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Dimethylformamide → N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide

HRID 1262354
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1262354
[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=3[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[N:6]2[N:5]=1)=[O:3].[C:25](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>>[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=3[N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])[N:6]2[N:5]=1)=[O:3]
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Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66712678N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-methanesulfonamide

Produkt 1

HCID 66712445N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide

Versuchsvorschrift

N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-methanesulfonamide (530 mg, 1.4 mmol) was dissolved in 20 mL of dry and warm DMF. The solution was cooled (ice bath). Potassium carbonate (0.80 g, 5.8 mmol) in N,N-Dimethylformamide (20 mL, 200 mmol) was added followed by methyl iodide (270 uL, 4.4 mmol). After 18 h, the mixture was stirred at room temperature overnight. The mixture was filtered and the solvent was evaporated. The product was purified by flash chromatography (ISCO, EtOAc to EtOAc: MeOH 90:10). The product, N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide, was obtained as a solid (320 mg, 58%). LCMS (E/I+) 379 (M+H).

Aufarbeitung

  1. customof dry
  2. temperaturewarm DMF
  3. temperatureThe solution was cooled (ice bath)
  4. filtrationThe mixture was filtered
  5. customthe solvent was evaporated
  6. customThe product was purified by flash chromatography (ISCO, EtOAc to EtOAc: MeOH 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-eb7c4eda7d9f4f03a13ed91432a80cab
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08471005B2

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