Triethylamine → (E)-3-Cyclopropyl-N-methyl-N-[2-[methyl-(2-methyl-4-quinolyl)amino]ethyl]prop-2-enamide

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Reaction Steps

(E)-3-Cyclopropylprop-2-enoic acid (22 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous THF and anhydrous DMF (2 ml). After 5 minutes N,N′-dimethyl-N-(2-methyl-4-quinolyl)ethane-1,2-diamine (52 mg, 0.23 mmol) and triethylamine (62 μl, 0.45 mmol) were added and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was removed under reduced pressure and purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 28.3 mg (0.087 mmol, 43.5%).

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