Hydroxyamine hydrochloride → 5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-[2-(2-methoxyethoxy)ethyl]pyridin-2-one

HRID 1617919Notes

Reaction equation

HRID 1617919 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:25])[N:16]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=2)=O)=[C:4]([CH3:36])[CH:3]=1.Cl.[NH2:38][OH:39].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:28][CH:27]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:25])[N:16]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=2)=[N:38]\[OH:39])=[C:4]([CH3:36])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666687605-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-(2-methoxyethoxy)ethyl)pyridin-2(1H)-one

Product 1

HCID 580435465-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-[2-(2-methoxyethoxy)ethyl]pyridin-2-one

Procedure

In analogy to example 151, step 3, 5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-(2-methoxyethoxy)ethyl)pyridin-2(1H)-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing 12% of the corresponding Z isomer as a light yellow solid, MS (ESI+): m/z=547.3 [M+H]+.

Sources & evidence

ORD record
ord-0953ba4daf2049fe93888152900d325a
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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