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Synthesis process of ezutromid

A synthetic process, the technology of Yezhu Yemi, which is applied in the field of organic chemical synthesis, can solve the problems of high energy consumption and low condensation yield, and achieve the effects of high yield, easy quality and quality control

Inactive Publication Date: 2019-11-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the existing synthesis of edutrami, 2-naphthoyl chloride is condensed with 2-amino-4-(ethylsulfonyl)phenol, and the strong electric absorption of the sulfonyl group makes the condensation process require a high temperature of 210°C. , will inevitably bring about high energy consumption in actual industrial production; in addition, the condensation yield of this process is also low

Method used

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  • Synthesis process of ezutromid
  • Synthesis process of ezutromid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Put 12.6g (100mmol) of compound 1,11.7g (110mmol) of sodium carbonate, 100mL of dichloromethane into the substitution kettle, slowly add 15.6g (130mmol) of ethyl iodide at 0°C, transfer to room temperature and stir for 10h. Filtration, solvent distillation, and column chromatography to obtain 11.55 g of compound 2 (yield 75%);

[0036] Take 3.084g (20mmol) of compound 2 in the nitrification kettle, add 2g of silica gel with a particle size of 300-400 mesh, 2g of distilled water and 60mL of DMSO into the nitrification kettle and place it in an ice water bathtub to cool, then slowly add 2.14g (20mmol) Sulfuric acid and 3.204g (40mmol) potassium nitrite were transferred to room temperature and stirred for 10h, filtered, extracted, dried, and separated by column chromatography to obtain 3.669g of compound 3 (yield 92%);

[0037] Into the reduction kettle, add 2.16g (36.9mmol) of nickel powder and 50mL of dichloromethane, then slowly add dropwise 0.15M sulfuric acid solution, ref...

Embodiment 2

[0043] Put 12.6g (100mmol) of compound 1,15.3g (110mmol) of potassium carbonate, and 100mL of acetone into the substitution kettle, slowly add 14.2g (130mmol) of bromoethane at 0°C, transfer to room temperature and stir for 10h, filter, Solvent distillation and column chromatography to obtain 10.01 g of compound 2 (yield 65%);

[0044] Take 3.084g (20mmol) of compound 2 in the nitrification kettle, add 2g of silica gel with a particle size of 300-400 mesh, 2g of distilled water and 60mL of DMF into the nitrification kettle and place it in an ice water bathtub to cool, then slowly add 0.73g (20mmol) HCl in sequence And 2.760g (40mmol) of sodium nitrite, and transferred to room temperature and stirred for 10h, filtered, extracted, dried, and separated by column chromatography to obtain 3.35g of compound 3 (yield 84%);

[0045] To the reduction kettle, add 2.07g (36.9mmol) manganese powder and 50mL dichloromethane, then slowly add 0.15M sulfuric acid solution dropwise, reflux overnigh...

Embodiment 3

[0049] Put 12.6g (100mmol) of compound 1,15.3g (110mmol) of potassium carbonate, 100mL of acetone into the substitution kettle, slowly add 15.6g (130mmol) of ethyl iodide at 0°C, transfer to room temperature and stir for 10h, filter, Solvent distillation and column chromatography to obtain 10.780 g of compound 2 (yield 70%);

[0050] Take 3.084g (20mmol) of compound 2 in the nitrification kettle, add 2g of silica gel with a particle size of 300-400 mesh, 2g of distilled water and 60mL of acetonitrile into the nitrification kettle and place it in an ice water bathtub to cool, then slowly add 3.842g (20mmol) in sequence Citric acid and 2.760g (40mmol) of sodium nitrite were transferred to room temperature and stirred for 10h, filtered, extracted, dried, and separated by column chromatography to obtain 3.590g of compound 3 (yield 90%);

[0051] Into the reduction kettle, add 2.07g (36.9mmol) iron powder and 50mL ethanol, then slowly add 0.15M hydrochloric acid solution dropwise, reflu...

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Abstract

The invention discloses a synthesis process of ezutromid, and relates to the field of drug synthesis. 4-mercaptophenol and an ethyl halide are taken as raw materials, a compound 2 is prepared, then acompound 3 is prepared through nitration, a compound 4 obtained after nitro-reduction and a compound 5 are condensed, after a sulfur compound 6 is obtained, finally under a specific photosensitizer, specific oxygen and specific blue light irradiation, a sulphone compound, namely the ezutromid is obtained through oxidization. In an existing process, due to the presence of a strong electron-withdrawing group, namely sulphone, the high temperature is needed, the condensation effect is poor, the yield is poor, and the synthesis process has the advantages that when the final sulfur compound is converted into a sulfone structure, heating is not needed, conditions are mild, and the yield is high.

Description

Technical field [0001] The invention relates to the technical field of organic chemistry synthesis, in particular to a synthesis process of yizhuqu rice. Background technique [0002] Ezutromid (Ezutromid) is a drug for the treatment of Duchenne muscular dystrophy (DMD), which is developed and produced by Summit Therapeutics and is currently in phase II clinical trials. DMD is caused by the deficiency of Dystrophin protein. Utrophin protein is similar to its structure and function. It can compensate for the muscle fiber damage caused by insufficient Dystrophin protein. Yizumi can increase Utrophin mRNA by transcription up-regulating the Utrophin gene. And its protein, realize the treatment of DMD. Yizhuqu rice can be taken orally directly, and it has been verified to enhance the muscle function of mice with muscular dystrophy. And in a double-blind experiment, the placebo control group confirmed that ezutril is safe and well tolerated. Ezutrimi is another new drug with great d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57
CPCC07D263/57
Inventor 姜雪峰李一鸣王玉红周怡琳
Owner EAST CHINA NORMAL UNIV
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