Reaction #46140

Reaction equation

3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

1-(4-methoxyphenyl)cyclopropanecarboxylic acid

triethylamine

1-hydroxybenzotriazole hydrate

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

→

titled product

N-[2-(6-Methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl]-1-(4-methoxyphenyl)cyclopropanecarboxamide

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Otherthe mixture was partitioned between EtOAc and water
2. 2
   Washthe organic layer was washed with saturated NaHCO3 solution and brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude residue was triturated with ether-hexane solution

Procedure

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (70 mg, 0.20 mmol) in 3 mL of dimethylformamide was added 1-(4-methoxyphenyl)cyclopropanecarboxylic acid (0.39 mg, 0.20 mmol), triethylamine (0.085 mL, 0.61 mmol), 1-hydroxybenzotriazole hydrate (37 mg, 0.24 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (47 mg, 0.24 mmol). After three hours, the mixture was partitioned between EtOAc and water, and the organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was triturated with ether-hexane solution to provide the titled product. HRMS (ES) exact mass calculated for C30H30N2O4 (M+H+): 483.2258. Found 483.2279.

Source