Ethyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689797, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4,6-dichloropyridazine-3-carboxylate (0.45 g, 2.04 mmol) and 2-(6-aminopyridin-2-yl)propan-2-ol (620 mg, 4.07 mmol) was dissolved in acetonitrile (3.00 mL) and heated at 130° C. for 18 h. The mixture was cooled, concentrated, the residue was adsorbed on silica gel and purified by flash chromatography (silica gel 45 μM, 160 g, Thomson) eluting with 0 to 100% hexanes/ethyl acetate over 40 min, to yield ethyl 6-chloro-4-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxylate (405 mg, 59.1% yield). 1H NMR (CHLOROFORM-d) δ: 10.72 (s, 1H), 9.00 (s, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.34 (d, J=7.9 Hz, 1H), 6.89 (d, J=7.9 Hz, 1H), 5.21 (br. s., 1H), 4.60 (q, J=7.2 Hz, 2H), 1.67 (s, 6H), 1.54 (t, J=7.9 Hz, 3H); LC-MS 337.0, 339.0 [M+H]+.

Provenance & Evidence