N-[(2,4-Difluorophenyl)methyl]-1,8-dihydro-9-hydroxy-2-[(1R)-3-hydroxy-1-methylpropyl]-1,8-dioxo-2H-pyrido[1,2-a]pyrazine-7-carboxamide

• CAT Number: C000386
• CAS Number: 1973402-05-9
• Molecular Formula: C₂₀H₁₉F₂N₃O₅
• Molecular Weight: 419.38
• Purity: ≥95%
• Synonyms: Dolutegravir impurity E; (R)-N-(2,4-Difluorobenzyl)-9-hydroxy-2-(4-hydroxybutan-2-yl)-1,8-dioxo-2,3,4,8-tetrahydro-1H-pyrido[1,2-a]pyrazine-7-carboxamide
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Appearance: Yellow Solid
• Storage: -20°C, Inert atmosphere
• IUPAC Name: N-[(2,4-difluorophenyl)methyl]-9-hydroxy-2-[(2R)-4-hydroxybutan-2-yl]-1,8-dioxopyrido[1,2-a]pyrazine-7-carboxamide
• InChI: InChI=1S/C20H19F2N3O5/c1-11(4-7-26)25-6-5-24-10-14(17(27)18(28)16(24)20(25)30)19(29)23-9-12-2-3-13(21)8-15(12)22/h2-3,5-6,8,10-11,26,28H,4,7,9H2,1H3,(H,23,29)/t11-/m1/s1
• InChIKey: NQVIDZANHVWALI-LLVKDONJSA-N
• SMILES: C[C@H](CCO)N1C=CN2C=C(C(=O)C(=C2C1=O)O)C(=O)NCC3=C(C=C(C=C3)F)F

(R)-N-(2,4-Difluorobenzyl)-9-hydroxy-2-(4-hydroxybutan-2-yl)-1,8-dioxo-2,3,4,8-tetrahydro-1H-pyrido[1,2-a]pyrazine-7-carboxamide(CAT: C000386) is identified as Impurity E of Dolutegravir, a second-generation HIV-1 integrase strand transfer inhibitor (INSTI). Dolutegravir is in Phase III clinical trials for HIV treatment, demonstrating potent inhibition of HIV replication in peripheral blood mononuclear cells (PBMCs), MT-4 cells, and CIP4 cells infected with a self-inactivating PHIV lentiviral vector. Studying Impurity E is crucial in pharmaceutical quality control to ensure drug safety and efficacy. Understanding its formation and behavior aids in refining the synthesis process and maintaining Dolutegravir’s therapeutic integrity in antiviral research.