Sodium hydride → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy) methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 385873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385873
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1.Br[CH2:32][CH2:33][O:34][CH3:35]>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][CH2:32][CH2:33][O:34][CH3:35])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

Produkt 1

HCID 595257925-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy) methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of NaH (7.5 mg, 0.19 mmol) in DMF (1.25 mL) at 0° C. under argon was added 5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 43) (50 mg, 0.13 mmol) and the mixture was allowed to stir for 10 minutes. 1-Bromo-2-methoxyethane (26 mg, 0.187 mmol) was then added and the reaction was allowed to warm to room temperature overnight. The reaction was then quenched by the addition of water, extracted with ethyl acetate and concentrated in vacuo. The crude residue was reverse phase HPLC (acteonitrile/water with formic acid as a modifier) to afford the title compound.

Aufarbeitung

  1. customThe reaction was then quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-92db7a6066574ad2989834fe3ccc069d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

Notizen zur Reaktion

Wird geladen…