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Preparation method of vonoprazan fumarate

A technology of vonoprazan fumarate and acetic acid, which is applied in the field of preparation of vonoprazan fumarate, can solve the problems of easy generation of impurities in the refining process, unstable process, and low total yield, so as to improve the reaction conversion High efficiency, good stability, and the effect of improving yield

Pending Publication Date: 2022-04-22
HANGZHOU ZHONGMEI HUADONG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In summary, there have been a lot of research on the synthesis process of vonoprazan fumarate, but the existing synthesis process of methylaminomethyl fragments has long route, low overall yield, unstable process, and easy to produce Impurities and other defects are not suitable for industrial production, so it is of great significance to develop a synthetic route and method that is suitable for industrial production, has no safety and environmental protection pressure, stable process, and good impurity control.

Method used

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  • Preparation method of vonoprazan fumarate
  • Preparation method of vonoprazan fumarate
  • Preparation method of vonoprazan fumarate

Examples

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Embodiment 1

[0039] At 20°C, methanol (400ml), 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (50g, 150.15 mmol) and 33% methylamine ethanol (42.75 g, 450.45 mmol) solution, after stirring for 1 hour, acetic acid (45.5 g, 450.45 mmol) was added dropwise at a temperature of 20°C. The temperature was lowered, and sodium triacetoxyborohydride (36.4 g, 600.6 mmol) was added under temperature control at 5°C. Keep warm and stir for 2 hours. The cooling device was removed, the temperature was raised to 20°C, and the mixture was stirred for 1 hour. Concentrate under reduced pressure to remove solvent. Add purified water (300ml) to the concentrate, stir until dissolved, then add ammonia water dropwise to adjust the pH value to 9-10. Ethyl acetate was added, stirred, extracted and separated. The organic phase was washed once with 5% aqueous sodium bicarbonate solution and saturated brine, dried with anhydrous sodium sulfate for 30 minutes, and filtered. After concentratin...

Embodiment 2

[0041] At 20°C, methanol (80ml), 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (10g, 30.3 mmol) and 33% methylamine ethanol (5.7g, 60.6mmol) solution, after stirring for 1 hour, acetic acid (3.64g, 60.6mmol) was added dropwise at a temperature of 20°C. The temperature was lowered, and sodium triacetoxyborohydride (25.69 g, 121.2 mmol) was added under temperature control at 5°C. Keep warm and stir for 2 hours. The cooling device was removed, the temperature was raised to 20°C, and the mixture was stirred for 1 hour. Concentrate under reduced pressure to remove solvent. Add purified water (60ml) to the concentrated solution, stir until dissolved, then add ammonia water dropwise to adjust the pH value to 9-10. Ethyl acetate was added, stirred, extracted and separated. The organic phase was washed once with 5% aqueous sodium bicarbonate solution and saturated brine, dried with anhydrous sodium sulfate for 30 minutes, and filtered. After concentrating t...

Embodiment 3

[0043] At 20°C, methanol (80ml), 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (10g, 30.3 mmol) and 33% methylamine ethanol (14.25 g, 151.5 mmol) solution, after stirring for 1 hour, acetic acid (9.1 g, 151.5 mmol) was added dropwise at a temperature of 20°C. The temperature was lowered, and sodium triacetoxyborohydride (25.69 g, 121.2 mmol) was added under temperature control at 5°C. Keep warm and stir for 2 hours. The cooling device was removed, the temperature was raised to 20°C, and the mixture was stirred for 1 hour. Concentrate under reduced pressure to remove solvent. Add purified water (60ml) to the concentrated solution, stir until dissolved, then add ammonia water dropwise to adjust the pH value to 9-10. Ethyl acetate was added, stirred, extracted and separated. The organic phase was washed once with 5% aqueous sodium bicarbonate solution and saturated brine, dried with anhydrous sodium sulfate for 30 minutes, and filtered. After concentr...

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Abstract

The invention provides a preparation method of vonoprazan fumarate, and the vonoprazan fumarate is prepared by taking 5-(2-fluorophenyl)-1-(pyridine-3-yl sulfonyl)-1H-pyrrole-3-formaldehyde as a starting material through amination, reduction and salt forming reaction. The method has the advantages of low impurity content and high yield, does not need to introduce toxic reactants, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical raw materials, in particular to a preparation method of vonoprazan fumarate. Background technique [0002] Vonoprazan fumarate, the chemical name is 5-(2-fluorophenyl)-1-(3-pyridylsulfonyl)-3-methylaminomethyl-1H-pyrrole fumarate , developed by Japan's Takeda Pharmaceutical (Takeda), was first launched in Japan in December 2014. Vonoprazan fumarate is a reversible proton pump inhibitor that inhibits K + with H + -K + - The combination of ATPase (proton pump) exerts early termination and strong and long-lasting inhibitory effect on gastric acid secretion, clinically treats gastric acid-related diseases such as erosive esophagitis, Helicobacter pylori infection, duodenal ulcer and gastric ulcer Has good curative effect. In addition, vonoprazan fumarate has relatively high tolerance and safety. [0003] Different impurities will be produced due to different synthesis processes o...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07C57/15C07C51/41
CPCC07D401/12C07C51/412C07C57/15
Inventor 余睿陈禹叶凯王忠平张建勇
Owner HANGZHOU ZHONGMEI HUADONG PHARMA
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