3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid Chemical Properties

storage temp. 

2-8°C

Appearance

White to off-white Solid

3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid Usage And Synthesis

Uses

3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic Acid acts as a synthetic reagent used in the preparation and in antitumor activity of pyrrolo[2,3-d]pyrimidine derivatives against A375 human melanoma cells.

Synthesis

The general steps for the synthesis of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid by nitrile hydrolysis reaction using 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzonitrile as raw material were as follows: General method: standard operating procedure for nitrile hydrolysis: 1. dissolve 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid nitrile in dioxane to prepare a 0.13 M solution. 2. aqueous NaOH solution (10 equiv. at a concentration of 1 g/L) was added to the above solution. 3. The reaction mixture was heated to reflux and the reaction was continued overnight. 4. Upon completion of the reaction, the dioxane solvent was removed by evaporation. 5. 5. The remaining aqueous phase was washed with ethyl acetate (AcOEt). 6. The aqueous phase was acidified with 2N HCl and extracted again with ethyl acetate (AcOEt). 7. The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4). 8. The desiccant was removed by filtration and the filtrate was concentrated to give the target product 3-(4-methylimidazol-1-yl)-5-trifluoromethylbenzoic acid.

References

[1] Patent: WO2014/102376, 2014, A1. Location in patent: Page/Page column 46
[2] Patent: WO2014/102377, 2014, A1. Location in patent: Page/Page column 50-51
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5439 - 5448
[4] Patent: WO2006/79791, 2006, A1. Location in patent: Page/Page column 41
[5] Patent: WO2004/29038, 2004, A1. Location in patent: Page 39

3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid(641571-13-3)Related Product Information

• Benzenamine, 3-(2-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-
• Methyl 3-amino-4-methylbenzoate
• Nilotinib Impurity 10
• Nilotinib N-Oxide
• Nilotinib Impurity 7
• Nilotinib genotoxic impurity 3
• Nilotinib Impurity 1
• Nilotinib Impurity 20
• 3-Amino-4-methylbenzoic acid
• Nilotinib Impurity 28
• Nilotinib impurity 3
• 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzamide
• 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid
• 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzonitrile
• 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester
• 1H-IMidazole, 4-Methyl-1-[3-nitro-5-(trifluoroMethyl)phenyl]-
• 3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate
• 3-(5-Methyl-1H-iMidazol-1-yl)-5-(trifluoroMethyl)benzenaMine