Reacción #68097

Ecuación de reacción

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

Rendimiento 19.2%

Disolventes

chloroform

chloroform

ethyl acetate

acetic acid

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   Otrothe organic layer was separated
3. 3
   Extracciónthe aqueous layer was extracted with chloroform
4. 4
   Lavadowashed sequentially with water and aqueous saturated sodium chloride solution
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   OtroThe residue thus obtained
8. 8
   Otrowas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1], diethyl ether
9. 9
   workup.ADDITIONwas added to the foam
10. 10
    Otrothus obtained
11. 11
    Filtraciónthe resulting solid was filtered
12. 12
    Otroto afford a yellow solid
13. 13
    Temperaturaafter heating
14. 14
    Filtraciónthe resulting solid was filtered

Procedimiento

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.

Fuente