Method for preparing indobufen

A technology of indobufen and its compounds, which is applied in the field of preparation of indobufen, can solve the problems of low product purity and difficult removal, and achieve the effects of simple purification process, material cost saving, and simple post-treatment

Pending Publication Date: 2022-07-01
SHANGHAI GAOZHUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the final zinc powder reduction reaction, excessively reduced or incompletely reduced impurities are unavoidably produced, and are difficult to remove, resulting in lower purity of the final product

Method used

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  • Method for preparing indobufen
  • Method for preparing indobufen
  • Method for preparing indobufen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1. Synthesis of compound 2

[0037] Dissolve 2-(4-nitrophenyl)butyric acid (50g, 1.0eq) in methanol, add concentrated sulfuric acid, heat under reflux for 2h with stirring, TLC detects the end of the reaction, and the reaction solution can be directly put into the next step.

[0038] 2. Synthesis of compound 3

[0039] To the reaction solution in the previous step, add reduced iron powder (46.4g, 3.5eq), add concentrated hydrochloric acid dropwise at room temperature, react for 3 hours, remove the solvent after TLC detection, add water and ethyl acetate, and add solid sodium carbonate The pH was adjusted to about 8, the layers were separated, the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, dried, filtered, and the filtrate was concentrated to obtain compound 3 with a yield of 85.6%.

[0040] 3. Synthesis of compound 4

[0041] Compound 3 (20g, 1.0eq), o-carboxybenzaldehyde (17.1g, 1.1eq), and sodium borohydride (1.96g, 0.5eq...

Embodiment 2

[0047] 1. Synthesis of compound 2

[0048] Dissolve 2-(4-nitrophenyl)butyric acid (50g, 1.0eq) in methanol, add concentrated sulfuric acid, heat under reflux for 2h with stirring, TLC detects the end of the reaction, and the reaction solution can be directly put into the next step.

[0049] 2. Synthesis of compound 3

[0050] To the reaction solution in the previous step, add reduced iron powder (60.1g, 4.5eq), add concentrated hydrochloric acid dropwise at room temperature, react for 3 hours, remove the solvent after TLC detection, add water and ethyl acetate, and add sodium carbonate solid The pH was adjusted to about 8, the layers were separated, the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, dried, filtered, and the filtrate was concentrated to obtain compound 3 with a yield of 85.3%.

[0051] 3. Synthesis of compound 4

[0052] Compound 3 (20g, 1.0eq), o-carboxybenzaldehyde (17.1g, 1.1eq), formic acid (7.15g, 1.5eq), triethylam...

Embodiment 3

[0057] 1. Synthesis of compound 2

[0058] Dissolve 2-(4-nitrophenyl)butyric acid (50 g, 1.0 eq) in methanol, add concentrated sulfuric acid, heat under reflux for 2 h with stirring, TLC detects the end of the reaction, and the reaction solution can be directly put into the next step.

[0059] 2. Synthesis of compound 3

[0060] Zinc powder (62.5g, 4eq) was added to the reaction solution in the previous step, concentrated hydrochloric acid was added dropwise at room temperature, reacted for 3 hours, the solvent was removed after the reaction was detected by TLC, water and ethyl acetate were added, and sodium carbonate solid was added to adjust the pH. Adjusted to about 8, separated, the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, dried, filtered, and the filtrate was concentrated to obtain compound 3 with a yield of 85.6%.

[0061] 3. Synthesis of compound 4

[0062] Compound 3 (20g, 1.0eq), o-carboxybenzaldehyde (17.1g, 1.1eq), an...

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Abstract

The invention discloses a method for synthesizing indobufen, which comprises the following steps: adding carboxybenzaldehyde, sodium borohydride and other reagents into a methanol solution of 2-(4-nitrophenyl) butyric acid, and finally reacting to generate the indobufen. According to the method, excessive reduction or incomplete reduction impurities generated in the final zinc powder reduction reaction are avoided, the purification process of the reaction is simpler, aftertreatment is easy, the raw materials are low in price, and the material cost is reduced.

Description

technical field [0001] The present invention relates to a preparation method of a compound, in particular to a preparation method of indobufen. Background technique [0002] With the progress of society, the continuous improvement of people's living standards, the improvement of dietary structure, the reduction of labor intensity, the aggravation of social aging and other factors, the high-risk groups of cardiovascular and cerebrovascular diseases are also increasing. Most of the cardiovascular and cerebrovascular diseases are closely related to thrombosis and thromboembolism. There are many factors that lead to thrombosis, such as platelet aggregation, blood stasis, and the activation of coagulation factors to promote the formation of thrombin. Therefore, looking for high-efficiency and low-toxic anti-platelet aggregation drugs can effectively reduce the morbidity and mortality of cardiovascular and cerebrovascular diseases. [0003] Indobufen (Indobufen), chemical name 2-...

Claims

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Application Information

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IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 李维华华岳庭王江淮
Owner SHANGHAI GAOZHUN PHARMA CO LTD
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