Aminopyrazine → 2-(4-(3-(1-(Hydroxyimino)-2,3-dihydro-1h-inden-5-ylamino)imidazo[1,2-a]pyrazin-2-yl)phenoxy)-n-methylacetamide

HRID 230124

Reaktionsgleichung

Reaktionsgleichung von HRID 230124
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].[CH:8]([C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([NH:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)=O.[Si]([O:29][N:30]=[C:31]1[C:39]2[C:34](=[CH:35][C:36]([N+:40]#[C-:41])=[CH:37][CH:38]=2)[CH2:33][CH2:32]1)(C(C)(C)C)(C)C>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]>[OH:29][N:30]=[C:31]1[C:39]2[C:34](=[CH:35][C:36]([NH:40][C:41]3[N:1]4[CH:6]=[CH:5][N:4]=[CH:3][C:2]4=[N:7][C:8]=3[C:10]3[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([NH:18][CH3:19])=[O:17])=[CH:12][CH:11]=3)=[CH:37][CH:38]=2)[CH2:33][CH2:32]1

Komponenten

6

Edukt 3

HCID 78747AminopyrazineHCID 152705192-(4-formylphenoxy)-N-methylacetamideHCID 577620625-isocyano-2,3-dihydroinden-1-one O-tert-butyldimethylsilyl oxime

Produkt 1

HCID 1371945672-(4-(3-(1-(Hydroxyimino)-2,3-dihydro-1h-inden-5-ylamino)imidazo[1,2-a]pyrazin-2-yl)phenoxy)-n-methylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571Scandium(III) triflateKatalysatorHCID 21226129Dichloromethane methanolLösungsmittel2×

Versuchsvorschrift

A mixture of pyrazin-2-amine (12) (1.1 eq.), 2-(4-formylphenoxy)-N-methylacetamide (9) (1.1 eq.) and a catalytic amount of Sc(OTf)3 was stirred in 2 mL of 1:1 DCM/MeOH at room temperature for 30 minutes. To this was added 5-isocyano-2,3-dihydroinden-1-one O-tert-butyldimethylsilyl oxime (1 eq.) as a 2 mL solution in 1:1 DCM/MeOH and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated under vacuum and the residue taken up in EtOAc (with a small amount of methanol added to help with dissolution) and purified by column using 1-5% MeOH/EtOAc+1% NH4OH. The desired product (14) was isolated as a light yellow solid. MS (APCI) m/z 443.1 (M+1).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. additionadded
  3. dissolutionto help with dissolution) and
  4. custompurified by column

Quellen und Nachweise

ORD-Eintrag
ord-96fcc8a891764c2cbf2c88da8dd3c11d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566716B2

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