Potassium Carbonate → 6-[(Dimethylamino)methyl]-7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

HRID 1258465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258465
[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:7][N:8]([CH2:12][C:3]1[C:4]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[CH:5][C:6]2[N:10]=[C:9]([CH3:11])[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:7]=2[C:2]=1[OH:1])[CH3:9]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 672205657-Hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

Produkt 1

HCID 672203476-[(Dimethylamino)methyl]-7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamideAusbeute 142 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide (1.0 g, 3.6 mmol, Step 2) and potassium carbonate (748 mg, 5.4 mmol) in N,N-dimethylformamide (36 mL) at 0° C. was added N,N-dimethylmethyleneiminium iodide (867 mg, 4.7 mmol). After stirring at the same temperature for 4 hours, the reaction mixture was quenched with saturated sodium hydrogencarbonate aqueous solution and extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on NH-gel eluting with ethyl acetate/methanol (30:1) to afford the title compound (855 mg, 71%) as a white amorphous.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated sodium hydrogencarbonate aqueous solution
  2. extractionextracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on NH-gel
  7. washeluting with ethyl acetate/methanol (30:1)

Quellen und Nachweise

ORD-Eintrag
ord-b40c95a2048b4cc7bfbb476514732319
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466166B2

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