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Triethylamine → 2-ethyl-7-[2-(methylsulfonyl)ethenyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 244872
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244872
[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:37]1[CH:38]=[CH:39][C:40]2[C:41]3[N:50]([CH2:51][CH:52]4[CH2:57][CH2:56][O:55][CH2:54][CH2:53]4)[C:49]([CH2:58][CH3:59])=[N:48][C:42]=3[C:43]([NH2:47])=[N:44][C:45]=2[CH:46]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O.C(#N)C>[CH2:58]([C:49]1[N:50]([CH2:51][CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)[C:41]2[C:40]3[CH:39]=[CH:38][C:37]([CH:2]=[CH:1][S:3]([CH3:6])(=[O:5])=[O:4])=[CH:46][C:45]=3[N:44]=[C:43]([NH2:47])[C:42]=2[N:48]=1)[CH3:59]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 19354Methyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 690807877-bromo-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 866293922-ethyl-7-[2-(methylsulfonyl)ethenyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amineAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (7 mg, 0.03 mmol), acetonitrile (15 mL), N,N-dimethylformamide (15 mL), methyl vinyl sulfone (150 mg, 1.41 mmol), triethylamine (0.53 mL, 3.8 mmol), tri-o-tolylphosphine (23 mg, 0.08 mmol) and 7-bromo-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine (500 g, 1.28 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath for 16 hours. The reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure. The resulting solid was partitioned between chloroform (100 mL) and 1% aqueous sodium carbonate (100 mL). The fractions were separated and the aqueous fraction was extracted with chloroform (2×50 mL). The combined organic fractions were sequentially dried (MgSO4), filtered, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient, 0-15% CMA over 1200 mL followed by 15-20% CMA over 1100 mL). Recrystallization from methanol provided 315 mg of 2-ethyl-7-[2-(methylsulfonyl)ethenyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a pale 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 mixture was cooled to ambient temperature
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was partitioned between chloroform (100 mL) and 1% aqueous sodium carbonate (100 mL)
  7. customThe fractions were separated
  8. extractionthe aqueous fraction was extracted with chloroform (2×50 mL)
  9. dry with materialThe combined organic fractions were sequentially dried (MgSO4)
  10. filtrationfiltered
  11. custompurified by chromatography
  12. washeluting with a CMA
  13. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-c3bb327c0c654ae4ac5c7f667b19d43b
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658666B2

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