4-[(3-chloro-4-fluorophenyl)amino]-6-[3-(morpholin-4-yl)propoxy]quinazolin-7-ol

• ChemBase ID: 166259
• Molecular Formular: C21H22ClFN4O3
• Molecular Mass: 432.8757832
• Monoisotopic Mass: 432.13644648
• SMILES: c1c(c(cc2c1c(ncn2)Nc1cc(c(cc1)F)Cl)O)OCCCN1CCOCC1
• Canonical SMILES: Oc1cc2ncnc(c2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
• InChI: InChI=1S/C21H22ClFN4O3/c22-16-10-14(2-3-17(16)23)26-21-15-11-20(19(28)12-18(15)24-13-25-21)30-7-1-4-27-5-8-29-9-6-27/h2-3,10-13,28H,1,4-9H2,(H,24,25,26)
• InChIKey: IFMMYZUUCFPEHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3-chloro-4-fluorophenyl)amino]-6-[3-(morpholin-4-yl)propoxy]quinazolin-7-ol
• IUPAC Traditional name: 4-[(3-chloro-4-fluorophenyl)amino]-6-[3-(morpholin-4-yl)propoxy]quinazolin-7-ol
• Synonyms: 4-[(3-Chloro-4-fluorophenyl)amino]-6-[3-(4-morpholinyl)propoxy]-7-quinazolinol; M523595; O-Desmethyl Gefitinib

Database IDs

• CAS Number: 847949-49-9
• PubChem SID: 162260392
• PubChem CID: 11281905

CALCULATED PROPERTIES

• Acid pKa: 7.8204184
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.191499
• LogD (pH = 7.4): 3.3438892
• Log P: 3.3039048
• Molar Refractivity: 113.0245 cm^3
• Polarizability: 44.015247 Å^3
• Polar Surface Area: 79.74 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 117-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291680

A major metabolite of Gefitinib.

REFERENCES

• Ranson, M., et al.: J. Clin. Oncology, 20, 2240 (2002)
• Mendelsohn, J., et al.: J. Clin. Oncology, 21, 2787 (2002)
• McKillop, D., et al.: Xenobiotica, 10, 917 (2002)