Trifluoroacetic acid → TFA acetonitrile

Participants

Reaction Steps

6-Chloro-4-(1-((4-(4-fluorophenyl)-1-methylpiperidin-4-yl)methoxy)ethyl)-1,3-bis((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2(3H)-one (58 mg, 0.085 mmol) was dissolved in TFA (40% in dichloromethane, 1 mL) and stirred at room temperature for 1 h. The reaction was concentrated, loaded onto a strong cation exchange cartridge, and flushed with several volumes of methanol which were discarded. The crude product was eluted with 2M ammonia in methanol and concentrated. preparative HPLC (29% B, isocratic method, ACN/TFA) gave 12.5 mg (27%) as a colorless film. 1H-NMR (CD3OD, 500 MHz) δ 7.30-7.60 (m, 2H), 7.00-7.25 (m, 2H), 6.92 (s, 1H), 6.60-6.70 (m, 1H), 4.49 (q, J=6.4 Hz, 1H), 3.46 (m, 2.4H), 3.23 (m, 1H), 2.40-3.00 (m, 7H), 1.90-2.25 (m, 2H), 1.38 (d, J=6.1 Hz, 3H). Mass spec.: 418.15 (MH)+.

Provenance & Evidence