1,1'-Carbonyldiimidazole → 6-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

HRID 333157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333157
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[C:5]([NH2:18])=[N:4][CH:3]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[NH:14][CH:13]=[CH:12]4)[C:19](=[O:20])[NH:18][C:5]2=[N:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 727136316-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine

Produkt 1

HCID 727136326-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 6-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine (0.450 g, 1.48 mmol) in THF (5 mL) was added carbonyldiimidazole (1.20 g, 7.40 mmol). The resulting mixture was heated at 65° C. for 48 hr, after which it was concentrated in vacuo and partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo to yield a residue that was purified via silica gel chromatography eluting with EtOAc to yield the title compound (0.20 g, 41%). HPLC retention time: 2.07 minutes; MS ESI (m/z): 330.2/332.2 (M+1)+, calc. 329.

Aufarbeitung

  1. concentrationafter which it was concentrated in vacuo
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified via silica gel chromatography
  9. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5d5c31191c61420cb1a0f70cd3b14431
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877772B2

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