Acrylic Acid → 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 2223684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223684
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=O)=O.C(O)(=O)C=C.[CH:19]1[CH:20]=[CH:21][C:22]2[N:27](O)N=[N:25][C:23]=2[CH:24]=1.CCN=C=NCCCN(C)C.[O:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]1[O:46][NH2:47].CCN(C(C)C)C(C)C>CCO.CN(C=O)C.O>[NH:27]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:24][C:23]=2[N:25]=[C:1]1[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]([NH:47][O:46][CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][O:40]2)=[O:10])[CH:11]=[CH:12][CH:13]=1

Komponenten

10

Edukt 6

HCID 6581Acrylic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 542035293-Formylcinnamic acid

Produkt 1

HCID 724240283-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the appropriate 3-formyl-cinnamic acid (3, 0.57 mmol) and the appropriate substituted-phenyl-1,2-diamine (0.57 mmol) in EtOH (5.0 mL) was refluxed for 24 hrs. The reaction was cooled, evaporated to dryness, and the resulting acrylic acid was used without further purification. To a solution of the acrylic acid (0.25 mmol) and HOBt (0.38 mmol) in DMF (5.0 mL) was added EDCI (0.38 mmol), O-(tetrahydro-pyran-2-yl)-hydroxylamine (0.38 mmol), and DIEA (0.75 mmol). The reaction was stirred at ambient temperature for 18 hrs. The resulting mixture was poured into H2O, extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated to dryness. The resulting material was purified via flash chromatography to yield the desired 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (11).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customevaporated to dryness
  3. customthe resulting acrylic acid was used without further purification
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe resulting material was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-52466af1f79a42f5bf863e7dadd7a418
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375228B2

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