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Preparation method of 5-(chloromethyl)-2-(trifluoromethyl)-1, 3, 4 oxadiazole

A technology of trifluoromethyl and chloromethyl, which is applied in the field of preparation of 5--2--1,3,4 oxadiazole, can solve the problems of difficult removal of water in acetonitrile, unfavorable industrial production, and high price of acetonitrile. Achieve the effect of convenient solvent recovery, strong reactivity and low cost

Inactive Publication Date: 2021-03-12
台州达辰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above technical route uses acetonitrile, a water-soluble solvent, as the reaction solvent. The price of acetonitrile is relatively high. After the post-treatment is cracked with isopropyl acetate or ethyl acetate and water, acetonitrile enters the water layer and produces a large amount of organic waste liquid. It is difficult to remove the water in acetonitrile , it is difficult to apply mechanically, the cost is high, and it is not conducive to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In a 500ml reaction flask, add 200g of 1,2-dichloroethane, 40.8g of 1-(chloroacetyl)-2-(trifluoroacetyl)hydrazine, add 61.32g of phosphorus oxychloride under stirring at room temperature, and heat up to Keep the reaction at 80-85°C for 20-24 hours, lower the temperature to below 10°C, add 200g of water dropwise, separate the organic layer, add 100g of 5% sodium bicarbonate aqueous solution, stir and wash until neutral, separate the organic layer, concentrate and recover 1, 2-dichloroethane, 33.64 g of oily product was obtained, the yield was 90.2%, and the purity was 97.3%.

Embodiment 2

[0015] In a 500ml reaction flask, add 150g of toluene, 40.8g of 1-(chloroacetyl)-2-(trifluoroacetyl)hydrazine, add 45.99g of phosphorus oxychloride under stirring at room temperature, heat up to 95-100°C and keep it warm for 20 -24 hours, lower the temperature to below 10°C, add 200 g of water dropwise, separate the organic layer, add 100 g of 5% aqueous sodium bicarbonate solution, stir and wash until neutral, separate the organic layer, concentrate and recover toluene to obtain 33.31 g of an oily product, and collect The yield is 89.3%, and the purity is 96.8%.

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Abstract

The invention relates to a preparation method of a sitagliptin intermediate 5-(chloromethyl)-2-(trifluoromethyl)-1, 3, 4 oxadiazole. The preparation method comprises the following steps: by taking 1-(chloroacetyl)-2-(trifluoroacetyl) hydrazine as a raw material, carrying out heating reaction with phosphorus oxychloride in the presence of a solvent to obtain a product solution, cooling, dropwise adding water for cracking, layering, washing an organic layer with a sodium bicarbonate aqueous solution until the organic layer is neutral, and finally concentrating and recovering the solvent to obtain the 5-(chloromethyl)-2-(trifluoromethyl)-1, 3, 4 oxadiazole. Aiming at the defects of the existing production process, the method provided by the invention has the advantages of obvious improvement,simple operation, convenient solvent recovery, easy scale-up production, good product purity and high yield.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and more specifically relates to a preparation method of 5-(chloromethyl)-2-(trifluoromethyl)-1,3,4 oxadiazole. Background technique [0002] 5-(Chloromethyl)-2-(trifluoromethyl)-1,3,4 oxadiazole is an important intermediate of sitagliptin phosphate developed by Merck. Sitagliptin phosphate is a kind of dipeptidyl peptidase-4 (DDP-4) inhibitor, and the trade name is Genovi, which was approved by the U.S. FDA in October 2006. sugar drug. It has been approved for use in 80 countries around the world. It can respond to glucose around the clock, can reduce postprandial blood sugar and fasting blood sugar at the same time, thereby effectively reducing blood sugar levels, and has good tolerance and safety, and does not increase patient weight. Compared with the traditional oral hypoglycemic drugs that are easy to gain weight at present, the curative effect is obvious, and it is a safe, eff...

Claims

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Application Information

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IPC IPC(8): C07D271/10
CPCC07D271/10
Inventor 缪炳林贺银翠徐龙曹俊爽周魏魏关键姜辉徐海斌
Owner 台州达辰药业有限公司
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