5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide

• ChemBase ID: 174202
• Molecular Formular: C14H16N4O3S
• Molecular Mass: 320.36684
• Monoisotopic Mass: 320.09431139
• SMILES: n1cc(ncc1C(=O)NCCc1ccc(cc1)S(=O)(=O)N)C
• Canonical SMILES: Cc1cnc(cn1)C(=O)NCCc1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C14H16N4O3S/c1-10-8-18-13(9-17-10)14(19)16-7-6-11-2-4-12(5-3-11)22(15,20)21/h2-5,8-9H,6-7H2,1H3,(H,16,19)(H2,15,20,21)
• InChIKey: IMEZLHZLIANIAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide
• IUPAC Traditional name: 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide
• Synonyms: N-[2-[4-(Aminosulfonyl)phenyl]ethyl]-5-methyl-2-pyrazinecarboxamide; 4-[2-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzenesulfonamide; 5-Methyl-N-(p-sulfamoylphenethyl)pyrazinecarboxamide; 4-[β-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzene Sulfonamide

Database IDs

• CAS Number: 33288-71-0
• PubChem SID: 164230112
• PubChem CID: 9883549

CALCULATED PROPERTIES

• Acid pKa: 10.223715
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.25140586
• LogD (pH = 7.4): -0.25197405
• Log P: -0.2513971
• Molar Refractivity: 81.4643 cm^3
• Polarizability: 31.75173 Å^3
• Polar Surface Area: 115.04 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 237-239°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M325946

An intermediate in the synthesis of Glipizide (G410225).

REFERENCES

• Singh, S., et al.: J. Pharm. Biomed. Anal., 41, 1037 (2006)
• Youssef, N., et al.: Chem. Pharm. Bull., 55, 541 (2006)