Method for preparing 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid

A technology of benzyl and benzo, applied in the field of chemical synthesis

Inactive Publication Date: 2013-06-12
史慎德
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chemical researchers have not stopped researching on obtaining new drugs with high activity and low to

Method used

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  • Method for preparing 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid
  • Method for preparing 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid
  • Method for preparing 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid

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Experimental program
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Embodiment 1

[0037] Embodiment 1: preparation compound I

[0038] Add 180g (1.75mol) of o-phenylenediamine, 188g (2mol) of chloroacetic acid, and 1500ml of phosphoric acid into the flask, reflux for 1.5 hours, cool to room temperature naturally after the reaction is complete, and neutralize with 10% sodium hydroxide solution until a large amount of Solid precipitated, cooled, and suction filtered to obtain a crude product, which was then recrystallized from a mixture of absolute ethanol and water to obtain yellow needle-like crystals, suction filtered, and dried to obtain 269 g of solid product Compound I, with a yield of 93%.

Embodiment 2

[0039] Embodiment 2: preparation compound II

[0040] Add 275g (2.54mol) of o-phenylenediamine and 210ml of concentrated hydrochloric acid to the flask and heat to reflux, add dropwise 220ml (2.6mol) of cyanamide solution with a concentration of 50% to the reaction solution, continue to reflux for 7 hours after the addition, and cyclize After completion, 215ml of 50% (2.68mol) sodium hydroxide solution was added dropwise, and then refluxed for 3 hours after the dropwise addition, cooled to room temperature to precipitate a solid, suction filtered, washed with water, and dried to obtain 235g of light yellow solid product Compound II, yield 90 %.

Embodiment 3

[0041] Embodiment 3: preparation compound III

[0042] Add 100 g (0.6 mol) of compound I, 500 ml of tetrahydrofuran, and 139 g (0.63 mol) of tert-butoxycarbonyl anhydride into the flask. After mixing evenly, 7.33 g (0.06 mol) of 4-N,N-dimethylaminopyridine was added in batches, and after the addition, the reaction mixture was stirred and reacted at 75°C for 3 hours. TLC (PE:EA=2:1) ​​showed that the reaction was complete, concentrated the reaction solution to dryness, added 600ml of ethyl acetate to dissolve it, washed it twice with saturated sodium bicarbonate, water, saturated brine, and anhydrous sodium sulfate. The organic phase was dried and concentrated to dryness to obtain 145 g of liquid product Compound III with a yield of 91%.

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Abstract

The invention belongs to the field of chemical synthesis, relates to a method for preparing 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid and concretely relates to the 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid and a preparation method of an intermediate compound for synthesis of the 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid. The 2-(((1H-benzo[d]imidazolyl-2-yl)methyl)(1-phenmethyl-1H-benzo[d]imidazolyl-2-yl)amino)acetic acid shown in the formula VII is a dibenzoimidazolyl amino acid compound having potential biological activity. The method provides a train of thought for similar compound synthesis and also provides a raw material for pharmacological research on the similar compounds.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for preparing bisbenzimidazole amino acid derivatives, more specifically, to 2-(((1H-benzo[d]imidazol-2-yl)methyl)( A method for preparing 1-benzyl-1H-benzo[d]imidazol-2-yl)amino)acetic acid. Background technique [0002] The nitrogen atoms in benzimidazole and its derivatives have lone pairs of electrons that can coordinate with metals in the body, so these compounds have important medicinal uses in anti-cancer, anti-fungal, analgesic and anti-inflammatory, anti-rheumatic, and anthelmintic. value. For example, the amino acid derivatives of benzimidazole, carbendazim and benomyl, are highly active systemic fungicides, and their mechanism of action is to bind to proteins in pathogens to inhibit mitosis, thereby playing a bactericidal effect. [0003] Because benzimidazole and its derivatives have good biological activity and are important drug intermediates, and many pro...

Claims

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Application Information

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IPC IPC(8): C07D235/30
Inventor 史慎德陈佰英陈朗秋
Owner 史慎德
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