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Nitration synthesis process applicable to industrial sildenafil midbody

A technology of sildenafil and intermediates, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of discomfort, low yield, long reaction time, etc., and achieve the effect of good reactivity, high yield and short reaction time

Inactive Publication Date: 2016-06-01
JINLIN MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has long reaction time, low yield and discomfort (Journal of Tianjin Urban Construction Institute, 2002, 8(1), 5~8)

Method used

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  • Nitration synthesis process applicable to industrial sildenafil midbody
  • Nitration synthesis process applicable to industrial sildenafil midbody
  • Nitration synthesis process applicable to industrial sildenafil midbody

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] Example 1: Dissolve 5.00g of 1-methyl-3-propylpyrazole-5-carboxylic acid in 28.40g of concentrated sulfuric acid at 50°C, slowly add 8.01g of mixed acid dropwise, and react at 65~70°C for 4.5~5h, Cool down to room temperature, add 106.92g of ice water, stir, and immediately precipitate 5.78g of solid, moisture 1.41%, yield 89.19%.

example 2

[0028] Example 2: Dissolve 20.00g of 1-methyl-3-propylpyrazole-5-carboxylic acid in 113.61g of concentrated sulfuric acid at 50°C, slowly add 31.9g of mixed acid dropwise, and react at 65~70°C for 4.5~5h, Cool down to room temperature, add 427.67g of ice water, stir, and immediately precipitate 23.58g of solid, moisture 2.28%, yield 90.40%.

example 3

[0029] Example 3: Dissolve 40.00g of 1-methyl-3-propylpyrazole-5-carboxylic acid in 227.21g of concentrated sulfuric acid at 50°C, slowly add 64.08g of mixed acid dropwise, and react at 65~70°C for 4.5~5h, Cool down to room temperature, add 855.34g of ice water, stir, and immediately precipitate 50.21g of solid, moisture 6.65%, yield 92.40%.

[0030] As can be seen from the above examples, the synthesis process of the present invention has the advantages of simple and convenient operation, high product yield, and concentrated sulfuric acid can be recycled, which greatly reduces the industrial cost.

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Abstract

The invention discloses a synthesis process applicable to a sildenafil midbody, namely 1-methyl-3-propyl-4-nitropyrazole-5-formic acid, in a large production scale. The invention discloses a synthesis process which is simple and convenient to operate and applicable to large-scale production of the sildenafil midbody, namely 1-methyl-3-propyl-4-nitropyrazole-5-formic acid. The synthesis process aims to solve the problem that conditions for nitration of 1-methyl-3-propyl-4-nitropyrazole-5-formic acid are not easy to control, and is simple and convenient to operate, very rapid in production separation, relatively high in yield and applicable to industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of pharmaceutical intermediate, especially relate to a kind of sildenafil intermediate 1-methyl-3-propyl group-4-nitropyrazole-5- Synthesis of formic acid. Background technique [0002] Sildenafil is a selective inhibitor of phosphodiesterase type 5 (PDE-5), and PDE-5 is a subtype of phosphodiesterase exclusive to cGMP, which is an effective treatment for male erectile dysfunction ( ED) drugs. The chemical name of sildenafil is 1-methyl-3-n-propyl-5-[2-ethoxy-5-(4-methylpiperazine-1-sulfonyl)phenyl]-1,6 -Dihydro-7H-pyrazolo[4,2-d]pyridin-7-one citrate, the structural formula is as follows figure 1 . [0003] The main synthetic route of sildenafil is 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide (1) and 2-ethoxybenzoyl chloride or 2-ethoxybenzene Formyl acid is used as the starting material, and it is obtained through condensation reaction, pyrimidinone ring closure reaction, chlorosul...

Claims

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Application Information

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IPC IPC(8): C07D231/16
CPCC07D231/16
Inventor 梁承武昌盛张秀荣凌志义冯波金瑛李晓光
Owner JINLIN MEDICAL COLLEGE
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