Tetrahydrofuran → 5-{[Acetyl-(2-hydroxy-ethoxy)-amino]-methyl}-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

HRID 20764

Reaktionsgleichung

Reaktionsgleichung von HRID 20764
[F:1][C:2]1[C:3]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])=[C:4]([CH:12]=[C:13]([CH2:16][NH:17][O:18][CH2:19][CH2:20][OH:21])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6].CCN(CC)CC.C1C[O:41][CH2:40][CH2:39]1>>[C:40]([N:17]([CH2:16][C:13]1[C:14]([F:15])=[C:2]([F:1])[C:3]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])=[C:4]([CH:12]=1)[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6])[O:18][CH2:19][CH2:20][OH:21])(=[O:41])[CH3:39]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 115774573,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethoxyamino)-methyl]-benzamide

Produkt 1

HCID 593480155-{[Acetyl-(2-hydroxy-ethoxy)-amino]-methyl}-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

Versuchsvorschrift

CH3CO2H (300 mg), EDC HCl (958 mg), and HODhbt (816 mg) were mixed in CH2Cl2 (5 mL) for 2 hours to give an active ester solution. A portion of this solution (0.2 mL) was added to a solution of 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethoxyamino)-methyl]-benzamide (80 mg) obtained in Example 6 and NEt3 (29 μL) in THF, and the mixture was stirred for 12 hours. The reaction mixture was washed with 0.3 N aqueous HCl and aqueous NaHCO3, and subjected to silica gel chromatography (CH2Cl2/MeOH as a developing solvent) to give the title compound (12.0 mg).

Aufarbeitung

  1. washThe reaction mixture was washed with 0.3 N aqueous HCl and aqueous NaHCO3

Quellen und Nachweise

ORD-Eintrag
ord-f808c5794fc44c8581f8426907727d88
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745663B2

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