Reacción #3608

Ecuación de reacción

3-methylbenzo[b]thiophene-2-acetyl chloride

triethylamine

dimethylaminopyridine

3-methylbenzo[b]thiophene-2-acetyl chloride

triethylamine

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

→

desired product

Rendimiento 39.5%

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

Rendimiento 39.5%

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
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for an additional 18 hours
5. 5
   Lavadowashed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   OtroThe reaction mixture is dried with Na2 SO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo
9. 9
   Otroto give a solid which
10. 10
    Otrois purified by flash chromatography

Procedimiento

To a stirred solution of 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl 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 72 hours at room temperature. An additional 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride, 0.346 g of triethylamine and 30 mg of dimethylaminopyridine is added and stirring continued for an additional 18 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 Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give 0.320 g of the desired product as a yellow foam.

Fuente