1,3-Benzodioxol-5-amine → 2-(3,4-Methylenedioxyphenylamino)-6-(3-acetamidophenyl)pyrazine

Participants

Reaction Steps

Using Method F with 200 mg (0.33 mmol) 4a and 138 mg (1.0 mmol) 3,4-methylendioxyaniline, 84 mg (29.0%) pure title compound were obtained after preparative HPLC (eluent: AcOEt) purification of the whole batch. Reaction time: 18 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 2.08 (s, 3H, CH3CO), 5.99 (s, 2H, OCH2O), 6.91 (d, 1H, Harom 5, J=8.40), 7.32 (q, 1H, Harom 6, Jo=8.43, Jm=1.99), 7.40 (d, 1H, Harom 2, J=1.85), 7.43 (t, 1H, Harom 5′, J=7.87), 7.65 (d, 1H, Harom 4′ or 6′, J=8.93), 7.68 (d, 1H, Harom 6′ or 4′, J=7.83), 8.12 (s, 1H, HP5), 8.30 (s, 1H, Harom 2′), 8.35 (s, 1H, HP3), 9.42 (s, 1H, NHamino), 10.09 (s, 1H, NHamido); MS, (C19H16N4O3), m/z: 349.1 [M++1, 100].

Provenance & Evidence