反应详情

温度

50 °C

A mixture of methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate (134 mg, 0.32 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 50° C. for 5 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (100 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was purified by chromatography on silica gel eluted with MeOH/DCM=1/5 to afford the crude product. It was then made a further purification by prep-HPLC to afford the desired product as a yellow solid (64 mg, 50%); LC/MS: MS (ES+) m/e 403 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.63 (s, 3H), 3.48 (t, J=4.2 Hz, 4H), 3.65 (t, J=4.2 Hz, 4H), 6.03 (s, 2H), 6.97 (d, J=7.8 Hz, 1H), 7.28 (s, 1H), 7.42 (t, J=7.5 Hz, 1H), 7.58-7.67 (m, 2H), 7.91 (d, J=7.8 Hz, 1H), 8.01 (d, J=7.8 Hz, 1H), 8.33 (d, J=7.8 Hz, 1H).

1. temperatureIt was cooled to room temperature
2. filtrationthe precipitate was collected by filtration
3. additionIt was then poured into water (100 mL)
4. filtrationIt was filtered
5. customthe solid was purified by chromatography on silica gel
6. washeluted with MeOH/DCM=1/5
7. customto afford the crude product
8. customa further purification by prep-HPLC