Solketal → HCID 178431368, compound

HRID 1645625

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

Reactant 4

HCID 7528Solketal

HCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

HCID 667758472-(((4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HCID 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-ff6610614c054fd3bb2a3f0cc5d2356c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124780B2

Linked notes

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