1397836-41-7

Basic information

• Product Name: (Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate
• Synonyms: 2-Ethoxy-1-[[2'-[(hydroxyamino)iminomethyl][1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid ethyl ester;ethyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate;(Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate;Azilsartan Impurity 26;Ethyl 2-ethoxy-1-((2-(N-hydroxycarbamimidoyl)-[1,1-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;(Z)-ethyl 2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
• CAS NO: 1397836-41-7
• Molecular Formula: C₂₆H₂₆N₄O₄
• Molecular Weight: 458.50904
• Mol File: 1397836-41-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 664.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 6.77±0.69(Predicted)
• CAS DataBase Reference: (Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate(1397836-41-7)
• EPA Substance Registry System: (Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl) biphenyl-4-yl) Methyl)-3H-benzo[d] iMidazole-4-carboxylate(1397836-41-7)

Safety Data

• Hazardous Substances Data: 1397836-41-7(Hazardous Substances Data)

Usage

General Description

(Z)-Ethyl-2-ethoxy-3-((2'-(N'-hydroxycarbamimidoyl) biphenyl-4-yl) methyl)-3H-benzo[d] imidazole-4-carboxylate is a complex organic compound containing the chemical elements carbon, hydrogen, nitrogen, and oxygen. It is a derivative of benzo[d] imidazole with an ethyl and ethoxy group, and a biphenyl-4-yl methyl portion attached to the molecule. This chemical possesses a carboxylate functional group and a hydroxycarbamimidoyl moiety, making it potentially useful in pharmaceutical applications where it may interact with biological systems and produce therapeutic effects. The compound's specific structure and properties make it a target for further research and potential development as a drug candidate for various medical conditions.

Upstream product

• 139481-41-7 ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate 

Downstream Products

• 1403474-70-3 ethyl ester of 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]-imidazole-7-carboxylic acid 
• 1403474-75-8 ethyl 2-ethoxy-1-((2'-(N'-((ethoxycarbonyl)oxy)carbamimidoyl)[biphenyl]-4-yl)methyl)-1H-benzoimidazole-7-carboxylate 
• 147403-03-0 azilsartan 
• 1417575-99-5 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid dimethylacetamide 
• 863031-21-4 Azilsartan medoxomil 
• 147403-52-9 methyl 2-ethoxy-1-((2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]-imidazole-7-carboxylate 
• 1417576-01-2 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-((2′-(4-ethyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate 
• 1417576-00-1 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-oxo-3-((2’-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1’-biphenyl]-4-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate 

Relevant articles and documents

Improved process for azilsartan medoxomil: A new angiotensin receptor blocker

An improved process for the active pharmaceutical ingredient of a new angiotensin II AT1 receptor antagonist, azilsartan medoxomil, has been developed. The results include reinvestigation of the described process as well as its novel modifications. This new process includes transformation of the CN group into amidoxime moiety by aqueous hydroxylamine, its cyclization into the corresponding oxadiazole by treatment with dialkyl carbonates, and the following hydrolysis of the ester and transformation into the medoxomil ester. Several thus far undocumented side products were identified, and some of them were synthesized and duly characterized as potential impurities. Formation and control of possible critical impurities are described.

Azilsartan synthesis process

The invention provides an azilsartan synthesis process which is characterized by comprising the following steps: dissolving hydroxylamine hydrochloride into dimethyl sulfoxide, adding sodium bicarbonate at 20-25 DEG C, increasing the temperature to 45-55 DEG C, performing stirring for 45-60 minutes, further adding AQST-SM, increasing the temperature to 80-85 DEG C, and performing a temperature-keeping reaction for 20-22 hours so as to obtain AQST-1; dissolving the AQST-1 into tetrahydrofuran, dropping DBU (diazabicyclo) at 20-25 DEG C, further adding carbonyl diazole, and performing a reactionfor 1.5-2.5 hours at 20-25 DEG C so as to obtain AQST-3; mixing the AQST-3 with a sodium hydroxide solution, increasing the temperature to 70-75 DEG C, and performing a temperature-keeping reaction for 1-2 hours so as to obtain a crude product of AQST; and adding methanol into the crude product of AQST, increasing the temperature to 60-65 DEG C, performing pulping for 45-50 minutes, reducing thetemperature to the room temperature, performing filtering, bleaching filter cakes by using methanol, performing suction filtration till dryness, and performing vacuum drying, so as to obtain an AQST product. By adopting the azilsartan synthesis process provided by the invention, the AQST product is prepared, the yield is high, the content of AQST is high, the content of impurities is low, the quality of the AQST product is remarkably improved, and the azilsartan synthesis process is well applied to production of high-quality azilsartan tablets.

Novel preparation method of azilsartan

The invention relates to a novel preparation method of azilsartan with relatively high yield and relatively high purity. A multi-refining or column chromatography method is not needed, in addition, the final yield reduction can not be caused. According to the preparation route provided by the application, the contents of an impurity A and an impurity B can be effectively reduced, the refining frequency is reduced, and the yield is also increased.