Triethylamine → HCID 178434310, compound

Participants

Reaction Conditions

Reaction Steps

(±)-tert-Butyl 4-((1-(3-methyl-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (94 mg, 0.15 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 1 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 concentrated to afford a crude product which was dissolved in dichloromethane (3 mL), cooled to 0° C., and treated with di-tert-butyl carbonate (63 mg, 0.29 mmol) and triethylamine (30 μL, 0.22 mmol). After 1 h, the reaction was treated with a few drops of 2 M ammonia in methanol and concentrated. The residue was dissolved in ethyl acetate, washed with water (2×), brine (2×), dried over sodium sulfate, filtered and concentrated. Flash chromatography on silica gel (15% ethyl acetate/hexanes) afforded 62 mg (83%). 1H-NMR (CDCl3, 500 MHz) δ 7.81 (s, 1H), 7.38-7.41 (m, 2H), 7.30-7.35 (m, 3H), 7.19 (m, 1H), 4.56 (q, J=6.4 Hz, 1H), 3.76 (m, 2H), 3.40 (d, J=9.2 Hz, 1H), 3.29 (d, J=8.9 Hz, 1H), 2.99-3.06 (m, 2H), 2.54 (s, 3H), 2.11-2.31 (m, 2H), 1.75-1.87 (m, 2H), 1.42 (s, 9H), 1.40 (m, 3H). Mass spec.: 518.28 (MH)+.

Provenance & Evidence