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

• ChemBase ID: 170473
• Molecular Formular: C22H25ClN2O3
• Molecular Mass: 400.8985
• Monoisotopic Mass: 400.15537035
• SMILES: C1Cc2c(C(c3c1cccn3)(C1CCN(CC1)C(=O)OCC)O)ccc(c2)Cl
• Canonical SMILES: CCOC(=O)N1CCC(CC1)C1(O)c2ccc(cc2CCc2c1nccc2)Cl
• InChI: InChI=1S/C22H25ClN2O3/c1-2-28-21(26)25-12-9-17(10-13-25)22(27)19-8-7-18(23)14-16(19)6-5-15-4-3-11-24-20(15)22/h3-4,7-8,11,14,17,27H,2,5-6,9-10,12-13H2,1H3
• InChIKey: WVWGYTXDYNKXEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 133284-74-9
• PubChem SID: 164226383
• PubChem CID: 69455764

CALCULATED PROPERTIES

• Acid pKa: 12.586842
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.7544434
• LogD (pH = 7.4): 3.8003025
• Log P: 3.800925
• Molar Refractivity: 108.7159 cm^3
• Polarizability: 42.054302 Å^3
• Polar Surface Area: 62.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941370

11-Hydroxy Dihydroloratadine is an impurity of Loratadine (L469575).

REFERENCES

• Zhong, D., et al.: Pharmazie, 49, 736 (1994)
• Squella, J., et al.: Talanta, 43, 2029 (1994)
• Ruperez, F., et al.: J. Pharm. Biomed. Anal., 29, 35 (1994)