Pyridine → 5-bromo-2-((hydroxyimino)methyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595666Notes

Reaction equation

HRID 595666 reaction equation
[Br:1][C:2]1[C:3]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:4][C:5]2[O:9][C:8]([CH:10]=O)=[C:7]([C:12]([NH:14][CH3:15])=[O:13])[C:6]=2[CH:16]=1.Cl.[NH2:24][OH:25].N1C=CC=CC=1>CS(C)=O.O>[Br:1][C:2]1[C:3]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:4][C:5]2[O:9][C:8]([CH:10]=[N:24][OH:25])=[C:7]([C:12]([NH:14][CH3:15])=[O:13])[C:6]=2[CH:16]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 903324905-bromo-2-formyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903327815-bromo-2-((hydroxyimino)methyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 5-bromo-2-formyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (700 mg, 1.8 mmol), hydroxylamine hydrochloride (280 mg, 4.05 mmol) and pyridine (284 mg, 3.6 mmol) in DMSO (5 mL) was stirred at room temperature for 2 h. The mixture was diluted with water, then filtered, the residue was crude product of 5-bromo-2-((hydroxyimino)methyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (650 mg, yield: 75%). 1H-NMR (DMSO-d6, 400 MHz) δ 12.26 (s, 1H), 8.46 (s, 1H), 8.41 (d, J=4.4 Hz, 1H), 8.18 (s, 1H), 8.06 (s, 1H), 3.20 (s, 3H), 3.19 (s, 3H), 2.83 (d, J=4.4 Hz, 3H). MS (M+H)+: 404/406.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-1e939596859f444ba54193adbdb7eae7
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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