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 598273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598273
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), prepared in Example 44, 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-f6d6822fd3734817b11ee069897eec5e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

Notizen zur Reaktion

Wird geladen…