Acetic Acid → HCID 86642027, compound

Participants

Reaction Steps

1.50 g (7.97 mmol) of the compound from Example 5A, 1.86 g (9.57 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)], 91 μl (1.59 mmol) of acetic acid and 158 μl (1.59 mmol) of piperidine are dissolved in 30 ml of anhydrous dichloromethane and stirred under reflux with a water trap overnight. The mixture is then washed with water, the organic phase is dried with magnesium sulfate, and the volatile components are removed in a rotary evaporator. 2.91 g (approx. 7.33 mmol) of the 2-cyanoethyl (2Z)-2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylidene]-3-oxobutanoate crude product obtained in this way are mixed with 0.990 g (9.00 mmol) of 4-amino-5-methylpyridin-2(1H)-one [Bisagni, E., Hung, N. C., Synthesis, 765-766 (1984)], taken up in 40 ml of 2-propanol and stirred at the reflux temperature overnight. After cooling, the resulting precipitate is filtered off and washed with a little diethyl ether. Drying under high vacuum results in 1.20 g (38% of theory) of the title compound.

Provenance & Evidence