Trifluoroacetic acid → HCID 178523573, compound

Participants

Reaction Steps

To a solution of N-[(1R,3S)-3-[[5-fluoro-2-(5-fluoro-1-trityl-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]pyrrolidine-1-carboxamide, 22, (0.100 g, 0.146 mmol) in dichloromethane (5 mL) was added triethylsilane (0.350 mL, 2.190 mmol) followed by trifluoroacetic acid (0.337 mL, 4.380 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted into 30 ml CH2Cl2 and aqueous saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4 and the solvent was removed under reduced pressure. The crude residue was purified by silica gel chromatography (12% MeOH and 88% CH2Cl2) to afford 64 mg of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.42 (dd, J=2.7, 1.4 Hz, 1H), 7.90 (d, J=3.2 Hz, 1H), 7.51 (dd, J=8.6, 2.7 Hz, 1H), 5.15 (d, J=5.5 Hz, 1H), 4.26 (d, J=7.9 Hz, 1H), 3.99-3.79 (m, 1H), 3.38 (d, J=3.2 Hz, 4H), 3.09 (d, J=6.6 Hz, 1H), 2.82 (d, J=11.3 Hz, 1H), 2.16-2.05 (m, 1H), 2.01-1.85 (m, 5H), 1.78 (d, J=13.2 Hz, 1H), 1.32-1.04 (m, 4H), 0.92 (dd, J=21.7, 11.8 Hz, 1H); LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=2.31 min, (M+H) 443.34.

Provenance & Evidence