Cyclohexylamine → 6-(Cyclohexylamino)-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxamide

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Reaction Conditions

Reaction Steps

A suspension of 6-chloro-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxamide (100 mg, 345 μmol, prepared as described for example 12) and cyclohexylamine (342 mg, 395 μL, 3.45 mmol) in N-methyl-2-pyrrolidinone (0.5 mL) was heated at 130° C. for 14 h. The mixture was cooled and concentrated under high vacuum at 120° C. to remove all residual solvent and amine starting material. The brown solid obtained was purified by chromatography (silica, 11 g spherical, 0-20% acetone in dichloromethane, 20 min) to give 6-(cyclohexylamino)-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxamide (81 mg, 230 μmol, 67% yield) as a white solid. 1H NMR (DMSO-d6) δ: 11.72 (br. s., 1H), 8.37 (br. s., 1H), 7.83 (s, 1H), 7.62 (br. s., 1H), 7.56 (t, J=7.7 Hz, 1H), 7.10 (d, J=7.8 Hz, 1H), 6.88 (d, J=7.3 Hz, 1H), 6.66 (d, J=8.1 Hz, 1H), 3.52-3.69 (m, 1H), 2.04-2.18 (m, 1H), 1.90-2.00 (m, 2H), 1.72-1.82 (m, 2H), 1.63 (d, J=12.6 Hz, 1H), 1.24-1.45 (m, 4H), 1.09-1.23 (m, 1H), 0.95-1.03 (m, 4H); MS (EI/CI) m/z: 353.1 [M+H].

Provenance & Evidence