反应详情

3-{tert-Butoxycarbonyl-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-amino}benzoic acid (42 mg, 0.10 mmol), ethylamine (12 M aq., 42 μL, 0.50 mmol), and triethylamine (28 μL, 0.20 mmol) are stirred in DMF (0.30 mL) and PyBOP (57 mg, 0.11 mmol) is added. Stirring is continued overnight. The reaction mixture is partitioned between EtOAc (7 mL) and NaHCO3 (sat. aq., 7 mL) and the layers are separated. The combined organic layers are washed with brine (2×5 mL) and dried over Na2SO4. Evaporation of the solvent affords an oil which is dissolved in MeOH (0.3 mL) containing HCl (12 M aq., 0.15 mL) and stirred overnight. Triethylamine (0.25 mL) and EtOH (2 mL) are added and the solvents removed under reduced pressure. The residue is purified by preparative HPLC to afford the title compound as a white solid (7 mg). 1H NMR (DMSO-d6, 400 MHz): δ=13.29 ppm (s, 0.8H); 10.01 (s, 0.9H); 8.77 (s, 1.0H); 8.65 (s, 1.0H); 8.52 (s, 1.1H); 8.41-8.37 (m, 2.1H); 8.25 (s, 1.0H); 8.08 (d, 1.0H); 7.47 (d, 1.0H); 7.41 (t, 1.1H); 7.04-7.03 (m, 0.5H); 3.32 (s, 29.2H (water)); 1.14 (t, 3.5H). LCMS: Rt=0.95 min (100%), m/z (ESI) 349 (M+H)+.

1. customThe reaction mixture is partitioned between EtOAc (7 mL) and NaHCO3 (sat. aq., 7 mL)
2. customthe layers are separated
3. washThe combined organic layers are washed with brine (2×5 mL)
4. dry with materialdried over Na2SO4
5. customEvaporation of the solvent
6. customaffords an oil which
7. stirringstirred overnight
8. customthe solvents removed under reduced pressure
9. customThe residue is purified by preparative HPLC