Reacción #3610

Ecuación de reacción

4-chloro-2-methoxybenzoyl chloride

triethylamine

4-chloro-2-methoxybenzoyl chloride

triethylamine

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

→

desired product

Rendimiento 41.1%

N-[4-(5H-Pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)ylcarbonyl)phenyl]-4-chloro-2-methoxybenzamide

Rendimiento 41.1%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 18 hours at room temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITis continued for 2 hours
5. 5
   Lavadowashed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   SecadoThe reaction mixture is dried with Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo
9. 9
   Otroto give a residue which
10. 10
    Otrois purified by flash chromatography
11. 11
    Otroto give a solid which
12. 12
    Otrois crystallized from ethyl acetate

Procedimiento

To a stirred solution of 0.406 g of 4-chloro-2-methoxybenzoyl chloride in 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 18 hours at room temperature. An additional 0.406 g of 4-chloro-2-methoxybenzoyl chloride and 0.346 g of triethylamine is added and stirring is continued for 2 hours. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, 1M NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a residue which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl acetate to give 0.320 g of the desired product as a white crystals, m.p. 222°-224° C.

Fuente