8-(Acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine → 2-[[(2,3-dimethylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazole

HRID 1789205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789205
C(O[CH2:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1)(=O)C.[SH:17][C:18]1[NH:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>Br.C(O)(=O)C>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]([CH2:5][S:17][C:18]3[NH:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[N:19]=3)=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

Komponenten

5

Edukt 2

HCID 201888548-(Acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridineHCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 201888452-[[(2,3-dimethylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazoleAusbeute 106,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

A mixture of 2.0 g (12 mmole) of 3-(acetoxymethyl)-2-pyridinamine, 1.7 g (17 mmole) of 3-chloro-2-butanone, and one crystal of potassium iodide was heated at 100° for 4.5 hours. The mixture was allowed to cool and was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The solid was triturated with diethyl ether and collected by filtration to yield 738 mg of 8-(acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra and by elemental analysis. [Calcd. for C12H14N2O2 : C, 66.04; H, 6.47; N, 12.84. Found: C, 66.01; H, 6.38; N, 13.05.] A mixture of 700 mg (3.2 mmole) of 8-(acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine and 482 mg (3.2 mmole) of 2-mercaptobenzimidazole in 10 ml of 15% hydrogen bromide in acetic acid was heated on a steam bath. After being cooled to room temperature, the mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to an oil. Spinning disk chromatography on silica gel (using 1% by volume ethanol-dichloromethane as eluent) yielded 1.05 g of the title compound Structure assignment was supported by the nmr and infrared spectra.

Aufarbeitung

  1. temperaturewas heated on a steam bath
  2. customthe mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-747991975c614cf3ace7cd83f57b627a
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04687775

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