ethyl 4-{13-chloro-7-cyano-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

• ChemBase ID: 165102
• Molecular Formular: C23H22ClN3O2
• Molecular Mass: 407.89268
• Monoisotopic Mass: 407.14005464
• SMILES: c12c(C(=C3CCN(CC3)C(=O)OCC)c3c(CC2)cc(cc3)Cl)nccc1C#N
• Canonical SMILES: CCOC(=O)N1CCC(=C2c3ccc(cc3CCc3c2nccc3C#N)Cl)CC1
• InChI: InChI=1S/C23H22ClN3O2/c1-2-29-23(28)27-11-8-15(9-12-27)21-19-6-4-18(24)13-16(19)3-5-20-17(14-25)7-10-26-22(20)21/h4,6-7,10,13H,2-3,5,8-9,11-12H2,1H3
• InChIKey: SEMUBDLGVZWDDH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{13-chloro-7-cyano-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-{13-chloro-7-cyano-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
• Synonyms: 4-(8-Chloro-4-cyano-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-Piperidinecarboxylic Acid Ethyl Ester; 4-Cyano Loratadine

Database IDs

• CAS Number: 860010-33-9
• PubChem SID: 162259235
• PubChem CID: 29976521

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.4106736
• LogD (pH = 7.4): 4.4106755
• Log P: 4.4106755
• Molar Refractivity: 122.6985 cm^3
• Polarizability: 43.09346 Å^3
• Polar Surface Area: 66.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol; Tetrahydrofuran
• Apperance: Pale Brown Solid
• Melting Point: 82-95°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C981805

Intermediate for the synthesis of 4-Hydroxymethyl Loratadine.

REFERENCES

• Cerrada, V., et al.: ARKIVOC, 9, 200 (2005).