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

Method for preparing zafirlukast important intermediate

A compound, the technology of nitroindole, which is applied in the field of preparation of C1-C4 alkyl 3-methoxy-4-[methyl]benzoate, can solve the problems of complex operation, high cost and tediousness, and achieve High yield, low cost and strong controllability

Active Publication Date: 2008-01-16
HAINAN SHENGKE LIFE SCI RES INST
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The yield reported in the literature of this method is 60%, but the yield of repeated actual operation is only about 30%, and the operation is complicated, loaded down with trivial details, and the cost is high

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
  • Method for preparing zafirlukast important intermediate
  • Method for preparing zafirlukast important intermediate
  • Method for preparing zafirlukast important intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Under nitrogen protection, 16.2 g of 5-nitroindole was added to 100 ml of dichloromethane, and 50 g of anhydrous aluminum trichloride was added. The temperature was lowered to -5-0°C, and 70 ml of dichloromethane and 25.1 g of methyl 4-carbonyl chloride-3-methoxybenzoate were added dropwise. After the dropwise addition was completed, the mixture was raised to room temperature and stirred overnight. The reaction solution was slowly poured into ice water, and stirred for 0.5 hours. Separate the organic phase, wash with 3×30 ml 5% sodium bicarbonate, and dry the organic phase with anhydrous sodium sulfate. After suction filtration, the filtrate was evaporated to remove the solvent under reduced pressure, 50 ml of isopropyl ether was added to stir and crystallize, and 31.8 g of a yellow solid product was obtained by filtration, with a yield of 90%.

Embodiment 2

[0030] Mix 17.7 grams of 3-methoxy-4-(5-nitro-1H-indole-3-carbonyl) methyl benzoate (formula III) obtained above with 70 milliliters of ethylene glycol, and add 8.4 grams Potassium hydroxide and 10 ml of 85% hydrazine hydrate were heated to reflux for 1.5 hours, the condenser was removed, and the water was evaporated from the reaction solution. When the temperature in the reaction flask rose to 195° C., install a condenser again, and continue heating to reflux for 5 hours. After cooling to room temperature, the reaction solution was poured into 300 ml of ice water and stirred for 0.5 hour. After suction filtration, 14.4 g of a light yellow solid product was obtained, with a yield of 85%.

[0031] Accompanying drawing is the schematic diagram of the chemical structural formula of compound (I).

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 the preparation method of formula (I) compound 3-methoxy-4-((5-nitro-1H-indole-3-base)methyl)benzoic acid C1-C4 alkyl esters. The compound is a crucial intermediate in the preparation of zafirlukast which is a leukotriene antagonist drug.

Description

technical field [0001] The present invention relates to 3-methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoic acid C 1 ~C 4 Preparation of alkyl esters, such compounds can be used to prepare leukotriene antagonist drug zafirlukast. Background technique [0002] Zafirlukast is a leukotriene receptor antagonist drug indicated for the prevention and long-term treatment of asthma. With the continuous development of the industrialization process, the living environment of human beings has also undergone continuous changes. With the decline of air quality and hundreds of millions of smokers, the number of asthma patients in my country's big cities is also increasing. Asthma is considered one of the four chronic diseases by the world medical community, and is listed as the top ten causes of death. Therefore, the development of zafirlukast will bring better economic and social benefits, and its chemical structural formula is as follows: [0003] [0004] Zafirlukast ...

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
IPC IPC(8): C07D209/18
Inventor 杨利民
Owner HAINAN SHENGKE LIFE SCI RES INST
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