Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

The preparation method of benzodiazepine compound

A technology for benzodiazepines and compounds, which is applied in the field of preparation of benzodiazepine compounds, can solve the problems of destroying isonitrile components, complicated reaction steps, etc., and achieves the advantages of low synthesis cost, shortened reaction steps, and simple and efficient synthesis method. Effect

Inactive Publication Date: 2014-10-29
中国人民解放军63975部队
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the resin-loaded method needs to separate the carrier excision and ring closure. After the carrier excision, the target compound can be finally obtained through a two-step reaction, and the reaction steps are still relatively cumbersome. The feed ratio of the components is 1:10; moreover, the method of resin loading destroys the isonitrile component during the removal process of the carrier, and only three components can modify the structure of the compound

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • The preparation method of benzodiazepine compound
  • The preparation method of benzodiazepine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1, the synthesis of N-cyclohexyl-2-(2,5-dioxo-1,4-benzodiazepine)-4-phenylbutanamide

[0020] 0.0286g (0.100mmol) amino functionalized ionic liquid boron tetrafluoride 1-[2-(aminoacetoxy) ethyl]-3-methylimidazolium salt, 0.0160g (0.120mmol) phenylpropanal was added to 50ml In the round bottom flask, pass nitrogen protection, add 10.0ml of anhydrous acetonitrile, add 2.00ml of triethylamine dropwise, stir at room temperature for 30min, cool to 0°C, add 0.0237g (0.100mmol) Boc-anthranilic acid in turn , 0.0109 g (0.100 mmol) cyclohexylisonitrile. After stirring at room temperature for 24 h, the filtrate was evaporated to dryness to obtain the Ugi product supported by ionic liquid, which was washed 3 times with 10.0 ml of anhydrous ether and 3 times with 10.0 ml of toluene.

[0021] After adding 5.00 ml of anhydrous methanol and 0.0142 ml (0.200 mmol) of acetyl chloride into the reaction bottle and stirring at room temperature for 24 h, a benzodiazepine compoun...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a preparation method of a benzodiazepine compound, which comprises the following steps: reacting amino functionalized ionic liquid, phenylpropyl aldehyde, Boc-anthranilic acid and cyclohexyl isonitrile to obtain an ionic-liquid-loaded Ugi product; reacting the ionic-liquid-loaded Ugi product under the catalytic action of hydrogen chloride gas to obtain a benzodiazepine compound of which the side chain is modified by Ugi reaction; and carrying out rotary evaporation on the reaction liquid, and washing out residues with anhydrous aether to obtain the required benzodiazepine compound. Compared with the existing preparation method, the preparation method provided by the invention shortens the reaction procedures and enhances the reaction efficiency; and the synthesis method is simple and efficient, and has wide application prospects.

Description

technical field [0001] The invention relates to a preparation method of a benzodiazepine compound, in particular to a benzodiazepine compound whose side chain is modified by a Ugi product through the reaction of ionic liquid loading Ugi. Background technique [0002] Benzodiazepines are a class of compounds with a wide range of biological activities. At present, such compounds are usually synthesized by Ugi reaction, which can not only shorten the synthetic route, improve the reaction efficiency, but also play the role of side chain modification. In 1996, Thomas et al directly synthesized benzodiazepines through Ugi reaction (J.Org.Chem., 1996, 61, 8935-8939). Conventional synthetic benzodiazepines method reaction formula is as follows: [0003] [0004] But this multi-component (four components) condensation reaction, in the case of no load, other components in the reaction system are difficult to remove, and finally can only be purified by the method of silica gel col...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D243/14
CPCY02P20/582
Inventor 肖军华董旭光毕晓静
Owner 中国人民解放军63975部队
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com