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Production method of omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride

A technology of methoxypyridine hydrochloride and methoxypyridine, which is applied in the field of chemical synthesis, can solve the problems of many by-products, unguaranteed product quality, and difficulty in realization, so as to reduce the generation of by-products and effectively Conducive to the effect of process safety and product quality safety

Pending Publication Date: 2022-02-15
上海卓鼎生物技术有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0006] 1. The starting materials are not easy to obtain, and it is difficult to realize the industrial production of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride, such as raw materials: 3,5-lutidine, 2-ethyl-3,5-lutidine, 2,4-dichloro-3,5,6-collidine, etc.
[0007] 2. There are many by-products, low conversion rate, low yield and other defects, so that the product quality cannot be guaranteed
[0009] 4. Due to the higher requirements for equipment caused by the selection of some highly corrosive and highly active catalysts and reagents, not only the catalyst and the actual price are high, but the equipment price is also raised at the same time, thereby increasing the production cost
[0010] 5. Further concerns about environmental pollution caused by the selection of some highly corrosive and highly active catalysts and reagents

Method used

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  • Production method of omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride
  • Production method of omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride
  • Production method of omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The method for the omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride, the specific operations are as follows:

[0037] 1. Preparation of 2,3,5-collidine-N-oxide:

[0038] Accurately weigh raw materials 2,3,5-collidine: 300g, acetic acid: 1L, 30 270ml of % hydrogen peroxide: Put it into a dry and clean reaction kettle at a temperature of 100°C, stir for 3.2 hours, then add 30% according to the ratio of (2,3,5-collidine: 30% hydrogen peroxide = 1g: 0.5ml) Hydrogen peroxide 150ml, continue to keep stirring at 100°C for 9.1h, after the reaction is over, concentrate under reduced pressure to recover acetic acid (recycled), recrystallize the concentrate with acetone:petroleum ether=2:3, filter the mother liquor through repeated recrystallization, The final crystals were combined and dried to obtain 292 g of 2,3,5-collidine-N-oxide, with a content of 98.3% and a yield of 95.7%;

[0039] 2. Preparation of 2,3,5-trimethyl-4-nitropyridine-...

Embodiment 2

[0048] The method for the omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride, the specific operations are as follows:

[0049] 1. Preparation of 2,3,5-collidine-N-oxide:

[0050] Accurately weigh raw materials 2,3,5-collidine: 400g, acetic acid: 1.3L, 30% hydrogen peroxide 360ml: Put it into a dry and clean reaction kettle at a temperature of 100°C, stir for 3.4 hours and then add 30 % hydrogen peroxide 200ml, continue to keep stirring at 100°C for 9.3 hours, after the reaction is over, concentrate under reduced pressure to recover acetic acid (recycled), recrystallize the concentrate with acetone:petroleum ether=2:3, filter to obtain the mother liquor through repeated recrystallization , the final crystals were combined and dried to obtain 390 g of 2,3,5-collidine-N-oxide, with a content of 98.2% and a yield of 95.7%;

[0051] 2. Preparation of 2,3,5-trimethyl-4-nitropyridine-N-oxide:

[0052] Accurately weigh 2,3,5-collidine-N-oxide: ...

Embodiment 3

[0060] The method for the omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride, the specific operations are as follows:

[0061] 1. Preparation of 2,3,5-collidine-N-oxide:

[0062] Accurately weigh raw materials 2,3,5-collidine: 600g, acetic acid: 2L, 30 % Hydrogen peroxide 540ml: put it into a dry and clean reaction kettle, temperature 100°C, stir for 3.2 hours, then add 30% according to the ratio of (2,3,5-collidine: 30% hydrogen peroxide = 1g: 0.5ml) Hydrogen peroxide 300ml, continue to keep stirring at 100°C for 9.7h, after the reaction is over, concentrate under reduced pressure to recover acetic acid (recycled), recrystallize the concentrate with acetone:petroleum ether=2:3, filter the mother liquor through repeated recrystallization, The final crystals were combined and dried to obtain 590 g of 2,3,5-collidine-N-oxide, with a content of 97.9% and a yield of 96.2%;

[0063] 2. Preparation of 2,3,5-trimethyl-4-nitropyridine-N-oxide:

...

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Abstract

The invention discloses a production method of an omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride, which comprises the following steps: s1, preparing the raw materials; s2, catalyzing and nitrifying the reactants; s3, carrying out alkoxylation; s4, carrying out acetylation and hydrolysis; s5, performing halogenating and salifying reaction. According to the method, 2,3,5-trimethylpyridine is taken as a raw material, 4-nitropyridine-N-oxide is obtained through oxidation and nitration, nitryl is substituted by methoxyl, the N-oxide and acetic anhydride are subjected to acylation esterification, hydrolysis, halogenation, salt formation and other reactions, 2-chloromethyl-3,5-dimethyl-4-methoxyl pyridine hydrochloride is obtained, generation of by-products is reduced, and the conversion rate is increased. Therefore, the product quality is guaranteed, some high-risk or dangerous chemicals are prevented from being used as catalysts and reagents, process safety, product quality safety and personal safety are facilitated, high-activity catalysts, reagents and the like are not used, and pollution to the environment is reduced to the minimum.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a production method of omeprazole drug intermediate 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride. Background technique [0002] Omeprazole is a new drug that went on the market in the late 1980s to treat duodenal ulcer and gastric ulcer. It was researched and developed by Astra Company in Sweden. By 1992, it had been approved for use in 65 countries, and its sales amounted to 1 billion US dollars, accounting for 17% of ulcer drugs, with sales of $2.23 billion in 1994. [0003] The vast majority of peptic ulcers occur in the stomach and duodenum, so they are also called gastric and duodenal ulcers. It is generally considered that the damage factors and mucosal damage of the local mucosa of the stomach and duodenum are caused by one or more causes When there is an imbalance between the protective factors, peptic ulcers result. Gastric acid and pepsin pla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/66
CPCC07D213/66
Inventor 杨青春滕院赵晓怡陶琪普倩
Owner 上海卓鼎生物技术有限公司
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