O-Phenylenediamine → HCID 66831845, compound

Participants

Reaction Steps

To a solution of 3-(methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (512 mg; 2.28 mmol) in DMF (50 mL) was added HBTU (908 mg; 2.40 mmol). The solution was stirred for 20 minutes, then added dropwise over 20 minutes to a solution of phenylenediamine (370 mg; 6.84 mmol) in DMF (50 mL). The reaction mixture was stirred for 24 hours, then poured onto ice (1 kg), and allowed to stand until the ice had melted. The resulting orange solid was filtered, and purified by column chromatography (DCM:MeOH 98:2) to give N-(2-aminophenyl)-3-(methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide as an orange solid. (474 mg; 70%). δH (DMSO d6): 9.76 (1H, s), 8.99 (1H, s), 7.43 (1H, dd, J=7.9, 1.0), 6.99 (1H, td, J=7.6, 1.5), 6.84 (1H, dd, J=8.0, 1.3), 6.67 (1H, dd, J=7.6, 1.3), 5.64 (2H, s), 4.91 (2H, s), 3.44 (3H, s).

Provenance & Evidence