creatinine → HCID 178439308, compound

Participants

Reaction Steps

To a solution of 200 mg (0.370 mmol) of N-(4-isopropylbenzenesulfonyl)-α-(4-carboxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide (from Step D) in 1 mL of dry THF was added 90 mg (0.556 mmol) of 1,1-carbonyldiimidazole. The solution was stirred at reflux under N2 for 2 hours. The cooled solution was evaporated to dryness. The residue was dissolved in 1 mL of acetonitrile and treated with 63 mg (0.556 mmol) of 2-amino-4,5-dihydro-1-methyl-1H-imidazol-4-one (creatinine) and 129 μL (93.7 mg; 0.925 mmol) of triethylamine. The mixture was stirred at reflux overnight. The cooled reaction mixture was quenched by addition of 1N HCl and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4, and filtered. The filtrate was concentrated, and the residue was flash chromatographed (silica gel, 27×3.5 cm; elution with 500 mL of 99:1:1 CHCl3 -MeOH-concentrated NH4OH followed by 1 L of 85:15:1 CHCl3 -MeOH-concentrated NH4OH) to give 142 mg (60%) of the title compound as a yellow solid, mp 137°-139 ° C.; homogeneous by TLC in 85:15:1 CHCl3 -MeOH-concentrated NH4OH. ESI mass spectrum m/e 635 (M+H)+.

Provenance & Evidence