170791-09-0

Basic information

• Product Name: Trityl candesartan cilexetil
• Synonyms: TRITYL CANDESARTAN CILETEXITIL;TRITYL CANDESARTAN CILEXETIL;TritylCandesartanCilexetil[CandesartanCilexetilIntermediates];Trityl;1-(cyclohexyloxycarbonyloxy)ethyl-2-ethoxy-1-[[(2(1-triphenylmethyl-1H-tetrazol-5-yl) biphenyl-4-yl)methyl]benzimidazole-7-carboxylate cas:(intermediate of candesartan cilexetil);Trityl candesartan Methyl ester;1-(CYCLOHEXYLOXYCARBONYLOXY)ETHYL-2-ETHOXY-1-[[(2''-(1-TRIPHENYLMETHYL-1H-TETRAZOL-5-YL) BIPHENYL-4-YL)METHYL]BENZIMIDAZOLE-7-CARBOXYLATE;TRIPHENYL CANDESARTAN CILEXETIL
• CAS NO: 170791-09-0
• Molecular Formula: C₅₂H₄₈N₆O₆
• Molecular Weight: 852.97
• EINECS: 1806241-263-5
• Product Categories: INTERMEDIATESOF;Candesartan Cilexetil;(intermediate of candesartan cilexetil)
• Mol File: 170791-09-0.mol
• Article Data: 15

Chemical Properties

• Appearance: white powder
• Density: 1.264 g/cm³
• Refractive Index: 1.652
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Hot DMSO, Hot Methanol
• PKA: 3.95±0.10(Predicted)
• CAS DataBase Reference: Trityl candesartan cilexetil(CAS DataBase Reference)
• NIST Chemistry Reference: Trityl candesartan cilexetil(170791-09-0)
• EPA Substance Registry System: Trityl candesartan cilexetil(170791-09-0)

Safety Data

• Hazardous Substances Data: 170791-09-0(Hazardous Substances Data)

Usage

Uses

Trityl Candesartan Cilexetil (Candesartan Cilexetil EP Impurity H) is an impurity of Candesartan (C175575), an angiotensin II type-1 receptor antagonist and used in treatment of congestive heart failure.

InChI:InChI=1/C52H48N6O6/c1-3-61-50-53-46-30-18-29-45(49(59)62-36(2)63-51(60)64-42-25-14-7-15-26-42)47(46)57(50)35-37-31-33-38(34-32-37)43-27-16-17-28-44(43)48-54-55-56-58(48)52(39-19-8-4-9-20-39,40-21-10-5-11-22-40)41-23-12-6-13-24-41/h4-6,8-13,16-24,27-34,36,42H,3,7,14-15,25-26,35H2,1-2H3

Upstream product

• 3970-35-2 2-chloro-3-nitrobezoic acid 
• 3979-45-1 ethyl 2-chloro-3-nitrobenzoate 
• 139481-58-6 ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate 
• 916891-91-3 ethyl 2-ethoxy-1-[[2'-[(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-[1,1']biphenyl-4-yl]methyl]-1H-benzoimidazole-7-carboxylate 
• 854538-89-9 ethyl 2-(4-bromobenzylamine)-3-nitrobenzoate 
• 916891-90-2 ethyl 3-amino-2-(4-bromobenzylamine)-benzoate 
• 854538-88-8 ethyl 1-(4-bromobenzyl)-2-ethoxy-benzimidazole-7-carboxylate 
• 76-83-5 trityl chloride 
• 139481-59-7 candesartan 
• 1239349-15-5 1-(cyclohexyloxycarbonyloxy)ethyl 2-bromo-3-(ethoxy(1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methylamino)methyleneamino)benzoate 
• 145040-37-5 candesartan cilexetil 
• 144873-97-2 2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid 
• 139481-72-4 2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid 
• 99464-83-2 1-chloroethyl cyclohexyl carbonate 

Downstream Products

• 145040-37-5 candesartan cilexetil 
• 869631-11-8 (1RS)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-oxo-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-2,3-dihydro-1H-benzimidazole-4-carboxylate 

Relevant articles and documents

A method for preparing ester

The invention provides a preparation method of candesartan cilexetil. The preparation method comprises steps I-IV. The step I concretely comprises the following substeps of adding candesartan and dichloromethane in a reaction container; slowly and dropwise adding triethylamine at the temperature of 10-15 DEG C; raising the temperature of a reaction system to 21-25 DEG C after dropwise adding of the triethylamine is fnished; adding triphenylchloromethane in batches; reacting for 3-4 hours; adding 0.1 mol/L HCl at one step after reaction is complete and adjusting pH (potential of hydrogen) to be 5-6; then slowly and dropwise adding 9 mol/L HCl and adjusting pH to be 2-3; leaving standstill; separating a water layer and an organic layer; adding saturated salt water in the organic layer to wash the organic layer; leaving standstill to achieve a layering effect; separating out the organic layer; performing decompress concentration on the organic layer to remove the dichloromethane; adding absolute ethyl alcohol in residual viscous substances; raising temperature to 45-50 DEG C; stirring for 3 hours; stopping heating after a large amount of white solids are separated out; reducing to room temperature; performing suction filtration; washing filter cakes with ethyl alcohol; and drying to obtain trityl candesartan.

A noveland practical synthesis of substituted 2-ethoxy benzimidazole: Candesartan cilexetil

A novel and practical synthetic route for the preparation of candesartan cilexetil from methyl 2-amino-3-nitrobenzoate is described.The key steps are the reaction of methyl 2-bromo-3-(diethoxy-methyleneamino)benzoate with (2-(1-trityl-1H-tetrazol-5-yl) biphenyl-4-yl) methanamine and the final formation of 2-ethoxy benzimidazole ring via intramolecular N-arylation.The final ring closure process could be utilized to prepare other 2-substituted benzimidazoles.The method is simple for operation and suitable for industrial production.

Process for the preparation of tetrazolyl compounds

The invention provides a method for preparing candesartan cilexetil and related tetrazolyl compounds. More particularly, the invention relates to the preparation of candesartan cilexetil and related tetrazolyl compounds and includes a method of removing a protective group (e.g., triphenylmethane (trityl) protecting group) from an N-protected tetrazolyl compound using a Lewis acid in an inert solvent and in the presence of an alcohol (e.g., reacting an N-protected tetrazolyl compound with ZnCl2 in the presence of an alcohol).