Trifluoroacetic acid → HCID 73504793, compound

Participants

Reaction Steps

A solution of (R)—N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (900 mg, 1.550 mmol) and triethylsilane (0.495 mL, 3.10 mmol) in DCM (14 mL) was treated with TFA (7.16 mL, 93 mmol). The reaction was stirred at room temperature for 1 h. The reaction mixture was evaporated in vacuo and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organics were washed with sat. aq. NaHCO3, brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography (0-10% MeOH/DCM) to afford (R)—N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd. For C17H18N6O2 [M+1]+ 339. found 339. 1H NMR (500 MHz, DMSO-d6) δ 12.56 (s, 1H), 10.71 (s, 1H), 8.99 (s, 1H), 8.94 (s, 1H), 7.80-7.72 (br s, 1H), 7.50 (s, 1H), 7.36-7.29 (m, 4H), 7.26-7.19 (m, 1H), 4.91-4.81 (m, 1H), 2.09 (s, 3H), 1.39 (d, J=6.9, 3H).

Provenance & Evidence