Reaction #3614

Reaction equation

10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

N,N-diisopropylethylamine

2-methylbenzoyl chloride

→

solid

Yield 65.9%

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

Yield 65.9%

Solvents

methylene chloride

Conditions

Workup

1. 1
   WashThe reaction mixture is washed with water
2. 2
   Dryingthe organic layer dried with Na2SO4
3. 3
   workup.ADDITIONHexane is added at the boil

Procedure

A solution of 0.83 g of 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.5 g of N,N-diisopropylethylamine and 0.6 g of 2-methylbenzoyl chloride in 50 ml of methylene chloride is stirred at room temperature for 18 hours. The reaction mixture is washed with water, the organic layer dried with Na2SO4 and passed through a pad of hydrous magnesium silicate. Hexane is added at the boil to give 0.75 g of a solid which is crystallized from methylene chloride-hexane to give 0.61 g of the desired product, m.p. 125°-130° C.

Source