4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium → 2-(((4-((2-(Fluoromethyl)-1,3-dioxan-2-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31667

Reaction equation

HRID 31667 reaction equation
[Na:1].C[C:3]1(C)[CH2:8][O:7][CH:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][S:18]([C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)=[O:19])[C:12]=2[CH3:29])[O:5][CH2:4]1.Cl[C:32]1C(C)=C[N+]([O-])=C(C)C=1C.[F:42][CH2:43]C1(CO)OCCCO1>>[Na:1].[F:42][CH2:43][C:6]1([CH2:9][O:10][C:11]2[C:16]([CH3:32])=[CH:15][N:14]=[C:13]([CH2:17][S:18]([C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)=[O:19])[C:12]=2[CH3:29])[O:7][CH2:8][CH2:3][CH2:4][O:5]1

Participants

4

Reactant 3

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-iumHCID 59792600(2-(Fluoromethyl)-1,3-dioxan-2-yl)methanolHCID 667765882-(((4-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667765372-(((4-((2-(Fluoromethyl)-1,3-dioxan-2-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 12%

Procedure

The same procedure as in the steps (1c) to (1g) of Example 1 was repeated using 4-chloro-2,3,5-trimethylpyridine 1-oxide and (2-(fluoromethyl)-1,3-dioxan-2-yl)methanol to obtain the title compound (331 mg, 5 steps: 12%) as a yellow solid.

Sources & evidence

ORD record
ord-8355213a781d4266a970f4324bc79970
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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