Methyl iodide → 5-[(E)-C-[2-(4-bromophenyl)-2-(4-methyl-1,3-thiazol-5-yl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617903Notes

Reaction equation

HRID 1617903 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[S:23][CH:22]=[N:21][C:20]=2[CH3:24])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=O)[NH:16][CH:17]=2)=O)=[CH:4][CH:3]=1.IC.[C:27](=[O:30])([O-])[O-].[K+].[K+].Cl.[NH2:34][OH:35].C(=O)([O-])O.[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[S:23][CH:22]=[N:21][C:20]=2[CH3:24])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:27](=[O:30])[N:16]([CH3:15])[CH:17]=2)=[N:34]\[OH:35])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666685555-(3-(4-bromophenyl)-3-(4-methylthiazol-5-yl)propanoyl)pyridin-2(1H)-one

Product 1

HCID 580435045-[(E)-C-[2-(4-bromophenyl)-2-(4-methyl-1,3-thiazol-5-yl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 161, step 1, 5-(3-(4-bromophenyl)-3-(4-methylthiazol-5-yl)propanoyl)pyridin-2(1H)-one was reacted with iodomethane in the presence of potassium carbonate. The product of this reaction was reacted in analogy to example 151, step 3 with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing less than 10% of the corresponding Z isomer as an off-white solid, MS (ESI+): m/z=432.1 [M+H]+.

Sources & evidence

ORD record
ord-b268511d744741cb88d4c5edfaab2a8e
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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