Trifluoroacetic acid → HCID 131728091, compound

Participants

Reaction Steps

Trifluoroacetic acid (45 mL) was added to a solution of Example 315C (5.72 g, 11.32 mmol) in dichloromethane (220 mL) at 0° C. After 5 minutes, the ice bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The residue was partitioned between dichloromethane and 1.0 N sodium hydroxide. The organic solvent was removed and the residue was purified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size) using a gradient of 5% to 75% acetonitrile to ammonium acetate (10 mM) over 20 minutes at a flow rate of 21 mL/min to provide the title compound. MS (ESI+) m/z 405.4 (M+H)+; Rt=1.37 min. 1H-NMR (400 MHz, DMSO-d6) δ 8.180 (m, 1H); 7.942 (m, 1H); 7.728 (m, 1H); 7.668 (m, 1H); 7.612 (m, 2H); 7.000 (m, 1H); 4.498 (m, 2H); 2.961 (m, 4H); 2.842 (m, 4H); 1.891 (m, 3H).

Provenance & Evidence