ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate → ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

HRID 244885

Reaktionsgleichung

Reaktionsgleichung von HRID 244885
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][C:4]=2[N:3]=1>[Pd].C(O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][C:4]=2[N:3]=1

Komponenten

4

Edukt 1

HCID 57657271ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

Produkt 1

HCID 57657240ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoateAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A glass Parr bottle was charged with 10% palladium on carbon (0.2 g) wetted with ethanol (10 mL) and a slurry of ethyl (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (1.81 g, 4.4 mmol) in ethanol (250 mL). The vessel was placed on a Parr apparatus, evacuated and charged with hydrogen (55 psi). The mixture was shaken at ambient temperature for 48 hours. The reaction mixture was filtered through a 0.2 micron PTFE membrane filter and the filter was rinsed with ethanol (300 ml). The filtrate was concentrated to dryness under reduced pressure. Recrystallization from acetonitrile provided 1.51 g of ethyl 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate as a white crystalline solid, mp 172-173° C.

Aufarbeitung

  1. customevacuated
  2. additioncharged with hydrogen (55 psi)
  3. filtrationThe reaction mixture was filtered through a 0.2 micron PTFE membrane
  4. filtrationfilter
  5. washthe filter was rinsed with ethanol (300 ml)
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-19c8f872a2554c9dae152e33978ae134
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

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