4-Chloro-2-chloromethyl-3,5-dimethylpyridinium chloride → 5-methoxy-2-[(4-chloro-3,5-dimethyl-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine

HRID 1819273Notes

Reaction equation

HRID 1819273 reaction equation
[Cl-].[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][NH+:6]=[C:5]([CH2:10]Cl)[C:4]=1[CH3:12].[CH3:13][O:14][C:15]1[N:20]=[C:19]2[N:21]=[C:22]([SH:24])[NH:23][C:18]2=[CH:17][CH:16]=1>>[CH3:13][O:14][C:15]1[N:20]=[C:19]2[N:21]=[C:22]([S:24][CH2:10][C:5]3[C:4]([CH3:12])=[C:3]([Cl:2])[C:8]([CH3:9])=[CH:7][N:6]=3)[NH:23][C:18]2=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 685397504-Chloro-2-chloromethyl-3,5-dimethylpyridinium chlorideHCID 1784881412H-Imidazo(4,5-b)pyridine-2-thione, 1,3-dihydro-5-methoxy-

Product 1

HCID 685400155-methoxy-2-[(4-chloro-3,5-dimethyl-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine

Procedure

As a further example, 4-chloro-2-chloromethyl-3,5-dimethylpyridinium chloride could be reacted with 5-methoxy-1H-imidazo[4,5-b]pyridine-2-thiol according to the procedure described under Example 39 to give 5-methoxy-2-[(4-chloro-3,5-dimethyl-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine. Conversion of this product with methanol-d4 following the protocol described under Example 44 would then give rise to formation of 5-methoxy-2-[(3,5-dimethyl-4-trideuteriomethoxy-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine, which, in turn, could be oxidized according to the procedure used in Example 46 to rac-5-methoxy-2-[(3,5-dimethyl-4-trideuteriomethoxy-2-pyridinyl)methylsulfinyl]-1H-imidazo[4,5-b]pyridine.

Sources & evidence

ORD record
ord-31282510e78f4c08a935254db6ca9819
Source dataset
uspto-grants-2009_10
Patent number
US07601737B2

Reaction notes

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