Réaction #3021

Équation de réaction

[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride

compound 113

[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride

dimethylformamide

BOP

triethylamine

water

→

3-{2-[[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrile

Rendement 91.0%

Solvants

1-(2-cyanoethyl)-2-indolecarboxylic acid

Conditions de réaction

Traitement

1. 1
   Extractionthe aqueous phase is extracted with ethyl acetate
2. 2
   SéchageThe organic extracts are dried over anhydrous sodium sulphate
3. 3
   Autreevaporated to dryness
4. 4
   AutreThe residue is purified by flash chromatography on a column of silica gel, eluent

Mode opératoire

1.5 g of [(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride (compound 113) are dissolved in 10 ml of dimethylformamide and 0.918 g of 1-(2-cyanoethyl)-2-indolecarboxylic acid, 1.95 g of BOP and then, dropwise, 1.28 g of triethylamine are then successively added. The reaction mixture is left at room temperature for 3 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residue is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain 3-{2-[[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrile in the form of a pasty foam; Yield: 91%.

Source