Reacción #3587

Ecuación de reacción

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

2,4-dichlorobenzoyl chloride

triethylamine

→

desired product

Rendimiento 53.5%

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

Rendimiento 53.5%

Disolventes

ethyl acetate

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe bath is removed
2. 2
   workup.STIRRINGthe reaction mixture stirred at room temperature for 18 hours
3. 3
   ConcentraciónThe volatiles are concentrated in vacuo
4. 4
   Otroto give a residue which
5. 5
   Lavadowashed with water, 2N citric acid, 1M NaHCO3 and brine
6. 6
   SecadoThe organic layer is dried with Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto give a residue which
10. 10
    Otrois crystallized from ethyl acetate

Procedimiento

To a solution of 415 mg of 2,4-dichlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of 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 18 hours. The volatiles are concentrated in vacuo to give a residue which is dissolved in ethyl acetate, washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4, filtered and concentrated in vacuo to give a residue which is crystallized from ethyl acetate to give 420 mg of the desired product as a crystalline solid, m.p., 210°-212° C.

Fuente