Methyl Acrylate → Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

HRID 244823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244823
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[NH2:30][C:31]1[C:40]2[N:41]=[C:42]([CH2:49][O:50][CH2:51][CH3:52])[N:43]([CH2:44][C:45]([CH3:48])([OH:47])[CH3:46])[C:39]=2[C:38]2[CH:37]=[CH:36][C:35](Br)=[CH:34][C:33]=2[N:32]=1.[C:54]([O:58][CH3:59])(=[O:57])[CH:55]=[CH2:56]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:30][C:31]1[C:40]2[N:41]=[C:42]([CH2:49][O:50][CH2:51][CH3:52])[N:43]([CH2:44][C:45]([OH:47])([CH3:48])[CH3:46])[C:39]=2[C:38]2[CH:37]=[CH:36][C:35](/[CH:56]=[CH:55]/[C:54]([O:58][CH3:59])=[O:57])=[CH:34][C:33]=2[N:32]=1

Komponenten

7

Edukt 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 219842117-bromo-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 57657222Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A thick walled glass reaction vessel was charged with anhydrous DMF (2 mL), palladium (II) Acetate (0.01 equivalents (eq)), tri-o-tolylphosphine (0.02 eq) and triethylamine (3 eq). To this orange solution was added a solution of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol in 50 mL anhydrous DMF followed by the addition of methyl acrylate (1.0 eq). The reaction mixture was purged with nitrogen, sealed and heated at 120° C. overnight, and slowly cooled to room temperature. The reaction mixture was concentrated to dryness and then slurried in water (50 mL). Saturated potassium carbonate solution (25 mL) was added. The mixture was extracted with dichloromethane (4×50 mL). The combined extracts were concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-25% CMA in chloroform) to provide Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate as a white solid.

Aufarbeitung

  1. customA thick walled glass reaction vessel
  2. customThe reaction mixture was purged with nitrogen
  3. customsealed
  4. temperatureslowly cooled to room temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. additionSaturated potassium carbonate solution (25 mL) was added
  7. extractionThe mixture was extracted with dichloromethane (4×50 mL)
  8. concentrationThe combined extracts were concentrated under reduced pressure
  9. custompurified by chromatography
  10. washa HORIZON HPFC system (silica cartridge, eluting with 0-25% CMA in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a7145933cd4246dd876ebe6554d63e17
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

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