m, 1H), 2.97-2.88 (m, 1H), 2.86-2.76 (m, 1H), 2.68-2.60 (m, 1H), 2.37-2.21 (m, 3H), 2.08-1.97 (m, 2H) ppm. LC/MS: Rt=1.16 min, ES+ 444 (FA standard).

Provenance & Evidence