4-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium → 2-(((4-(2-(2-(Methoxymethyl)-1,3-dioxolan-2-yl)ethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31663Notes

Reaction equation

HRID 31663 reaction equation
[Na:1].[CH3:2][C:3]1[C:4]([CH2:22][S:23]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[N:26]=2)=[O:24])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10]C1(C)OCC2(OCCO2)CO1.ClC1C=C[N+]([O-])=C(C)C=1C.[CH3:44][O:45][CH2:46][C:47]1([CH2:52]CO)[O:51][CH2:50][CH2:49][O:48]1>>[Na:1].[CH3:44][O:45][CH2:46][C:47]1([CH2:52][CH2:10][O:9][C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:22][S:23]([C:25]3[NH:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[N:26]=3)=[O:24])[C:3]=2[CH3:2])[O:51][CH2:50][CH2:49][O:48]1

Participants

4

Reactant 3

HCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 597925682-(2-(Methoxymethyl)-1,3-dioxolan-2-yl)ethanolHCID 667765502-(((3-Methyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667766262-(((4-(2-(2-(Methoxymethyl)-1,3-dioxolan-2-yl)ethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 3.9%

Procedure

The same procedure as in the steps (5d) to (5h) of Example 5 was repeated using 4-chloro-2,3-dimethylpyridine 1-oxide and 2-(2-(methoxymethyl)-1,3-dioxolan-2-yl)ethanol to obtain the title compound (312 mg, 5 steps 3.9%) as a light yellow foam.

Sources & evidence

ORD record
ord-edb0fff28eba4b36bd4723dec06abb69
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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