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

HRID 1360519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360519
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-0d0ca69ec7764360b17270af44741b13
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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