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Process for preparing Vildagliptin by one-pot method

A process and a selected technology, applied in the field of one-pot preparation of vildagliptin, can solve the problems of many functional groups, many by-products, low yield and the like, and achieve the effect of simple and convenient process operation.

Active Publication Date: 2012-08-01
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the existing synthetic route, the yield from 3 to 4 is 50% to 70%, the yield is low, there are many by-products, and purification is inconvenient
The existing synthetic routes all adopt shrinkage and then dehydration, so that molecule 3 has more functional groups, and more by-products are generated during dehydration.

Method used

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  • Process for preparing Vildagliptin by one-pot method
  • Process for preparing Vildagliptin by one-pot method
  • Process for preparing Vildagliptin by one-pot method

Examples

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Effect test

Embodiment 1

[0022] The preparation one of embodiment 1 vildagliptin

[0023] Add 8 mL of chloroacetyl chloride 2 and 100 mL of anhydrous dichloromethane into a 1 L three-necked flask under the protection of nitrogen. Under the condition of cooling in an ice bath, 21 grams of (S)-pyrrole-2-cyano trifluoroacetate 6 was added dropwise in this reaction mixture (by the known literature Journal of Medicinal Chemistry, 2009, 52 (21) , 6672-6684) and 33 milliliters of triethylamine in 200 milliliters of anhydrous dichloromethane solution, after the dropwise addition, the reaction solution was raised to room temperature and continued to stir for 6 to 24 hours. Add 1.8 grams of tetrabutylammonium iodide to the reaction solution, then add 17 grams of 3-amino-1-adamantanol 5 and 20 milliliters of triethylamine dropwise in 100 milliliters of anhydrous dichloromethane solution, after the dropwise addition, the reaction solution was continuously stirred at 30-40° C. for 72 hours. Add 500 ml of water t...

Embodiment 2

[0026] The preparation two of embodiment 2 vildagliptin

[0027] Add 8.7 mL of bromoacetyl bromide 2 and 100 mL of anhydrous chloroform into a 1 L three-necked flask under the protection of nitrogen. Under the condition of cooling in an ice bath, 21 grams of (S)-pyrrole-2-cyano trifluoroacetate 6 was added dropwise in this reaction mixture (by the known literature Journal of Medicinal Chemistry, 2009, 52 (21) , 6672-6684 made) and 200 ml of anhydrous chloroform solution of 40 ml of diisopropylethylamine, after the dropwise addition, the reaction solution rose to room temperature and continued stirring for 10 hours. Add 1.8 grams of tetrabutylammonium iodide to the reaction solution, and then add 17 grams of 3-amino-1-adamantanol 5 and 20 milliliters of diisopropylethylamine dropwise to the reaction solution in 100 milliliters without Water chloroform solution, after the dropwise addition, the reaction solution was stirred for 24 hours. Add 500 ml of water to the reaction sol...

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Abstract

The invention relates to a process for preparing Vildagliptin by a one-pot method. The one-pot method is adopted, so the purification steps are reduced, the product yield is improved, and the process is particularly suitable for industrial production.

Description

technical field [0001] The invention relates to a process for preparing vildagliptin by a one-pot method. The biggest feature of the process is that the one-pot method is adopted, thereby reducing purification steps and improving product yield, and is especially suitable for large-scale industrial production. Background technique [0002] Vildagliptin is a dipeptidylase type IV (DDPIV) inhibitor developed by Novartis, which can be used to treat type 2 diabetes. In September 2007, it was approved as a low-dose drug by the European Union, and it has also been approved in Brazil and Mexico. [0003] The key of the existing synthetic route concentrates on the selection of the dehydrating agent when the amide compound (3) is converted into the cyano compound (4): the world patent-WO2000034241 applied by Novartis and the application of the Czech generic pharmaceutical company Zentiva The world patent-WO2010022690 all adopts trifluoroacetic anhydride (Trifluoroacetic anhydride) as...

Claims

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Application Information

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IPC IPC(8): C07D207/16
Inventor 林国强田平吴诺毅孙彩云
Owner JIANGSU HANSOH PHARMA CO LTD
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