Dimethylformamide → 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-5-(5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-1H-pyridin-2-one

HRID 917783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917783
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:18]([NH:20][NH2:21])=[O:19])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1.CN([CH:25]=[O:26])C>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:18]2[O:19][C:25](=[O:26])[NH:21][N:20]=2)=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1

Komponenten

3

Edukt 2

HCID 6228DimethylformamideHCID 112350284-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid hydrazide

Produkt 1

HCID 589628444-(2-Fluoro-4-iodo-phenylamino)-1-methyl-5-(5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-1H-pyridin-2-one

Versuchsvorschrift

4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid hydrazide was dissolved in DMF (20 mL) and treated with the 1,1′-carbonydiimidazole (2.90 g, 17.92 mmol). The mixture was stirred at room temperature for 24 hours. The solid was precipitate out. This material was isolated by filtration, washed well with water and hexanes, then dried to afford 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-5-(5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-1H-pyridin-2-one as an off white solid (5.0 g, 71%). (APCI+) calcd for C14H10FIN4O3 428.16 (M+1), found 428.9. Anal. Calcd for C14H10FIN4O3: C, 39.27; H, 2.35; N, 13.09. Found: C, 39.55; H, 2.88; N, 13.12.

Aufarbeitung

  1. additiontreated with the 1,1′-carbonydiimidazole (2.90 g, 17.92 mmol)
  2. customThe solid was precipitate out
  3. customThis material was isolated by filtration
  4. washwashed well with water and hexanes
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-76219ae72a9141b88af04a13ff925cff
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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