Hydroxyamine hydrochloride → 3-[5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-2-oxo-1-pyridinyl]propanamide

HRID 1617928Notes

Reaction equation

HRID 1617928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:23])[N:16]([CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[CH:17]=2)=O)=[C:4]([CH3:34])[CH:3]=1.Cl.[NH2:36][OH:37].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:23])[N:16]([CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[CH:17]=2)=[N:36]\[OH:37])=[C:4]([CH3:34])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666664123-(5-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-2-oxopyridin-1(2H)-yl)propanamide

Product 1

HCID 580433293-[5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-2-oxo-1-pyridinyl]propanamide

Procedure

In analogy to example 151, step 3, 3-(5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-2-oxopyridin-1(2H)-yl)propanamide was reacted 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=516.4 [M+H]+.

Sources & evidence

ORD record
ord-cc3aa3b49d584dae8466d788938cc768
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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