Reacción #3612

Ecuación de reacción

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

2-methylphenylacetyl chloride

triethylamine

→

desired product

Rendimiento 53.6%

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

Rendimiento 53.6%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 hours at room temperature
3. 3
   Lavadowashed with water, 2N citric acid, NaHCO3, and brine
4. 4
   SecadoThe reaction mixture is dried with Na2SO4
5. 5
   Filtraciónfiltered through a pad of hydrous magnesium silicate
6. 6
   Otroevaporated in vacuo
7. 7
   Otroto give a solid which
8. 8
   Otrois purified by flash chromatography
9. 9
   Otroto give a solid which
10. 10
    Otrois crystallized from ethyl acetate

Procedimiento

To a stirred solution of 0.334 g of 2-methylphenylacetyl chloride 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 72 hours at room temperature. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered through a pad of hydrous magnesium silicate and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl acetate to give 0.385 g of the desired product as white crystals, m.p. 198°-200° C.

Fuente