反应详情

温度

100 °C

30 mg (0.084 mmol) of 1-(4-aminocyclohexyl)-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride were dissolved in 2 ml of dimethylformamide. To the obtained solution 32 μl (0.42 mmol) of ethylisocyanate, 60 μl (0.336 mmol) of DIPEA, were added. The mixture was stirred at 100° C. for 18 hours, the solution was portioned between ethyl acetate and saturated aqueous solution of NaHCO3, and the organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum. The crude was purified by silica gel chromatography (DCM/MeOH/NH4OH 95/5/1) to provide 1-{4-[(ethylcarbamoyl)amino]cyclohexyl}-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide 4 mg (11%) as a white solid. LC/MS (254) HPLC method 2 Rt 4.38 min. 1H NMR (401 MHz, DMSO-d6) δ 9.47 (s, 1H), 8.27 (d, J=8.67 Hz, 1H), 7.74 (d, J=8.67 Hz, 1H), 7.59 (s, 2H), 6.06 (d, J=7.08 Hz, 1H), 5.89-6.02 (m, 1H), 5.81 (t, J=5.49 Hz, 1H), 3.78-3.88 (m, 1H), 3.00-3.07 (m, 2H), 2.71-2.74 (m, 3H), 2.15-2.29 (m, 2H), 1.99-2.11 (m, 3H), 1.90 (dd, J=3.54, 13.67 Hz, 2H), 1.65-1.79 (m, 2H), 1.01 (t, J=7.20 Hz, 3H). HRMS (ESI) calcd for C20H25N7O2S [M+H]+ 428.1863 found 428.1852.

1. washthe organic layer was washed with brine
2. dry with materialdried over Na2SO4
3. customevaporated under vacuum
4. customThe crude was purified by silica gel chromatography (DCM/MeOH/NH4OH 95/5/1)