Sodium hydride → 6-Cyclopropylmethoxy-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657874

Reaktionsgleichung

Reaktionsgleichung von HRID 657874
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Br.Cl[C:10]1[C:11]([CH3:21])=[C:12]([CH3:20])[C:13]2[N:14]([C:16]([NH2:19])=[N:17][N:18]=2)[N:15]=1>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:10]2[C:11]([CH3:21])=[C:12]([CH3:20])[C:13]3[N:14]([C:16]([NH2:19])=[N:17][N:18]=3)[N:15]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 86650797HCID 86650797, Verbindung

Produkt 1

HCID 580458766-Cyclopropylmethoxy-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Cyclopropylmethanol (2.84 ml) was initially charged in DMF (20 ml), admixed under argon with sodium hydride (862 mg) and stirred at 50° C. for 1 h. Subsequently, 6-chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.006, 2 g), dissolved in DMF (20 ml), and one equivalent of the alkoxide solution were added. After stirring at 50° C. for one hour, two further equivalents of alkoxide solution were added and the mixture was stirred further at 50° C. Then the reaction mixture was dried and purified using silica gel (40 g cartridge, dichloromethane/methanol gradient of 0-10% in 40 min). 625 mg of the title compound were obtained. LC-MS rt: 0.62 min [M+H]+: 234.1 (met. b)

Aufarbeitung

  1. stirringAfter stirring at 50° C. for one hour
  2. stirringthe mixture was stirred further at 50° C
  3. customThen the reaction mixture was dried
  4. custompurified
  5. customsilica gel (40 g cartridge, dichloromethane/methanol gradient of 0-10% in 40 min)

Quellen und Nachweise

ORD-Eintrag
ord-9bb26740a86049afbf94787c82376075
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076336B2

Verknüpfte Notizen

Wird geladen…