1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butane-1,3-dione

• ChemBase ID: 176063
• Molecular Formular: C16H12F6N4O2
• Molecular Mass: 406.2824992
• Monoisotopic Mass: 406.08644496
• SMILES: c1(cc(c(cc1F)CC(=O)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)F)F
• Canonical SMILES: O=C(Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F
• InChI: InChI=1S/C16H12F6N4O2/c17-10-6-12(19)11(18)4-8(10)3-9(27)5-14(28)25-1-2-26-13(7-25)23-24-15(26)16(20,21)22/h4,6H,1-3,5,7H2
• InChIKey: QAEDTLFWHIEVPK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butane-1,3-dione
• IUPAC Traditional name: 1-[3-(trifluoromethyl)-5H,6H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butane-1,3-dione
• Synonyms: 1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1,3-butanedione; rac-Sitagliptin 3-Ketone; 4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one

Database IDs

• CAS Number: 764667-65-4
• PubChem SID: 164231973
• PubChem CID: 9887588

CALCULATED PROPERTIES

• Acid pKa: 11.207747
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.9276186
• LogD (pH = 7.4): 1.9275582
• Log P: 1.9276258
• Molar Refractivity: 85.0148 cm^3
• Polarizability: 30.192507 Å^3
• Polar Surface Area: 68.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 82-84°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O864950

Sitagliptin intermediate.

REFERENCES

• Mohri, K., et al.: Chem. Pharm. Bull., 30, 3097 (1982)
• Cameron, M., et al.: J. Pharm. Biomed. Anal., 28, 137 (1982)