Trifluoroacetic acid → HCID 73054872, compound

Participants

Reaction Steps

TFA (954 μL, 12.5 mmol) was added to a solution of tert-butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate (A16) (220 mg, 0.415 mmol) in DCM (10 mL) and the resulting mixture stirred for 20 hours at room temperature. The volatiles were removed in vacuo and the resulting residue partitioned between EtOAc (100 mL) and 2 M aqueous NaOH (100 mL). The layers were separated and the organic layer washed with water (100 mL), brine (50 mL), dried (MgSO4) then evaporated in vacuo to yield a white solid. The solid was taken up in DCM (10 mL) and sonicated for 2 minutes then petroleum benzine 40-60° C. (100 mL) was added and sonication continued for a further 10 minutes. The resulting suspension was filtered and the filter cake dried to give the title compound 3 as a white solid (135 mg, 76%); 1H NMR (400 MHz, d4-MeOH) δ 8.57 (s, 1H), 7.68 (d, J=8.6 Hz, 2H), 7.33 (d, J=8.8 Hz, 2H), 7.31-7.17 (m, 4H), 3.81 (s, 2H), 3.69 (s, 2H), 3.22-3.06 (m, 4H). LCMS-A: rt 4.722 min; m/z 428 [M−1]−.

Provenance & Evidence