Trifluoroacetic acid → 1-(2-(2-(2-((4-(Piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Participants

Reaction Steps

A solution of TFA (0.65 mL, 8.5 mmol) and tert-butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A6) (0.13 mg, 0.21 mmol) in DCM (20 mL) was stirred for 24 hours at room temperature under nitrogen. The volatiles were removed in vacuo and the residue was taken up in MeOH and loaded onto an SCX cartridge (10 g). The column was eluted with 5 column volumes of MeOH and then 5 column volumes of 5% v/v aqueous ammonia in MeOH to elute the amine product. The ammoniacal filtrate was evaporated under reduced pressure and the resulting solid was dried under high vacuum to give the title compound 2 as a white solid (100 mg, 93%); 1H NMR (400 MHz, d6-DMSO) δ 10.14 (s, 1H), 8.67 (s, 1H), 7.66 (d, J=8.6 Hz, 2H), 7.37-7.27 (m, 3H), 7.25-7.14 (m, 3H), 6.99 (s, 1H), 6.00 (s, 1H), 3.22-3.13 (m, 2H), 3.13-3.06 (m, 2H), 3.01 (d, J=11.9 Hz, 2H), 2.62-2.52 (m, peaks obscured by solvent), 1.67 (d, J=10.7 Hz, 2H), 1.57-1.40 (m, 4H), 0.97 (s, 2H). LCMS-A: rt 4.963 min; m/z 510 [M+H]+.

Provenance & Evidence