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

• ChemBase ID: 173992
• Molecular Formular: C16H18N4O5S
• Molecular Mass: 378.40292
• Monoisotopic Mass: 378.0997907
• SMILES: c1c(ncc(n1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)OC)C
• Canonical SMILES: COC(=O)NS(=O)(=O)c1ccc(cc1)CCNC(=O)c1cnc(cn1)C
• InChI: InChI=1S/C16H18N4O5S/c1-11-9-19-14(10-18-11)15(21)17-8-7-12-3-5-13(6-4-12)26(23,24)20-16(22)25-2/h3-6,9-10H,7-8H2,1-2H3,(H,17,21)(H,20,22)
• InChIKey: LCIIQNPZVOQTFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-(4-{2-[(5-methylpyrazin-2-yl)formamido]ethyl}benzenesulfonyl)carbamate
• IUPAC Traditional name: methyl 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 Methyl Ester; N-[4-[β-(5-Methylpyrazine-2-carboxamido)ethyl]phenylsulfonyl]methylurethane; Methyl 4-[β-(5-Methylpyrazine-2-carboxamido)ethyl]benzene Sulfonamide Carbamate

Database IDs

• CAS Number: 33288-74-3
• PubChem SID: 164229902
• PubChem CID: 13340907

CALCULATED PROPERTIES

• Acid pKa: 2.9549704
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.5769686
• LogD (pH = 7.4): -0.58632135
• Log P: 0.35650235
• Molar Refractivity: 92.6538 cm^3
• Polarizability: 36.27275 Å^3
• Polar Surface Area: 127.35 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M322900

Methyl 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)