Reacción #3603

Ecuación de reacción

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

3-chlorobenzo[b]thiophen-2-carbonyl chloride

triethylamine

→

solid

Rendimiento 61.5%

N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-chlorobenzo[b]thiophene-2-carboxamide

Rendimiento 61.5%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 18 hours
3. 3
   LavadoThe reaction mixture is washed with water, 1N HCl, NaHCO3, and brine
4. 4
   SecadoThe reaction mixture is dried with Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated in vacuo
7. 7
   Otroto give a solid which
8. 8
   Otrois purified by flash chromatography

Procedimiento

To a stirred solution of 0.440 g of 3-chlorobenzo[b]thiophen-2-carbonyl chloride in 10 ml of methylene chloride is added 0.33 ml of triethylamine. After stirring for 15 minutes, 0.485 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 18 hours. The reaction mixture is washed with water, 1N HCl, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give 0.49 g of solid, m.p. 220°-222° C.

Fuente