4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino](4,5,6-13C3)pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile

• ChemBase ID: 168826
• Molecular Formular: C20H15BrN6O
• Molecular Mass: 438.25466451
• Monoisotopic Mass: 437.05913564
• SMILES: n1[13c]([13c]([13c](nc1Nc1ccc(cc1)C#N)Oc1c(cc(cc1C)C#N)C)Br)N
• Canonical SMILES: N#Cc1ccc(cc1)Nc1n[13c](N)[13c]([13c](n1)Oc1c(C)cc(cc1C)C#N)Br
• InChI: InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)/i16+1,18+1,19+1
• InChIKey: PYGWGZALEOIKDF-WTZVUXPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino](4,5,6-^1^3C₃)pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
• IUPAC Traditional name: 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino](4,5,6-^1^3C₃)pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
• Synonyms: 4-[[6-Amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl-13C3]oxy]-3,5-dimethyl-benzonitrile; R 165335-13C3; TMC 125-13C3; Etravirine-13C3

Database IDs

• CAS Number: 1189671-48-4
• PubChem SID: 162262958
• PubChem CID: 71316697

CALCULATED PROPERTIES

• Acid pKa: 12.491134
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.5185337
• LogD (pH = 7.4): 5.536277
• Log P: 5.5365114
• Molar Refractivity: 111.8711 cm^3
• Polarizability: 40.72325 Å^3
• Polar Surface Area: 120.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Off-White Solid
• Melting Point: >245°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E937002

A novel labelled HIV reverse transcriptase inhibitor useful in treatment of HIV infection.

REFERENCES

• Scholler-Gyure, M., et al.: J. Clin. Pharmacol., 48, 322 (2008)
• Thakur, A., et al.: Eur. J. Med. Chem., 43, 471 (2008)