4-(2-chloroethyl) thiazole-2-carboxylic acid ethyl ester and preparation method and application thereof

A technology of ethyl carboxylate and ethyl acetate, applied in the field of ethyl 4-thiazole-2-carboxylate and its preparation, achieving the effects of mild reaction conditions, easy operation and increased yield
CN113461635AInactive Publication Date: 2021-10-01上海毕得医药科技股份有限公司
9 Cites 0 Cited by

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
上海毕得医药科技股份有限公司
Publication Date
2021-10-01
Estimated Expiration
Not applicable · inactive patent

Smart Images

  • Figure 1
    Figure 1
  • Figure 2
    Figure 2
  • Figure 3
    Figure 3
Patent Text Reader

Abstract

The invention provides 4-(2-chloroethyl) thiazole-2-carboxylic acid ethyl ester and a preparation method and application thereof. The preparation method comprises the steps that 2-(2-aminothiazole-4-yl) ethyl acetate of a compound 1 is dissolved in dichloromethane, and 2-(2-bromothiazole-4-yl) ethyl acetate is obtained through diazotization and halogenation; then, under the condition of a reducing agent, 2-(2-bromothiazole-4-yl) ethane-1-ol is obtained; in a carbon monoxide atmosphere, carbonyl insertion reaction is performed through a proper catalyst to obtain 4-(2-ethoxyl) thiazole-2-carboxylic acid ethyl ester; and finally, thionyl chloride is used for chlorination to obtain 4-(2-chloroethyl) thiazole-2-carboxylic acid ethyl ester. The 4-(2-chloroethyl) thiazole-2-carboxylic acid ethyl ester can be used as an intermediate in synthesis of APJ receptor stimulant compounds. The invention provides a route method for synthesizing the 4-(2-chloroethyl) thiazole-2-carboxylic acid ethyl ester for the first time, the reaction condition is mild after the brominating reagent is optimized in the first step, and the yield is improved.
Need to check novelty before this filing date? Find Prior Art

Description

technical field

[0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to ethyl 4-(2-chloroethyl)thiazole-2-carboxylate and a preparation method and application thereof. Background technique

[0002] The APJ receptor is a member of the rhodopsin-like G protein-coupled receptor (GPCR) family. The apelin / APJ system has been observed in various tissues including the heart, kidney, pancreas, lung, and central nervous system, suggesting that this system plays diverse roles in mammalian physiology and pathology. Compounds capable of acting as APJ receptor agonists and compositions comprising compounds that act as APJ receptor agonists are useful for activating APJ receptors and treating various diseases. An example is one area where such compounds could be used to treat cardiovascular disease. In particular, the compounds are useful for improving contractility and ejection fraction in patients with chronic heart failure, and for tre...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More