Trifluoroacetic acid → 3,4-Difluoro-2-[(2-Fluoro-4-Iodophenyl)amino]-N-(2-Hydroxyethoxy)-5-[(2-Hydroxyethoxy)methyl]benzamide

HRID 20724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20724
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:7]([F:29])=[C:8]([F:28])[C:9]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[C:10]([CH:18]=1)[C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12].[BH4-].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1COCC1>[F:28][C:8]1[C:9]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[C:10]([CH:18]=[C:6]([CH2:2][O:1][CH2:5][CH2:4][OH:3])[C:7]=1[F:29])[C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 593480285-[1,3]dioxolan-2-yl-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

Produkt 1

HCID 115337913,4-Difluoro-2-[(2-Fluoro-4-Iodophenyl)amino]-N-(2-Hydroxyethoxy)-5-[(2-Hydroxyethoxy)methyl]benzamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-[1,3]dioxolan-2-yl-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (21.69 g) obtained in Step G in anhydrous THF (100 ml) were added sodium borohydride (4.21 g, 111.4 mmol) and trifluoroacetic acid (5.08 ml, 66.8 mmol) with ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (SiO2 600 g, 100% AcOEt to AcOEt/MeOH (50:1 to 20:1)) to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(2-hydroxy-ethoxymethyl)-benzamide (13.9 g, 80%) as a white powder.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (SiO2 600 g, 100% AcOEt to AcOEt/MeOH (50:1 to 20:1))

Quellen und Nachweise

ORD-Eintrag
ord-8c1f75a1519a4c70ab298985d235dc5d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745663B2

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