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Synthesis process of rufinamide

A rufinamide and process technology, applied in the field of medicinal chemistry, can solve the problems of long reaction time, low catalytic efficiency, complicated operation and the like, and achieve the effects of reducing reaction time, improving catalytic efficiency and speeding up the reaction process

Inactive Publication Date: 2014-01-29
XUHE TIANJIN YIYAO KEJI YOUXIAN GONGSI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems of cumbersome operation, unsafety, long reaction time and low catalytic efficiency in the existing rufinamide production route, the present invention improves it and provides a simple, safe, fast and efficient rufinamide synthetic route

Method used

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  • Synthesis process of rufinamide
  • Synthesis process of rufinamide
  • Synthesis process of rufinamide

Examples

Experimental program
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preparation example Construction

[0025] Preparation of 1 nanometer cuprous oxide catalyst

[0026] In a 1000ml three-necked bottle, add 1.6g PVP, 0.44g copper acetate, and 200ml water, and slowly add 40ml of sodium borohydride solution containing 0.75g of sodium borohydride into the copper acetate solution under vigorous stirring. After that, the vigorous stirring was continued for 2 h. Centrifuge the reaction solution in the previous step (6000rpm) to discard the supernatant, add water to wash, and centrifuge again (6000rpm) to obtain about 2g of a black solid, wherein the copper content is about 60%.

Embodiment 1

[0027] The preparation of embodiment 1 rufinamide

[0028] Add 2.88g of sodium azide, 0.9g of tetrabutylammonium chloride, and 10ml of water into a 100ml three-necked flask, stir at room temperature, and add 20ml of acetonitrile containing 3g of 2,6-difluorobenzyl bromide after all the solids are dissolved solution. The mixture was stirred at room temperature and monitored by TLC (petroleum ether:ethyl acetate=30:1). The reaction takes about 2 hours to complete. Stirring was stopped, the layers were allowed to stand, and the acetonitrile layer was separated to obtain an acetonitrile solution of 2-(azidomethyl)-1,3-difluorobenzene. Under the protection of nitrogen, add 1.4ml methyl propiolate and nano Cu to the acetonitrile solution of 2-(azidomethyl)-1,3-difluorobenzene 2 O (0.01 equivalent, 0.034 g), and the reaction was stirred at room temperature under nitrogen protection, and monitored by TLC (dichloromethane:methanol=30:1). The reaction takes about 3 hours to complete...

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Abstract

The invention provides an improved synthesis process for synthesizing rufinamide. The process comprises the following steps of a, reacting 2, 6-difluorobenzyl halide with azide and tetrabutylammonium chloride to obtain 2-(azide methyl)-1,3-difluorobenzene; b, reacting 2-(azide methyl)-1, 3-difluorobenzene with methyl propiolate under the catalyzing of nano-cuprous oxide (Cu2O) to obtain 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-methyl formate; and c, reacting 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-methyl formate with ammonium hydroxide to obtain rufinamide. The process has the advantages of short reaction time and high catalytic efficiency, and is simple and safe to operate.

Description

technical field [0001] The invention relates to a synthesis process of rufinamide and belongs to the field of medicinal chemistry. Background technique [0002] Rufinamide (compound of formula (I)), English name is Rufinamide, trade name is Banzel, developed by Swiss Novartis, and in November 2008, it was approved by the FDA to be listed in the United States for epilepsy Lennox-Gastaut syndrome (LGS ) adjuvant therapy. Its chemical name is 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide, and its structural formula is as follows: [0003] [0004] At present, it is under development in China, and there is no official manufacturer of the drug. The existing production process of rufinamide is to first use 2,6-difluorobenzyl halide to react with sodium azide in aqueous solution. Then the prepared azide reacts with methyl propiolate under the action of copper sulfate and ascorbic acid to prepare the intermediate 1-(2,6-difluorobenzyl)-1H-1,2,3-triazol Methyl azole-4...

Claims

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Application Information

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IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 杨诚陈悦王静晗李永涛白翠改
Owner XUHE TIANJIN YIYAO KEJI YOUXIAN GONGSI
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