Sodium hydride → 1-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

HRID 598415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598415
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[C:14](=[CH:15][N:16]([CH3:22])[C:17](=[O:21])[C:18]=2[CH3:20])[NH:13]C1=O.[Si]([O:31][CH2:32][CH2:33][C:34]1([S:37](Cl)(=[O:39])=[O:38])[CH2:36][CH2:35]1)(C(C)(C)C)(C)C>CN(C=O)C.C1COCC1>[OH:31][CH2:32][CH2:33][C:34]1([S:37]([NH:13][C:14]2[C:19]([NH:11][C:5]3[CH:6]=[CH:7][C:8]([I:10])=[CH:9][C:4]=3[F:3])=[C:18]([CH3:20])[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=2)(=[O:39])=[O:38])[CH2:36][CH2:35]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 582598911-(2-fluoro-4-iodophenyl)-5,7-dimethyl-1H-imidazo[4,5-c]pyridine-2,6(3H,5H)-dioneHCID 593863261-[2-(Tert-butyldimethylsilanyloxy)ethyl]-cyclopropanesulfonyl chloride

Produkt 1

HCID 589908331-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (60% in mineral oil) (21.8 mg, 0.544 mmol) is added to a solution of 1-(2-fluoro-4-iodophenyl)-5,7-dimethyl-1H-imidazo[4,5-c]pyridine-2,6(3H,5H)-dione (100 mg, 0.251 mmol) in dry DMF (5 mL) at 0° C. The cooling bath is removed and the solution stirred at room temperature for 1 hour. The solution is re-cooled to −5° C. in a dry-ice/acetone bath, and 1-[2-(tert-butyldimethylsilanyloxy)ethyl]-cyclopropanesulfonyl chloride (300 mg, 1 mmol) in dry THF (2 mL) is added. The mixture is warmed to room temperature and stirred for an additional 16 hours. The mixture is concentrated to give an oily residue and purified via flash chromatography (SiO2, EtOAc:MeOH=9:1) to give the title compound.

Aufarbeitung

  1. customThe cooling bath is removed
  2. temperatureThe solution is re-cooled to −5° C. in a dry-ice/acetone bath
  3. temperatureThe mixture is warmed to room temperature
  4. stirringstirred for an additional 16 hours
  5. concentrationThe mixture is concentrated
  6. customto give an oily residue
  7. custompurified via flash chromatography (SiO2, EtOAc:MeOH=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-4d76636721c74f31bd0e4a29cd7f8431
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897624B2

Notizen zur Reaktion

Wird geladen…