Reaction #155369

Reaction equation

1c

3-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester

→

crude product

Yield 58.0%

3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid methyl ester

Yield 58.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperatureto reflux for one hour
2. 2
   OtherThe solution was then evaporated to dryness
3. 3
   Otherthe remaining solid triturated with water

Procedure

A solution of the product of 1c (22.6 mmol) in 100 mL concentrated acetic acid was heated to reflux for one hour. The solution was then evaporated to dryness, the remaining solid triturated with water and under stirring the pH was adjusted to about 8-9. The crude product was isolated through extraction with ethyl acetate and purified by chromatography on silica gel (eluent: dichloromethane/ethanol 1:1).

Source