Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

Crude tert-butyl (S)-3-((5-(1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)(methyl)amino)azetidine-1-carboxylate was dissolved in dichloromethane (1 mL). To this solution was added TFA (0.462 mL, 6.00 mmol) at room temperature. The reaction mixture was stirred at room temperature for 5 minutes. The solvent was removed with a stream of nitrogen and the crude product was purified by preparative HPLC (acid mode, 1-25% ACN/water gradient) to give a TFA salt of the title compound as a clear film (5.9 mg, 19% over two steps). 1H NMR (400 MHz, CD3OD) δ ppm 1.73-1.82 (m, 3H), 2.49-2.56 (m, 3H), 2.82-2.89 (m, 3H), 3.94-4.08 (m, 4H), 4.19-4.33 (m, 3H), 4.46-4.57 (m, 1H), 5.97-6.09 (m, 1H), 6.70-6.77 (m, 1H), 7.85-7.94 (m, 1H), 8.32-8.47 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C20H25N9, 392. found 392.

Provenance & Evidence