N,N-Dimethylethylenediamine → 5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

HRID 1451488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451488
Cl[C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[N:6]=[C:5]3[C:12]4[CH:13]=[CH:14][N:15]=[CH:16][C:17]=4[C:18](=[O:19])[C:3]=1[C:4]=23.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24]>>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[N:6]=[C:5]3[C:12]4[CH:13]=[CH:14][N:15]=[CH:16][C:17]=4[C:18](=[O:19])[C:3]=1[C:4]=23

Komponenten

3

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 199747705-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

Produkt 1

HCID 199747415-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

Versuchsvorschrift

5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one of Example 6 (0.013 g) is added to 2-(dimethylamino)ethylamine (0.34 mL). The yellow mixture is heated quickly to reflux for 1 hour. The excess diamine is removed from the orange solution by a gentle stream of nitrogen. The orange mixture obtained is purified by silica gel column chromatography with a gradient elution (1% methanol/chloroform (25 mL), 2% methanol/chloroform (25 mL), 4% methanol/chloroform (25 mL), 8% methanol/chloroform (25 mL), 12% methanol/chloroform (25 mL), 16% methanol/chloroform (25 mL), 24% methanol/chloroform (50 mL)) to yield 5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one (0.010 g) as a reddish orange solid.

Aufarbeitung

  1. temperatureThe yellow mixture is heated quickly
  2. temperatureto reflux for 1 hour
  3. customThe excess diamine is removed from the orange solution by a gentle stream of nitrogen
  4. customThe orange mixture obtained
  5. customis purified by silica gel column chromatography with a gradient elution (1% methanol/chloroform (25 mL), 2% methanol/chloroform (25 mL), 4% methanol/chloroform (25 mL), 8% methanol/chloroform (25 mL), 12% methanol/chloroform (25 mL), 16% methanol/chloroform (25 mL), 24% methanol/chloroform (50 mL))

Quellen und Nachweise

ORD-Eintrag
ord-29101702fcd14bcf99bc393362805ba3
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604246

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