Method for synthesizing Mirabegron intermediate by microchannel reactor

A microchannel reactor, Mirabegron technology, applied in chemical instruments and methods, chemical/physical/physical-chemical reactors, preparation of organic compounds, etc. problems such as low yield, to achieve the effects of stable online production and post-processing, reduction of production costs, and improvement of yield and purity

Inactive Publication Date: 2018-12-07
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the problems of large potential safety hazards, low yield, poor purity, and low times of catalyst recovery and mechanical use in the synthesis of Mirabegron intermediates in traditional high-pressure catalytic hydrogenation reactors, the invention provides a microchannel reactor for synthesizing Mirabegron The method of the Peron intermediate, the chemical reaction formula is as follows:

Method used

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  • Method for synthesizing Mirabegron intermediate by microchannel reactor
  • Method for synthesizing Mirabegron intermediate by microchannel reactor
  • Method for synthesizing Mirabegron intermediate by microchannel reactor

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Embodiment 1

[0043] Embodiment 1: the method for the synthesis of mirabegron intermediate in microchannel reactor.

[0044] This embodiment provides a kind of method that microchannel reactor synthesizes Mirabegron intermediate, and concrete steps are as follows:

[0045] 1) Weigh 180g of the raw material (ALPHAR)-ALPHA-[[[2-(4-nitrophenyl)ethyl]amino]methyl]benzyl alcohol into 3L of methanol, stir well and add 10g of Pd The Pd / C catalyst with a content of 10% is fully stirred and mixed to form a material I, and the material I is transported to the preheating module 1 of the microchannel reactor for preheating, and then enters the reaction module group of the microchannel reactor after preheating.

[0046] 2) Hydrogen is delivered to the reaction module group of the microchannel reactor and step 1) reacts with the preheated material I in the reaction module group, wherein: adjust the flow rate of the slurry pump so that the flow rate of the material I is 40.0g / min , adjust H 2 The flow r...

Embodiment 2

[0047] Embodiment 2: the method for the synthesis of mirabegron intermediate in microchannel reactor.

[0048] This embodiment provides a kind of method that microchannel reactor synthesizes Mirabegron intermediate, and concrete steps are as follows:

[0049] 1) Weigh 180g of the raw material (ALPHAR)-ALPHA-[[[2-(4-nitrophenyl)ethyl]amino]methyl]benzyl alcohol into 3L of ethanol, stir well and add 12g of Pd mass The Pd / C catalyst with a content of 5% is fully stirred and mixed to form a material I, and the material I is transported to the preheating module 1 of the microchannel reactor for preheating, and then enters the reaction module group of the microchannel reactor after preheating.

[0050] 2) Hydrogen is delivered to the reaction module group of the microchannel reactor and step 1) reacts with the preheated material I in the reaction module group, wherein: adjust the flow rate of the slurry pump to make the flow rate of the material I 30.0g / min , adjust H 2 The flow r...

Embodiment 3

[0051] Embodiment 3: the method for the synthesis of mirabegron intermediate in microchannel reactor.

[0052] This embodiment provides a kind of method that microchannel reactor synthesizes Mirabegron intermediate, and concrete steps are as follows:

[0053] 1) Weigh 240g of the raw material (ALPHAR)-ALPHA-[[[2-(4-nitrophenyl)ethyl]amino]methyl]benzyl alcohol into 4.5L of ethanol, stir well and add 16g of Pt The Pt / C catalyst with a mass content of 5% is fully stirred and mixed to form a material I, and the material I is transported to the preheating module 1 of the microchannel reactor for preheating, and then enters the reaction module group of the microchannel reactor after preheating.

[0054] 2) Hydrogen is delivered to the reaction module group of the microchannel reactor and step 1) the material I after preheating is reacted in the reaction module group, wherein: adjust the flow rate of the slurry pump so that the flow rate of the material I is 25.0g / min , adjust H 2...

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Abstract

The invention relates to a method for synthesizing a Mirabegron intermediate by a microchannel reactor, and belongs to the field of drug synthesis in organic synthesis. The invention aims to solve problems of existing Mirabegron intermediate synthesis process, such as large potential safety hazard, low yield, poor purity, low frequency for recycling and reusing of a catalyst and the like. According to the method, a raw material, an organic solvent and an activated carbon-supported precious metal catalyst are mixed and then react with hydrogen in a microchannel reactor to obtain the Mirabegronintermediate (ALPHAR)-ALPHA-[[[2-(4-aminophenyl)ethyl]amino]methyl]benzyl alcohol. The concentration of the raw material in the organic solvent is 0.1 mol / L-0.5 mol / L; mass ratio of the raw material to the activated carbon-supported precious metal catalyst is 1: (0.01-0.10); and the molar ratio of the raw material in the material I to hydrogen is 1: (3.0-3.5). The method of the invention is suitable for long-term safe and stable online production of the Mirabegron intermediate.

Description

technical field [0001] The invention belongs to the field of drug synthesis in organic synthesis, and in particular relates to a method for synthesizing mirabegron intermediates in a microchannel reactor. Background technique [0002] Mirabegron, chemical name is 2-amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazole ethyl Amide, the structural formula is as follows: [0003] [0004] Developed and manufactured by Japan Astellas Corporation, it was approved for marketing in Japan and the United States around 2012 for the treatment of adult overactive bladder. Symptoms such as frequent urination, urgency and urinary incontinence caused by hyperactivity have received good market feedback. Therefore, it is of great significance to study the synthesis method of mirabegron and its related intermediates. [0005] (alphaR)-alpha-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol is the key intermediate for the synthesis of Mirabegron, and the most...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/30C07C213/02B01J19/00
CPCB01J19/0093C07C213/02C07C215/30
Inventor 任吉秋杨昆李海涛
Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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