Synthesis method of Anagliptin key intermediate

A synthetic method and intermediate technology, applied in the field of drug synthesis, can solve the problems of less reported synthetic routes of pyrimidine-6-carboxylic acid, and achieve the effects of environmental friendliness, high product purity, and less side reactions

Active Publication Date: 2014-07-30
安徽安腾药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, there are few reports on the synthesis route of 2-methyl-pyrazolo[1,5-A]pyrimidine-6-carboxylic acid of formula (I)

Method used

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  • Synthesis method of Anagliptin key intermediate
  • Synthesis method of Anagliptin key intermediate
  • Synthesis method of Anagliptin key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 69.06g (1.0mol) of cyanoacetaldehyde, dissolved in 300ml of methanol, added 132g (1.1mol) of N,N-dimethylformamide dimethyl acetal, reacted at 20-25°C for 20-25h, and reduced Concentrate under reduced pressure to obtain an orange-yellow solid, which is recrystallized from ethanol to obtain a light yellow crystal, which is air-dried at 50°C for 10 hours to obtain 87 g of a solid, with a yield of 70%.

Embodiment 2

[0044] 69.06g (1.0mol) of cyanoacetaldehyde, dissolved in 400ml of ethanol, added 132g (1.1mol) of N,N-dimethylformamide dimethyl acetal, reacted at 20-25°C for 20-25h, and reduced Concentrate under reduced pressure to obtain an orange-yellow solid, which is recrystallized from ethanol to obtain light-yellow crystals, and air-dried at 50°C for 10 hours to obtain 75 g of solid, with a yield of 61.3%.

Embodiment 3

[0046] 69.06g (1.0mol) of cyanoacetaldehyde, dissolved in 550ml of isopropanol, add 132g (1.1mol) of N,N-dimethylformamide dimethyl acetal, react at 20-25℃ for 20-25h, end Concentrate under reduced pressure to obtain an orange-yellow solid, which is recrystallized from ethanol to obtain a light yellow crystal, which is air-dried at 50°C for 10 hours to obtain 76 g of a solid, with a yield of 70%.

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Abstract

The invention discloses a synthesis method of Anagliptin key intermediate. The synthesis method comprises the following steps: jointing cyanoacetaldehyde with N,N-dimethylformamide dimethyl acetal to obtain (2E)-3-(dimethylamino)-2-formylacrylonitrile, further performing ring closing with 3-amino-5-methylpyrazole to obtain 2-methyl-pyrazolo[1,5-a]pyrimidine-6-carbonitrile, and then hydrolyzing to obtain the Anagliptin key intermediate. The invention relates to a brand-new method for synthesizing 2-methyl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, and the method has the advantages of use of raw materials, less side products, high product purity, and low whole cost.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing 2-methyl-pyrazolo[1,5-A]pyrimidine-6-carboxylic acid, a key intermediate of alalogliptin. Background technique [0002] Alalogliptin is a dipeptidyl peptidase IV inhibitor, which prevents and treats diseases such as diabetes (especially type 2 diabetes) and diabetic syndrome by blocking the activity of dipeptidyl peptidase IV. Effect. [0003] Generally, alogliptin of formula (V) can be prepared according to the key intermediate of formula (I) 2-methyl-pyrazolo[1,5-A]pyrimidine-6-carboxylic acid obtained in the present invention. [0004] [0005] So far, there are few reports on the synthesis route of 2-methyl-pyrazolo[1,5-A]pyrimidine-6-carboxylic acid of formula (I). Contents of the invention [0006] The purpose of the present invention is to overcome the deficiencies of the prior art and provide a new method for synthesizing the key intermediate...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李新涓子汪迅李勇刚夏小波林祥义高艳吕兴红
Owner 安徽安腾药业有限责任公司
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