Diisopropylethylamine → HCID 60162558, compound

Participants

Reaction Steps

(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (1.0 g, 3.05 mmol), 4,5-dichloro-2-methyl-2H-pyridazin-3-one (J. Org. Chem. 2473-76, 46, 1981) (0.546 g, 3.05 mmol) and diisopropylethylamine (2.1 mL, 12.8 mmol) in isopropanol (5 mL) was heated to reflux for 4.25 h then at 75° C. for 20 h. The reaction mixture was cooled, diluted with EtOAc (20 mL) and washed with 1M sodium carbonate (10 mL). The organic extracts were dried (Na2SO4), evaporated to dryness and purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM then gradient 20-100% EtOAc in DCM). Fractions containing the less polar product were evaporated and freeze dried to give 323 as a yellow solid, (78 mg, 6.4%). LCMS (Method C): RT 4.80 min [M+H]+ 398.00. 1H NMR δ (ppm) (DMSO-d): 7.77 (1H, dd, J=8.82, 4.85 Hz), 7.56-7.55 (6H, m), 7.14 (1H, ddd, J=9.9, 8.9, 2.50 Hz), 6.89 (1H, dd, J=8.91, 2.51 Hz), 6.61 (1H, d, J=9.09 Hz), 5.94 (1H, t, J=7.66 Hz), 3.56 (3H, s), 1.51 (3H, d, J=6.65 Hz)

Provenance & Evidence