2-Chloromethyl-3,4-dimethoxypyridinium chloride → 1-((3,4-dimethoxypyridin-2-yl)methyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione

HRID 658732Notes

Reaction equation

HRID 658732 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[CH2:16][NH:15][C:14]3=[O:19])[CH:10]=[N:9]2)=[C:5]([CH3:20])[O:4][N:3]=1.Cl.[CH3:22][O:23][C:24]1[C:25]([CH2:32]Cl)=[N:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>>[CH3:22][O:23][C:24]1[C:25]([CH2:32][N:15]2[CH2:16][C:17](=[O:18])[N:13]([C:11]3[CH:10]=[N:9][N:8]([CH2:7][C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:20])[CH:12]=3)[C:14]2=[O:19])=[N:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideHCID 574224243-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione

Product 1

HCID 579449231-((3,4-dimethoxypyridin-2-yl)methyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dioneYield 26%

Procedure

Prepared as in example 10-5 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione and 3,4-dimethoxy-2-chloromethyl pyridine hydrochloride. Yield: 26%. MS M+H calculated 360.2; found 360.2. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 1.0 μM.

Sources & evidence

ORD record
ord-5a30a88055ba45f5aa501dc62179d55f
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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