Method for producing n-ethyl-n-[3-(3-cyanopyrazolo[1,5a]pyrimidine-7-yl)phenyl]acetamide
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United States of America Patent
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Apr 25, 2006
Grant Date -
Aug 4, 2005
app pub date -
Jan 17, 2003
filing date -
Feb 14, 2002
priority date (Note) -
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Abstract
N-ethyl-N-[3-(3-cyanopyrazolo[1,5-a]pyrimidine-7-yl)phenyl]acetamide (Zaleplon) can be produced by condensing 3-(N-acetyl-N-ethyl-amino)-β-oxo-phenylpropanal sodium salt with 3-amino-4-cyanopyrazole. Said sodium salt can be produced by first treating 3-acetylamino-acetophenone with an alkali metal hydroxide, in particular with powdered potassium hydroxide and then with an ethylating reagent, in particular ethyl bromide and the N-(3-acetylphenyl)-N-ethyl-acetamide that is obtained is reacted with a formic acid alkyl ester in the presence of an alkali metal alkanolate, in particular in the presence of sodium ethanolate. Zaleplon is the active ingredient of the soporific licensed under the trade name Sonata®.
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