5-methyl-N-[3-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide

• ChemBase ID: 172258
• Molecular Formular: C12H9F3N2O2
• Molecular Mass: 270.2072696
• Monoisotopic Mass: 270.0616122
• SMILES: c1noc(c1C(=O)Nc1cccc(c1)C(F)(F)F)C
• Canonical SMILES: O=C(c1cnoc1C)Nc1cccc(c1)C(F)(F)F
• InChI: InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-3-8(5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
• InChIKey: KBFQQKBZIFSAMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-N-[3-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide
• IUPAC Traditional name: 5-methyl-N-[3-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide
• Synonyms: 5-Methyl-N-[3-(trifluoromethyl)phenyl]-4-isoxazolecarboxamide; Leflunomide Imp. E (EP); Leflunomide 3-Isomer

Database IDs

• CAS Number: 61643-23-0
• PubChem SID: 164228168
• PubChem CID: 7314718

CALCULATED PROPERTIES

• Acid pKa: 10.032718
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.5070732
• LogD (pH = 7.4): 2.5061257
• Log P: 2.5070858
• Molar Refractivity: 64.1569 cm^3
• Polarizability: 21.993309 Å^3
• Polar Surface Area: 55.13 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L322765

Leflunomide analogue, with potential antiinflammatory and anti-viral activity. Leflunomide (L322750) Impurity E.

REFERENCES

• Bertolini, G., et al.: J. Med. Chem., 40, 2011 (1997)
• Huang, W., et al.: Chem. Pharm. Bull., 51, 313 (1997)