Diisopropylethylamine → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3 (2.90 g, 9.28 mmol), 4-(2-(dimethylamino)ethoxy)benzenamine dihydrochloride (2.58 g, 10.2 mmol), 4-Dimethylaminopyridine (56.7 mg, 0.464 mmol) in CH2Cl2 (100 ml) was added O-Benzotriazoyl-N,N,N′,N′-tetramethyluronium Hexafluorophosphate (3.87 g, 10.2 mmol) under ice cooling, and the mixture was stirred at 0° C. for 10 min. Then N,N-Diisopropylethylamine (4.19 g, 32.4 mmol) was added under ice cooling. The mixture was stirred at 0° C. for 5 min, and at room temperature for 15 h. The reaction was quenched with saturated aqueous NaHCO3 under ice cooling, and the whole was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by Biotage (eluent: CH2Cl2 to CH2Cl2/MeOH, 6:1) gave the colorless solid. The solid was triturated with Et2O-hexane to give 4 (65%).

Provenance & Evidence