Réaction #3614

ord-a0865d39ece04d7ca18701901cb148a2

Équation de réaction

Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N
10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
Cc1ccccc1C(=O)Cl
2-methylbenzoyl chloride
Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccccc1C
solid
Rendement 65.9%
Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccccc1C
N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)-2-methylphenyl]-2-methylbenzamide
Rendement 65.9%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05733905uspto-grants-1998_03