Methyl 3-Bromopyruvate → HCID 59233216, Verbindung

HRID 1925140

Reaktionsgleichung

Reaktionsgleichung von HRID 1925140
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:20])([F:19])[C:12]3[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[N:9][N:10]=2)[CH:7]=1.Br[CH2:22][C:23](=O)[C:24]([O:26][CH3:27])=[O:25].C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:20])([F:19])[C:12]3[CH:13]=[CH:14][C:15]4[N:16]([CH:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[N:18]=4)[N:17]=3)=[N:9][N:10]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 352524Methyl 3-BromopyruvateHCID 516892Sodium BicarbonateHCID 59233207HCID 59233207, Verbindung

Produkt 1

HCID 59233216HCID 59233216, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A reaction mixture of 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine (11.0 g, 32.2 mmol), methyl 3-bromo-2-oxopropanoate (11.67 g, 64.5 mmol), and NaHCO3 (10.84 g) in dioxane (150 mL) was heated at 80° C. for 4 hrs to provide a red reaction mixture. Solids were filtered off, rinsed with dioxane, and the combined filtrates were concentrated via rotary evaporation. The resulting residue was dissolved in EtOAc and washed with 0.1 N NaOH until the red color no longer persisted. The organic phase was then separated and concentrated to dryness. The resulting material was purified via MPLC (5:95, MeOH/EtOAc) to provide the title compound, 45I (4.0 g, 9.45 mmol, 30%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.88 (s, 3 H) 7.77 (dd, J=9.73, 1.64 Hz, 1 H) 7.85 (d, J=9.60 Hz, 1 H) 7.97-8.08 (m, 1 H) 8.53 (d, J=9.60 Hz, 1 H) 8.98 (d, J=1.01 Hz, 1 H) 9.02 (s, 1 H). ESI-MS:m/z 423.1 (M+H)+.

Aufarbeitung

  1. customto provide a red reaction mixture
  2. filtrationSolids were filtered off
  3. washrinsed with dioxane
  4. concentrationthe combined filtrates were concentrated via rotary evaporation
  5. dissolutionThe resulting residue was dissolved in EtOAc
  6. washwashed with 0.1 N NaOH until the red color
  7. customThe organic phase was then separated
  8. concentrationconcentrated to dryness
  9. customThe resulting material was purified via MPLC (5:95, MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8969949d90cd41ceb02c5d5572e19037
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178534B2

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