2-Imidazolidinone → HCID 53492514, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (720 mg, 2 mmol), imidazolidin-2-one (861 mg, 10 mmol), copper(I) iodide (229 mg, 1.2 mmol), N,N-dimethylglycine hydrochloride (224 g, 1.6 mmol) and potassium carbonate (829 mg, 6 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120° C. for 12 h. Then the reaction mixture cooled to room temperature. Iodo-benzene (2.17 mL, 20 mmol), copper(I) iodide (229 mg, 1.2 mmol), N,N-dimethylglycine hydrochloride (224 g, 1.6 mmol) and potassium carbonate (829 mg, 6 mmol) was added. The reaction mixture was stirred at 120° C. for 12 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×200 mL), washed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 3,3-dimethyl-2-[3-(2-oxo-3-phenyl-imidazolidin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (82 mg, 9%) as a white solid: LC/MS m/e calcd for C27H27N3O3 (M+H)+: 442.53, observed: 442.1.

Provenance & Evidence