Trifluoroacetic acid → HCID 118307530, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.5 mL) was added to a cooled (0° C.) mixture of (1R)-1-(3′-amino-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-yl)-2,2-difluoroethanol (100 mg, 0.244 mmol) and sodium cyanoborohydride (30.6 mg, 0.487 mmol) in dichloromethane (0.5 mL) at 0° C. Trifluoroacetaldehyde (85 mg, 0.731 mmol) was added to the reaction mixture, and then stirred at room temperature for 3 hours. Aqueous sodium carbonate was added to the reaction mixture, extracted with ethyl acetate and the combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to give (1R)-2,2-difluoro-1-(3′-[(2,2,2-trifluoroethyl)amino]-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-yl)ethanol as a yellow solid. MS ESI calc'd. for C21H17F8N4O [M+H] 493. found 493. 1H NMR (400 MHz, CDCl3): δ 8.66 (d, J=5.0 Hz, 1H); 7.70 (s, 1H); 7.63 (d, J=8.0 Hz, 2H); 7.52 (d, J=8.0 Hz, 2H); 7.39 (s, 1H); 7.13 (s, 1H); 7.08 (d, J=5.0 Hz, 1H); 6.65 (s, 1H); 5.83 (td, J=56.0, 4.8 Hz, 1H); 4.91 (td, J=10.1, 4.8 Hz, 1H); 3.87 (q, J=8.9 Hz, 2H).

Provenance & Evidence