Lithium borohydride → HCID 68770584, Verbindung

HRID 1628402Notizen

Reaktionsgleichung

[BH4-].[Li+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][C:19](OCC)=[O:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1>O1CCCC1.[Cl-].[NH4+].C(=O)([O-])O.[Na+]>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][CH2:19][OH:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a suspension of lithium borohydride (22.5 mg, 1.03 mmol) in tetrahydrofuran (3.5 mL) was added ethyl 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]propanoate (Reference Example 28; 155 mg, 0.345 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 20 hr, the mixture was diluted with aqueous ammonium chloride at 0° C. and stirred at 0° C. for 30 min. The resultant mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture to give the title compound as a solid (35.7 mg, 0.0876 mmol, 25%).

Aufarbeitung

extractionextracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture

Quellen und Nachweise

ORD-Eintrag: ord-1be540d0f4b44ff9858403443c44adfa
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08785460B2

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