chloromethyl 6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl carbonate

• ChemBase ID: 164425
• Molecular Formular: C13H8Cl2N4O4
• Molecular Mass: 355.13302
• Monoisotopic Mass: 353.99226012
• SMILES: c1cnc2c(n1)C(=O)N(C2OC(=O)OCCl)c1ncc(cc1)Cl
• Canonical SMILES: ClCOC(=O)OC1N(c2ccc(cn2)Cl)C(=O)c2c1nccn2
• InChI: InChI=1S/C13H8Cl2N4O4/c14-6-22-13(21)23-12-10-9(16-3-4-17-10)11(20)19(12)8-2-1-7(15)5-18-8/h1-5,12H,6H2
• InChIKey: LTLOOQRIMYDJAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloromethyl 6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl carbonate
• IUPAC Traditional name: chloromethyl 6-(5-chloropyridin-2-yl)-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl carbonate
• Synonyms: Chloromethyl Carbonic Acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl Ester; N-Desmethyl Zopicolone; 7-Chloromethyloxy-carbonyloxy-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Database IDs

• CAS Number: 508169-18-4
• PubChem SID: 162258560
• PubChem CID: 11210448

CALCULATED PROPERTIES

• Acid pKa: 12.450795
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.0786629
• LogD (pH = 7.4): 2.078661
• Log P: 2.078665
• Molar Refractivity: 77.6283 cm^3
• Polarizability: 30.532303 Å^3
• Polar Surface Area: 94.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - C369268

Zoplicone intermediate.

REFERENCES

• Koeller, K., et al.: Nature, 409, 232 (2001)
• Terreni, M., et al.: Bioorg. Med. Chem. Lett., 18, 2429 (2001)
• Wegman, M., et al.: Biotechnol. Bioeng. 79, 356 (2002)