Synthese of substitutd pyrazolopyrimidines

A technology of halogenated pyrazolopyrimidines and pyrazolopyrimidines, which is applied in the field of synthesis of pyrazolopyrimidines, and can solve the problems of time-consuming and large-scale synthesis that are not particularly economical or effective

Inactive Publication Date: 2002-10-02
NEUROCRINE BIOSCI INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] 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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Embodiment

[0109] Formation of Enaminones 8 of Reaction Schemes 1, 2 and / or 3 under Phase Transfer Conditions

[0110] To enaminone 8' (25 g, 107.6 mmol) in trifluorotoluene (92 mL) and dichloromethane (160 mL) was added tetrabutylammonium sulfate (2 g, 5.9 mmol). To the mixture was added dimethyl sulfate (16 g, 126.7 mmol). To this mixture was added 200 g of a 50% aqueous sodium hydroxide solution, and the mixture was stirred vigorously 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 bring the reaction temperature below 40°C. The aqueous phase was separated and the organic phase was washed three times with water and dried over magnesium sulfate. Dichloromethane was removed in vacuo to yield a yellow solid. The solid was filtered, washed with trifluorotoluene and dried under vacuum to give 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 range of indications, including the treatment of insomnia. Background of the Invention [0002] US 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, such compounds are active as anxiolytics, anticonvulsants, sedative-hypnotics and musculoskeletal relaxants. Such compounds can generally be classified as "substituted pyrazolopyrimidines" having the following structure (I): 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 chart for the various R groups). [0003] Compounds of structure (I) are described in US Pat. No. 4,521,422 by combining an appropriately substituted pyrazole (a) with an appropriately substituted 3-dimethylamino-2-propen-1-one (b) as shown in Scheme A belo...

Claims

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Application Information

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Patent Type & Authority Applications(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
Owner NEUROCRINE BIOSCI INC
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