Sodium hydride → 2-{4-[2-(2,4-dimethyl-imidazol-1-yl)-acetyl]-piperazin-1-yl}-N-phenyl-benzamide

HRID 1810961

Reaktionsgleichung

Reaktionsgleichung von HRID 1810961
[CH3:1][C:2]1[NH:3][C:4]([CH3:7])=[CH:5][N:6]=1.[H-].[Na+].Cl[CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[CH2:16][CH2:15]1)=[O:13]>CS(C)=O>[CH3:1][C:2]1[N:6]([CH2:11][C:12]([N:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=3[C:22]([NH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:23])[CH2:18][CH2:19]2)=[O:13])[CH:5]=[C:4]([CH3:7])[N:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 702592,4-DimethylimidazoleHCID 57516318HCID 57516318, Verbindung

Produkt 1

HCID 595487242-{4-[2-(2,4-dimethyl-imidazol-1-yl)-acetyl]-piperazin-1-yl}-N-phenyl-benzamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 2,5-dimethyl imidazole (0.060 g, 0.630 mmol) in 1 mL of DMSO in a reaction tube is added 60% NaH (0.030 g, 0.730 mmol). The mixture bubbles as deprotonation occurs. The mixture is stirred for 0.5 h and then 0.5 mL of a DMSO solution containing 2-[4-(2-chloro-acetyl)-piperazin-1-yl]-N-phenyl-benzamide (0.075 g, 0.210 mmol) is added. The flask is sealed and heated at 80° C. for 60 h. The product is purified via Prep HPLC (20-100% CH3CN/H2O) to give 74.7 mg of 2-{4-[2-(2,4-dimethyl-imidazol-1-yl)-acetyl]-piperazin-1-yl}-N-phenyl-benzamide in 85% yield. MS: MH+=418.9

Aufarbeitung

  1. additionis added
  2. customThe flask is sealed
  3. customThe product is purified via Prep HPLC (20-100% CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-c633281c91134e22bb1ccd9c8a230193
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362249B2

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