Réaction #77837

Équation de réaction

triethylamine

ethyl isocyanate

2-(amino)-N-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamide

HCl

→

benzamide

Rendement 17.5%

2-((Ethylaminocarbonyl)amino)-N-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamide

Rendement 17.5%

Solvants

THF

EtOAc

Conditions de réaction

Traitement

1. 1
   LavageThe EtOAc layer was washed with 1 N HCl and brine
2. 2
   SéchageThe EtOAc was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   AutreReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA)

Mode opératoire

2-(amino)-N-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamide (Example 114a) (50 mg) was dissolved in THF (2.5 mL) prior to the addition of triethylamine (30 mg) and ethyl isocyanate (21 mg). After stirring for 72 h, EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) provided the title benzamide (10 mg). MS found: (M+Na)+=602.4.

Source