Hydroxyamine hydrochloride → 5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-[3-fluoro-4-(2-hydroxyethoxy)phenyl]ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617898Notes

Reaction equation

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

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 670155955-{3-(4-Chloro-2-methyl-phenyl)-3-[3-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-propionyl}-1-methyl-1H-pyridin-2-one

Product 1

HCID 580432045-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-[3-fluoro-4-(2-hydroxyethoxy)phenyl]ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 151, step 3, 5-{3-(4-chloro-2-methyl-phenyl)-3-[3-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-propionyl}-1-methyl-1H-pyridin-2-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as a colourless solid, MS (ESI+): m/z=459.3 [M+H]+.

Sources & evidence

ORD record: ord-675f6e52067c4b1aaf4dc7637e4d1f5c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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