1403474-70-3

Basic information

• Product Name: 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester
• Synonyms: 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester;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 ethyl ester;ethyl 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;Ethyl 2-ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;ethyl ester of azilsartan
• CAS NO: 1403474-70-3
• Molecular Formula: C₂₇H₂₄N₄O₅
• Molecular Weight: 484.50326
• EINECS: 200-258-5
• Mol File: 1403474-70-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.34±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.99±0.20(Predicted)
• CAS DataBase Reference: 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester(1403474-70-3)
• EPA Substance Registry System: 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester(1403474-70-3)

Safety Data

• Hazardous Substances Data: 1403474-70-3(Hazardous Substances Data)

Usage

Description

1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester is a complex organic compound with a unique chemical structure. It is characterized by the presence of a benzimidazole core, an ethoxy group, and an ester functional group. This molecule is known to be an impurity in Azilsartan, which is an analgesic and anti-inflammatory drug containing angiotensin II antagonists.

Uses

Used in Pharmaceutical Industry:
1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, ethyl ester is used as an impurity in the production of Azilsartan (A926900). As an analgesic and anti-inflammatory drug, Azilsartan contains angiotensin II antagonists, which help in managing pain and inflammation by blocking the action of angiotensin II, a potent vasoconstrictor.
The presence of this compound as an impurity in Azilsartan may have implications for the drug's efficacy, safety, and overall quality. It is essential to monitor and control the levels of this impurity during the manufacturing process to ensure the drug meets the required standards and provides the desired therapeutic effects without causing adverse side effects.

Upstream product

• 1397836-41-7 2-ethoxy-3-[[2'-(N-hydroxycarbamimidoyl)biphenyl-4-yl]methyl]benzimidazole-4-carboxylic acid ethyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 105-58-8 Diethyl carbonate 
• 139481-41-7 ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate 
• 1397836-41-7 ethyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate 
• 1403474-75-8 ethyl 2-ethoxy-1-((2'-(N'-((ethoxycarbonyl)oxy)carbamimidoyl)[biphenyl]-4-yl)methyl)-1H-benzoimidazole-7-carboxylate 

Downstream Products

• 863031-21-4 Azilsartan medoxomil 
• 147403-03-0 azilsartan 

Relevant articles and documents

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.

Aitch sand smooth intermediate and its and Aitch of preparation method

The invention discloses a preparation method of an intermediate 5B and azilsartan 1. The preparation method of the azilsartan 1 comprises the following steps: 1) in a solvent, mixing a compound 2B with hydroxylamine to react to obtain a compound 3B; 2) in a solvent, mixing the compound 3B prepared in the step 1) with chloroformate to react under the action of alkali to obtain a compound 4B; 3) in a solvent, carrying out cyclization reaction on the compound 4B prepared in the step 2) to obtain a compound 5B; and 4) in a solvent, carrying out esterolysis reaction on the compound 5B prepared in the step 3) under the action of alkali to obtain the azilsartan 1, wherein R is a C6-C10 aryl group or C1-C4 straight-chain or branched-chain alkyl group. The preparation method of the azilsartan intermediate 5B is described as the step 3). The preparation method has the advantages of fewer impurities, short reaction time, higher technical yield and higher product purity, and is suitable for industrial production.