Diisopropylethylamine → 4-((S)-2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazine-1-carbonyl)imidazolidin-2-one

Participants

Reaction Steps

A solution of 3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2, Compound 90) (100 mg, 0.273 mmol), in CH2Cl2:DMF (1:1, 3 mL), then treated with 2-oxo-imidazolidine-4-carboxylic acid (50 mg, 0.321 mmol), followed by the addition of diisopropylethylamine (100 μL, 0.819 mmol) and PyBOP (198 mg, 0.383 mmol). The reaction stirred at room temperature for 8 h. The solution was washed with a saturated aqueous solution of NaHCO3 (10 mL) followed by brine (10 mL). The organic portion was dried over MgSO4, filtered and evaporated to an oil which was purified by reversed phase HPLC to afford product as a colorless solid (39 mg, 30%). LC/MS (Method B) 3.60 min, [M+1]+ 479. Potency class A.

Provenance & Evidence