Reaction #587106

Reaction equation

3-chloropropan-1-amine hydrochloride

triethylamine

1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid

1-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid

HATU

→

N-(3-Chloropropyl)-1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-carboxamide

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture is stirred overnight
2. 2
   OtherThe reaction mixture is purified by preparative HPLC
3. 3
   OtherThe product-containing fractions are evaporated in vacuo

Procedure

140 mg (0.36 mmol) of 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid (Example 29A) are dissolved in 8 ml of DMF and, after addition of 204 mg (0.54 mmol) of HATU and 66 mg (0.54 mmol) of DMAP, stirred at room temperature for 15 minutes. Then a solution of 93 mg (0.72 mmol) of 3-chloropropan-1-amine hydrochloride and 80 mg (0.79 mmol) of triethylamine in 1 ml of DMF is added dropwise, and the reaction mixture is stirred overnight. The reaction mixture is purified by preparative HPLC. The product-containing fractions are evaporated in vacuo.

Source