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Method for producing 4-methoxy pyrrole derivative

A technology for methoxypyrrole and derivatives, which is applied in the field of preparation of 4-methoxypyrrole derivatives, can solve the problems of low yield, unsuitability for large-scale industrial production and the like, and achieves the effect of improving process efficiency and yield

Pending Publication Date: 2021-04-30
DAEWOONG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, the preparation process of this patent has a lower yield, and the total yield of the four preparation steps is 51.4%, and dangerous reagents (such as sodium hydride, diisobutyl aluminum hydride, etc.) and environment-polluting reagents ( Such as pyridinium chlorochromate), so it is not suitable for large-scale industrial production

Method used

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  • Method for producing 4-methoxy pyrrole derivative
  • Method for producing 4-methoxy pyrrole derivative
  • Method for producing 4-methoxy pyrrole derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0110]

[0111] (step 1)

[0112] 100.0g of 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylic acid methyl ester (chemical formula 2), 9.2g of 4-(dimethylamino)- Pyridine and 393.0 g of acetonitrile were added to the flask, and stirred at room temperature for 10 minutes. After cooling the temperature in the flask to 5°C to 10°C, add 80.1g of 3-fluorobenzenesulfonyl chloride (chemical formula 3) and 53.2g of N,N-diisopropylethylamine, and at a temperature of 20 to 30°C Stir for 2 hours to complete the reaction.

[0113] Then, 500.0 g of purified water and 451.0 g of ethyl acetate were added, stirred for 10 minutes, and left to stand for 10 minutes. After this time, the aqueous layer was discarded.

[0114] Thereafter, 500.0 g of purified water was added to the organic layer, and a 1N-hydrochloric acid aqueous solution was gradually added in a temperature range of 20°C to 30°C to adjust the pH to 3.5 to 5.0, followed by stirring for 10 minutes and standing for 10 min...

Embodiment 2

[0144]

[0145] (step 1)

[0146] 100.0g of 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylic acid methyl ester (chemical formula 2), 9.2g of 4-(dimethylamino)- Pyridine and 393.0 g of acetonitrile were added to the flask, and stirred at room temperature for 10 minutes. After the temperature in the flask was cooled to 5°C to 10°C, 80.1g of 3-fluorobenzenesulfonyl chloride (chemical formula 3) and 53.2g of N,N-diisopropylethylamine were added, and at a temperature of 20°C to 35°C Stirring was continued for 2 hours to complete the reaction.

[0147] Then, 500.0 g of purified water and 451.0 g of ethyl acetate were added, stirred for 10 minutes, and left to stand for 10 minutes. After this time, the aqueous layer was discarded.

[0148] Thereafter, 500.0 g of purified water was added to the organic layer, and a 1N-hydrochloric acid aqueous solution was gradually added in a temperature range of 20°C to 30°C to adjust the pH to 3.5 to 5.0, followed by stirring for 10 m...

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Abstract

The present invention relates to a method for producing a 4-methoxy pyrrole derivative. According to one embodiment, the present invention can provide a useful advantage of industrial mass production of a 4-methoxy pyrrole derivative, as the process efficiency and yield are improved and the use of hazardous reagents and environmental pollution reagents is excluded.

Description

technical field [0001] The disclosure relates to a preparation method of 4-methoxypyrrole derivatives. Background technique [0002] When the balance between aggressive factors (such as gastric acid, Helicobacter pylori pepsin, stress, alcohol, tobacco, etc.) and defensive factors (such as gastric mucosa, bicarbonate, prostaglandins, blood supply, etc.) Gastrointestinal ulcers, gastritis, and reflux esophagitis can occur. Therefore, therapeutic agents for gastrointestinal injuries such as gastrointestinal ulcers, gastritis, reflux esophagitis are classified into drugs that inhibit aggressive factors and drugs that enhance defensive factors. [0003] Meanwhile, ulcers have been reported in gastrointestinal ulcers, gastritis, and reflux esophagitis even in the absence of increased gastric acid secretion. Therefore, with the increase of aggressive factors, the decrease of defensive factors due to the pathological changes of gastric mucosa is considered to be an important reas...

Claims

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Application Information

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IPC IPC(8): C07D207/48A61K31/40A61P1/00
CPCA61K31/40A61P1/00C07D207/48
Inventor 辛政泽孙正贤严德基
Owner DAEWOONG PHARM CO LTD
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