Hydrochloric Acid → (Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[3,2-e]benzoxazol-7-one

HRID 1859061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859061
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[CH:8]=O.[C:10]1([C:16]2[O:17][C:18]3[C:19]([N:28]=2)=[C:20]2[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.Cl>N1CCCCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:21]1\[C:22](=[O:27])[NH:23][C:24]2[CH:25]=[CH:26][C:18]3[O:17][C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[N:28][C:19]=3[C:20]\1=2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 112864661H-Pyrrole-2-carboxaldehyde, 3-methoxy-HCID 212534362-Phenyl-6,8-dihydro-oxazolo[4,5-e]indol-7-one

Produkt 1

HCID 9841676(Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[3,2-e]benzoxazol-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Methoxypyrrole-2-carboxaldehyde (15 mg, 0.12 mmol) (prepared according to F. Bellamy et. al., J. Chem. Research (S) (1979), 18-19; J Chem Research (M) (1979) 0101-0116), piperidine (3 drops)(Aldrich), and 2-phenyl-6,8-dihydro-oxazolo[4,5-e]indol-7-one (25 mg, 0.10 mmol)(from Example 2) were dissolved in DMF (1 mL). The mixture was heated to 90° C. and stirred at that temperature for 1 h. The mixture was cooled, poured into water, and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined organic extracts were washed with water, brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the crude product was purified by reverse phase HPLC with acetonitrile-water mixture as solvent. (Yield 3.6 mg, 8.4%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe crude product was purified by reverse phase HPLC with acetonitrile-water mixture as solvent

Quellen und Nachweise

ORD-Eintrag
ord-d543721749fb4f10b9ccc65e19e74e8c
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153634

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