Dimethylformamide → 5-[(E)-2-acetamidoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

HRID 2038627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038627
[NH2:1][CH2:2][CH2:3][O:4]/[N:5]=[CH:6]/[C:7]1[C:8]([F:30])=[C:9]([F:29])[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=1)[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13].CN(C)C=O.CON(C(C)=O)[C:39](=[O:41])[CH3:40]>CO>[C:39]([NH:1][CH2:2][CH2:3][O:4]/[N:5]=[CH:6]/[C:7]1[C:8]([F:30])=[C:9]([F:29])[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=1)[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13])(=[O:41])[CH3:40]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 538412N,N-Diacetyl-O-methylhydroxylamineHCID 113072055-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

Produkt 1

HCID 231323375-[(E)-2-acetamidoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (E)-5-[(2-amino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (8.14 mg, 0.02 mmol) described in Step C in a mixed solvent of dimethylformamide (1 ml) and methanol (5 ml) was added N-methoxydiacetamide (100 mg, 0.76 mmol), and the mixture was stirred at room temperature for 14 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resultant residue was purified with Mega Bond Elut silica gel (Varian, 5 g). (E)-5-[(2-Acetylamino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (8.10 mg, 92% yield) was obtained as a pale yellow solid from fractions eluted with 6% methanol/methylene chloride.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resultant residue was purified with Mega Bond Elut silica gel (Varian, 5 g)

Quellen und Nachweise

ORD-Eintrag
ord-23c42eead4984e04a57192095552f39a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575391B2

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