7-Benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2203540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203540
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH2:24][CH3:25])[C:21]([CH2:26][O:27][CH2:28][CH3:29])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>[Pd].C(O)C>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]([CH2:26][O:27][CH2:28][CH3:29])[N:22]([CH2:23][CH2:24][CH3:25])[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=2[N:16]=1

Komponenten

4

Edukt 1

HCID 575452997-Benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 1360752014-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

7-Benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.9 g, 9.99 mmol) was mixed with ethanol and added to a Parr flask charged with 10% palladium on carbon (0.390 g) in ethanol. The flask was placed under hydrogen pressure and shaken for 18 hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with warm DMF. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from methanol to yield 2.4 g of 4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol as a white solid, mp>250° C.

Aufarbeitung

  1. additionadded to a Parr flask
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with warm DMF
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-54897ad8462d43c3b31282a66405acad
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365567B2

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