Reacción #3588

Ecuación de reacción

2-chlorobenzoyl chloride

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

→

desired product

Rendimiento 72.1%

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

Rendimiento 72.1%

Disolventes

methylene chloride

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 methylene chloride

Procedimiento

To a solution of 347 mg of 2-chlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamineo 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 methylene chloride, 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 methylene chloride to give 525 mg of the desired product as a white crystalline solid, m.p. 228°-230° C.

Fuente