Trifluoroacetic acid → HCID 73055446, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-3-(trifluoromethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A97) (0.075 g, 0.12 mmol) in DCM (5 mL) was added TFA (0.20 mL, 2.6 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The volatiles were evaporated under reduced pressure and the residue partitioned between water (20 mL) and EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (2×20 mL). The combined organic extracts were dried using a phase separation cartridge then the volatiles were removed under reduced pressure. The residue was triturated with Et2O and the resulting precipitate collected by filtration to give the title compound 22 (56 mg, 88%); 1H NMR (400 MHz, d6-DMSO) δ 10.22 (s, 1H), 8.67 (s, 1H), 8.29 (brs, 1H), 7.68 (d, J=8.6 Hz, 2H), 7.57 (d, J=7.9 Hz, 1H), 7.52 (d, J=7.6 Hz, 1H), 7.48 (s, 1H), 7.41 (t, J=7.8 Hz, 1H), 7.19 (d, J=8.6 Hz, 2H), 6.94 (s, 1H), 3.73 (s, 2H), 3.38 (m, 2H), 3.10 (m, 4H), 2.98 (td, J=12.8, 2.6 Hz, 2H), 2.79 (tt, J=11.7, 2.7 Hz, 1H), 1.93 (d, J=15.8 Hz, 2H), 1.74 (qd, J=13.8, 4.0 Hz, 2H). LCMS-A: rt 4.99 min; m/z 552.3 [M+H]+.

Provenance & Evidence