Reaction #452469

Reaction equation

isothiourea

1-benzoyl-3-[3-[N-(4-bromobenzyl)-N-(quinolin-2-yl)amino]-propyl]-2-methylisothiourea

3-(1H-imidazol-4-yl)propyl amine

→

title compound

Yield 58.0%

1-[3-[N-(4-bromobenzyl)-N-(quinolin-2-yl)amino]propyl]-2-Benzoyl-3-[3-(1H-imidazol-4-yl)propyl]guanidine

Yield 58.0%

Solvents

pyridine

Conditions

Workup

1. 1
   Temperatureat reflux temperature for 10 h
2. 2
   workup.STIRRINGby stirring at room temperature for 48 h
3. 3
   OtherThe solvent was evaporated in vacuo
4. 4
   Otherthe residue was purified by column chromatography on silica gel (600 ml)
5. 5
   workup.ADDITIONa mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent

Procedure

To a solution of the above isothiourea (5.0 g, 9.133 mmol) in dry pyridine (70 ml) was added 3-(1H-imidazol-4-yl)propyl amine (1.26 g, 10.05 mmol) and the resulting mixture was stirred at reflux temperature for 10 h followed by stirring at room temperature for 48 h. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (600 ml) using a mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent affording 3.31 g (58%) of the title compound as an amorphous solid.

Source