Preparation method of 2-methyl-3-carbonyl pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride

A technology of carboxylic acid hydrochloride and carbonylpyrazole, which is applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as no preparation method, and achieve the effect of simple reaction operation

Pending Publication Date: 2022-03-11
CHEMSHUTTLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride has reports of this compound, but there is no synthetic preparation method

Method used

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  • Preparation method of 2-methyl-3-carbonyl pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride
  • Preparation method of 2-methyl-3-carbonyl pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride
  • Preparation method of 2-methyl-3-carbonyl pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride

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Experimental program
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Embodiment 1

[0023] A preparation method of 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid hydrochloride, the preparation method comprising the following steps:

[0024] Compound 1 (ethyl 2-methyl-3-carbonyl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride) (2.6g, 0.01 mol) was slowly added to distilled water (5.4mL) heated to 80°C in batches, stirred at 80°C for 0.5h in a stuffy tank, then raised to 160°C and stirred for 2h. When concentrated to dryness by pressure distillation, the reaction solution was poured into tert-butyl methyl ether for beating and washing and filtered twice, and 1.8 g of solid product was collected. After adding 9 mL of methanolic hydrochloric acid solution (concentration: 4 mol / L) to the solid product, stir at room temperature for 3 h, and then Concentrated under reduced pressure to obtain a yellow solid, namely 1.9 g of the 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride, with a yield of 82% and a pu...

Embodiment 2

[0027] A preparation method of 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid hydrochloride, the preparation method comprising the following steps:

[0028] Compound 1 (ethyl 2-methyl-3-carbonyl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride) (2.6g, 0.01 mol) was slowly added to distilled water (50mL) heated to 80°C in batches, stirred at 80°C in a stuffy tank for 0.5h, then raised to 140°C and continued to react and stir for 24h. LCMS central control detected that the reaction was complete, and the hydrolysis reaction solution was decompressed. When distilling and concentrating to dryness, pour tert-butyl methyl ether into the reaction solution to make slurry, wash and filter twice, collect 1.75 g of solid product, add 1.8 mL of methanolic hydrochloric acid solution (concentration: 4 mol / L) to the solid product, stir at room temperature for 16 h, reduce Concentrated under reduced pressure to obtain a yellow solid, namely 1.85 g of the 2-m...

Embodiment 3

[0030] A preparation method of 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid hydrochloride, the preparation method comprising the following steps:

[0031] Compound 1 (ethyl 2-methyl-3-carbonyl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride) (2.6g, 0.01 mol) was slowly added in batches to distilled water (180mL) heated to 80°C, stirred at 80°C in a stuffy tank for 0.5h, then heated to 160°C and continued to react and stir for 48h, the LCMS central control detected that the reaction was complete, and the hydrolysis reaction solution was decompressed When distilling and concentrating to dryness, pour tert-butyl methyl ether into the reaction solution to make slurry, wash and filter twice, collect 1.9 g of solid product, add 9.5 mL of methanolic hydrochloric acid solution (concentration: 4 mol / L) to the solid product, stir at room temperature for 24 h, reduce Concentrate under reduced pressure to obtain a yellow solid, namely 2.0 g of the 2-...

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Abstract

The invention discloses a preparation method of 2-methyl-3-carbonyl-pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps: (1) dissolving a compound 1 in distilled water, and heating for hydrolysis reaction to prepare a hydrolysis reaction solution; and (2) concentrating the hydrolysis reaction solution, and reacting the concentrated hydrolysis reaction solution with a hydrochloric acid methanol solution to prepare a target product, namely the 2-methyl-3-carbonyl pyrazolo [4, 3-c] pyridine-7-carboxylic acid hydrochloride. The method is simple to operate and relatively high in yield, and a target product with very high purity is obtained.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylate hydrochloride. Background technique [0002] Drug molecular building blocks are important fragments that make up drug molecules, just like Lego building blocks, and are the raw materials for the synthesis of drug molecules. The 2-methyl-3-carbonyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid hydrochloride that this method synthesizes, owing to containing the functional group of acid group, thereby in organic chemistry, high Molecular materials, biomedicine, pharmaceutical and pesticide intermediates and other fields have very important application prospects. The acid group contained in this kind of compound is a very valuable synthetic building block in synthesis. [0003] Organic carboxylic acid compounds widely exist in natural products, drug molecules, pesti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 李欢
Owner CHEMSHUTTLE
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