Diisopropylethylamine → methyl (S)-2-(4-ethylpiperazin-1-yl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)benzoylamino]propanoate

Participants

Reaction Steps

0.6 g (2.1 mmol) of 4-(2-methylquinolin-4-ylmethoxy)benzoic acid are dissolved in 10 ml of dimethylformamide then 0.7 g (2.3 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate and 1.1 ml (6.3 mmol) of diisopropylethylamine are added. After stirring for 15 minutes at ambient temperature, a solution of 700 mg (2.1 mmol) of methyl 3-amino-2-(4-ethylpiperazin-1-yl)propanoate trihydrochloride and 1.1 ml (6.3 mmol) of diisopropylethylamine in 10 ml of dimethylformamide is added. The reaction medium is stirred at ambient temperature for 18 h then is hydrolysed with a saturated aqueous solution of sodium hydrogen carbonate. After extraction with ethyl acetate, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under vacuum. The product is purified by chromatography over silica gel eluted with a 93/7 dichloromethane/methanol mixture to give 840 mg (81%) of methyl (S)-2-(4-ethylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzoylamino]propanoate in the form of a colourless oil.

Provenance & Evidence