Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

(R)-methyl (6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (0.622 mmol) was taken up in TFA (5 ml) and the reaction mixture stirred at room temperature for 1 h. Triethylsilane (0.113 ml, 0.705 mmol) was added drop wise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford (R)-methyl (6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate, TFA (190 mg, 0.406 mmol, 57.5% yield) as a white solid. MS ESI calc'd. For C17H19N6O3 [M+H]+ 355. found 355. 1H NMR (600 MHz, DMSO): 12.69 (br s, 1H); 10.39 (br s, 1H); 9.27 (br s, 1H); 8.95 (s, 1H); 7.76 (br s, 1H); 7.43 (s, 1H); 7.31 (d, J=4.5 Hz, 4H); 7.21 (m, 1H); 4.85 (t, J=7.3 Hz, 1H); 3.68 (s, 3H); 1.39 (d, J=6.9 Hz, 3H).

Provenance & Evidence