Methyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689754, compound

Participants

Reaction Conditions

Reaction Steps

A heavy walled resealable tube was charged with methyl 4,6-dichloropyridazine-3-carboxylate (1.3 g, 6.28 mmol) and 6-cyclobutylpyridin-2-amine (931 mg, 6.28 mmol) in acetonitrile (6.00 mL). The tube was heated with stirring in an oil bath at 80° C. for 48 h. Solvent was evaporated under vacuum, the residue was dissolved in dichloromethane and then purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco) eluting with 0 to 10% over 20 min dichloromethane/acetone to give methyl 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxylate (350 mg, 17.5% yield) as a light yellow solid. 1H NMR (CHLOROFORM-d) δ: 10.62 (s, 1H), 9.49 (s, 1H), 7.59 (t, J=7.9 Hz, 1H), 6.85 (d, J=7.6 Hz, 1H), 6.73 (d, J=8.3 Hz, 1H), 4.10 (s, 3H), 3.67 (quin, J=8.6 Hz, 1H), 2.24-2.58 (m, 4H), 1.85-2.22 (m, 2H); LC-MS 319.0 [M+H]+.

Provenance & Evidence