5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 173591
• Molecular Formular: C21H22N2O5S
• Molecular Mass: 414.47478
• Monoisotopic Mass: 414.12494281
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C1(OCCO1)C
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCc1ccc(cn1)C1(C)OCCO1
• InChI: InChI=1S/C21H22N2O5S/c1-21(27-10-11-28-21)15-4-5-16(22-13-15)8-9-26-17-6-2-14(3-7-17)12-18-19(24)23-20(25)29-18/h2-7,13,18H,8-12H2,1H3,(H,23,24,25)
• InChIKey: BKGURYFSOKOYPR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione

Database IDs

• CAS Number: 184766-66-3
• PubChem SID: 164229501
• PubChem CID: 4288290

CALCULATED PROPERTIES

• Acid pKa: 6.6176434
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.7662385
• LogD (pH = 7.4): 2.0226028
• Log P: 2.8461576
• Molar Refractivity: 108.1496 cm^3
• Polarizability: 42.383274 Å^3
• Polar Surface Area: 86.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethanol; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 59-61°C

DETAILS

Toronto Research Chemicals - M303670

An intermediate for the synthesis of the metabolite of Pioglitazone (P471000).

REFERENCES

• Tanis, S.P., et al.: J. Med. Chem., 39, 5053 (1996)