反应详情

温度

70 °C

The mixture of 5-amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione (585 mg, 2.0 mmol) and Pd/C (60 mg) in MeOH (95 mL) was stirred under atmospheric H2 for 2.5 h and filtered through Celite. The filtrate was mixed with 4-chloro-2-methoxynicotinic aldehyde (343.2 mg, 2.0 mmol) and HOAc (5 mL), stirred at the room temperature for 62 h, and evaporated under reduced pressure to afford an oil crude which was mixed with HCl in dioxane (4 M, 25 mL) and H2O (2 mL), heated at 70° C. for 1 h and evaporated. The residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL), basified with 28% aqueous NH4OH, and concentrated. Chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (60:10:1) afforded the title compound (642 mg, 80%). 1H NMR (DMSO-d6) δ 1.39 (d, J=6 Hz, 3H, CH3), 2.14 (s, 6H, 2CH3), 2.29 (m, 1H), 3.04 (m, 1H), 4.40 (m, 1H), 6.59 (d, J=8 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 8.04 (s, 1H), 8.05 (s, 1H); ESI-MS m/z 400.3 (MH+).

1. filtrationfiltered through Celite
2. stirringstirred at the room temperature for 62 h
3. customevaporated under reduced pressure
4. customto afford an oil crude which
5. customevaporated
6. additionThe residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL)
7. concentrationconcentrated