5-chloro-7-{4-[(3-phenylphenyl)methyl]piperazin-1-yl}-2,3-dihydro-1,3-benzoxazol-2-one; methanesulfonic acid

• ChemBase ID: 164095
• Molecular Formular: C25H26ClN3O5S
• Molecular Mass: 516.00904
• Monoisotopic Mass: 515.12816963
• SMILES: C1N(CCN(C1)Cc1cccc(c1)c1ccccc1)c1c2c(cc(c1)Cl)[nH]c(=O)o2.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.Clc1cc(N2CCN(CC2)Cc2cccc(c2)c2ccccc2)c2c(c1)[nH]c(=O)o2
• InChI: InChI=1S/C24H22ClN3O2.CH4O3S/c25-20-14-21-23(30-24(29)26-21)22(15-20)28-11-9-27(10-12-28)16-17-5-4-8-19(13-17)18-6-2-1-3-7-18;1-5(2,3)4/h1-8,13-15H,9-12,16H2,(H,26,29);1H3,(H,2,3,4)
• InChIKey: GZUPEWPMZPFBNP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-7-{4-[(3-phenylphenyl)methyl]piperazin-1-yl}-2,3-dihydro-1,3-benzoxazol-2-one; methanesulfonic acid
• IUPAC Traditional name: 5-chloro-7-{4-[(3-phenylphenyl)methyl]piperazin-1-yl}-3H-1,3-benzoxazol-2-one; methanesulfonic acid
• Synonyms: 7-[4-([1,1'-Biphenyl]-3-ylmethyl)-1-piperazinyl]-5-chloro-2(3H)-benzoxazolone Mesylate; 5-Chloro Bifeprunox Mesylate

Database IDs

• CAS Number: 1217042-05-1
• PubChem SID: 162258230
• PubChem CID: 57369197

CALCULATED PROPERTIES

• Acid pKa: 9.377686
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.0559282
• LogD (pH = 7.4): 4.7642283
• Log P: 5.0944037
• Molar Refractivity: 121.2965 cm^3
• Polarizability: 46.85562 Å^3
• Polar Surface Area: 44.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 257-259°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C364550

Used as an antipsychotic compound. Activates the serotonin 5-hydroxytryptamine (5-HT)1A receptor.

REFERENCES

• Wolf, W., et al.: Curr. Opin. Invest. Drugs, 4, 72 (2003)
• Assie, M.B., et al.: J. Pharmacol. Exp. Ther., 315(2003)
• 265 (2005)