Reaction #3683

Reaction equation

5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine

4-[(5-fluoro-2-methylbenzoyl)amino]-2-chlorobenzoyl chloride

diisopropylethylamine

→

N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)-3-chlorophenyl]-5-fluoro-2-methylbenzamide

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe mixture is washed with H2 O, 1N HCl, H2O, 1M NaHCO3, brine
2. 2
   Dryingdried (Na2SO4)
3. 3
   Washthe filter cake washed with dichloromethane
4. 4
   ConcentrationThe filtrate is concentrated
5. 5
   Otherthe solid crystallized from ethyl acetate
6. 6
   Otherto give crystals, m.p. 137°-140° C.

Procedure

A mixture of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 0.391 g of 4-[(5-fluoro-2-methylbenzoyl)amino]-2-chlorobenzoyl chloride and 0.158 g of diisopropylethylamine in 10 ml of dichloromethane is stirred at room temperature overnight. The mixture is washed with H2 O, 1N HCl, H2O, 1M NaHCO3, brine and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is again passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and the solid crystallized from ethyl acetate to give crystals, m.p. 137°-140° C.

Source