Chloroform → 4(2'-Aminoethyl)amino-1,8-dimethylimidazo(1,2-a)quinoxaline

HRID 984843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984843
Cl[C:2]1[C:3]2[N:4]([C:13]([CH3:16])=[CH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([CH3:12])[CH:6]=2.C(Cl)(Cl)Cl>C(N)CN>[NH2:4][CH2:3][CH2:2][NH:11][C:2]1[C:3]2[N:4]([C:13]([CH3:16])=[CH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([CH3:12])[CH:6]=2

Komponenten

4

Edukt 2

HCID 6212ChloroformHCID 225089424-Chloro-1,8-dimethyl-imidazo[1,2-A]quinoxaline2×

Produkt 1

HCID 98137584(2'-Aminoethyl)amino-1,8-dimethylimidazo(1,2-a)quinoxalineAusbeute 174,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3301EthylenediamineLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-1,8-dimethylimidazo(1,2-a)quinoxaline (compound 5) (4.8 g, 21 mmol) in ethylenediamine (300 mL) was heated at 60° C. under nitrogen gas (N2) for 16 hours. The solvent was evaporated under vacuum. The residue was diluted with EtOAc (200 mL), washed with saturated Na2CO3 and brine, dried over MgSO4, filtered and concentrated. Flash chromatography using methanol (MeOH) provided a solid, which was then dissolved with CHCl3 and filtered to remove any dissolved silica gel. The filtrate was concentrated under vacuum, providing the title compound 6 as a white solid (4.67 g). 1H NMR (500 MHz, CDCl3) δ 7.88 (s, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.26 (s, 1H), 7.22 (d, J=8.3 Hz, 1H), 6.31 (s, 1H), 3.63 (apparent q, J=5.9 Hz, 2H), 2.96 (t, J=6.0 Hz, 2H), 2.88 (s, 3H), 1.38 (br, 2H); MS (ESI), m/z 256.15 [(M+H)+; calculated for compound 6, C14H17N5:255.15].

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. additionThe residue was diluted with EtOAc (200 mL)
  3. washwashed with saturated Na2CO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customprovided a solid, which
  8. filtrationfiltered
  9. customto remove any dissolved silica gel
  10. concentrationThe filtrate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-af9636153a5740eab03ffebc23f5d2ac
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869956B2

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