Phosphorus oxychloride → N-[4-(Cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

HRID 1297588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297588
[C:1]([C:4]([C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13](=[O:28])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([F:31])[CH:8]=1)([CH3:6])[CH3:5])(=O)[NH2:2].P(Cl)(Cl)(Cl)=O>>[C:1]([C:4]([CH3:6])([CH3:5])[C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13](=[O:28])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([F:31])[CH:8]=1)#[N:2]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 10295972N-[4-(1-Carbamoyl-1-methyl-ethyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

Produkt 1

HCID 17832827N-[4-(Cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamideAusbeute 82,1 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To N-[4-(1-Carbamoyl-1-methyl-ethyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide (3.00 g) in a 50 mL flask was added phosphorous oxychloride (3.29 mL). The solution was heated for 1 h at 90° C. The solution was then cooled in an ice bath, poured over satd. aq. sodium carbonate (50 mL), then extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo, yielding the title compound (2.36 g).

Aufarbeitung

  1. temperatureThe solution was then cooled in an ice bath
  2. additionpoured over satd
  3. extractionaq. sodium carbonate (50 mL), then extracted with ethyl acetate (4×100 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ebaace09f7c54565877232c0ad3c12a7
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250518B2

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