反应详情

温度

160 °C

A mixture of 56.3 mg (0.150 mmol) of 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and 1.0 ml (15.0 mmol) of 1,2-ethylenediamine was heated at 160° C. for 30 min. The mixture was mixed with water and extracted with ethyl acetate. The organic extracts were washed with water 3 times, brine, dried over MgSO4 and concentrated. The residue was heated in a mixture of 4 M of hydrogen chloride in 6 ml of dioxane and 2 ml of conc. hydrochloric acid at 60° C. for 18 hours. The mixture was concentrated in high vacuum and triturated with ethyl ether. The solid material was filtered out and washed with ethyl ether to give 143. Yield 37.5 mg (56%) over two steps. ESI MS m/z 332.1 (M+1). 1H NMR (400 MHz, DMSO): 14.27 (s, 1H), 9.57 (s, 1H), 9.30 (s, 1H), 9.19 (d, J=8.0 Hz, 1H), 9.11 (s, 1H), 8.90 (d, J=4.8 Hz, 1H), 8.23 (s, 3H), 8.11 (dd, J=7.9, 5.6 Hz, 1H), 7.68 (d, J=7.5 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 6.71 (d, J=7.3 Hz, 1H), 3.75 (t, J=6.0 Hz, 2H), 3.17 (dd, J=11.4, 5.7 Hz, 2H)

1. extractionextracted with ethyl acetate
2. washThe organic extracts were washed with water 3 times, brine
3. dry with materialdried over MgSO4
4. concentrationconcentrated
5. temperatureThe residue was heated in a mixture of 4 M of hydrogen chloride in 6 ml of dioxane and 2 ml of conc. hydrochloric acid at 60° C. for 18 hours
6. concentrationThe mixture was concentrated in high vacuum
7. customtriturated with ethyl ether
8. filtrationThe solid material was filtered out
9. washwashed with ethyl ether