Trifluoroacetic acid methylene chloride → HCID 178506217, compound

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tert-Butyl 4-(((3-cyclopropyl-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (18 mg, 0.03 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 to afford 9 mg (77%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.92 (s, 1H), 7.31-7.45 (m, 5H), 7.22-7.33 (m, 1H), 4.67 (s, 2H), 3.52 (s, 2H), 2.95-2.99 (m, 2H), 2.76-2.81 (m, 2H), 2.15-2.24 (m, 3H), 1.89-1.95 (m, 2H), 1.04-1.02 (m, 4H). Mass spec.: 430.16 (MH)+. Accurate mass spec.: m/z 430.2097 [MH]+, Δ=2.1 ppm.

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