Triethylamine → 2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dione

HRID 244868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244868
[CH:1]([N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13])=[CH2:2].C(N(CC)CC)C.Br[C:22]1[CH:31]=[CH:30][C:29]2[N:28]=[CH:27][C:26]3[N:32]=[C:33]([CH2:44][CH2:45][O:46][CH3:47])[N:34]([CH2:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][C:39]4=[O:43])[C:25]=3[C:24]=2[CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[CH3:47][O:46][CH2:45][CH2:44][C:33]1[N:34]([CH2:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][C:39]2=[O:43])[C:25]2[C:24]3[CH:23]=[C:22]([CH:2]=[CH:1][N:3]4[C:7](=[O:8])[C:6]5[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:4]4=[O:13])[CH:31]=[CH:30][C:29]=3[N:28]=[CH:27][C:26]=2[N:32]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 219843071-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one

Produkt 1

HCID 690814342-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dioneAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (17 mg, 0.08 mmol), acetonitrile (50 mL), N-vinylphthalimide (716 mg, 4.13 mmol), triethylamine (1.6 mL, 11 mmol), tri-o-tolylphosphine (69 mg, 0.22 mmol) and 1-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one (1.62 g, 3.76 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath for 15 hours. The reaction was cooled to ambient temperature and methanol (50 mL) and chloroform (50 ml) were added. After filtering through a 0.2 micron PTFE membrane, the solution was concentrated under reduced pressure and then purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-8% gradient of methanol in dichloromethane) to provide 2.0 g of 2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dione as a bright yellow solid.

Aufarbeitung

  1. customA thick walled glass tube, equipped with a stir bar
  2. customThe reaction mixture was purged with nitrogen
  3. customthe tube was sealed
  4. temperatureThe reaction was cooled to ambient temperature
  5. additionmethanol (50 mL) and chloroform (50 ml) were added
  6. filtrationAfter filtering through a 0.2 micron PTFE membrane
  7. concentrationthe solution was concentrated under reduced pressure
  8. custompurified by chromatography
  9. washeluting with a 0-8% gradient of methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-14ff085203a346ac8f5fbe8d490f62ad
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

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