Hydroxide → 3-amino-N-methyl-6-[3-({[(3-morpholin-4-ylphenyl)methyl]amino}methyl) phenyl]pyrazine-2-carboxamide

Beteiligte Stoffe

Reaktionsschritte

A solution of 3-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoic acid (0.081 g, 0.30 mmol), HOBt (0.048 g, 0.36 mmol) and HBTU (0.17 g, 0.45 mmol) in DMF (1.0 mL) was stirred at r.t. for 10 min. A solution of [(3-morpholin-4-ylphenyl)methyl]amine trifluoroacetate (0.13 g, 0.30 mmol) in DMF (1.0 mL) was added and the resulting solution was stirred for 12 h at r.t. The solution was concentrated in vacuo and the crude mixture was purified via HPLC (reverse-phase, CH3CN/H2O with 0.1% TFA). Upon removal of CH3CN/H2O, the product was taken up in EtOAc (100 mL) and washed with 1M NaOH(aq) (50 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Trituration and collection of a solid by vacuum filtration provided 11.6 mg (and treated with Bio-Rad AG 1-X8 resin (hydroxide form) until pH 8. The product was filtered and concentrated in vacuo, to provide 14.1 mg (9% yield) of 3-amino-N-methyl-6-[3-({[(3-morpholin-4-ylphenyl)methyl]amino}methyl) phenyl]pyrazine-2-carboxamide: 1H NMR (400 MHz, d6-DMSO): 9.15 (t, 1H), 8.91 (s, 1H), 8.87 (m, 1H), 8.55 (s, 1H), 8.37 (d, 1H), 7.88 (d, 1H), 7.57 (t, 1H), 7.19 (t, 1H), 6.95 (s, 1H), 6.82 (m, 2H), 4.48 (d, 2H), 3.72 (t, 4H), 3.08 (t, 2H), 2.85 (d, 3H); MS (EI) for C24H26N6O3: 447 (MH+).

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