5-Chloro-4-[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethylamino]-2-methyl-2H-pyridazin-3-one → 4-[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethylamino]-2-methyl-2H-pyridazin-3-one

Participants

Reaction Steps

5-Chloro-4-[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamino]-2-methyl-2H-pyridazin-3-one (0.06 g, 0.15 mmol) in ethyl acetate (5 mL) and sat. aq sodium hydrogen carbonate (1 mL) was hydrogenated over 10% palladium on carbon (20 mg) at room temperature and pressure for 3 h. The reaction mix was filtered, evaporated to dryness and purified by column chromatography (Si—PCC, gradient 50-100% EtOAc in DCM). Fractions containing the product were evaporated and freeze dried to give 326 as a white solid, (30 mg, 55%). LCMS (Method C): RT 4.0 min [M+H]+ 364.09. 1H NMR δ (ppm) (DMSO-d): 7.76 (1H, dd, J=8.83, 4.84 Hz), 7.58-7.56 (5H, m), 7.44 (1H, d, J=4.98 Hz), 7.13 (1H, ddd, J=9.9, 8.9, 2.5 Hz), 6.85 (1H, dd, J=8.90, 2.47 Hz), 6.74 (1H, d, J=7.91 Hz), 5.90 (1H, d, J=5.04 Hz), 4.81 (1H, dq, J=7.12 Hz), 3.59 (3H, s), 1.49 (3H, d, J=6.65 Hz)

Provenance & Evidence