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Dichloromethane → 5-[(2-acetylamino-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

HRID 2038628
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2038628
[C:1]([NH:4][CH2:5][CH2:6][O:7]/[N:8]=[CH:9]/[C:10]1[C:11]([F:33])=[C:12]([F:32])[C:13]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:14]([CH:22]=1)[C:15]([NH:17][O:18][CH2:19][CH2:20][OH:21])=[O:16])(=[O:3])[CH3:2].ClCCl.ClC(Cl)C(O)=O.C(=O)(O)[O-].[Na+]>O>[C:1]([NH:4][CH2:5][CH2:6][O:7][NH:8][CH2:9][C:10]1[C:11]([F:33])=[C:12]([F:32])[C:13]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:14]([CH:22]=1)[C:15]([NH:17][O:18][CH2:19][CH2:20][OH:21])=[O:16])(=[O:3])[CH3:2]
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Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6597Dichloroacetic AcidHCID 516892Sodium BicarbonateHCID 231323375-[(E)-2-acetamidoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

Produkt 1

HCID 116571505-[(2-acetylamino-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide
Ausbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To (E)-5-[(2-acetylamino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (57.6 mg, 99.3 μmol) obtained in Step D was added dichloromethane (2.5 ml). The mixture was stirred at room temperature, and borane-pyridine complex (80 μl, 0.79 mmol) and dichloroacetic acid (67 μl, 0.80 mmol) were added thereto. After stirring for 3 hours, water (10 ml) and saturated aqueous sodium bicarbonate (2 ml) were added to the reaction mixture, which was then extracted with methylene chloride (15 ml and 2×8 ml). The combined organic layers were washed with aqueous sodium bicarbonate (8 ml) and saturated aqueous sodium chloride (8 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol (10:1)) to give 5-[(2-acetylamino-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (Compound C-7, 44.0 mg, 76%).

Aufarbeitung

  1. stirringAfter stirring for 3 hours
  2. extractionwas then extracted with methylene chloride (15 ml and 2×8 ml)
  3. washThe combined organic layers were washed with aqueous sodium bicarbonate (8 ml) and saturated aqueous sodium chloride (8 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol (10:1))

Quellen und Nachweise

ORD-Eintrag
ord-f5e6e469bb704564aa82efacae30b739
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575391B2

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