HCID 68540198, compound → 2-{[(4-Chloro-3-methylpyridin-2-yl)methyl]sulfanyl}-1H-benzimidazole
Reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][NH+:6]=[C:5]([CH2:9]Cl)[C:4]=1[CH3:11].[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[SH:21]>>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:21][C:13]2[NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:12]=2)[C:4]=1[CH3:11]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-a52e5b6e53744f6588e819ef7a46744d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601737B2
Reaction notes
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