반응 #820938

반응 방정식

hydrochloric acid

4-chloro-1,2-dimethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine

3-chloroaniline

methanesulfonic acid

→

title compound

N-(3-Chlorophenyl)-1,2-dimethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine hydrochloride

용매

ethyl acetate

diethyl ether

1,4-dioxan

반응 조건

후처리

1. 1
   기타The reaction mixture was transferred to a round bottom flask
2. 2
   기타evaporated
3. 3
   기타The residue was partitioned between ethyl acetate (10 ml) and saturated sodium bicarbonate solution
4. 4
   세척washed with saturated sodium bicarbonate solution and water
5. 5
   건조The organic layer was dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타to afford a brown oil
8. 8
   기타The oil was purified by Biotage chromatography on silica gel loading the column
9. 9
   세척eluting with 5% ethyl acetate/hexane (200 ml)
10. 10
    온도increasing the percentage of ethyl acetate to 20%, 50% and 100%
11. 11
    기타to afford a white foam
12. 12
    기타The mixture was evaporated
13. 13
    기타the residue triturated with diethyl ether
14. 14
    기타to afford a white solid which
15. 15
    여과was filtered off
16. 16
    세척washed with diethyl ether
17. 17
    기타dried

실험 절차

A mixture of 4-chloro-1,2-dimethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (68 mg), 3-chloroaniline (0.05 ml) and methanesulfonic acid (0.03 ml) in dry 1,4-dioxan was heated under microwave conditions at 180° C. for fifteen minutes. The reaction mixture was transferred to a round bottom flask and evaporated. The residue was partitioned between ethyl acetate (10 ml) and saturated sodium bicarbonate solution and washed with saturated sodium bicarbonate solution and water. The organic layer was dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by Biotage chromatography on silica gel loading the column using dichloromethane and eluting with 5% ethyl acetate/hexane (200 ml) increasing the percentage of ethyl acetate to 20%, 50% and 100% to afford a white foam. The foam was dissolved in warm ethyl acetate and treated with 1M hydrochloric acid in diethyl ether. The mixture was evaporated, the residue triturated with diethyl ether to afford a white solid which was filtered off, washed with diethyl ether and dried to afford the title compound (59 mg).

출처