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Process for synthesizing cimetidine

A cimetidine and process technology, applied in the field of synthesizing cimetidine, can solve the problems of not overcoming the reaction route, having malodorous methyl mercaptan, long reaction route and the like, avoiding the malodor problem, improving environmental protection and safety , the effect of high product yield

Active Publication Date: 2021-06-18
YANCHENG KAILI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, US4328349, CN101838241A, etc. all disclose that 4-((2-aminoethyl)thiomethyl)-5-methylimidazole reacts with dimethyl cyanamide to form a condensate, and then reacts with methylamine to form The process route of cimetidine, but the scheme will produce a large amount of volatile, toxic and odorous methyl mercaptan during the generation of condensate and amination, which will cause serious pollution to the environment and
Although CN104557720A has adopted cyanamide carbonic acid diester to replace cyanamide carbonic acid dimethyl ester, but cyanamide carbonic acid diester needs to be prepared by condensation of cyanamide and orthocarbonic acid tetraester, and productive rate is not high, and in 4-( After (2-aminoethyl) thiomethyl)-5-methylimidazole condenses with dimethyl cyanocarbamate, it also needs to react with methylamine to get to cimetidine, and the reaction route is longer. The total yield is not high
GB2111044 first condenses cyanoaminocarbonate with methylamine, and then reacts with 4-((2-aminoethyl)thiomethyl)-5-methylimidazole. Although the reaction sequence is changed, it does not Overcome the problems of long reaction route and low total yield

Method used

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  • Process for synthesizing cimetidine
  • Process for synthesizing cimetidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 4-((2-aminoethyl)thiomethyl)-5-methylimidazole (2.06g, 12.0mmol), cyanamide (0.53g, 12.6mmol), methyl isocyanate in a 250mL three-necked flask Ester (0.72g, 12.6mmol), CuI (0.11g, 0.6mmol), triphenylphosphine (0.31g, 1.2mmol), toluene (100mL), stirred for 10min, then heated to reflux to continue the reaction. The reaction progress was monitored by TLC until the point where the raw material 4-((2-aminoethyl)thiomethyl)-5-methylimidazole completely disappeared, and then the reaction was continued for 2 hours, and the total reaction time was about 8 hours. After the reaction, the reaction solution was naturally cooled to room temperature, washed with 0.1M aqueous hydrochloric acid (100 mL), and then washed with saturated sodium chloride solution (100 mL) and water (100 mL×2). The oil phase was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was separated by column chromatography. The eluent was ethyl acetate / pe...

Embodiment 2

[0024] Add 4-((2-aminoethyl)thiomethyl)-5-methylimidazole (2.06g, 12.0mmol), cyanamide (0.53g, 12.6mmol), methyl isocyanate in a 250mL three-necked flask Ester (0.72g, 12.6mmol), Cu2O (0.086g, 0.6mmol), triphenylphosphine (0.31g, 1.2mmol), toluene (100mL), stirred for 10min, then heated to reflux to continue the reaction. The reaction progress was monitored by TLC until the point where the raw material 4-((2-aminoethyl)thiomethyl)-5-methylimidazole completely disappeared, and then the reaction was continued for 2 h, and the total reaction time was about 10 h. After the reaction, the reaction solution was naturally cooled to room temperature, washed with 0.1M aqueous hydrochloric acid (100 mL), and then washed with saturated sodium chloride solution (100 mL) and water (100 mL×2). The oil phase was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was separated by column chromatography, and the eluent was ethyl acetate / pet...

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Abstract

The invention provides a process for synthesizing cimetidine. According to the technology, cimetidine can be obtained through one-step condensation of 4-((2-aminoethyl)thiomethyl)-5-methylimidazole, the technological process is very simple, and particularly, compared with multi-step synthesis, the technological process is greatly simplified, and the cost is reduced; cyanamido dimethyl dithiocarbamate is not used, so that volatile methyl mercaptan is not generated, the problem of stink is avoided, and the environmental protection property and the safety are greatly improved.

Description

technical field [0001] The invention relates to the field of medicine and chemistry, in particular, the invention relates to a process for synthesizing cimetidine. Background technique [0002] Cimetidine, also known as Cimetidine (CIM for short), is the first-generation H2 receptor antagonist, which mainly acts on H2 receptors on gastric parietal cells, competitively inhibits the effect of histamine, thereby inhibiting gastric acid secretion . Cimetidine can inhibit gastric acid secretion caused by food, histamine, pentagastrin, caffeine and insulin, and has preventive and protective effects on corrosive gastritis caused by bile salts, ethanol and other stimuli. Gastric mucosal injury, stress gastric ulcer and upper gastrointestinal bleeding caused by anti-inflammatory drugs also have obvious curative effect and can pass through the blood-brain barrier. [0003] Cimetidine has been on the market earlier, so a large number of synthetic methods have been developed specifica...

Claims

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Application Information

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IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 马向东黄伟杨毅跃
Owner YANCHENG KAILI PHARMA
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