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Synthesis method of 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide

A technology of aminothiazole acetyl and aminothiazole, which is applied in the field of drug synthesis, can solve the problems of inability to synthesize and high cost of mirabegron, and achieve the effects of fewer reaction steps, high product yield and good quality.

Active Publication Date: 2020-02-28
SUZHOU UUGENE BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The prior art cannot synthesize 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide, resulting in high cost of synthesizing mirabegron

Method used

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  • Synthesis method of 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide
  • Synthesis method of 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide
  • Synthesis method of 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide

Examples

Experimental program
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Effect test

Embodiment 1

[0029] At room temperature, add 300ml of dichloromethane and 158g of aminothiazole acetic acid to the reaction bottle to cool down to 0-10°C, slowly add 119g of thionyl chloride dropwise, and after the dropwise addition, raise the temperature of the mixture to 35-40°C, stir Reflux for 3h.

[0030] Cool down to 10-15°C, add 155g of 4-(2chloroethyl)aniline to the reaction liquid, slowly add 111g of triethylamine dropwise, react at 10-25°C for 3h, add 200g of water, stir for 1h, separate liquid, cool down Filtrate at -10 degrees to obtain 290g off-white solid 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide, yield 98.3%, purity 99.81%.

Embodiment 2

[0032] At room temperature, add 300ml of toluene and 158 grams of aminothiazole acetic acid to the reaction bottle to cool down to 0-10 degrees, slowly add 119 g of thionyl chloride dropwise, after the addition, warm up the mixture to 35-40 degrees, stir and reflux for 3 hours .

[0033] Cool down to 10-15°C, add 155g of 4-(2chloroethyl)aniline to the reaction liquid, slowly add 111g of triethylamine dropwise, react at 10-25°C for 3h, add 200g of water, stir for 1h, separate liquid, cool down Filtrate at -10 degrees to obtain 280g off-white solid 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide, yield 95%, purity 99.71%.

Embodiment 3

[0035] At room temperature, add 300ml of toluene and 158 grams of aminothiazole acetic acid to the reaction bottle to cool down to 0-10 degrees, slowly add 121 g of thionyl chloride dropwise, after the addition, warm up the mixture to 35-40 degrees, stir and reflux for 3 hours .

[0036] Cool down to 10-15°C, add 165g of 4-(2chloroethyl)aniline to the reaction solution, slowly add 131g of triethylamine dropwise, react at 10-25°C for 3h, add 100g of water, stir for 1h, separate the liquid, and cool down Filtrate at -10 degrees to obtain 267g off-white solid 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide, yield 90.5%, purity 99.21%.

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Abstract

The invention discloses a synthesis method of 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide. The synthesis method comprises following steps: step one, adding amino thiazole acetic acid into a solvent, slowly dropwise adding sulfoxide chloride, and carrying out reactions at a temperature of 35 to 40 DEG C to obtain amino thiazole acetyl chloride; step two, adding amino thiazole acetyl chloride and 4-(2-chloroethyl) aniline into dichloromethane, maintaining a temperature of 10 to 25 DEG C, slowly dropwise adding triethylamine, and carrying out reactions for 3 hours after addition; and step three, pumping the reaction liquid into water, carrying out liquid separation, and reducing the pressure to separate dichloromethane so as to obtain a white solid namely 2-(2-aminothiazole-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide. The synthesis method has the advantages of few steps, high yield, and good product quality, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide. 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] And 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide is an important intermediate in the synthesis of mirabegron. [0005] The prior art cannot synthesize 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl)-phenyl]-acetamide, resulting in high cost of synthesizing ...

Claims

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Application Information

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IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE BIOPHARMA
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