Trifluoroacetic acid methylene chloride → HCID 178506216, compound

Participants

Reaction Steps

tert-Butyl 4-(((3-bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (34 mg, 0.06 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 4 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvent was evaporated and the compound purified by reverse phase HPLC to afford 5 mg (27%) as a clear oil. 1H-NMR (CD3OD, 500 MHz) δ 7.87 (s, 1H), 7.53 (s, 1H), 7.37-7.43 (m, 4H), 7.29-7.30 (m, 1H), 4.77 (s, 2H), 3.56 (s, 2H), 3.27-3.31 (m, 2H), 2.90-2.95 (m, 2H), 2.50-2.53 (m, 2H), 2.14-2.20 (m, 2H). Mass spec.: 468.08 (MH)+. Accurate mass spec.: m/z 468.1322 [MH]+, Δ=0.5 ppm.

Provenance & Evidence