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Method for synthesizing osimertinib by molecular sieve catalysis

A technology of molecular sieves and alcohol solvents, which is applied in organic chemistry and other fields, can solve the problems of 3-chloropropionyl chloride's high toxicity and volatility, its inapplicability to large-scale industrial production, and the difficulty of post-processing, so as to reduce highly toxic raw materials Use, easy industrial production, and efficient response

Inactive Publication Date: 2019-10-11
滨州市鸿源工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The conditions of this method are complicated, the toxicity and volatility of 3-chloropropionyl chloride used are high, and the price is high, which leads to an increase in production cost, and the difficulty of post-treatment is relatively large, so it is not suitable for large-scale industrial production

Method used

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  • Method for synthesizing osimertinib by molecular sieve catalysis
  • Method for synthesizing osimertinib by molecular sieve catalysis
  • Method for synthesizing osimertinib by molecular sieve catalysis

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Add N-2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indole- 3-yl)-2-pyrimidinyl]amino]aniline (4.45g, 0.010mol), add acrylic acid (0.86g, 0.012mol), HY molecular sieves (0.44g, 0.002mol), isopropanol (32mL, 7.2ml / g), heated to 35°C with microwave, reacted for 4h, dried over anhydrous sodium sulfate, and finally removed the solvent by rotary evaporation to obtain 4.07g of a foamy off-white solid with a yield of 81.6%.

Embodiment 2

[0030] Add N-2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indole- 3-yl)-2-pyrimidinyl]amino]aniline (4.45g, 0.010mol), add acrylic acid (0.86g, 0.012mol), HY molecular sieves (0.66g, 0.003mol), isopropanol (32mL, 7.2ml / g), microwave heated to 35°C, reacted for 4 hours, dried over anhydrous sodium sulfate, and finally removed the solvent by rotary evaporation to obtain 4.88 g of a foamy off-white solid with a yield of 97.9%.

Embodiment 3

[0032] Add N-2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indole- 3-yl)-2-pyrimidinyl]amino]aniline (4.45g, 0.010mol), add acrylic acid (0.86g, 0.012mol), HY molecular sieves (0.66g, 0.003mol), isopropanol (32mL, 7.2ml / g), heated to 30°C with microwave, reacted for 4h, dried over anhydrous sodium sulfate, and finally removed the solvent by rotary evaporation to obtain 4.78g of a foamy off-white solid with a yield of 95.9%.

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Abstract

The invention relates to the field of organic synthesis, in particular to a novel method for synthesizing osimertinib through molecular sieve catalysis. N-1-[2-(dimethylamino) ethyl]-5-methoxy-N1-methyl-N4-[4-(1-methyl-1H-indole-3-yl-2-pyrimidinyl]-1,2,4-triaminobenzene and acrylic acid as raw materials, acrylic acid is added into an alcohol solvent, reaction is carried out through molecular sievecatalysis and microwave heating, and after the reaction is completed, post-treatment is carried out to obtain the osimertinib. According to the method, the reaction conditions are mild, industrial production is facilitated, the raw materials are environmentally friendly in use, used highly toxic raw materials are decreased, the yield is high, and the reaction efficiency is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing osimertinib by catalyzing molecular sieves. Background technique [0002] AZD9291 is a third-generation irreversible epidermal growth factor receptor tyrosine kinase inhibitor for the activation of resistant mutant EGFR. In April 2014, the U.S. Food and Drug Administration (FDA) awarded AZD9291 the title of "Breakthrough Therapy Drug". Targeted drugs for side effects such as rashes. [0003] AZD9291 chemical name: N-{2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indole -3-base)-2-pyrimidinyl]amino]phenyl}-2-acrylamide, its structural formula is: [0004] [0005] Aniline Osimertinib intermediate N1-[2-(dimethylamino)ethyl]-5-methoxy-N1-methyl-N4-[4-(1-methyl-1H-indole-3 -yl)-2-pyrimidinyl]-1,2,4-benzenetriamine and 3-chloropropionyl chloride to synthesize osimertinib N-{2-[[2-(dimethylamino)ethyl]methyl Amino]-4-methoxy-5-[...

Claims

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Application Information

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IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 崔召华崔召新栾信松
Owner 滨州市鸿源工程有限公司
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