2-[(3,5-dimethyl-4-nitropyridin-2-yl)methanesulfinyl]-5-methoxy-1H-1,3-benzodiazole

• ChemBase ID: 166356
• Molecular Formular: C16H16N4O4S
• Molecular Mass: 360.38764
• Monoisotopic Mass: 360.08922601
• SMILES: c1cc(cc2c1[nH]c(n2)S(=O)Cc1c(c(c(cn1)C)[N+](=O)[O-])C)OC
• Canonical SMILES: COc1ccc2c(c1)nc([nH]2)S(=O)Cc1ncc(c(c1C)[N+](=O)[O-])C
• InChI: InChI=1S/C16H16N4O4S/c1-9-7-17-14(10(2)15(9)20(21)22)8-25(23)16-18-12-5-4-11(24-3)6-13(12)19-16/h4-7H,8H2,1-3H3,(H,18,19)
• InChIKey: PFDONLPWKWJOCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3,5-dimethyl-4-nitropyridin-2-yl)methanesulfinyl]-5-methoxy-1H-1,3-benzodiazole
• IUPAC Traditional name: 2-[(3,5-dimethyl-4-nitropyridin-2-yl)methanesulfinyl]-5-methoxy-1H-1,3-benzodiazole
• Synonyms: 2-[[(3,5-Dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-5-methoxy-1H-benzimidazole; 5-Methoxy-2-{(S)-[(4-nitro-3,5-dimethyl-pyridine-2-yl)methyl]sulfinyl}-1H-benzimidazole; 4-Desmethoxy-4-nitro Omeprazole

Database IDs

• CAS Number: 317807-10-6
• PubChem SID: 162260489
• PubChem CID: 9906891

CALCULATED PROPERTIES

• Acid pKa: 9.677481
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.531086
• LogD (pH = 7.4): 2.529158
• Log P: 2.5311646
• Molar Refractivity: 94.5238 cm^3
• Polarizability: 36.724457 Å^3
• Polar Surface Area: 113.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 165-167°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D290500

Impurity C from the synthesis of Omeprazole.

REFERENCES

• Kohl, B., et al.: J. Med. Chem., 35, 1049 (1992)