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Preparation method for buparvaquone

A technology of bupavaquinone and acetic acid, which is applied in the field of chemical drug synthesis, can solve the problems of unavailable raw materials, increase the cost of synthesizing bupavaquinone, increase the difficulty of synthesizing bupavaquinone, and achieve low reaction cost and short reaction steps , post-processing simple effects

Inactive Publication Date: 2015-12-30
山东川成医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, 1,4-benzopyrandione and p-tert-butylcyclohexylacetaldehyde are used as raw materials for reaction. There is currently no stable market supplier for these two raw materials. The raw materials are extremely difficult to obtain, and the source of raw materials is an inevitable problem. This also directly increases the difficulty of synthesizing bupavaquinone by this route, and also directly increases the cost of synthesizing bupavaquinone by using this route

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A preparation method for bupavaquinone, the steps are as follows:

[0045] (1) Synthesis of 2-mercaptopyridine oxide p-tert-butylcyclohexyl acetate

[0046] Add 60g (0.3mol) of p-tert-butylcyclohexylacetic acid into a 1000mL four-necked flask, add 400mL of dichloromethane, stir to dissolve, then cool the reaction system with an ice-water bath, and drop di Thionyl chloride 65mL (0.9mol), after the dropwise addition, remove the ice-water bath, heat the above reaction solution to reflux, react under reflux for 4 hours, the solution is yellowish brown, stop heating, the reaction system is heated and concentrated under normal pressure, concentrated After the completion, a yellow-brown solid was obtained, and then 100 mL of dichloromethane was added to the reaction flask for further concentration, and the residual thionyl chloride was removed. After the removal was completed, 600 mL of dichloromethane was added to the reaction flask of the residual solid at room temperature ...

Embodiment 2

[0062] Embodiment 2: comparative example

[0063] (1) Synthesis of 2-mercaptopyridine p-tert-butylcyclohexylacetic acid ester (adjust the molar ratio of p-tert-butylcyclohexylacetic acid and 2-mercaptopyridine sodium salt to 1:1.5)

[0064] Add 30g (0.15mol) of p-tert-butylcyclohexylacetic acid into a 500mL four-neck flask, add 200mL of dichloromethane, stir to dissolve, then cool the reaction system with an ice-water bath, and add di Thionyl chloride 32.5mL (0.45mol), after the dropwise addition, remove the ice-water bath, heat the above reaction solution to reflux, react under reflux for 4 hours, the solution is yellowish brown, stop heating, the reaction system is heated and concentrated under normal pressure, After the concentration is complete, a yellow-brown solid is obtained, and then 50 mL of dichloromethane is added to the reaction flask for further concentration, and the residual thionyl chloride is removed. After the removal, 300 mL of dichloromethane is added to th...

Embodiment 3

[0072] Embodiment 3: comparative example

[0073] (1) Synthesis of 2-mercaptopyridine p-tert-butylcyclohexylacetic acid ester (adjust the molar ratio of p-tert-butylcyclohexylacetic acid and 2-mercaptopyridine sodium salt to 1:1)

[0074]Add 30g (0.15mol) of p-tert-butylcyclohexylacetic acid into a 500mL four-neck flask, add 200mL of dichloromethane, stir to dissolve, then cool the reaction system with an ice-water bath, and add di Thionyl chloride 32.5mL (0.45mol), after the dropwise addition, remove the ice-water bath, heat the above reaction solution to reflux, react under reflux for 4 hours, the solution is yellowish brown, stop heating, the reaction system is heated and concentrated under normal pressure, After the concentration is complete, a yellow-brown solid is obtained, and then 50 mL of dichloromethane is added to the reaction flask for further concentration, and the residual thionyl chloride is removed. After the removal, 300 mL of dichloromethane is added to the r...

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PUM

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Abstract

The invention discloses a preparation method for buparvaquone. The method comprises taking tert-butylcyclohexyl acetic acid, sodium omadine and 1,4-naphthoquinone as initial raw materials, firstly reacting tert-butylcyclohexyl acetic acid with sodium omadine to generate tert-butylcyclohexyl acetic acid 2-thioxo-pyridin-1-yl ester, then reacting with 1,4-naphthoquinone for addition, so as to generate 2-[(4-tert-butylcyclohexyl)methyl]-3-(2-pyridinylsulfanyl)-1,4-naphthalenedione, then mixing the obtained 2-[(4-tert-butylcyclohexyl)methyl]-3-(2-pyridinylsulfanyl)-1,4-naphthalenedione, methanol, tripotassium phosphate trihydrate and water, performing heating hydrolysis, processing the solution and acidifying, and filtering to obtain a buparvaquone crude product, and then recrystallizing by utilizing isopropanol, so as to obtain a buparvaquone competitive product. The method is simple in operation, relatively low in cost, high in product yield and relatively suitable for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and in particular relates to a preparation method of bupavaquinone. Background technique [0002] A quinone compound is an aromatic organic compound with a six-carbon atom ring diketone structure containing two double bonds. It exists widely in nature. The main active ingredients of many important traditional Chinese medicines contain quinone compounds. Many quinone compounds Have antibacterial, antiviral or antitumor activity. [0003] The English name of Buparvaquone is Buparvaquone, the chemical name is 2-[(4-tert-butylcyclohexyl)methyl]-3-hydroxy-1,4-naphthalenedione, CAS number: 88426-33-9, and its structural formula is as follows : [0004] . [0005] A drug developed by Pitman-Moore Company for the treatment of bovine theilesiosis, which is a blood protozoan disease that is seriously harmful to cattle. After the pathogen of the disease is transmitted to cattle by tick...

Claims

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Application Information

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IPC IPC(8): C07C46/00C07C46/10C07C50/32C07D213/70C07D213/89
CPCC07C46/00C07C46/10C07D213/70C07D213/89
Inventor 沈乃涛韩立霞李文丽郭明刘怀振周艳明董洪涛
Owner 山东川成医药有限公司
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