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The synthetic method of mirabegron

A synthetic method, aminomethyl technology, applied in the direction of organic chemistry, etc., can solve the problems of low mirabegron yield, high processing cost, and human health hazards, and achieve high product yield, few reaction steps, good The effect of market competitiveness

Active Publication Date: 2022-04-19
SUZHOU UUGENE BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The yield of Mirabegron prepared by this method is low, and the steps are long. In the reaction step, borane dimethyl sulfide and high temperature and high pressure are used, wherein borane dimethyl sulfide is harmful to human health, and high temperature and high pressure are not only dangerous but also Processing costs will be high

Method used

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  • The synthetic method of mirabegron
  • The synthetic method of mirabegron
  • The synthetic method of mirabegron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] At room temperature, add methanol 300ml, R-2 (aminomethyl) benzyl alcohol 137 grams, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl) -Phenyl]-acetamide 295g and 111g of triethylamine, heat the mixed solution to 60-65°C, stir and reflux for 8h, pump the reaction solution into 500g of water while it is hot, cool to 10-15°C, filter 380 g of off-white solid Mirabegron was obtained with a yield of 96% and a purity of 99.9%.

Embodiment 2

[0030] At room temperature, 300 ml of isopropanol, 137 grams of R-2 (aminomethyl) benzyl alcohol, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethane base)-phenyl]-acetamide 295g and 111g of triethylamine, warm up the mixture to 60-65°C, stir and reflux for 8h, pump the reaction liquid into 500g of water while it is hot, and cool down to 10-15°C , and filtered to obtain 360g off-white solid mirabegron, with a yield of 91% and a purity of 99.47%.

Embodiment 3

[0032] At room temperature, add methanol 300ml, R-2 (aminomethyl) benzyl alcohol 137 grams, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl) -Phenyl]-acetamide 295g and 141g of triethylamine, heat the mixture to 60-65°C, stir and reflux for 8h, pump the reaction liquid into 500g of water while it is hot, cool down to 10-15°C, filter 370 g of off-white solid mirabegron was obtained, with a yield of 94% and a purity of 98.3%.

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Abstract

The invention discloses a synthesis method of Mirabegron, which comprises the following processing steps: S1. Under room temperature conditions, R-2 (aminomethyl) benzyl alcohol, 2-(2-aminothiazole-5-yl)- N-[4-(2-chloro-ethyl)-phenyl]-acetamide and triethylamine were added to the solvent and refluxed for 8h; S2, after the reaction was completed, the reaction solution was pumped into water, filtered to obtain Mirabegron . The solvent in the step S1 is one or more of methanol, ethanol, propanol, dichloromethane, chloroform, acetone, butanone, and toluene. The present invention not only does not use irritating organic solvents, but also does not use dangerous borane dimethyl sulfide and high temperature and high pressure, not only the reaction process is green and environmentally friendly, clean production is realized, but also the cost is reduced, which has better market competition force.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of mirabegron. Background technique [0002] Mirabegron is used to treat overactive bladder in adults. The clinical trial data show that compared with the existing clinical treatment of adults with overactive bladder, mirabegron has the characteristics of rapid onset of action, good tolerance, no sexual dysfunction for patients, and small adverse reactions. Its chemical name is 2-amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide, and its chemical formula is : [0003] [0004] There is a patent application (publication number: EP1440969,2004, A1) in the literature about the synthesis of Mirabegron in the prior art, and this patent application relates to the preparation method of Mirabegron, and the steps of the preparation method are as follows: a) in an organic solvent, Condensate D-mandelic acid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE BIOPHARMA
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