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Methanol → 5-Chloro-1-[4-fluoro-3-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 447835
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 447835
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=1.CO.C(OCC)(=O)C>CN(C=O)C>[ClH:11].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)[CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 668768832-Amino-5-chloronicotinamideHCID 668776264-(Bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene

Produkt 1

HCID 669700475-Chloro-1-[4-fluoro-3-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochlorideAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(Step 2) A solution of 2-amino-5-chloronicotinamide (685 mg) and 4-(bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene obtained in Step 1 (1.6 g) in DMF (10 ml) was stirred at 90° C. for 24 hr. The mixture was allowed to cool to room temperature, methanol and ethyl acetate were added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=4:1). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (510 mg).

Aufarbeitung

  1. filtrationthe precipitated crystals were collected by filtration
  2. dissolutionThe obtained crystals were dissolved in 1N sodium hydroxide solution
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=4:1)
  8. dissolutionThe obtained yellow solid was dissolved in methanol
  9. addition4N hydrogen chloride-ethyl acetate solution (2 ml) was added
  10. filtrationthe precipitated crystals were collected by filtration
  11. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-8b25574088e04cf68790004b4012d5e5
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481569B2

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