Trifluoroacetic acid → HCID 73054871, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (A10) (28 mg, 0.053 mmol) in DCM (8 mL) was added TFA (2 mL) and the resulting solution was stirred at 25° C. for 24 hours. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (10 mL) and 2 M NaOH (20 mL). The aqueous layer was extracted with EtOAc (2×10 mL) then the combined organic layers washed with brine (10 mL) and dried (MgSO4). The solvent was removed in vacuo to give a brown solid which was taken up in MeOH and purified by SCX cartridge (5 g, MeOH followed by 0.5 M NH3 in MeOH). The volatiles from the ammoniacal filtrate were removed in vacuo and the resulting solid residue suspended in cyclohexane and sonicated. The resulting suspension was filtered and the filter cake dried to give the title compound 2 as a light brown solid (8 mg, 35%); 1H NMR (400 MHz, d6-DMSO) δ 9.08 (s, 1H), 8.11 (s, 1H), 7.60 (dd, J=9.2, 2.2 Hz, 2H), 7.41 (s, 1H), 7.26-7.20 (m, 1H), 7.19-7.13 (m, 3H), 6.92 (s, 1H), 6.85 (d, J=9.1 Hz, 2H), 4.02 (s, 1H), 3.50 (s, 2H), 3.03 (dd, J=10.1, 5.7 Hz, 2H), 2.97 (m, 2H), 2.85 (m, 4H), 2.69-2.64 (m, 2H), 2.36-2.30 (m, 2H), 2.05 (s, 3H). LCMS-A: rt 4.364 min; m/z 431.1 [M+H]+.

Provenance & Evidence