Реакция #68097

Уравнение реакции

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

Выход 19.2%

Растворители

chloroform

chloroform

ethyl acetate

acetic acid

methanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   Другоеthe organic layer was separated
3. 3
   Экстракцияthe aqueous layer was extracted with chloroform
4. 4
   Промывкаwashed sequentially with water and aqueous saturated sodium chloride solution
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was removed under reduced pressure
7. 7
   ДругоеThe residue thus obtained
8. 8
   Другоеwas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1], diethyl ether
9. 9
   workup.ADDITIONwas added to the foam
10. 10
    Другоеthus obtained
11. 11
    Фильтрацияthe resulting solid was filtered
12. 12
    Другоеto afford a yellow solid
13. 13
    Температураafter heating
14. 14
    Фильтрацияthe resulting solid was filtered

Методика

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.

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