1,2-Dichloroethane → HCID 21837225, compound

Participants

Reaction Steps

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-4-fluorophenylacetic acid (0.15 g, 0.60 mmol) from Step 5 above and 2-carbamoyl-4-(2-methylphenyl)piperazine (0.13 g, 0.66 mmol) from Step 4 of Example 1 in DMF (3 mL) was added HOBT (0.11 g, 0.78 mmol), EDC (0.17 g, 0.9 mmol), and DIEA (0.16 mL, 0.9 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 (50 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated and washed with H2O (10 mL) and saturated aqueous NaHCO3 (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 5:95 MeOH:CH2Cl2 as eluant. Evaporation of the product-containing fractions gave the title compound as an amorphous solid. HPLC retention time=9.16 min (method A) TLC Rf =0.25 (5:95 MeOH:CH2Cl2); FAB MS: m/z=454 (M+ +H), 0.4 CH2Cl2 ; combustion analysis: C22H23F4N3O3, 0.4 CH2Cl2 ; Calculated C, 57.43; H, 5.12; N, 8.97; Found C, 57.44; H, 4.89; N, 9.22

Provenance & Evidence