Water → HCID 15595653, Verbindung

HRID 329616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 329616
[N:1]1[N:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1)=[N:5]2.[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH3:22][N:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:6]2[CH:7]=[CH:8][C:9]3[N:4]([CH:3]=[N:2][N:1]=3)[N:5]=2)[CH:11]=1)[C:17](=[O:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 75321466-(m-Acetamidophenyl)-1,2,4-triazolo[4,3-b]pyridazine

Produkt 1

HCID 15595653HCID 15595653, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2.53 g of N-[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide in 100 ml of dry dimethylformamide was added 0.6 g of sodium hydride (50% in oil). This mixture was stirred under argon, for 1 hour, then 0.78 ml of methyl iodide was added. This mixture was stirred overnight, then poured into 300 ml of water and extracted with 50 ml portions of dichloromethane. The extracts were combined, dried and evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with dichloromethane:methanol (98:2). The active fractions were combined, evaporated and the solid recrystallized from dichloromethane-hexane, giving 1.39 g of the desired product as light orange crystals mp 166°-169° C.

Aufarbeitung

  1. stirringThis mixture was stirred overnight
  2. extractionextracted with 50 ml portions of dichloromethane
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with dichloromethane:methanol (98:2)
  7. customevaporated
  8. customthe solid recrystallized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a44811dab2ea4461841e6b881d372e09
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892873

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