Tetrahydrofuran → N-{2-[5-(Hydroxymethyl)-1,3-thiazol-2-yl]-1-(methoxymethyl)-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide
Reaktionsgleichung
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:23]1[S:24][C:25]([C:28](OCC)=[O:29])=[CH:26][N:27]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(O)C>[OH:29][CH2:28][C:25]1[S:24][C:23]([C:5]2[N:4]([CH2:3][O:2][CH3:1])[C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])=[N:27][CH:26]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a mixture of ethyl 2-{1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate (2.13 g) and tetrahydrofuran (30 mL) was added lithium aluminum hydride (0.21 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added ethanol (5 mL) and then saturated aqueous ammonium chloride solution (4 mL). The resulting inorganic salt was filtered off, and the filtrate was concentrated. The obtained crystals were subjected to silica gel column chromatography and eluted with ethyl acetate to give the title compound (1.95 g, quantitative) as pale-yellow crystals. melting point 156-157° C.
Aufarbeitung
- filtrationThe resulting inorganic salt was filtered off
- concentrationthe filtrate was concentrated
- washeluted with ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-56bc1f4c55e34099bedd06d9afc3af86
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08957070B2
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