Sodium hydride → N-[4-(5H-Imidazo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-2 4-dichlorobenzamide

HRID 55244

Reaktionsgleichung

Reaktionsgleichung von HRID 55244
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][N:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>O1CCOCC1>[N:21]1[CH:20]=[CH:19][N:11]2[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:27]=4[Cl:26])=[CH:23][CH:22]=3)=[O:7])[CH2:9][C:10]=12

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 666452,4-Dichlorobenzoyl chlorideHCID 2183708710,11-Dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c]-[1,4]benzodiazepine

Produkt 1

HCID 21837155N-[4-(5H-Imidazo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-2 4-dichlorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel3×

Versuchsvorschrift

A slurry of 0.330 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 15 ml of dioxane is stirred and warmed slightly to obtain a nearly complete solution. The reaction mixture is cooled to room temperature and 43 mg of sodium hydride in oil added. The mixture is warmed slightly. Gas evolution stops in a few minutes. The reaction mixture is cooled to room temperature and 153 μl of 2,4-dichlorobenzoyl chloride in 2.5 ml of dioxane added. An additional 3.5 ml of dioxane is added and the reaction mixture stirred at room temperature for 2 days. The volatiles are evaporated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is separated and the aqueous phase extracted with chloroform two more times. The combined organic layers are trated with activated carbon and filtered through MgSO4. The filtrate is evaporated in vacuo to a tan foam which is purified by flash chro- matography on silica gel by elution with CHCl3 and 3-7% CH3OH in chloroform to give 310 mg of tan foam.

Aufarbeitung

  1. temperaturewarmed slightly
  2. customto obtain a nearly complete solution
  3. temperatureThe mixture is warmed slightly
  4. waitGas evolution stops in a few minutes
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customThe volatiles are evaporated in vacuo to a residue which
  7. customis partitioned between water and chloroform
  8. customThe organic layer is separated
  9. extractionthe aqueous phase extracted with chloroform two more times
  10. filtrationfiltered through MgSO4
  11. customThe filtrate is evaporated in vacuo to a tan foam which
  12. customis purified by flash chro- matography on silica gel by elution with CHCl3 and 3-7% CH3OH in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-9189f16ec8ed4833a5a9293a78b37e17
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624923

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