3-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylprop-2-enamide → 3-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylpropanamide

HRID 244841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244841
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][C:29]2=[O:33])[C:7]2[C:16]3[CH:15]=[C:14]([CH:17]=[CH:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:24]=1>[Pd].CO>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][C:29]2=[O:33])[C:7]2[C:16]3[CH:15]=[C:14]([CH2:17][CH2:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:24]=1

Komponenten

4

Edukt 1

HCID 690822943-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylprop-2-enamide

Produkt 1

HCID 690823003-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylpropanamideAusbeute 108,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A glass Parr vessel was charged with 10% palladium on carbon (0.07 g), methanol (50 mL) and 3-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylprop-2-enamide (0.66 g, 1.47 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The mixture was shaken at 50° C. for approximately 72 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to provide 720 mg of crude 3-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylpropanamide as a white semi-solid. MS (ESI) m/z 452 (M+H)+.

Aufarbeitung

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-05921736f5d54d52afacd06e9e1ab7ae
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

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