Reaktion #3585

Reaktionsgleichung

10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

2,5-dichlorobenzoyl chloride

triethylamine

→

desired product

Ausbeute 35.0%

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

Ausbeute 35.0%

Lösungsmittel

ethyl acetate

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   SonstigeThe bath is removed
3. 3
   EinengenThe volatiles are concentrated in vacuo
4. 4
   Sonstigeto give a residue which
5. 5
   Waschenwashed with water, 2N citric acid, 1M NaHCO3 and brine
6. 6
   TrocknenThe organic layer is dried with Na2SO4
7. 7
   Einengenconcentrated in vacuo to a residue which
8. 8
   Sonstigeis purified by thick layer chromatography by elution with 1:1 ethyl acetate-hexanes
9. 9
   Sonstigeto give a residue
10. 10
    SonstigeThe residue is crystallized from ethyl acetate

Vorschrift

To a solution of 414.5 mg of 2,5-dichlorobenzoyl chloride in 5 ml of methylene chloride is added 276 μl of triethylamine. After stirring at 0° C. for 3 minutes 400 mg of the 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 3 hours. The volatiles are concentrated in vacuo to give a residue which is dissolved in ethyl acetate and washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4 and concentrated in vacuo to a residue which is purified by thick layer chromatography by elution with 1:1 ethyl acetate-hexanes to give a residue. The residue is crystallized from ethyl acetate to give 220 mg of the desired product as white crystals, m.p. 218°-220° C.

Quelle