136304-78-4

Basic information

• Product Name: Azilsartan pharMaceutical interMediate
• Synonyms: Methyl 3-aMino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)Methyl)aMino)benzoate;Azilsartan pharMaceutical interMediate###136304-78-4
• CAS NO: 136304-78-4
• Molecular Formula: C₂₂H₁₉N₃O₂
• Molecular Weight: 357.40516
• Mol File: 136304-78-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 106-110℃
• Boiling Point: 584.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.27
• PKA: 4.54±0.11(Predicted)
• CAS DataBase Reference: Azilsartan pharMaceutical interMediate(CAS DataBase Reference)
• NIST Chemistry Reference: Azilsartan pharMaceutical interMediate(136304-78-4)
• EPA Substance Registry System: Azilsartan pharMaceutical interMediate(136304-78-4)

Safety Data

• Hazardous Substances Data: 136304-78-4(Hazardous Substances Data)

Usage

Uses

Methyl Ester Candersartan Reduzate is an impurity of the antihypertensive drug candesartan and azilsartan.

Upstream product

• 139481-28-0 methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate 
• 134-20-3 2-carbomethoxyaniline 
• 1228755-48-3 methyl 2-((2'-cyanobiphenyl-4-yl)methylamino)-5-iodo 3-nitrobenzoate 
• 856414-36-3 2-Azidocarbonyl-3-nitro-benzoic acid methyl ester 
• 21606-04-2 methyl 2-carboxy-3-nitrobenzoate 
• 67-56-1 methanol 
• 139481-38-2 methyl 2-amino>-3-nitrobenzoate 
• 57113-90-3 methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate 
• 603-11-2 3-nitrophthalic acid 
• 73833-13-3 acid chloride of 1-methylhydrogen-3-nitrophthalate 

Downstream Products

• 139481-47-3 3-(2'-Cyano-biphenyl-4-ylmethyl)-2-methoxy-3H-benzoimidazole-4-carboxylic acid methyl ester 
• 150058-16-5 methyl 2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>-3-<3-ethyl(thioureido)>benzoate 
• 139481-44-0 methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate 
• 139481-54-2 2-Butoxy-3-(2'-cyano-biphenyl-4-ylmethyl)-3H-benzoimidazole-4-carboxylic acid methyl ester 
• 147404-04-4 methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-cyclopropyl-1H-benzimidazole-7-carboxylate 
• 136285-44-4 methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-pentylbenzimidazole-7-carboxylate 
• 139481-55-3 2-Allyloxy-3-(2'-cyano-biphenyl-4-ylmethyl)-3H-benzoimidazole-4-carboxylic acid methyl ester 
• 136304-79-5 methyl 2-(2-chloroethyl)-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate 
• 150058-17-6 methyl 3-<3-butyl(thioureido)>-2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>benzoate 
• 145040-37-5 candesartan cilexetil 
• 139481-72-4 2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid 
• 147403-52-9 methyl 2-ethoxy-1-[[2’-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate 
• 912357-50-7 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-cyclopropyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate 
• 147403-32-5 2-cyclopropyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid 

Relevant articles and documents

New practical synthesis of the key intermediate of candesartan

The development of a new, practical synthesis of methyl 3-amino-N-(2′-cyanobiphenyl-4-yl)methyl]anthranilate, key intermediate of candesartan, is described, starting from methyl anthranilate. The features of our approach are as follows: (i) introduction of the 3-nitro group by acid catalysed rearrangement of the corresponding methyl N-nitroanthranilate; (ii) introduction of a (2′-cyanobiphenyl-4-yl)methyl side chain by N-alkylation of the appropriate N-nitroanthranilic acid derivative. In the most efficient procedure methyl N,3-dinitroanthranilate was N-alkylated with 4′-bromomethyl-biphenyl-2-nitrile. Catalytic reduction of the aromatic nitro group was accompanied with the removal of the N-nitro function to afford the required key intermediate in good yield.

PROCESS FOR PREPARATION OF CANDESART AN CILEXETIL SUBSTANTIALLY FREE OF DES-CANDESARTAN CILEXETIL IMPURITY

The present invention provides a process for preparation of candeartan cilexetil substantially free of 2,3-dihydro-2-oxo-3-[[2'-(2H-tetrazol-5-yl)[l,l-biphenyl]-4- yl]methyl]-l-[[(cyclohexyloxy)carbonyl]oxy]ethylester-lH-benzimidazole-7- carboxylate (des-candesartan cilexetil) impurity.

CRYSTAL AND PROCESS FOR PRODUCING THE SAME

A process for producing crystals of 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimdazole-7-carboxylic acid (compound (I)), characterized by dissolving or suspending the compound (I) or a salt thereof in a solvent comprising an aprotic polar solvent and crystallizing it. By the process, the contaminants which are contained in the compound (I) or its salt and are difficult to remove, such as tin compounds, analogues of the compound (I), and a residual organic solvent, can be easily removed. Crystals of the compound (I) can be efficiently and easily mass-produced in high yield on an industrial scale.