1,2-Diaminocyclohexane, cis- → 6-(cis-2-Amino-cyclohexylamino)-4-(6-[1,2,3]triazol-1-yl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-(6-[1,2,3]triazol-1-yl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (44 mg, 0.139 mmol) was dissolved in N-methylpyrrolidinone (0.9 mL). cis-Cyclohexane-1,2-diamine (95 mg, 0.834 mmol) was added and the mixture was warmed to 150° C. After 16 h the mixture was cooled and concentrated in vacuo. The residue obtained was diluted with saturated aqueous sodium bicarbonate solution, then extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by chromatography (silica, 0:0:10 to 0.1:1:10 ammonium hydroxide:methanol:dichloromethane) gave 6-(cis-2-amino-cyclohexylamino)-4-(6-[1,2,3]triazol-1-yl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (13 mg, 23%) as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.33 (s, 1H) 9.13 (d, J=8.3 Hz, 1H) 8.84 (d, J=1.1 Hz, 1H) 8.16-8.26 (m, 1H) 8.03 (d, J=0.8 Hz, 1H) 7.96 (d, J=7.9 Hz, 1H) 7.67 (s, 1H) 7.51-7.57 (m, 1H) 7.51-7.57 (m, 1H) 7.43-7.50 (m, 1H) 3.60 (br. s., 1H) 2.96-3.03 (m, 1H) 1.21-1.64 (m, 8H); MS (EI/CI) m/z: 395 [M+H].

Provenance & Evidence