Hydrochloric Acid → 5-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

HRID 2038626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038626
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([C:19](=[O:25])[NH:20][O:21][CH2:22][CH2:23][OH:24])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:15]([F:35])[C:14]=1[F:36])(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[C:14]([F:36])=[C:15]([F:35])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:17]([CH:18]=1)[C:19]([NH:20][O:21][CH2:22][CH2:23][OH:24])=[O:25]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11445081HCID 11445081, Verbindung

Produkt 1

HCID 113072055-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of {2-[2,3-difluoro-4-(2-fluoro-4-iodo-phenylamino)-5-(2-hydroxy-ethoxycarbamoyl)-benzylideneaminooxy]-ethyl}-carbamic acid tert-butyl ester (55 mg, 0.31 mmol) prepared in Step B in ethyl acetate (5 ml) was added 1 N HCl solution in ethyl acetate (1 ml), and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was neutralized with saturated solution of sodium bicarbonate (50 ml), and extracted with ethyl acetate (3×100 ml). The extract was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and after washing with diethyl ether (10 ml), the residue was recrystallized from methanol to give (E)-5-[(2-amino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (17.31 mg, 37% yield) as a pale yellow solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washafter washing with diethyl ether (10 ml)
  8. customthe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-27617004e4fc4f469f81a0f58d64ec34
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575391B2

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