40253-44-9

Basic information

• Product Name: ETHYL4-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE
• Synonyms: ETHYL4-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE;4-Methyl-1H-imidazole-2-carboxylic acid ethyl ester;5-Methyl-1H-imidazole-2-carboxylic acid ethyl ester;ethyl 5-Methyl-1H-iMidazole-2-carboxylate;1H-IMidazole-2-carboxylic acid, 5-Methyl-, ethyl ester
• CAS NO: 40253-44-9
• Molecular Formula: C7H10N2O2
• Molecular Weight: 154.17
• Mol File: 40253-44-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 287℃
• Flash Point: 128℃
• Appearance: /
• Density: 1.171
• Vapor Pressure: 0.00252mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 2-8°C
• PKA: 11.81±0.10(Predicted)
• CAS DataBase Reference: ETHYL4-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL4-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE(40253-44-9)
• EPA Substance Registry System: ETHYL4-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE(40253-44-9)

Safety Data

• Hazardous Substances Data: 40253-44-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1437, 1973 DOI: 10.1021/jo00947a052

InChI:InChI=1/C7H10N2O2/c1-3-11-7(10)6-8-4-5(2)9-6/h4H,3H2,1-2H3,(H,8,9)

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 78-98-8 2-oxopropanal 
• 822-36-6 4-methyl-1H-imidazole 
• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 70631-93-5 4-methyl-1H-imidazole-2-carboxylic acid 
• 1171125-20-4 ethyl 4-bromo-5-methyl-1H-imidazole-2-carboxylate 
• 1357114-39-6 ethyl 5-methyl-1-phenyl-1H-imidazole-2-carboxylate 

Relevant articles and documents

Synthesis of 4-Methylimidazole-2-Carboxylic Acid

4-Methylimidazole-2-carboxylic acid was synthesized from 4-methylimidazole with a total yield of 65% over four steps including an N-benzyl protection, acylation, debenzylation, and ester hydrolysis. The solvent, base, temperature, and reaction time are op

4-alkyl-imidazole-2-carboxylic acid synthesizing method

The invention provides a method for synthesizing 4-alkylimidazole-2-carboxylic acid I. The method comprises the steps of firstly, reacting 2-alkyl-imidazole II as a raw material with BnX in the presence of a base to generate a mixture of a pair of position isomers IIIa and IIIb; secondly, on the premise that the mixture is not separated, reacting the mixture with halogenated formate (i.e., XCOOR2) in the presence of a base to generate a pair of corresponding isomers IVa and IVb; thirdly, hydrogenating to remove a benzyl group V in the presence of a hydrogenation catalyst; and fourthly, in the presence of a base, hydrolyzing to obtain the desired product 4-alkylimidazole-2-carboxylic acid I. The reaction route is shown in the specification, wherein R1 is selected from hydrogen atom and lower alkyl groups such as methyl and ethyl and R2 is selected from C1-C6 alkyl, C1-C6 alkoxy substituted group, a phenyl group or a benzyl group. The method disclosed by the invention has ingenious concept, since an inexpensive reagent is used in the respective step, and the yield of each step is high, the final target product 4-alkylimidazole-2-carboxylic acid I can be obtained in efficiency, convenience and low cost.

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.