Preparation method of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride

A technology of dimethoxypyridine hydrochloride and dimethoxypyridine, which is applied in the field of preparation of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxypyridine hydrochloride, can Solve the problems of low safety, complex reaction, and many by-products, and achieve the effect of improving work efficiency, reducing reaction steps, and increasing yield

Active Publication Date: 2015-04-29
SHOUGUANG FUKANG PHARMA
View PDF0 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In the prior art, the preparation method of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxypyridine hydrochloride generally starts from 3-hydroxyl-2-methyl-4-pyrone The raw material is completed in seven steps of etherification, nitriding, chlorination, oxidation, methoxidation, acetic acid hydrolysis, and chlorination. The reaction is complicated, the by-products are more, and the yield is low; the raw material contains phosphorus oxychloride and sodium methoxide. The use of products is less safe

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
  • Preparation method of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 3-hydroxy-2-methyl-4-pyridone.

[0021] Add 40g of 3-hydroxy-2-methyl-4-pyrone and 200g of ammonia water (20%) into the reaction bottle, slowly heat up to dissolve, keep at 40°C for 2h, slowly add 30g of ammonium carbonate, keep at 40°C for 2h, slowly add 62g of ammonium carbonate, kept at 40°C for 3h, slowly raised to reflux and maintained at reflux for 5h, then cooled to 0°C, filtered with suction and rinsed with a small amount of water, dried to obtain 38g of 3-hydroxy-2-methyl-4-pyridone ( Yield 95.7%); MS: m / z = 125.2 [M] + . 1H NMR ([D6]DMSO, 400 Hz): δ 2.17 (s, 3H, CH 3 ), 6.07–6.10(d,1H,5-H), 7.38–7.57 (d, 1H, 6-H), 11.4 (s, 1H, NH).

Embodiment 2

[0022] Example 2: Preparation of 3-hydroxy-2-methyl-4-pyridone.

[0023] Add 40g of 3-hydroxy-2-methyl-4-pyrone and 120g of methanol to the reaction flask, slowly heat up to dissolve, slowly add 120g of ammonium bicarbonate at 40°C, keep warm at 40°C for 2h, slowly add 90g of ammonium bicarbonate, Insulate for 3 hours, slowly raise the temperature to reflux and maintain reflux for 5 hours, then cool down to -10°C, filter with suction and rinse with a small amount of ice methanol, and dry to obtain 25g of 3-hydroxy-2-methyl-4-pyridone (yield 63.1%) ; MS: m / z = 125.2 [M] + . 1H NMR ([D6]DMSO, 400 Hz): δ 2.17 (s, 3H, CH 3 ), 6.07–6.10(d,1H,5-H), 7.38–7.57 (d, 1H, 6-H), 11.4 (s, 1H, NH).

Embodiment 3

[0024] Example 3: Preparation of 3-hydroxy-2-methyl-4-pyridone.

[0025] Add 40g of 3-hydroxy-2-methyl-4-pyrone and 100ml of water to the reaction flask, heat up to dissolve, slowly add 153g of ammonium bicarbonate at 40°C, keep warm at 40°C for 3h, slowly add 90g of ammonium bicarbonate, Insulate for 5 hours, slowly raise the temperature to reflux and maintain reflux for 5 hours, then cool down to 0°C, filter with suction and rinse with a small amount of water, and dry to obtain 30g of 3-hydroxy-2-methyl-4-pyridone (yield 75.6%);

[0026] MS: m / z = 125.2 [M] + . 1H NMR ([D6]DMSO, 400 Hz): δ 2.17 (s, 3H, CH 3 ), 6.07–6.10(d,1H,5-H), 7.38–7.57 (d, 1H, 6-H), 11.4 (s, 1H, NH).

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 belongs to the technical field of medicine, and particularly relates to a preparation method of a pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method comprises the following steps: using 3-hydroxyl-2-methyl-4-pyrone as a starting raw material, and then only performing five-step reaction to obtain the pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method reduces the reaction steps, shortens the reaction cycle, improves the working efficiency, and increases the yield coefficient.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a preparation method of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxypyridine hydrochloride. Background technique [0002] In the prior art, the preparation method of pantoprazole intermediate 2-chloromethyl-3,4-dimethoxypyridine hydrochloride generally starts from 3-hydroxyl-2-methyl-4-pyrone The raw material is completed in seven steps of etherification, nitriding, chlorination, oxidation, methoxidation, acetic acid hydrolysis, and chlorination. The reaction is complex, the by-products are more, and the yield is low; the raw material contains phosphorus oxychloride and sodium methoxide. The use of products is less safe. [0003] Contents of the invention [0004] The present invention aims at the shortcomings existing in the prior art, and proposes a new preparation method, using 3-hydroxyl-2-methyl-4-pyrone as the starting material, and only five s...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/89C07D213/69
CPCC07D213/69C07D213/89
Inventor 董良军孙继国刘杰国建辉甲宗青杨大伟王海鹏王洪明侯俊杰
Owner SHOUGUANG FUKANG PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap