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Synthetic method for 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid

An ethoxycarbonyl group and a synthesis method technology, which is applied in the field of synthesis of compound 1-imidazo[1,5]pyridine-6-carboxylic acid, can solve the problems of no suitable industrial synthesis method, and achieve reasonable reaction process design and reaction Ease of use and convenient operation

Inactive Publication Date: 2019-08-30
WUXI APPTEC
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Synthetic method for 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid
  • Synthetic method for 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid

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Embodiment 1

[0012] Compound 1 (330 g, 2.09 mol) and 4-dimethylaminopyridine (25.6 g, 209 mmol) were dissolved in tetrahydrofuran, heated to 70 ° C, and then Boc anhydride (480 g, 2.20 mol) dissolved in tetrahydrofuran Slowly added dropwise to the reaction liquid, reacted at 70° C. for 1 hour, TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. Spin the reaction system to dryness, then dissolve in ethyl acetate (3000 mL) and water (3000 mL), adjust the pH to 3 with 2 molar hydrochloric acid in ice bath, and then add ethyl acetate (1000 mL * 2) After extraction, the organic phase was washed with brine (1000 mL), then dried and concentrated to obtain crude compound 2 (1.3 kg).

[0013] Compound 2 (231 g, 1.08 mol), compound 5 (367 g, 3.24 mol) and cesium carbonate (704 g, 2.16 mol) were dissolved in N,N-dimethylformamide (1400 mL) at 85 °C The reaction was carried out for 16 hours. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the ...

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Abstract

The invention relates to a synthetic method for 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid, and mainly solves the technical problem that a current method is not suitable for industrial synthesis. The method comprises the following three steps: step 1, firstly performing a reaction on a compound 1 and di-tert-butyl dicarbonate in solvent tetrahydrofuran under the action of 4-dimethylaminopyridine to obtain a compound 2; step2, performing a reaction on the compound 2 and ethyl cyanoacetate in solvent N,N-dimethylformamide under the action of cesium carbonate to obtain a compound 3;and step 3, performing a reaction on the compound 3 under the action of hydrochloric acid-ethyl acetate to obtain the 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid. The reaction formula isshown in the description.

Description

technical field [0001] The invention relates to a synthesis method of compound 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid. Background technique [0002] Compound 1 -(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, the method of 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid is rarely reported in the literature. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of the present invention is to develop a synthetic method of 1-(ethoxycarbonyl)imidazo[1,5]pyridine-6-carboxylic acid with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and high yield. It mainly solves the technical problem that there is no suitable indust...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陈冬枝王密杨云龙毛晶刘爽庞洲汪永生韩冰洋于凌波马汝建
Owner WUXI APPTEC
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