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

• ChemBase ID: 165516
• Molecular Formular: C22H23ClN2O2
• Molecular Mass: 382.88322
• Monoisotopic Mass: 382.14480567
• SMILES: C1Cc2c(C(=C3CCN(CC3)C(=O)OCC)c3c1cccn3)cccc2Cl
• Canonical SMILES: CCOC(=O)N1CCC(=C2c3cccc(c3CCc3c2nccc3)Cl)CC1
• InChI: InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-13-10-15(11-14-25)20-18-6-3-7-19(23)17(18)9-8-16-5-4-12-24-21(16)20/h3-7,12H,2,8-11,13-14H2,1H3
• InChIKey: LMPBOVWBDYPSQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{12-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
• IUPAC Traditional name: ethyl 4-{12-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
• Synonyms: Ethyl 4-(7-Chloro-5,6-dihydro-11H-benzo[5,6] cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxyate; 8-Dechloro-7-chloro Loratadine; 4-(7-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester

Database IDs

• PubChem SID: 162259649
• PubChem CID: 71315241

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.527412
• LogD (pH = 7.4): 4.5542254
• Log P: 4.5545793
• Molar Refractivity: 116.9769 cm^3
• Polarizability: 41.255592 Å^3
• Polar Surface Area: 42.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D226325

Loratadine (L469575) impurity.

REFERENCES

• Bruttmann, G., et al.: J. Allergy Clin. Immunol., 83, 411 (1989)
• Haria, M., et al.: Drugs, 48, 617 (1994)