Solketal → HCID 178431368, compound

HRID 31680

Reaction equation

HRID 31680 reaction equation
[Na:1].[CH3:2][C:3]1([CH3:31])[O:8]C[CH:6]([CH2:9][O:10][C:11]2[C:16](C)=[CH:15][N:14]=[C:13]([CH2:18][S:19]([C:21]3[NH:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[N:22]=3)=[O:20])[C:12]=2[CH3:30])[CH2:5][O:4]1.CC1(C)OC(CO)CO1.ClC1C=C[N+]([O-])=C(C)C=1C.[F:51]C1C=CC2NC(S)=NC=2C=1>>[Na:1].[CH3:2][C:3]1([CH3:31])[O:8][CH:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:18][S:19]([C:21]3[NH:25][C:24]4[CH:26]=[CH:27][C:28]([F:51])=[CH:29][C:23]=4[N:22]=3)=[O:20])[C:12]=2[CH3:30])[CH2:5][O:4]1

Participants

5

Reactant 4

HCID 7528SolketalHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 667758472-(((4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltHCID 178505474HCID 178505474, compound

Product 1

HCID 178431368HCID 178431368, compoundYield 14.1%

Procedure

The same procedure as in the step (10b) of Example 10 and the step (14b) of Example 14, the step (5f) of Example 5, the steps (11h) and (11i) of Example 11 was repeated using solketal, 4-chloro-2,3-dimethylpyridine 1-oxide, and 5-fluoro-1H-benzimidazole-2-thiol to obtain the title compound (210 mg, yield: 14.1%) as a white solid. Note that methanol was used as a solvent instead of ethanol in the same operation as in the step (5f).

Sources & evidence

ORD record
ord-a11e91989b544cc486de35037d86b48b
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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