Succinic anhydride → HCID 89437178, compound

Participants

Reaction Steps

The 5-aminopyrazine-2-carbonitrile (commercially available, 1.0 g, 8.32 mmol) was dissolved in tetrahydrofuran then succinic anhydride (1.04 g, 10.4 mmol) was added, the mixture was stirred at room temperature for 2 h and at reflux overnight. Then 1.0 equivalent of succinic anhydride was added and the solution was refluxed for 4 days. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated, acidified and extracted with ethyl acetate (3×). The combined organic layer was dried on magnesium sulfate and concentrated under vacuum. The residue was purified by flash chromatography eluting with cyclohexane-ethyl acetate (1/3) with acid acetic (1%) to give 4-[(5-cyanopyrazin-2-yl)amino]-4-oxo-butanoic acid A1 (1.30 g, 71%). M.p.=201-202° C., 1H NMR (400 MHz, DMSO-d6) δ 12.09 (bs, 1H), 11.40 (s, 1H), 9.41 (s, 1H), 8.96 (s, 1H), 2.73 (t, 2H), 2.55 (t, 2H) ppm. LC-MS (Method B): RT 0.96, 219 (M−H+)

Provenance & Evidence