4-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyrimidin-5-yl)pyrimidin-2-yl]amino}phenyl)-3-(trifluoromethyl)benzamide

• ChemBase ID: 161102
• Molecular Formular: C30H31F3N8O
• Molecular Mass: 576.6153496
• Monoisotopic Mass: 576.25729231
• SMILES: c1cnc(nc1c1cncnc1)Nc1c(ccc(c1)NC(=O)c1cc(c(cc1)CN1C[C@@H](CC1)N(C)C)C(F)(F)F)C
• Canonical SMILES: CN([C@@H]1CCN(C1)Cc1ccc(cc1C(F)(F)F)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cncnc1)C)C
• InChI: InChI=1S/C30H31F3N8O/c1-19-4-7-23(13-27(19)39-29-36-10-8-26(38-29)22-14-34-18-35-15-22)37-28(42)20-5-6-21(25(12-20)30(31,32)33)16-41-11-9-24(17-41)40(2)3/h4-8,10,12-15,18,24H,9,11,16-17H2,1-3H3,(H,37,42)(H,36,38,39)/t24-/m1/s1
• InChIKey: ZGBAJMQHJDFTQJ-XMMPIXPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyrimidin-5-yl)pyrimidin-2-yl]amino}phenyl)-3-(trifluoromethyl)benzamide
• IUPAC Traditional name: 4-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyrimidin-5-yl)pyrimidin-2-yl]amino}phenyl)-3-(trifluoromethyl)benzamide
• Synonyms: N-[3-([4,5'-Bipyrimidin]-2-ylamino)-4-methylphenyl]-4-[[(3S)-3-(dimethylamino)-1-pyrrolidinyl]methyl]-3-(trifluoromethyl)benzamide; INNO 406; NS 187; Bafetinib

Database IDs

• CAS Number: 859212-16-1
• PubChem SID: 162255237
• PubChem CID: 11215316

CALCULATED PROPERTIES

• Acid pKa: 12.337041
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.275333
• LogD (pH = 7.4): 2.6107388
• Log P: 4.66941
• Molar Refractivity: 158.2598 cm^3
• Polarizability: 58.95202 Å^3
• Polar Surface Area: 99.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B109050

A substituted benzamide derivative structurally related to STI-571 (Imatinib Mesylate). It was identified as highly potent Bcr-Abl kinase inhibitor.

REFERENCES

• Li, Q., et al.: J. Med. Chem., 39, 3070 (1996)
• Ptasznik, A., et al.: Nat. Med., 10, 1187 (1996)
• Tetsuo, A., et al.: Bioorg. Med. Chem. Lett., 16, 1421 (1996)