Water → 2-Methylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide
Reaktionsgleichung
C(O[CH2:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9])C.[BH4-].[Na+].O>CS(C)=O>[CH3:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 2-(ethoxymethyl-amino)-N-(5-phenoxy-thiophene-2-ylmethyl)-nicotinamide described in Preparation Example A+-6 (148 mg, 0.385 mmol) in dimethylsulfoxide (3 mL) was added sodium borohydride (44 mg, 1.15 mmol), and the solution was stirred for 30 minutes at 100° C., followed by stirring for 20 minutes at 110° C. Furthermore, sodium borohydride (35 mg, 0.925 mmol) was added thereto, followed by stirring for 20 minutes at 110° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate, the organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (86 mg, 0.26 mmol, 67%) was obtained.
Aufarbeitung
- stirringby stirring for 20 minutes at 110° C
- stirringby stirring for 20 minutes at 110° C
- extractionwas then extracted with ethyl acetate
- washthe organic layer was sequentially washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-678f674f3e75494cb9068c34d2c9f122
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07932272B2
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