2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

• ChemBase ID: 160286
• Molecular Formular: C16H19FN4O3
• Molecular Mass: 334.3454632
• Monoisotopic Mass: 334.14411871
• SMILES: n1(c(nc(c(c1=O)O)C(=O)NCc1ccc(cc1)F)C(N)(C)C)C
• Canonical SMILES: Fc1ccc(cc1)CNC(=O)c1nc(n(c(=O)c1O)C)C(N)(C)C
• InChI: InChI=1S/C16H19FN4O3/c1-16(2,18)15-20-11(12(22)14(24)21(15)3)13(23)19-8-9-4-6-10(17)7-5-9/h4-7,22H,8,18H2,1-3H3,(H,19,23)
• InChIKey: AQLZTHZLYFFVIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide
• IUPAC Traditional name: 2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide
• Synonyms: 2-(1-Amino-1-methylethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide; 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide; 2-(2-Aminopropan-2-yl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Database IDs

• CAS Number: 518048-03-8
• PubChem SID: 162254421
• PubChem CID: 54721880

CALCULATED PROPERTIES

• Acid pKa: 7.384401
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9314082
• LogD (pH = 7.4): -0.48303422
• Log P: -0.4515086
• Molar Refractivity: 87.6339 cm^3
• Polarizability: 32.801697 Å^3
• Polar Surface Area: 108.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 105-107°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95+%; 97%

DETAILS

Toronto Research Chemicals - A616150

An intermediate in the preparation of HIV-integrase inhibitors

REFERENCES

• Summa, V., et al.: J. Med. Chem., 51, 5843 (2008)