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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
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  • 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

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  • 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).

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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

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Application Information

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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
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