64736-53-4

Usage

Preparation

A mixture of 137 g (1 mol) of 4,5-dichloroimidazole, 414 g (3 mol) of K2CO3 and 1,000 ml of carbon dioxide was stirred in an autoclave at 200° C. under autogenous pressure for 10 hours. The solid output was pulverized, suspended in 2 1 of water and brought to pH 3-4 with concentrated hydrochloric acid while being cooled with ice. The resulting precipitate was filtered off and recrystallized from water to give 136 g (75%) of 4,5-dichloroimidazole-2-carboxylic acid; mp. 240° C. (dec.).

Upstream product

• 16042-25-4 1H-imidazole-2-carboxylic acid 
• 124-38-9 carbon dioxide 
• 7682-38-4 2,4,5-trichloro-1H-imidazole 
• 16076-27-0 2-bromo-4,5-dichloro-1 H-imidazole 
• 584-08-7 potassium carbonate 
• 15965-30-7 4,5-dichloroimidazole 
• 64738-53-0 2,3,7,8-tetrachloro-5H,10H-diimidazo<1,2-a:1',2'-d>pyrazine-5,10-dione 

Downstream Products

• 15965-30-7 4,5-dichloroimidazole 

Relevant academic research and scientific papers

IMIDAZOLE CARBONYL COMPOUND

To develop an antibiotic having a novel mechanism of action, the present inventors have searched for a compound that has weak cytotoxicity, the physical property of high solubility in water, the effect of inhibiting both DNA gyrase GyrB and topoisomerase IV ParE subunits, and sufficient antibacterial activity. As a result, the present inventors have completed the present invention by finding that a compound of the present invention represented by the general formula (1), a pharmacologically acceptable salt thereof, and a prodrug thereof have desirable properties. The present invention provides a pharmaceutical composition (particularly, a preventive or therapeutic composition for infectious disease) comprising a compound represented by the formula (1), a pharmacologically acceptable salt thereof, or a prodrug thereof as an active ingredient.

Preparation of imidazole-2-carboxylic acids

4,5-Disubstituted imidazole-2-carboxylic acids are prepared by reacting 4,5-disubstituted imidazoles with carbon dioxide under superatmospheric pressure at from 150° to 300° C. in the presence of a base.

Azoles. Part 5. Metal-Halogen Exchange Reactions of Polybromoimidazoles

1,2-Dilithiated imidazoles were prepared by treating 2-bromo-4,5-dichloro- and 2,4,5-tribromoimidazole with 2 equivalents of butyl-lithium and trapped with various electrophiles to give moderate yields of the 2-substituted 4,5-dihalogeno compounds (4)-(10

A CONVENIENT SYNTHESIS OF 4(5)-MONO-, 4,5-DI-, AND 2,4,5-TRI-SUBSTITUTED IMIDAZOLES

A procedure is described for the stepwise introduction of substituents (hydrogen included) into the imidazole ring by FGI of the bromine atoms in 1-protected 2,4,5-tribromo-imidazoles in the order 2-5-4 using halogen-metal exchange techniques.

Syntheses and Reactions of Some 4,5-Dihaloimidazole-2-carboxylic Acid Derivatives

The preparation of 5H,10H-diimidazopyrazine-5,10-dione (2a) and its 2,3,7,8-tetrabromo- and 2,3,7,8-tetrachloro- analogs (2b and 2c, respectively) is reported.These dimers, when allowed to react with various anilines, afford imidazole-2-carboxamides (3a-c).