反应详情

Dimethylamine hydrochloride (686 mg, 8.4 mmol) was added to 30 mL of anhydrous N,N-dimethylformamide, and potassium carbonate (3.48 g, 25.2 mmol) was added and stirred for minutes at room temperature. Then compound 11a (4.2 mmol), HBTU (benzotriazole-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 4.77 g, 12.6 mmol), and triethylamine (2.9 mL, 21 mmol) were added and reacted overnight at room temperature under nitrogen atmosphere. The reaction mixture was poured into water and filtered. The filtrate was extracted once with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was combined with the filter cake. The crude product was purified by column chromatography (dichloromethane:methanol=100:1) to give white compound 12a (922 mg, 60.0%). m.p. 238-239° C. 1H NMR (300 MHz, CDCl3): δ 8.08 (d, J=8.6 Hz, 2H), 7.82 (d, J=1.4 Hz, 1H), 7.02 (d, J=1.4 Hz, 1H), 6.73 (d, J=8.6 Hz, 2H), 4.11 (t, J=4.4 Hz, 4H), 3.86 (t, J=4.4 Hz, 4H), 3.20 (br, s, 6H). MS (EI) m/e (%): 366 (M+, 100).

1. additionwas added
2. customreacted overnight at room temperature under nitrogen atmosphere
3. filtrationfiltered
4. extractionThe filtrate was extracted once with ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. customThe crude product was purified by column chromatography (dichloromethane:methanol=100:1)