Water → N-methyl-N-{2-[5-(2-oxoethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl)thiophene-2-sulfonamide
Reaktionsgleichung
[OH:1][CH2:2][CH2:3][CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[N:18]([CH3:27])[S:19]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)(=[O:21])=[O:20])=[N:6][CH2:5]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>C(#N)C>[CH3:27][N:18]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[NH:10][C:9]([C:7]1[S:8][CH:4]([CH2:3][CH:2]=[O:1])[CH2:5][N:6]=1)=[CH:17]2)[S:19]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:21]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a solution of N-{2-[5-(2-hydroxyethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (2.78 g) in acetonitrile (150 mL) was added Dess-Martin reagent (3 g), and the mixture was stirred under heating at 70° C. for 30 min. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (27 mg, yield 22%) as a brown amorphous solid from a fraction eluted with ethyl acetate:hexane=25:75. MS: 420(MH+).
Aufarbeitung
- temperatureto cool to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-e599c8490ba74a1d97f5f86fa1356bc3
- Quelldatensatz
- uspto-grants-2013_04
- Patentnummer
- US08410087B2
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