Hydrazine hydrate (1:1) → O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamine

HRID 599394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599394
O.NN.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:22][O:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1>C(O)C>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:22][O:23][NH2:24])[N:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 67052437HCID 67052437, Verbindung

Produkt 1

HCID 11414929O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamineAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Hydrazine hydrate (9 mL) was added to a suspension of 2-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}isoindole-1,3-dione (3.9 g) in ethanol (90 mL). The resulting solution was stirred at ambient temperature for 3 hours. The reaction mixture was filtered to remove a precipitate and the filter cake was washed with ethanol and dichloromethane. The filtrate was concentrated under reduced pressure, diluted with aqueous 1N hydrochloric acid (100 mL), and then washed sequentially with dichloromethane (2×50 mL) and ethyl acetate (1×50 mL). Analysis of the organic washes by LCMS indicated that they did not contain product. The aqueous acidic layer was made basic (˜pH 9) with solid sodium carbonate and then extracted sequentially with dichloromethane (1×100 mL), ethyl acetate (1×100 mL), and dichloromethane (1×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide 2.07 g of O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamine as a tan foam.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove a precipitate
  3. washthe filter cake was washed with ethanol and dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiondiluted with aqueous 1N hydrochloric acid (100 mL)
  6. washwashed sequentially with dichloromethane (2×50 mL) and ethyl acetate (1×50 mL)
  7. extractionextracted sequentially with dichloromethane (1×100 mL), ethyl acetate (1×100 mL), and dichloromethane (1×100 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-42a057faa4c145a4bfc4cacecb2da938
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897767B2

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