Trifluoroacetic acid → HCID 118511965, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)oxy)piperidine-1-carboxylate (117 mg, 0.25 mmol) in DCM (3.0 mL) at 0° C. was added TFA (0.5 mL, 6.73 mmol). The reaction was stirred at 0° C. for 20 min then at RT for 2 h. The solution was concentrated, the residue was dissolved in DCM and washed with a saturated aq. solution of NaHCO3. The organic layer was separated, and the aq. layer was extracted with DCM (2×). The combined organic layers were then concentrated, and the residue was dissolved in DMSO (3 mL). Purification by rpHPLC (Silicycle Silichrome XT C18 column; 30×150 mm, 5 m, 5-95% 0.1% TFA/ACN in 0.1% TFA/water by volume over 10 min.), then drying in a Genevac Series II Evaporator afforded (S)-2-(2-(piperidin-3-yloxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (27.3 mg, 0.057 mmol, 22.7% yield) as an amorphous brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.62 (br. s., 1H), 8.69-8.85 (m, 2H), 8.33 (d, J=8.8 Hz, 1H), 7.95 (d, J=7.4 Hz, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.7 Hz, 1H), 7.16 (d, J=2.0 Hz, 1H), 7.09 (d, J=8.8 Hz, 1H), 7.02 (br. s., 1H), 5.51 (br. s., 1H), 3.40-3.53 (m, 4H), 3.14 (br. s., 2H), 2.89 (t, J=6.8 Hz, 2H), 2.11-2.23 (m, 1H), 1.94-2.05 (m, 2H), 1.81-1.90 (m, 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −74.35 (s, 3F). m/z (ESI, +ve ion) 363.0 (M+H)+.

Provenance & Evidence