N-(2-chloro-6-methylphenyl)-2-{[2-methyl-6-(piperazin-1-yl)pyrimidin-4-yl]amino}-1,3-thiazole-5-carboxamide

• ChemBase ID: 166286
• Molecular Formular: C20H22ClN7OS
• Molecular Mass: 443.95298
• Monoisotopic Mass: 443.12950704
• SMILES: c1ccc(c(c1C)NC(=O)c1cnc(s1)Nc1cc(nc(n1)C)N1CCNCC1)Cl
• Canonical SMILES: Cc1nc(Nc2ncc(s2)C(=O)Nc2c(C)cccc2Cl)cc(n1)N1CCNCC1
• InChI: InChI=1S/C20H22ClN7OS/c1-12-4-3-5-14(21)18(12)27-19(29)15-11-23-20(30-15)26-16-10-17(25-13(2)24-16)28-8-6-22-7-9-28/h3-5,10-11,22H,6-9H2,1-2H3,(H,27,29)(H,23,24,25,26)
• InChIKey: DOBZFFWLHXORTB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-chloro-6-methylphenyl)-2-{[2-methyl-6-(piperazin-1-yl)pyrimidin-4-yl]amino}-1,3-thiazole-5-carboxamide
• IUPAC Traditional name: N-(2-chloro-6-methylphenyl)-2-{[2-methyl-6-(piperazin-1-yl)pyrimidin-4-yl]amino}-1,3-thiazole-5-carboxamide
• Synonyms: N-(2-Chloro-6-methylphenyl)-2-[[2-methyl-6-(1-piperazinyl)-4-pyrimidinyl]amino]-5-thiazolecarboxamide; Dasatinib metabolite M4; N-Deshydroxyethyl Dasatinib

Database IDs

• CAS Number: 910297-51-7
• PubChem SID: 162260419
• PubChem CID: 11669430

CALCULATED PROPERTIES

• Acid pKa: 8.282942
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.60259223
• LogD (pH = 7.4): 2.8701763
• Log P: 3.483615
• Molar Refractivity: 121.4892 cm^3
• Polarizability: 44.43826 Å^3
• Polar Surface Area: 95.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D290000

A metabolite of Dasatinib. Used in the treatment of cancers and immune diseases.

REFERENCES

• Trentham, D., et al.: Biochem. J., 126, 635 (1972)
• Matsuguchi, T., et al.: J. Biol. Chem., 269, 5016 (1972)
• Berman, E., et al.: Leukemia Res., 24, 289 (1972)
• Tokarski, J., et al.: Cancer Res., 2006, 66, 5790 (1972)