Trifluoroacetic acid → HCID 86709785, compound

Participants

Reaction Conditions

Reaction Steps

TFA (0.5 mL, 6.49 mmol) was added to a solution of (4R)-tert-butyl 4-((6-(1-(tetrahydro-2H-pyran-2-yl)-5-(1-(trifluoromethyl)cyclopropyl)-1H-indazol-3-yl)pyrazin-2-yl)oxy)-6-azaspiro[2.5]octane-6-carboxylate (25.2 mg, 0.041 mmol) in DCM (0.5 mL) and the resulting solution was stirred at 25° C. for 2 h. The mixture was concentrated in vacuo and the residue was taken up in DMSO (2.0 mL) and purified by rpHPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% CH3CN/H2O+0.1% TFA, 15 min, 254 nm) to provide 3-(6-((4R)-6-azaspiro[2.5]oct-4-yloxy)-2-pyrazinyl)-5-(1-(trifluoromethyl)cyclopropyl)-1H-indazole tris(2,2,2-trifluoroacetate) (12.0 mg, 0.016 mmol, 38% yield) as a yellow foam: 1H NMR (400 MHz, MeOH-d4) δ ppm 9.04 (1 H, s), 8.42-8.46 (1 H, m), 8.31 (1 H, s), 7.60-7.64 (1 H, m), 7.55-7.59 (1 H, m), 5.07 (1 H, s), 3.89 (1 H, d, J=12.7 Hz), 3.57 (1 H, m, J=13.3, 1.0 Hz), 3.47-3.54 (1 H, m), 3.34-3.39 (1 H, m), 2.72 (1 H, td, J=13.9, 4.5 Hz), 1.45-1.49 (2 H, m), 1.22-1.27 (1 H, m), 1.17-1.22 (2 H, m), 0.99 (1 H, dt, J=8.9, 5.6 Hz), 0.77-0.85 (2 H, m), 0.67-0.73 (1 H, m). 19F NMR (377 MHz, MeOH) δ ppm −71.41 (3 F, s), −77.45 (9 F, br. s.). MS (ESI, pos. ion) m/z: 430.1 (M+1).

Provenance & Evidence