반응 #68097

반응 방정식

sodium hydrogen carbonate

1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one

3-oxo-3,4-dihydro-2H-1,4-benzooxazine-6-carbaldehyde

sodium cyanoborohydride

→

6-(((1-(2-(7-methoxy-2-oxoquinoxaline-1-(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzooxazine-3(4H)-one

수율 19.2%

용매

chloroform

chloroform

ethyl acetate

acetic acid

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   기타the organic layer was separated
3. 3
   추출the aqueous layer was extracted with chloroform
4. 4
   세척washed sequentially with water and aqueous saturated sodium chloride solution
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   기타The residue thus obtained
8. 8
   기타was purified by silica gel column chromatography [eluent; chloroform:methanol=5:1], diethyl ether
9. 9
   workup.ADDITIONwas added to the foam
10. 10
    기타thus obtained
11. 11
    여과the resulting solid was filtered
12. 12
    기타to afford a yellow solid
13. 13
    온도after heating
14. 14
    여과the resulting solid was filtered

실험 절차

To 3.0 mL of a methanol solution containing 0.20 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one, 0.12 g of 3-oxo-3,4-dihydro-2H-1,4-benzooxazine-6-carbaldehyde, 38 μL of acetic acid and 83 mg of sodium cyanoborohydride were added at room temperature and stirred at the same temperature for 6.5 hours. To the reaction mixture, chloroform and aqueous saturated sodium hydrogen carbonate solution were added to be adjusted to pH 10.2, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=5:1], diethyl ether was added to the foam thus obtained, and the resulting solid was filtered to afford a yellow solid. To this solid, ethyl acetate and chloroform were added, the mixture was cooled to the room temperature after heating, and the resulting solid was filtered to give 59 mg of 6-(((1-(2-(7-methoxy-2-oxoquinoxaline-1-(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzooxazine-3(4H)-one a pale yellow solid.

출처