2-[(4,4,4-2H3)butyl]-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carbaldehyde

• ChemBase ID: 172404
• Molecular Formular: C22H21ClN6O
• Molecular Mass: 420.89474
• Monoisotopic Mass: 420.146537
• SMILES: c1(c(cccc1)c1ccc(cc1)Cn1c(nc(c1C=O)Cl)CCCC)c1nn[nH]n1
• Canonical SMILES: CCCCc1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)C=O)Cl
• InChI: InChI=1S/C22H21ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,14H,2-3,8,13H2,1H3,(H,25,26,27,28)
• InChIKey: FQZSMTSTFMNWQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4,4,4-^2H₃)butyl]-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carbaldehyde
• IUPAC Traditional name: 2-[(4,4,4-^2H₃)butyl]-5-chloro-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carbaldehyde
• Synonyms: 2-(Butyl-d3)-4-chloro-1-[[2’-(1H-tetrazol-5-yl)[1,1’-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxaldehyde; EXP 3179; DUP 167; Losartan Carboxaldehyde-d3

Database IDs

• PubChem SID: 164228314
• PubChem CID: 45038506

CALCULATED PROPERTIES

• Acid pKa: 7.399731
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.5464892
• LogD (pH = 7.4): 5.264376
• Log P: 5.553504
• Molar Refractivity: 131.6177 cm^3
• Polarizability: 45.91553 Å^3
• Polar Surface Area: 89.35 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF; DMSO; Ethanol; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 82-84°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L470507

A labelled intermediate in the synthesis of the EXP 3174, a metabolite of Losartan.

REFERENCES

• Pieter, B.M.W.M., et al.: Hypertension, Supp. III, 18, 5, (1991)
• Chang, L.L., et al.: J. Med. Chem., 36, 2558 (1993)