Trifluoroacetic acid → HCID 73054870, compound

Participants

Reaction Steps

TFA (0.5 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-5-methylphenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A90) (0.106 g, 0.177 mmol) in DCM (5 mL) and the resulting mixture stirred at room temperature for 17 hours. The solvent was removed in vacuo and the residue partitioned between EtOAc (20 mL) and 2 M aqueous NaOH (20 mL). The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layers washed with water (20 mL), brine (20 mL) and dried over MgSO4. The volatiles were removed in vacuo to give a solid which was suspended in DCM and cyclohexane. The resulting suspension was filtered to give the title compound 21 as a white solid (0.085 g, 96%); 1H NMR (400 MHz, d4-MeOH) δ 8.54 (s, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 7.14 (d, J=7.7 Hz, 1H), 7.06-6.98 (m, 2H), 3.62 (s, 2H), 3.28-3.21 (m, 2H), 3.15-3.08 (m, 2H), 3.08-3.01 (m, 2H), 2.86 (td, J=12.6, 2.6 Hz, 2H), 2.78-2.67 (m, 1H), 2.26 (s, 3H), 1.91 (d, J=12.0 Hz, 2H), 1.74 (qd, J=12.9, 4.0 Hz, 2H). LCMS-A: rt 4.94 min; m/z 498.3 [M+H]+.

Provenance & Evidence