Reacción #3586

Ecuación de reacción

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

3-methyl-2-thiophenecarbonyl chloride

triethylamine

→

solid

Rendimiento 113.5%

N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methyl-2-thiophenecarboxamide

Rendimiento 113.5%

Disolventes

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
   Otrocrystallizes from ethyl acetate

Procedimiento

To a solution of 318 mg of 3-methyl-2-thiophenecarbonyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of the 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 crystallizes from ethyl acetate to afford 800 mg of solid. The solid is dissolved in methylene chloride washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is filtered through hydrous magnesium silicate, dried with Na2SO4 and concentrated in vacuo to give a residue which crystallizes from ethyl acetate to afford 400 mg of the desired product as a white solid, m.p. 232°-235° C.

Fuente