ChemicalBook--->CAS DataBase List--->641571-13-3

641571-13-3

641571-13-3 Structure

641571-13-3 Structure
IdentificationBack Directory
[Name]

3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid
[CAS]

641571-13-3
[Synonyms]

Nilotinib Impurity 14
3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid
3-(4-METHYL-1H-IMIDAZOL-1-YL)-5-(TRIFLUOROMETHYL)BENZOIC ACID
[Molecular Formula]

C12H9F3N2O2
[MDL Number]

MFCD09998833
[MOL File]

641571-13-3.mol
Chemical PropertiesBack Directory
[storage temp. ]

2-8°C
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[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]

3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzonitrile

641571-12-2

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

641571-13-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

3-(4-Methylimidazol-1-yl)-5-trifluoromethylbenzoic acid(641571-13-3)1HNMR
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