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Method for preparing telmisartan intermediate

A technology for telmisartan and intermediates, which is applied in the field of intermediate synthesis, can solve problems such as the lack of practical significance in synthesis, and achieve the effects of good industrialization prospects, effective recovery and high product purity

Inactive Publication Date: 2011-05-25
SHANGHAI ECUST BIOMEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Method for preparing telmisartan intermediate
  • Method for preparing telmisartan intermediate
  • Method for preparing telmisartan intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0031] In a 250ml three-necked flask, add 8gNaOH, 13.5ml water, 1.0gTBAB and 11g2-n-propyl-4-methyl-6-(1'-methylbenzimidazol-2'-yl) benzimidazole, 40ml 1 , 2-dichloroethane. A mixture of 9g of 2-cyano-4'-bromomethylbiphenyl and 60ml of 1,2-dichloroethane was added dropwise while stirring under cooling at 0-10°C. After the dropwise addition was completed, the reaction was continued for 5 hours. After the reaction was completed, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, the residue was washed with 100ml of tertiary methyl ether, washed with water, and dried in an oven to constant weight to obtain 2-cyano-4'-[2"-n-propyl-4"-methyl-6"-( 1'"-methylbenzimidazol-2'"-yl)benzimidazol-1"-ylmethyl]biphenyl, yield 92%, HPLC content 99.6%.

Embodiment 2

[0033] Add 20ml K to a 250ml three-neck flask 2 CO 3 Saturated solution, 0.9g TBAB and 11 grams of 2-n-propyl-4-methyl-6-(1'-methylbenzimidazol-2'-yl)benzimidazole, 40ml of 1,2-dichloroethane. A mixture of 9 g of 2-cyano-4'-bromomethylbiphenyl and 60 ml of 1,2-dichloroethane was added dropwise while stirring under cooling at -10°C-0°C. After the dropwise addition was completed, the reaction was continued for 6 hours. After the reaction was completed, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, the residue was washed with 100ml of ether and then washed with water, and dried in an oven to constant weight to obtain 2-cyano-4'-[2"-n-propyl-4"-methyl-6"-(1' "-Methylbenzimidazol-2'"-yl)benzimidazol-1"-ylmethyl]biphenyl, yield 87%, HPLC content 99.2%.

Embodiment 3

[0035] In a 250ml three-necked flask, add 8gNaOH, 20ml water, 1.2gTBAHS and 11 grams of 2-n-propyl-4-methyl-6-(1'-methylbenzimidazol-2'-yl)benzimidazole, 40ml carbon tetrachloride. Add dropwise a mixture of 9g of 2-cyano-4'-bromomethylbiphenyl and 60ml of carbon tetrachloride while stirring under cooling at 0-10°C. After the dropwise addition was completed, the reaction was continued for 4 hours. After the reaction was completed, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, the residue was washed with 100ml of petroleum ether, washed with water, and dried in an oven to constant weight to obtain 2-cyano-4'-[2"-n-propyl-4"-methyl-6"-(1 '"-methylbenzimidazol-2'"-yl)benzimidazol-1"-ylmethyl]biphenyl, yield 90.5%, HPLC content 99.5%.

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Abstract

The invention discloses a method for preparing 2-cyan-4'-[2''-n-propyl-4''-methyl-6''-(1'''-methylbenzimidazole-2'''-yl) benzimidazole-1''-yl methyl] biphenyl serving as a telmisartan intermediate by a phase transfer catalytic method. In the method, the 2-cyan-4'-[2''-n-propyl-4''-metyl-6''-(1'''-metylbenzimidazole-2'''-yl)nzimidazole-1''-yl methyl] biphenyl is obtained by reacting 2-n-propyl-4-methyl-6-(1'-methylbenzimidazole-2'-yl) benzimidazole with 2-cyan-4'-bromomethyl biphenyl which serve as raw materials in a solvent such as hydrocarbon or halohydrocarbon and the like under the action of a phase transfer catalyst.

Description

technical field [0001] The invention relates to the synthesis of an intermediate of the blood pressure-lowering drug telmisartan. Background technique [0002] Telmisartan (Telmisartan), chemical name 4'-[2"-n-propyl-4"-methyl-6"-(1'"-methylbenzimidazol-2'"-yl)benzimidazole -1"-ylmethyl] biphenyl-2-carboxylic acid is an angiotensin II receptor antagonist, mainly used in the treatment of hypertension and other medical conditions, its structural formula is as follows: [0003] [0004] The synthesis of telmisartan is mainly obtained by the further reaction of the intermediate 2-n-propyl-4-methyl-6-(1'-methylbenzimidazol-2'-yl)benzimidazole (II). The main methods of reporting in the literature are as follows: [0005] Literature (J.Med.Chem.1993, 36, 4040-4051; WO2006 / 044648; CN1344712) uses the intermediate 2-n-propyl-4-methyl-6-(1'-methylbenzimidazole-2' -yl) benzimidazole (II) and 4'-bromomethylbiphenyl-2-carboxylate (IV) obtained by nucleophilic substitution reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18
Inventor 吴范宏杨雪艳肖时俊俞晓东
Owner SHANGHAI ECUST BIOMEDICINE CO LTD
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