Methyl 4,6-dichloropyridazine-3-carboxylate → Methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate

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Reaction Steps

A stirred solution of methyl 4,6-dichloropyridazine-3-carboxylate (255 mg, 1.23 mmol) and 6-isopropylpyridin-2-amine (252 mg, 1.85 mmol) in acetonitrile (8.0 mL) was heated at 140° C. for 21 h. After cooling to room temperature the reaction mixture was concentrated in vacuo, then the residue purified by chromatography (silica, 20-45 μm, 80 g, Thomson, 0 to 10% acetone in dichloromethane, 20 min) to give methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (113 mg, 30%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.64 (br. s., 1H) 9.39 (s, 1H) 7.63 (t, J=7.83 Hz, 1H) 6.94 (d, J=7.58 Hz, 1H) 6.78 (d, J=8.08 Hz, 1H) 4.12 (s, 3H) 3.01-3.19 (m, 1H) 1.31-1.42 (m, 6H). LCMS (EI/CI) m/z: 307 [M+H].

Provenance & Evidence