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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

Inactive Publication Date: 2021-10-01
上海毕得医药科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] About the synthesis of 4-(2-chloroethyl) thiazole-2-carboxylate ethyl ester, there is no report yet in the prior art

Method used

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

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Embodiment

[0060] The preparation process of the 4-(2-chloroethyl) thiazole-2-carboxylate ethyl ester of the present embodiment comprises the following steps:

[0061] (1), the preparation of compound 2:

[0062]

[0063] 35g of 2-(2-aminothiazol-4-yl) ethyl acetate of compound 1 was added to 700mL of dichloromethane, and then 230g of benzyltriethylammonium bromide (4.5eq) was added, and then slowly dripped 97g of tert-butyl nitrite (5eq) was added, and the reaction was carried out at room temperature (25° C.) for 18 hours. Poured into ice water, extracted with EA, backwashed with 10% HCl, backwashed with saturated aqueous sodium chloride solution, dried and spin-dried to obtain 41.72g of 2-(2-bromothiazol-4-yl) ethyl acetate of compound 2, yield It is 85% and the purity is 95.8%.

[0064] (2), the preparation of compound 3:

[0065]

[0066] Add 41.72g of 2-(2-bromothiazol-4-yl)ethyl acetate of compound 2 into 500mL of ethanol, cool down to 0°C in an ice-salt bath, add 15g of s...

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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.

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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56C07D277/32
CPCC07D277/56C07D277/32
Inventor 郦荣浩许慧敏王治国罗春艳
Owner 上海毕得医药科技股份有限公司
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