HCID 57545979, compound → HCID 25159918, compound

Participants

Reaction Steps

(±)-tert-Butyl 4-phenyl-4-((1-(5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)piperidine-1-carboxylate (62 mg, 0.098 mmol) was dissolved in trifluoroacetic acid (50% in dichloromethane, 1.5 mL) and stirred at room temperature for 3 h. The reaction was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was flushed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated to give 41 mg (quant.). 1H-NMR (CDCl3, 500 MHz) δ 10.03 (bs, 1H), 8.08 (m, 1H), 7.95 (m, 1H), 7.32-7.55 (m, 5H), 7.26 (m, 1H), 4.66 (m, 1H), 3.54 (m, 2H), 3.36 (m, 2H), 2.72-3.06 (m, 4H), 2.36 (m, 1H), 2.16 (m, 1H), 1.97 (m, 1H), 1.85 (m, 1H), 1.49 (m, 3H); 13C-NMR (CDCl3, 126 MHz) δ 143.8, 138.1, 135.2, 128.8, 127.5, 127.1, 126.8, 124.7 (q, J=272 Hz), 123.3, 119.7 (q, J=3.8 Hz), 118.1 (q, J=3.8 Hz), 79.2, 78.3, 42.8, 42.6, 41.7, 33.8, 33.7, 22.2. Mass spec.: 404.19 (MH)+. Accurate mass spec.: m/z 404.1960 [MH]+, Δ=2.5 ppm.

Provenance & Evidence