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Preparation method of benzene substituent oxadiazole compound

A compound, oxadiazole technology, applied in the field of new preparation of pharmaceutical intermediates, can solve problems such as synthesis difficulties

Inactive Publication Date: 2015-08-05
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of N-((3-(2-bromo-5-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)ethylamine is difficult at present

Method used

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  • Preparation method of benzene substituent oxadiazole compound
  • Preparation method of benzene substituent oxadiazole compound
  • Preparation method of benzene substituent oxadiazole compound

Examples

Experimental program
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Embodiment 1

[0026] (1) Synthesis of 2-bromo-5-methoxybenzaldehyde

[0027] Add 20g of 4-bromoanisole to 230ml of tetrahydrofuran, lower the temperature to -78°C, add 130ml of 2.5M n-butyllithium, stir and react for 2 hours, then add N,N-dimethylformamide, and naturally warm to Stir at room temperature overnight, add 1N hydrochloric acid, add ethyl acetate, extract and separate the layers, collect the organic phase, dry, and concentrate to obtain 17 g of 2-bromo-5-methoxybenzaldehyde.

[0028] (2) Synthesis of 2-bromo-5-methoxybenzaldehyde oxime

[0029] 17g of 2-bromo-5-methoxybenzaldehyde was added to 210ml of ethanol, 14g of hydroxylamine hydrochloride was added, heated to reflux for 4 hours, water and ethyl acetate were added for extraction, the organic phase was collected, dried, and concentrated to obtain 15g of 2- Bromo-5-methoxybenzaldehyde oxime.

[0030] (3) Synthesis of 2-bromo-5-methoxybenzonitrile

[0031] Add 15g of 2-bromo-5-methoxybenzaldehyde oxime to 150ml of tetrahydrofuran, add...

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Abstract

The invention discloses a preparation method of a benzene substituent oxadiazole compound N-((3-(2-bromine-5-methoxy phenyl)-1, 2, 4-oxadiazole-5-radical) methyl) ethylamine. 4-bromoanisole serves as a starting material and is subjected to aldehydes, oximate, elimination, addition, cyclization and substitution reaction to obtain a target product 7. The product serving as a template micro-molecule for synthesizing diversified compound libraries.

Description

Technical field [0001] The invention relates to a novel preparation method of pharmaceutical intermediates, in particular to a benzene-substituted oxadiazole compound N-((3-(2-bromo-5-methoxyphenyl)-1,2,4-oxa Diazol-5-yl)methyl)ethylamine preparation method. technical background [0002] The compound N-((3-(2-bromo-5-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)ethylamine, the structural formula is: [0003] [0004] This compound N-((3-(2-bromo-5-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)ethylamine and related derivatives are used in medicinal chemistry and It is widely used in organic synthesis. Currently, the synthesis of N-((3-(2-bromo-5-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)ethylamine is difficult. Therefore, it is necessary to develop a synthetic method that is easy to obtain, easy to operate, easy to control the reaction, and suitable for the overall yield. Summary of the invention [0005] The invention discloses a benzene-substituted oxadiazole compound N-((3-(2-bro...

Claims

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Application Information

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IPC IPC(8): C07D271/06
CPCC07D271/06
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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