Reaction Steps
A mixture of (R)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)amino)piperidine-1-carboxylate (78.0 mg, 0.169 mmol) and TFA (0.45 mL, 5.84 mmol) in DCM (1.5 mL) was stirred at 0° C. for 10 min, then at 25° C. for 1 h. The mixture was concentrated in vacuo, and the residue was taken up in DMSO (2.0 mL) and purified by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) to provide (R)-2-(2-(piperidin-3-ylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (30.7 mg, 0.065 mmol, 38% yield) as a yellowish-brown solid: 1H NMR (400 MHz, MeOH-d4) δ ppm 8.08 (1H, dd, J=9.6, 4.1 Hz), 7.85 (1H, dd, J=7.5, 1.3 Hz), 7.65 (1H, d, J=7.4 Hz), 7.43 (1H, br. s.), 7.37 (1H, t, J=7.5 Hz), 6.96 (1H, d, J=7.2 Hz), 4.40-4.50 (1H, m), 3.79 (1H, dd, J=11.7, 2.3 Hz), 3.66 (2H, t, J=7.0 Hz), 3.43 (1H, dt, J=12.8, 4.3 Hz), 3.06-3.18 (2H, m), 3.03 (2H, t, J=7.1 Hz), 2.27-2.38 (1H, m), 2.10-2.22 (1H, m), 1.93-2.07 (1H, m), 1.72-1.85 (1H, m). 19F NMR (377 MHz, MeOH-d4) δ ppm −77.29 (3F, s). m/z (ESI, +ve) 362.1 (M+H)+.
