Reaction #3021

Reaction equation

[(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

Yield 91.0%

Solvents

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

Conditions

Workup

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

Procedure

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