Trifluoroacetic acid → {7-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-oxo-3,4-dihydro-2H-quinolin-1-yl}-acetic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 7-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-3,4-dihydro-1H-quinolin-2-one (233 mg, 0.557 mmol) in DMF (3.0 mL) is treated with NaH (67 mg, 1.67 mmol, 60%). The resulting suspension is heated at 57° C. for 40 minutes and cooled to room temperature. The t-butyl bromoacetate (217 mg, 1.11 mmol) is added and the suspension is stirred for 2 hours and then quenched with water. The mixture is extracted with EtOAc (30 mL×2) and the combined organics are dried (Na2SO4), concentrated, and purified on silica gel chromatography column with 20% EtOAc/Hexanes to obtain the intermediate compound. The intermediate is then treated with TFA (1.0 ml), CH2Cl2 (1.0 ml), H2O (0.1 mL) and stirred for 2 hours, concentrated and purified on silica gel chromatography (Hexanes/EtOAc/HOAc, 5/5/0.02) afford the title compound (65 mg, 25%). MS (MH+): 477.1; the structure is also confirmed by proton NMR.

Provenance & Evidence