Reaction #77833

Reaction equation

BOP Reagent

diisopropylethylamine

2-amino-5-iodobenzoic acid

N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

NaHCO3

→

benzamide 2-amino-N-{2-[((cis)-2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethyl}-5-iodobenzamide

Yield 12.3%

Solvents

DMF

EtOAc

Conditions

Workup

1. 1
   DryingThe EtOAc was dried (MgSO4)
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated
4. 4
   OtherReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Procedure

The above material, (61b), N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide (59 mg) was dissolved in DMF (1 mL). After cooling to 0° C., diisopropylethylamine (0.1 mL) and 2-amino-5-iodobenzoic acid (43 mg) were added. BOP Reagent (72 mg) was added, and the mixture was stirred overnight. EtOAc was added along with NaHCO3 solution. The EtOAc was dried (MgSO4), filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide 2-amino-N-{2-[((cis)-2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethyl}-5-iodobenzamide (6 mg). MS found: (M+Na)+=622.2.

Source