Aminopyrazine → HCID 11965641, Verbindung

HRID 230125

Reaktionsgleichung

Reaktionsgleichung von HRID 230125
[N+:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2)#[C-:2].[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH2:19].[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=O)=[CH:22]1>C(Cl)Cl.CO.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:30]2[N:19]=[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][N:13]3[C:2]=2[NH:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6]3)=[CH:22]1

Komponenten

6

Edukt 3

HCID 78747AminopyrazineHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 187198135-Isocyano-2,3-dihydroinden-1-one

Produkt 1

HCID 11965641HCID 11965641, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571Scandium(III) triflateKatalysatorHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

5-Isocyano-2,3-dihydroinden-1-one (6) (60.0 mg, 379 μmol) was combined with pyrazin-2-amine (12) (36.1 mg, 379 μmol), 1-methyl-1H-indole-3-carbaldehyde (15) (60.4 mg, 379 μmol) and Sc(OTf)3 (18.7 mg, 37.9 μmol) in DCM/MeOH and stirred at room temperature overnight. The solvent was evaporated and purified by silica using 2% MeOH/EtOAc to provide 5-(2-(1-methyl-1H-indol-3-yl)imidazo[1,2-a]pyrazin-3-ylamino)-2,3-dihydroinden-1-one (16). MS (APCI) m/z (M+1)

Aufarbeitung

  1. customThe solvent was evaporated
  2. custompurified by silica using 2% MeOH/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-28ca106c0b57480d89a242c3d18c7b5f
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566716B2

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