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Preparation method of methanol solution of rupatadine fumarate intermediate methyl 5-methyl nicotinate

A technology of rupatadine fumarate and methyl nicotinate, which is applied in the field of methanol solution preparation, can solve the problems of large discharge of three wastes of solvents and reagents, frequent processing, and long processing time. The effect of short, high production efficiency, and small discharge of three wastes

Pending Publication Date: 2021-08-03
BEIJING JIALIN PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It avoids the defects of frequent post-reaction treatment process, long treatment time, large discharge of solvents and reagents and three wastes, high preparation cost and low production efficiency, and is green and environmentally friendly, suitable for large-scale industrial production

Method used

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  • Preparation method of methanol solution of rupatadine fumarate intermediate methyl 5-methyl nicotinate
  • Preparation method of methanol solution of rupatadine fumarate intermediate methyl 5-methyl nicotinate
  • Preparation method of methanol solution of rupatadine fumarate intermediate methyl 5-methyl nicotinate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 25g of 5-methylnicotinic acid into the reaction flask, add 141mL of methanol and stir to dissolve. Add 31.4 mL of thionyl chloride dropwise at room temperature, heat to 71°C and reflux for 3 hours after the dropwise addition, then concentrate under reduced pressure to remove 60%-70% of the solvent, cool the residue to room temperature, and add dropwise 2.5mol / L sodium methoxide methanol solution , so that the pH of the solution is about 7-8. After filtering, the filter cake was rinsed twice with 30 mL of methanol, and the filtrate was collected to obtain a methanol solution of methyl 5-methylnicotinate with a purity of 96.38%.

Embodiment 2

[0037] Add 136g of 5-methylnicotinic acid into the reaction flask, add 1000mL of methanol and stir to dissolve. Add 170mL of thionyl chloride dropwise at room temperature, heat to 71°C and reflux for 3h after the dropwise addition, then concentrate under reduced pressure to remove 60%-70% of the solvent, cool the residue to room temperature, add dropwise 5mol / L sodium methoxide methanol solution to make The pH of the solution is about 7-8. After filtering, the filter cake was rinsed twice with 160 mL of methanol, and the filtrate was collected to obtain a methanol solution of methyl 5-methylnicotinate with a purity of 93.6%.

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Abstract

The invention relates to a preparation method of a methanol solution of rupatadine fumarate intermediate methyl 5-methyl nicotinate, which comprises the following steps of: 1, adding 5-methyl nicotinic acid into methanol, stirring for dissolving, adding thionyl chloride, and heating for reflux reaction; and 2, carrying out vacuum concentration to remove part of the solvent, adding a sodium methoxide methanol solution at room temperature, adjusting the pH value, and filtering to obtain a methanol solution of 5-methyl nicotinate.

Description

technical field [0001] The invention relates to a method for preparing a pharmaceutical compound intermediate, in particular to a method for preparing a methanol solution of rupatadine fumarate intermediate 5-methylnicotinate. Background technique [0002] Rupatadine fumarate has the following structural formula: [0003] [0004] As a dual antagonist of histamine and platelet aggregation, rupatadine fumarate is mainly used in the treatment of allergic diseases such as allergic rhinitis and urticaria. Rupatadine fumarate has been listed in many countries around the world since it was first launched in Spain in March 2003. In 2013, my country approved domestic pharmaceutical companies to produce rupatadine fumarate raw materials and preparations. [0005] There are many public reports on the preparation of rupatadine fumarate, and the patent CN201610181976.2 provides a detailed overview of its synthetic routes, most of which involve an important intermediate, methyl 5-met...

Claims

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Application Information

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IPC IPC(8): C07D213/80C07D213/803
CPCC07D213/80C07D213/803
Inventor 徐贵远
Owner BEIJING JIALIN PHARM INC