2-{[(4-chloro-3,5-dimethylpyridin-2-yl)methyl]sulfanyl}-5-methoxy-1H-1,3-benzodiazole

• ChemBase ID: 166351
• Molecular Formular: C16H16ClN3OS
• Molecular Mass: 333.83574
• Monoisotopic Mass: 333.07026083
• SMILES: c1cc(cc2c1[nH]c(n2)SCc1c(c(c(cn1)C)Cl)C)OC
• Canonical SMILES: COc1ccc2c(c1)nc([nH]2)SCc1ncc(c(c1C)Cl)C
• InChI: InChI=1S/C16H16ClN3OS/c1-9-7-18-14(10(2)15(9)17)8-22-16-19-12-5-4-11(21-3)6-13(12)20-16/h4-7H,8H2,1-3H3,(H,19,20)
• InChIKey: UPVARCHBWKDWRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(4-chloro-3,5-dimethylpyridin-2-yl)methyl]sulfanyl}-5-methoxy-1H-1,3-benzodiazole
• IUPAC Traditional name: 2-{[(4-chloro-3,5-dimethylpyridin-2-yl)methyl]sulfanyl}-5-methoxy-1H-1,3-benzodiazole
• Synonyms: 2-[[(4-Chloro-3,5-dimethyl-2-pyridinyl)methyl]thio]-6-methoxy-1H-benzimidazole; 5-Methoxy-2-{[(4-chloro-3,5-dimethyl-pyridine-2-yl)methyl]thio}-1H-benzimidazole; 4-Desmethoxy-4-chloro Omeprazole Sulfide

Database IDs

• CAS Number: 220757-74-4
• PubChem SID: 162260484
• PubChem CID: 9797740

CALCULATED PROPERTIES

• Acid pKa: 10.749082
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.245207
• LogD (pH = 7.4): 4.3209257
• Log P: 4.322126
• Molar Refractivity: 90.6322 cm^3
• Polarizability: 36.15503 Å^3
• Polar Surface Area: 50.8 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 67-71°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D290400

Impurity G from the synthesis of Omeprazole.

REFERENCES

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