ethyl 3-[1-(2-{[(4-cyanophenyl)amino]methyl}-1-(2H3)methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate

• ChemBase ID: 165433
• Molecular Formular: C27H26N6O3
• Molecular Mass: 482.53374
• Monoisotopic Mass: 482.20663872
• SMILES: c1cnc(cc1)N(CCC(=O)OCC)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C#N
• Canonical SMILES: CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C#N)c1ccccn1
• InChI: InChI=1S/C27H26N6O3/c1-3-36-26(34)13-15-33(24-6-4-5-14-29-24)27(35)20-9-12-23-22(16-20)31-25(32(23)2)18-30-21-10-7-19(17-28)8-11-21/h4-12,14,16,30H,3,13,15,18H2,1-2H3
• InChIKey: OZBOESGNDSVMDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-[1-(2-{[(4-cyanophenyl)amino]methyl}-1-(^2H₃)methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate
• IUPAC Traditional name: ethyl 3-[1-(2-{[(4-cyanophenyl)amino]methyl}-1-(^2H₃)methyl-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate
• Synonyms: N-[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine Ethyl Ester Ethanedioate; Deacetamidine Cyano Dabigatran-d3 Ethyl Ester

Database IDs

• PubChem SID: 162259566
• PubChem CID: 71315197

CALCULATED PROPERTIES

• Acid pKa: 16.076275
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1506844
• LogD (pH = 7.4): 3.1600077
• Log P: 3.1601279
• Molar Refractivity: 136.8279 cm^3
• Polarizability: 52.57761 Å^3
• Polar Surface Area: 113.14 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D195652

Nonpeptide thrombin inhibitor intermediate.

REFERENCES

• Hauel, N. et al.: J. Med. Chem. 45, 1757 (2002)