Tetrahydrofuran → HCID 59349495, compound

Participants

Reaction Conditions

Reaction Steps

A dry round bottomed flask was charged with N1,N6-bis(5-bromo-2-methylphenyl)-5,10-dioxo-5,10-dihydrodiimidazo[1,5-a:1′,5′-d]pyrazine-1,6-dicarboxamide (490 mg, 0.8 mmol) and anhydrous THF (15 ml). To this suspension was added 4,5-dimethyl-1H-imidazol-2-amine (196 mg, 1.76 mmol) in anhydrous DMF (2 ml). The reaction mixture was then stirred at 53° C. for 16 hours. The reaction mixture was then allowed to cool to room temperature and concentrated at reduced pressure. The crude material was treated with methanol and 1M hydrochloric acid. Saturated potassium carbonate solution was then added to neutralize the mixture. The resulting solid was filtered off, washed with 1M hydrochloric acid, saturated potassium carbonate solution and dichloromethane. Purification by reverse phase HPLC (aqueous ammonium acetate/acetonitrile) gave 32 mg of N4-(5-bromo-2-methylphenyl)-N5-(4,5-dimethyl-1H-imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): 7.97 (d, 1H), 7.35 (d, 1H), 7.27 (d, 1H), 2.29 (s, 3H), 2.04 (s, 6H); MS (EI): 418.5 (MO.

Provenance & Evidence