反应详情

温度

150 °C

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].

1. temperatureAfter 16 h the mixture was cooled
2. concentrationconcentrated in vacuo
3. customThe residue obtained
4. extractionextracted with ethyl acetate
5. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by chromatography (silica, 0:0:10 to 0.1:1:10 ammonium hydroxide:methanol:dichloromethane)