Trifluoroacetic acid → 2-(5-Fluoro-2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

Participants

Reaction Steps

TFA (0.825 mL, 10.8 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-4-fluorophenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A37) (0.162 g, 0.269 mmol) in DCM (20 mL) under nitrogen and the resulting solution stirred for 24 hours at room temperature. 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 6 column volumes of 5% v/v aqueous ammonia in MeOH. The volatiles from the ammoniacal eluent were evaporated under reduced pressure to give the title compound 9 as a yellow solid (0.117 g, 87%); 1H NMR (400 MHz, d6-DMSO) δ 10.12 (s, 1H), 8.65 (s, 1H), 7.64 (d, J=8.6 Hz, 2H), 7.48 (s, 1H), 7.23-7.13 (m, 3H), 7.08 (dd, J=10.2, 2.8 Hz, 1H), 7.04-6.95 (m, 2H), 3.50 (s, 2H), 3.14-2.95 (m, 6H), 2.63-2.52 (m, 3H), 1.67 (d, J=10.8 Hz, 2H), 1.49 (qd, J=12.4, 3.9 Hz, 2H). LCMS-A: rt 4.853 min; m/z 502 [M+H]+.

Provenance & Evidence