Hydrochloric Acid → (Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[3,2-e]benzothiazol-7-one
Reaktionsgleichung
[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[S: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[S: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=2Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
3-Methoxypyrrole-2-carboxaldehyde (11 mg, 0.088 mmol)(Bellamy, supra), piperidine (3 drops)(Aldrich), and 2-phenyl-6,8-dihydro-thiazolo[4,5-e]indol-7-one (21.4 mg, 0.08 mmol) (Example 3) were dissolved in DMF (3 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 using acetonitrile—water as solvent, then crystallization from ethanol. (Yield 4.5 mg, 15%)
Aufarbeitung
- temperatureThe mixture was cooled
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic extracts were washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe solvent was concentrated under reduced pressure
- customthe crude product was purified by reverse phase
- customcrystallization from ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-12e6f80739e7429caf6c5c092b24f4a1
- Quelldatensatz
- uspto-grants-2001_03
- Patentnummer
- US06197804B1
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