HCID 68540198, compound → 2-{[(4-Chloro-3-methylpyridin-2-yl)methyl]sulfanyl}-1H-benzimidazole

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Reaction Steps

For example, 4-chloro-2-chloromethyl-3-methylpyridinium chloride could be reacted with 1H-benzimidazole-2-thiol according to the procedure described under Example 12 to give 2-[(4-chloro-3-methyl-2-pyridinyl)methylthio]-1H-benzimidazole. Conversion of this product with, for instance, 1,1-dideuterio-3-methoxy-1-propanol or 1,1-dideuterio-2,2,2-trifluoroethanol following the protocol described under Example 14 would then give rise to formation of 2-[(4-(1,1-dideuterio-3-methoxyprop-1-oxy)-3-methyl-2-pyridinyl)methylthio]-1H-benzimidazole and 2-[(4-(1,1-dideuterio-2,2,2-trifluoroethoxy)-3-methyl-2-pyridinyl)methylthio]-1H-benzimidazole, respectively. Finally, oxidation of these compounds according to the procedure used in Example 46 would provide rac-2-[(4-(1,1-dideuterio-3-methoxypropan-1-oxy)-3-methyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole and rac-2-[(4-(1,1-dideuterio-2,2,2-trifluoroethoxy)-3-methyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole, respectively.

Provenance & Evidence