ethyl 4-{13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate

• ChemBase ID: 171814
• Molecular Formular: C22H23ClN2O2
• Molecular Mass: 382.88322
• Monoisotopic Mass: 382.14480567
• SMILES: C1Cc2c(C(c3c1cccn3)C1=CCN(CC1)C(=O)OCC)ccc(c2)Cl
• Canonical SMILES: CCOC(=O)N1CCC(=CC1)C1c2ccc(cc2CCc2c1nccc2)Cl
• InChI: InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-9,11,14,20H,2,5-6,10,12-13H2,1H3
• InChIKey: ZORGYPXITGWTSB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate
• IUPAC Traditional name: ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-3,6-dihydro-2H-pyridine-1-carboxylate
• Synonyms: 4-(8-Chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-3,6-dihydro-1(2H)-pyridinecarboxylic Acid Ethyl Ester; Iso Loratadine

Database IDs

• CAS Number: 170727-59-0
• PubChem SID: 164227724
• PubChem CID: 59047051

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.325717
• LogD (pH = 7.4): 4.3590016
• Log P: 4.359444
• Molar Refractivity: 107.8879 cm^3
• Polarizability: 41.183517 Å^3
• Polar Surface Area: 42.43 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Low Melting Pink Solid
• Melting Point: 50-53°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I821050

Loratadine (L469575) impurity. An isomer of Loratadine used for preparation of tricyclic amides and ureas useful for inhibition of G-protein function and for treatment of proliferative diseases.

REFERENCES

• Billah., et al.: Lipids, 26, 1172 (1991)
• Piwinski., et al.: J. Med. Chem., 34, 457 (1991)