Réaction #3686

Équation de réaction

4-[(2-methylbenzoyl)amino]-3-chlorobenzoyl chloride

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

N,N-diisopropylethylamine

→

product

Rendement 106.0%

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

Rendement 106.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed with H2O and saturated NaHCO3
2. 2
   SéchageThe organic layer is dried (Na2SO4)
3. 3
   ConcentrationThe filtrate is concentrated
4. 4
   workup.DISSOLUTIONthe residue (4.0 g) dissolved in dichloromethane
5. 5
   Filtrationagain filtered through a pad of hydrous magnesium silicate
6. 6
   AutreThe filtrate is evaporated

Mode opératoire

To a mixture of 1.38 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1.11 g of N,N-diisopropylethylamine in 50 ml of dichloromethane is added 2.61 g of 4-[(2-methylbenzoyl)amino]-3-chlorobenzoyl chloride in 25 ml of dichloromethane. The mixture is stirred at room temperature overnight and then washed with H2O and saturated NaHCO3. The organic layer is dried (Na2SO4) and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated, the residue (4.0 g) dissolved in dichloromethane and again filtered through a pad of hydrous magnesium silicate. The filtrate is evaporated to give the product as a glass (3.62 g). A 1.8 g sample of the glass is crystallized from ethyl acetate to give 1.4 g of crystals, m.p. 176°-178° C.

Source