N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)(2H8)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide

• ChemBase ID: 165417
• Molecular Formular: C22H26ClN7O2S
• Molecular Mass: 488.00554
• Monoisotopic Mass: 487.15572179
• SMILES: c1ccc(c(c1C)NC(=O)c1cnc(s1)Nc1cc(nc(n1)C)N1CCN(CC1)CCO)Cl
• Canonical SMILES: OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
• InChI: InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
• InChIKey: ZBNZXTGUTAYRHI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)(^2H₈)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
• IUPAC Traditional name: N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)(^2H₈)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
• Synonyms: N-[2-Chloro-6-methylphenyl]-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl-d8]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide; BMS-354825-d8; Dasatinib-d8

Database IDs

• PubChem SID: 162259550
• PubChem CID: 25226418

CALCULATED PROPERTIES

• Acid pKa: 8.494367
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.7240891
• LogD (pH = 7.4): 3.7455697
• Log P: 3.8209383
• Molar Refractivity: 133.0762 cm^3
• Polarizability: 48.759987 Å^3
• Polar Surface Area: 106.51 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: Off-White to Light Tan Solid
• Melting Point: 259-262°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D193602

A new, oral, small-molecule Tyrosine Kinase Inhibitor (TKI) for the treatment of CML. Antineoplastic.

REFERENCES

• Lombardo, L.J., et al: J. Med. Chem., 47, 6658 (2004)
• Shah, N. P., et al.: Science, 305, 399 (2004)
• O’Hare, T., et al.: Curr. Opin. Genet. Dev., 16, 92 (2004)