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Preparation method of ACC (acetyl-coA carboxylase) inhibitor drug key intermediate

An intermediate and inhibitor technology, applied in the field of chemical synthesis, can solve the problems of low total yield, long reaction route and high synthesis cost

Inactive Publication Date: 2017-09-12
JIANGSU SKYRUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Among them, compound I is considered to be the key intermediate in the synthesis process of the substance. The method for synthesizing compound I disclosed in the patent US2015203510A1 is to use the following starting materials and routes, through Gewald aminothiophene reaction, amide synthesis, ring closure, alkali hydrolysis, and decarboxylation , bromination and other reactions to obtain the target compound I; the reaction route is long, the total yield is only 8.3%, and precious metal raw materials such as silver acetate are also used, and the synthesis cost is also high

Method used

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  • Preparation method of ACC (acetyl-coA carboxylase) inhibitor drug key intermediate
  • Preparation method of ACC (acetyl-coA carboxylase) inhibitor drug key intermediate

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Embodiment 1

[0018] step one:

[0019] Add acetone (200g, 3.444mol, 1eq), ethyl cyanoacetate (389.5g, 3.444mol, 1eq), sulfur (110.4g, 3.444mol, 1eq), 400ml of absolute ethanol into a 2L four-necked reaction flask, and stir , heated to an internal temperature of 30°C, controlled the temperature at 30-40°C, and added dropwise morpholine (300g, 3.444mol, 1eq). ), until the reaction of the raw materials is complete, stop the reaction, cool down to about 30°C, pour the reaction solution into 2L of water, solids precipitate out, stir for 15min, filter, rinse the filter cake with 200ml of 50% ethanol aqueous solution, and dry it with air at 50°C for 4h. Obtained yellow solid II: 454.2g, yield: 71.2%; the yellow solid II was subjected to nuclear magnetic detection, 1 H-NMR (500MHz, CDCl 3 ): δ 7.25(s, 2H), 6.53(s, 1H), 4.14-4.19 (q, 2H), 2.12 (s, 3H), 1.28-1.25 (t, 3H) .

[0020] Step two:

[0021] Take a clean 2L four-necked reaction flask, add a drying tube, and protect it with nitrogen...

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Abstract

The invention relates to a method for synthesizing key intermediates of ACC inhibitor drugs, which belongs to the field of chemical synthesis. The method of the invention mainly obtains target compounds by improving starting materials, Gewald aminothiophene reaction, amide synthesis, ring closure, bromination and other reactions , does not need the alkaline hydrolysis step of ethyl formate group, and also does not need the next step of decarboxylation reaction, shortens the reaction process, has the advantages of stable and safe route, low cost, cheap and easy-to-obtain raw materials, and high yield.

Description

technical field [0001] The invention relates to a method for preparing a compound, in particular to a method for preparing a key intermediate of an ACC inhibitor drug, and relates to the field of chemical synthesis. Background technique [0002] Acetyl-CoA carboxylase (ACC for short) gradually synthesizes various saturated fatty acids by catalyzing a series of reactions of condensation, reduction, dehydration and reduction of acetyl-CoA and malonyl-CoA. ACC inhibitors are substances that can inhibit the activity of ACC, thereby blocking the fatty acid synthesis process. Therefore, such substances are commonly used in the treatment of diseases such as human obesity, dyslipidemia and hyperlipidemia. [0003] Patent US2015203510A1 protects an ACC inhibitor of thienopyrimidine derivatives, which has curative effect in the prevention and treatment of human metabolic syndrome, and also has inhibitory effect on ACC enzymes in plants, parasites and bacteria. [0004] [0005] A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D333/38
CPCC07D495/04C07D333/38
Inventor 燕立波沈秋华金永华李佼佼
Owner JIANGSU SKYRUN PHARMA CO LTD
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