反应详情

温度

0 °C

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(pyridin-2-ylmethyl)quinoline-3,4-diamine (for a preparation see Intermediate 63, 500 mg) was dissolved in DCM (20 ml) and the reaction mixture was cooled to 0° C. 2-Methoxyacetyl chloride (1.1 eq) was added dropwise and the reaction mixture was stirred at room temperature for 30 min. The mixture was hydrolysed using a solution of sodium hydrogen carbonate and extracted with DCM. The organic was dried over Na2SO4, filtered and concentrated to dryness. The obtained residue was dissolved in acetic acid (5 ml) and the reaction mixture was heated to 130° C. for 16 h. The reaction mixture was treated with sodium hydroxide (1M) and extracted with DCM. The organic was dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, eluting with DCM/methanol (95:5). The resulting compound was recrystallised from acetonitrile and dried under vacuum to give 4-(8-methoxy-2-(methoxymethyl)-1-(pyridin-2-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole (50 mg) as a cream-coloured powder.

1. extractionextracted with DCM
2. dry with materialThe organic was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated to dryness
5. dissolutionThe obtained residue was dissolved in acetic acid (5 ml)
6. temperaturethe reaction mixture was heated to 130° C. for 16 h
7. additionThe reaction mixture was treated with sodium hydroxide (1M)
8. extractionextracted with DCM
9. dry with materialThe organic was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated to dryness
12. customThe residue was purified by chromatography on silica gel
13. washeluting with DCM/methanol (95:5)
14. customThe resulting compound was recrystallised from acetonitrile
15. customdried under vacuum