ethyl N-(4-{2-[(5-methylpyrazin-2-yl)formamido]ethyl}benzenesulfonyl)carbamate

• ChemBase ID: 168676
• Molecular Formular: C17H20N4O5S
• Molecular Mass: 392.4295
• Monoisotopic Mass: 392.11544076
• SMILES: c1c(ncc(n1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)OCC)C
• Canonical SMILES: CCOC(=O)NS(=O)(=O)c1ccc(cc1)CCNC(=O)c1cnc(cn1)C
• InChI: InChI=1S/C17H20N4O5S/c1-3-26-17(23)21-27(24,25)14-6-4-13(5-7-14)8-9-18-16(22)15-11-19-12(2)10-20-15/h4-7,10-11H,3,8-9H2,1-2H3,(H,18,22)(H,21,23)
• InChIKey: IWLIZOPQUBXCKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl N-(4-{2-[(5-methylpyrazin-2-yl)formamido]ethyl}benzenesulfonyl)carbamate
• IUPAC Traditional name: ethyl N-(4-{2-[(5-methylpyrazin-2-yl)formamido]ethyl}benzenesulfonyl)carbamate
• Synonyms: N-[[4-[2-[[(5-Methyl-2-pyrazinyl)carbonyl]amino]ethyl]phenyl]sulfonyl]carbamic Acid Ethyl Ester; Ethyl 4-[β-(5-Methylpyrazine-2-carboxamido)ethyl]benzene Sulfonamide Carbamate

Database IDs

• CAS Number: 1076198-09-8
• PubChem SID: 162262808
• PubChem CID: 29979992

CALCULATED PROPERTIES

• Acid pKa: 2.947542
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.2203194
• LogD (pH = 7.4): -0.22951545
• Log P: 0.7133103
• Molar Refractivity: 97.4024 cm^3
• Polarizability: 38.09861 Å^3
• Polar Surface Area: 127.35 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 143-155°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E925113

Ethyl 4-[β-(5-Methylpyrazine-2-carboxamido)ethyl]benzene Sulfonamide Carbamate is an intermediate in the synthesis of Glipizide (G410225).

REFERENCES

• Bakshi, M., et al.: J. Pharm. Biomed. Anal., 36, 769 (2004)
• Youssef, N., et al.: Chem. Pharm. Bull., 55, 541 (2004)