O-(2-(Vinyloxy)ethyl)hydroxylamine → 2-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-vinyloxyethoxy)-amide

HRID 1971191Notes

Reaction equation

HRID 1971191 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]([CH3:19])[C:11](=[O:18])[CH:12]=[CH:13][C:14]=2[C:15]([OH:17])=O)=[C:4]([F:20])[CH:3]=1.[CH:21]([O:23][CH2:24][CH2:25][O:26][NH2:27])=[CH2:22]>>[CH:21]([O:23][CH2:24][CH2:25][O:26][NH:27][C:15]([C:14]1[CH:13]=[CH:12][C:11](=[O:18])[N:10]([CH3:19])[C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:20])=[O:17])=[CH2:22]

Participants

3

Reactant 2

HCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 576369362-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 866723232-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-vinyloxyethoxy)-amideYield 60%

Procedure

2-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (0.020 g, 0.059 mmol) was coupled as described previously in Example 154 using O-(2-vinyloxy-ethyl)-hydroxylamine to yield 0.015 g (60%) pure desired product as a yellow solid.

Sources & evidence

ORD record
ord-ad45718cd8ba445a924bea1847612dbb
Source dataset
uspto-grants-2013_04
Patent number
US08431574B2

Reaction notes

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