1,2-Dichloroethane → HCID 18700097, compound

Participants

Reaction Steps

To a stirred solution of 2-(2,2,2-trifluoroethoxyphenyl-acetic acid (0.20 g, 0.90 mmol) from Step 2 of Example 16 and 1-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one prepared by the method of Ogawa, et al., J. Med. Chem. (1993), vol. 36, pp. 2011-2017) (0.24 g, 0.90 mmol) in DMF (15 mL) was added HOBT (0.15 g, 1.0 mmol), EDC (0.44 g, 1.5 mmol), and DIEA (0.3 mL, 1.7 mmol). The solution was stirred at ambient temperature for 14 h and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated and washed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:2 CH2Cl2 :MeOH as eluant to give the title compound as an amorphous solid.

Provenance & Evidence