Sodium hydride → 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamide

HRID 2242811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242811
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:7]([S:9]([NH:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])[CH:8]=1)#[N:2].Br[CH2:28][CH2:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].[H-].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][C:19]2[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=2)=[C:7]([S:9]([N:12]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH2:28][CH2:29][N:30]2[C:34](=[O:35])[CH2:33][CH2:32][C:31]2=[O:36])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 135613951-(2-Bromoethyl)pyrrolidine-2,5-dioneHCID 592083045-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzenesulfonamide

Produkt 1

HCID 111919305-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamideAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzene-sulfonamide (41.4 mg, 0.1 mmol) in dry DMF (2 ml) was added 1-(2-bromo-ethyl)-pyrrolidine-2,5-dione (30.9 mg, 0.15 mmol) and NaH (60%, 6.00 mg, 0.15 mmol). The mixture was stirred for 8 hours at 90° C. After cooled to room temperature, the solvent was evaporated. The mixture was diluted with EtOAc (60 ml), washed with brine, and dried over MgSO4. The solvent was evaporated and the residue was purified by preparative TLC (CH2Cl2/CH3OH=20/1) to give 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamide (44 mg, 81.6%) and the free base was converted into HCl salt by 4N HCl in dioxane.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was evaporated
  3. additionThe mixture was diluted with EtOAc (60 ml)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by preparative TLC (CH2Cl2/CH3OH=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-33dfae9ddd17442dbf6ecbea0c5a5d09
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674797B2

Notizen zur Reaktion

Wird geladen…