Preparation method of 5-(tert-butyloxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-C]pyridine-7-carboxylic acid

A technology of tert-butoxycarbonyl and pyrazolo, applied in 5-(tert-butoxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3- C] The field of preparation of pyridine-7-carboxylic acid can solve problems such as no suitable industrial synthesis method, and achieve the effects of convenient operation, easy reaction and short route

Inactive Publication Date: 2019-12-10
CHANGZHOU HEQUAN PHARMA CO LTD
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  • Abstract
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  • Claims
  • Application Information

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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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  • Preparation method of 5-(tert-butyloxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-C]pyridine-7-carboxylic acid

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Embodiment 1

[0010] Example 1: a. Compound 1 (19.5 g, 72 mmol) and N,N-dimethylformamide dimethyl acetal (27.8 g, 1.3 mol) were refluxed overnight. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the reaction was complete. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / ethyl acetate volume ratio = 10 / 1 to 2 / 1) to obtain compound 2 (19.5 g) as a yellow oil with a yield of 83.12%.

[0011] b. Compound 2 (12 g, 36.8 mmol) was dissolved in ethanol (120 mL), and hydrazine hydrate (2.3 g, 50 mmol) was slowly added dropwise into the reaction solution for 10 minutes at room temperature. The reaction solution was refluxed for 3 hours, cooled down and spin-dried, the residue was dissolved in EtOAc, washed with brine, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain a crude product. The crude product was purified by column chromatography to yellow oily compound 3 (4.6 g), yield 42.20%.

[0...

Embodiment 2

[0015] Example 2: a. Compound 1 (195 g, 719 mmol) and N,N-dimethylformamide dimethyl acetal (278 g, 13.2 mol) were refluxed overnight. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the reaction was complete. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / ethyl acetate volume ratio = 10 / 1 to 2 / 1) to obtain compound 2 (195 g) as a yellow oil with a yield of 83.12%.

[0016] b. Dissolve compound 2 (120 g, 0.37 mol) in ethanol (1.2 L), and slowly add hydrazine hydrate (23 g, 0.5 mol) into the reaction solution dropwise at room temperature. The reaction solution was refluxed for 3 hours, cooled down and spin-dried, the residue was dissolved in EtOAc, washed with brine, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain a crude product. The crude product was purified by column chromatography to yellow oily compound 3 (50 g), yield 45.87%.

[0017] c. A suspension of compou...

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Abstract

The invention relates to a preparation method of 5-(tert-butyloxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-C]pyridine-7-carboxylic acid, and mainly solves the technical problem that a method suitable for industrial synthesis does not exist at present. The method comprises four steps: firstly, carrying out a reaction of a compound 1 and N,N-dimethylformamide dimethylacetal to obtain a compound 2; then, carrying out a reaction of the compound 2 and hydrazine hydrate in ethanol to obtain a compound 3; carrying out a reaction of the compound 3 with methyl iodide in an ethyl acetate solvent and with cesium carbonate as an alkali, to generate a compound 4; and finally, hydrolyzing the compound 4 with sodium hydroxide in water and ethanol to obtain a target compound 5. The obtained compound is a useful intermediate or product for synthesizing many medicines.

Description

technical field [0001] The present invention relates to a kind of 5-(tert-butoxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-C]pyridine-7-carboxylic acid (CAS : 1391732-65-) synthetic method. Background technique [0002] 5-(tert-butoxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-7-carboxylic acid and related derivatives in pharmaceuticals It is widely used in chemistry and organic synthesis. At present, there is little synthesis about 5-(tert-butoxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-C]pyridine-7-carboxylic acid, There is a certain risk in similar literature reactions, and the route is long and the yield is low. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of the invention is to develop a kind of 5-(tert-butoxycarbonyl)-2-methyl-4,5,6,7-tetrahydro-...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 何燕平任文武周强刘胜攀汪冬冬刘月领徐富军焦家盛安自强王瑞琪余沛东杨芳张莉莉于凌波马汝建
Owner CHANGZHOU HEQUAN PHARMA CO LTD
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