Potassium Carbonate → 5-[(E)-C-[2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-cyclobutylpyridin-2-one

HRID 1617674Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=O)=[CH:4][CH:3]=1.[CH:27]1(Br)[CH2:30]C[CH2:28]1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:39][OH:40].C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH:18]3[CH2:30][CH2:27][CH2:28]3)[CH:17]=2)=[N:39]\[OH:40])=[CH:4][CH:3]=1

Participants

Reactant 5

HCID 11430Potassium Carbonate

HCID 78110Bromocyclobutane

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 666685075-[3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 580432195-[(E)-C-[2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-cyclobutylpyridin-2-one

Procedure

In analogy to example 161, step 1, 5-[3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one (example 162, step 3) was reacted with cyclobutylbromide 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 NaHCO3 to give the title compound as a colorless solid, MS (ESI+): m/z=465.2 [M+H]+.

Sources & evidence

ORD record: ord-8dfd30e9f1614c6f8fe39c475f83e30e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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