Diisopropylethylamine → HCID 68157292, compound

Participants

Reaction Steps

(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (1.0 g, 3.05 mmol), 6-amino-4,5-dichloro-2-methyl-2H-pyridazin-3-one (J. Het Chem, 5-10 37, 2000) (0.59 g, 3.05 mmol) and diisopropylethylamine (2.1 mL, 12.8 mmol) in butanol (5 mL) was heated to 115° C. in a sealed tube under argon for 19 h. The reaction mixture was cooled and diluted with EtOAc (50 mL) and washed with water (20 mL). The organic extracts were dried (Na2SO4), evaporated to dryness and purified by column chromatography (Si—PCC, gradient 1-8% (9:1 MeOH/0.880 NH3) in DCM then gradient 20-100% EtOAc in cyclohexane). Fractions containing the less polar product were evaporated and freeze dried to give 341 as a yellow solid, (167 mg, 13%). LCMS (Method C): RT 4.01 min [M+H]+ 313.02. 1H NMR δ (ppm DMSO-d6): 7.76 (1H, dd, J=8.81, 4.85 Hz), 7.56-7.40 (5H, m), 7.13 (1H, ddd, J=9.85, 8.80, 2.53 Hz), 6.88 (1H, dd, J=8.91, 2.51 Hz), 5.70 (1H, d, J=9.37 Hz), 5.61-5.60 (1H, m), 5.52 (2H, s), 3.37 (3H, s), 1.59 (3H, d, J=6.56 Hz)

Provenance & Evidence