144690-33-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester is used as an impurity in the synthesis of Tritylolmesartan Ethyl Ester, which is an impurity of olmesartan medoxomil (O550000). Olmesartan medoxomil is an angiotensin II receptor antagonist and anti-hypertensive drug, indicating the potential role of 1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester in the development and production of medications for hypertension treatment.
Used in Chemical Research:
Due to its complex structure and the presence of various functional groups, 1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester can be used as a starting material or intermediate in the synthesis of other complex organic compounds for various applications in chemical research and development.
Used in Material Science:
The unique structural features of 1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester may also find applications in material science, particularly in the development of new materials with specific properties, such as those with enhanced stability, reactivity, or selectivity in various chemical processes.

Upstream product

• 124750-51-2 N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole 
• 144689-93-0 ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate 
• 400747-06-0 C₁₆H₁₃O₂N 
• 873-32-5 2-Chlorobenzonitrile 
• 2403-54-5 2-(4-chlorophenyl)-1,3-dioxolane 
• 154709-18-9 4'-hydroxymethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl 
• 155983-56-5 5-<2-(4'-formylbiphenylyl)>-2-(triphenylmethyl)-2H-tetrazole 
• 168265-56-3 1-benzyl-5-(4'-methyl-[1,1'-biphenyl]-2-yl)-1H-tetrazole 
• 106-38-7 para-bromotoluene 
• 76-83-5 trityl chloride 
• 144689-23-6 ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{[2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate 
• 38612-13-4 4-bromobenzyl benzoate 
• 28386-90-5 5-benzyl-1-phenyl-1H-tetrazole 
• 1485-70-7 N-benzylbenzamide 

Downstream Products

• 936114-12-4 potassium 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate 
• 879097-59-3 sodium 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate 
• 157356-74-6 C₄₅H₄₂N₆O₂ 
• 1114761-92-0 lithium 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 
• 1337980-10-5 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate 
• 1301633-27-1 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-{[2'-(1H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-imidazole-5-carboxylate 
• 144690-92-6 trityl olmesartan medoxomil 
• 1301629-88-8 [1-(benzoyloxy)]ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1304676-48-9 (1-adamantyl)carbonyloxymethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1304689-26-6 [1-(cyclohexylcarbonyloxy)]ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1301629-90-2 (1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1335030-67-5 tetradecanoyloxymethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1301629-89-9 [1-(benzoyloxy)]ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 
• 1304676-50-3 (1-adamantyl)carbonyloxymethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 

Relevant academic research and scientific papers

Preparation and purification method of olmesartan medoxomil key intermediate

The invention relates to a preparation and purification method of a key intermediate 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{[2' -(triphenylmethyl-1H-tetrazole-5-yl) (1, 1'-biphenyl)-4-yl] methyl}-1H-imidazole-5-ethyl formate (I) for preparing a chemical drug olmesartan medoxomil for treating hypertension. The invention provides a preparation and purification method for generating a compound (I) by reacting 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (II) with N-(triphenylmethyl)-5-(4'-bromomethylbiphenyl-2-yl) tetrazole (III) in the presence of an organic solvent and an acid-binding agent. According to the preparation and purification method of the compound (I), the impurity content is effectively reduced, and the quality of a subsequent target productis improved. The method is stable in process, high in yield, good in quality, simple to operate, less in three wastes, low in production cost and suitable for industrial production, and the recoveredsolvent can be continuously used.

Preparation method of high purity olmesartan medoxomi I

The invention relates to a preparation method of high purity olmesartan medoxomi I. The preparation method comprises following steps: 1,5-(4'-bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole (A) and ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (B) are taken as raw materials to prepare an olmesartan medoxomi I intermediate 1 (C) through condensation reaction; theolmesartan medoxomi I intermediate 1 (C) is subjected to hydrolysis in the presence of sodium hydroxide so as to obtain a compound (D); without separation, the compound (D) and raw material 4-Cloromethyl-5-methyl-1,3-dioxol-2-one (E) are directly subjected to condensation reaction so as to obtain an olmesartan medoxomi I intermediate 2 (F); and the olmesartan medoxomi I intermediate 2 (F) is subjected to deprotection in a 75% acetic acid aqueous solution so as to obtain olmesartan medoxomi I crude product, and acetone is adopted for recrystallization so as to obtain high purity olmesartan medoxomi I (G). The reaction conditions are mild; side products are few; the finished product purity is high; the preparation method is safe, is friendly to the environment, and is suitable for industrialized production; residual solvent is less; and quality standards are achieved.

A olmesartan medoxomil and its preparation method (by machine translation)

The invention discloses a olmesartan medoxomil and its preparation method, the present invention discloses a olmesartan medoxomil, its chemical structure is: The present invention novel method for preparation method, comprises the following steps: (1) preparing AMST - 3 C45 H44 N6 O3 ; (2) preparing C43 H39 N6 NaO3 AMST - 4; (3) preparing C48 H44 N6 O6 AMST - 6; (4) preparing olmesartan sha tanzhi thick; (5) to make the C29 H30 N6 O6 Olmesartan medoxomil. The invention separation effect is good, relatively low viscosity system, split-phase required time is short, the time is saved but also reduces energy consumption. Filtering and separating the high recovery rate, the product quality is high, the running cost is low; process without the need to add chemical, solvent solvent, not into the secondary pollution material; equipment and automatic operation, good stability, easy to realize industrial demand. (by machine translation)

Preparation method of olmesartan medoxomil

The invention provides an improved synthesis method of olmesartan medoxomil. The improved synthesis method comprises the following steps: enabling ethyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate and 4-[2-(triphenylmethyl tetrazole-5-yl)phenyl]phenylmethyl bromide to make alkylation reaction; after carrying out hydrolysis on an ester group, enabling a product and a 4-substituted methyl-5-methyl-2-oxo-1,3-dioxole derivative to make nucleophilic substitution reaction, so as to form ester; then removing the protection of triphenylmethyl to obtain the olmesartan medoxomil. According to the improved synthesis method provided by the invention, alkylation, hydrolysis, esterification and protective group removal reaction are finished through a one-pot method, and a separation and purification process is not needed. A few of instruments and equipment are needed and a technology is simple; the whole process only utilizes an organic solvent, so that industrial production is facilitated; filtering and desalting are used for replacing extraction and washing operation, so that a few of three wastes are generated, and the improved synthesis method is environmentally friendly.

A process for the preparation of olmesartan

The invention relates to a method for preparing a medicine olmesartan medoxomil for treating hypertension, belongs to the field of medicines, and provides a method for preparing the olmesartan medoxomil with low material cost and mild reaction condition. The method comprises the following steps of: feeding two initial raw materials ( a compound 1 and a compound 2) according to a mole ratio of 1:1 during the process; adding the polyethylene glycol/N,N-dimethylacetamide composite catalyst to be completely reacted with the two initial raw materials so as to avoid a necessary impurity control process caused by excessive raw materials during classic reaction; and removing triphenylmethyl from a methanol/organic solvent mixed system to avoid participation of acid. Based on the improvement, the operation is greatly simplified, the cost is reduced, and the industrial production is facilitated.

Method for preparing olmesartan medoxomil

The invention provides a method for preparing olmesartan medoxomil and belongs to the field of medicine synthesis. The method comprises the steps that imidazole monoester and 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole (BBTT) are used as starting materials and subjected to condensation, hydrolysis and acidification through a one-pot method in an acetone system to obtain 4-(1-hydroxyl-1-methylethyl)-2-propyl-{4-[2-(triphenylmethyl tetrazole-5-base) phenyl] phenyl} methylimidazole-5-carboxylic acid; the obtained product is then esterified with 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone, wherein the purity of the esterified product through purification is larger than or equal to 99.5%; the esterified product is subjected to deprotection under the action of a 22.5% sulfuric acid solution to obtain highly purified olmesartan medoxomil. Condensation and esterification are performed through the one-pot method, so that the operation procedure is simplified, control is facilitated, the key intermediate esterified product is purified and then subjected to deprotection in the reaction, the olmesartan medoxomil with purity larger than or equal to 99.5% can be obtained, the total yield can reach 60%-75%, the raw materials are easy to obtain, cost is low, and the method is applicable to industrial production.

A process for the preparation of olmesartan

The invention discloses a preparation method of Olmesartan Medoxomil. The method is used for synthesizing an important intermediate 4-[2-(2-triphenylmethyl tetrazole-5-yl) phenyl] benzyl bromide (a compound III) so as to prepare the compound Olmesartan Medoxomil. The method is high in yield, easy to separate and purify, simple to operate and suitable for industrial production.

Improved synthesis process of olmesartan medoxomil derivatives

The present invention relates to an improved olmesartan medoxomil derivative preparation method. More specifically, the olmesartan medoxomil derivative preparation method includes the steps of: initiating a coupling reaction between imidazole compounds and biphenyl methyl halide compounds; initiating a de-esterification reaction of the products of the coupling reaction; and initiating a condensation reaction between the de-esterified products with dioxolen derivatives. The present invention can optimize the reaction conditions of the coupling and de-esterification reactions to minimixe the content of the conventionally produced byproducts and residual solvent to significantly increase the yield and purity of the target products. The final olmesartan medoxomil derivatives obtained by using the method has the residual solvent content less than or equal to 500 ppm, thereby being lowered to 1/10 or less of the ICH guidelines.

DEPROTECTION METHOD FOR TETRAZOLE COMPOUND

The present invention relates to a method of deprotecting a tetrazole compound, useful as an intermediate for angiotensin II receptor blockers, and provides a novel production method of angiotensin II receptor blockers. Provided is a production method of a compound represented by the formula [3] or [4] or a salt thereof, including (i) reducing a compound represented by the formula [1] or [2] or a salt thereof in the presence of a metal catalyst and an alkaline earth metal salt, or (ii) reacting the compound with a particular amount of Br?nsted acid: wherein each symbol is as defined in the present specification.

METHOD FOR PRODUCING BIARYL COMPOUND

Provided is a novel production method capable of producing a biaryl compound, which is useful as an intermediate for angiotensin II receptor blockers, economically under conditions suitable for industrial production. A production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more kinds of compounds selected from the group consisting of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by RAxP(O)(OM)y wherein each symbol is as defined in the DESCRIPTION.