4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide → HCID 178489626, compound

Participants

Reaction Conditions

Reaction Steps

A mixture comprising ethyl 2-(5-hydroxy-1H-benzoimidazol-2-yl)propionate (148 mg, 0.63 mmol), 4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide (200 mg, 0.63 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (0.5 mL) was stirred at room temperature until homogeneous, degassed under vacuum and concentrated by heating at 170° C. for 2 hours under a stream of N2. The residue was cooled to room temperature and rinsed with an excess of ethyl ether. The resulting amorphous material was taken up in 50% aqueous acetonitrile and purified by preparative reverse phase HPLC (2-50% CH3CN/H2O) to provide 2-[1-(5-hydroxy-1H-benzoimidazol-2-yl)ethyl]-N-[2-(2-methoxyphenoxy)ethyl]-3-methyl-3H-benzoimidazole-5-carboxamide (40 mg, 13% yield) as a light pink solid; MS (BioIon) C27H27N5O4 m/e calc 485.59; found 486.5 (MH+).

Provenance & Evidence