Synthese of substitutd pyrazolopyrimidines

一种唑并嘧啶、吡唑的技术，应用在吡唑并嘧啶的合成领域，能够解决耗时、大规模的合成不是特别经济或有效的等问题，达到简化反应条件、好产率、提高效率的效果

Inactive Publication Date: 2004-06-02
NEUROCRINE BIOSCIENCES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Although U.S. Patent Nos. 4,521,422 and 4,900,836 teach synthetic techniques for compounds of structure (I), these methods are relatively time-consuming, involve many steps, and are not particularly economical or efficient for large-scale syntheses

Method used

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  • Synthese of substitutd pyrazolopyrimidines
  • Synthese of substitutd pyrazolopyrimidines
  • Synthese of substitutd pyrazolopyrimidines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0141] Formation of enaminone 8 of reaction schemes 1, 2 and / or 3 under phase transfer conditions

[0142]

[0143] To enaminone 8' (25 g, 107.6 mmol) in benzotrifluoride (92 mL) and dichloromethane (160 mL) was added tetrabutylammonium sulfate (2 g, 5.9 mmol). Dimethyl sulfate (16 g, 126.7 mmol) was added to the mixture. To this mixture was added 200 g of a 50% aqueous sodium hydroxide solution, and the mixture was vigorously stirred for 6 hours, keeping the reaction temperature below 40°C. Depending on the consumption of starting material, 200 mL of water was carefully added to keep the reaction temperature below 40°C. The aqueous phase was separated off and the organic phase was washed three times with water and dried over magnesium sulfate. The dichloromethane was removed in vacuo to give a yellow solid. The solid was filtered, washed with benzotrifluoride and dried under vacuum to give the alkylated enaminone 8 (19 g, 72% yield).

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Abstract

Methods of making substituted pyrazolopyrimidines generally and, more particularly, N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5- alpha ]-pyrimidin-7-yl}phenyl)acetamide. Such compounds have utility over a wide range of indications, including treatment of insomnia. In the practice of the present invention, improved techniques which do not require use and / or isolation of the pyrazole intermediate are disclosed, as well as improved techniques for making the reaction intermediates themselves. Such techniques offer significant advantages, including enhanced efficiency, particularly in the context of large scale manufacture.

Description

technical field [0001] The present invention relates to the synthesis of substituted pyrazolopyrimidines which are effective for a wide variety of indications, including the treatment of insomnia. Background of the invention [0002] U.S. Patent No. 4,521,422 to the American Cyanamid Company relates to certain aryl and heteroaryl [7-(aryl and heteroaryl)-pyrazolo(1,5-a)pyrimidines -3-yl]methanone, a class of compounds that are active as anxiolytics, anticonvulsants, sedative-hypnotics and skeletal muscle relaxants. Such compounds can generally be classified as "substituted pyrazolopyrimidines" and have the following structure (I): [0003] [0004] where R 2 , R 3 , R 5 , R 6 and R 7 As defined in US Patent No. 4,521,422 (but in a different numbered scheme for each R group). [0005] Compounds of structure (I) are prepared according to U.S. Patent No. 4,521,422 by combining an appropriately substituted pyrazole (a) with an appropriately substituted 3-dimethylamino-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B61/00C07C231/08C07C233/43C07D487/04
CPCC07C231/08C07C233/43C07D487/04C07D333/22C07D409/12
Inventor R·S·戈罗斯K·M·维尔考克森理查德·C·奥格尔斯比
Owner NEUROCRINE BIOSCIENCES INC
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