Sodium Iodide → 4-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl acetate

HRID 1984442

Reaktionsgleichung

Reaktionsgleichung von HRID 1984442
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH3:21])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19].[C:22]([O-:25])(=[O:24])[CH3:23].[K+].[I-].[Na+].CN(C=O)C>O>[C:22]([O:25][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH3:21])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19])(=[O:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 577175141-(4-chlorobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Produkt 1

HCID 577175744-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl acetateAusbeute 1,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1-(4-Chlorobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine (3.8 g, 12.5 mmol, prepared as described in Example 19) was combined with potassium acetate (3.68 g, 37.5 mmol), sodium iodide (470 mg, 3.12 mmol), and DMF (21 mL). The mixture was heated at 90° C. for 2 hours, allowed to cool to ambient temperature, diluted with water (100 mL), stirred for 20 minutes, and then filtered to remove a black solid. The filtrate was allowed to stand for 1 week at which time crystals had formed. The crystals were isolated by filtration, purified by chromatography on a HORIZON HPFC system (25+M cartridge eluting with chloroform/CMA in a gradient from 100:0 to 70:30), and then recrystallized from acetonitrile to provide 55 mg of 4-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl acetate as a tan crystalline solid, mp 128-129° C. MS (APCI) m/z 327 (M+H)+;

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. customto remove a black solid
  4. waitto stand for 1 week at which time crystals
  5. customhad formed
  6. customThe crystals were isolated by filtration
  7. custompurified by chromatography on a HORIZON HPFC system (25+M cartridge
  8. washeluting with chloroform/CMA in a gradient from 100:0 to 70:30), and
  9. customthen recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-585f28843b7948c09a8d69e109b8d02d
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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