Hydroxyamine hydrochloride → 2-[5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-2-oxo-1-pyridinyl]acetamide

HRID 1617926Notes

Reaction equation

HRID 1617926 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:22])[N:16]([CH2:18][C:19]([NH2:21])=[O:20])[CH:17]=2)=O)=[C:4]([CH3:33])[CH:3]=1.Cl.[NH2:35][OH:36].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:25][CH:24]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:22])[N:16]([CH2:18][C:19]([NH2:21])=[O:20])[CH:17]=2)=[N:35]\[OH:36])=[C:4]([CH3:33])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666669532-(5-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-2-oxopyridin-1(2H)-yl)acetamide

Product 1

HCID 580432382-[5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-2-oxo-1-pyridinyl]acetamide

Procedure

In analogy to example 151, step 3, 2-(5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-2-oxopyridin-1(2H)-yl)acetamide was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as an off-white solid, MS (ESI−): m/z=500.1 [M−H]−.

Sources & evidence

ORD record
ord-b7a76b755fe247a993ef90bec1df676b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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