Hydroxyamine hydrochloride → N-[4-[(3E)-1-(4-chloro-2-methylphenyl)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)propyl]phenyl]cyclopropanesulfonamide

HRID 1617957Notes

Reaction equation

HRID 1617957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH:30]3[CH2:32][CH2:31]3)(=[O:29])=[O:28])=[CH:22][CH:21]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH3:19])[CH:13]=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:20]2[CH:21]=[CH:22][C:23]([NH:26][S:27]([CH:30]3[CH2:31][CH2:32]3)(=[O:29])=[O:28])=[CH:24][CH:25]=2)[CH2:9]/[C:10](=[N:35]\[OH:36])/[C:12]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH3:19])[CH:13]=2)=[C:4]([CH3:33])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67015678Cyclopropanesulfonic acid {4-[1-(4-chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-phenyl}-amide

Product 1

HCID 58043396N-[4-[(3E)-1-(4-chloro-2-methylphenyl)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)propyl]phenyl]cyclopropanesulfonamide

Procedure

In analogy to example 151, step 3, cyclopropanesulfonic acid {4-[1-(4-chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-phenyl}-amide was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing 7% of the corresponding Z isomer as a colourless solid, MS (ESI+): m/z=500.3 [M+H]+.

Sources & evidence

ORD record
ord-366f6805e9f84f56a89814115ab21508
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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