Reacción #68131

Ecuación de reacción

sodium cyanoborohydride

(2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine

sodium hydrogen carbonate

1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile

→

4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile

Rendimiento 44.7%

1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Rendimiento 44.7%

Disolventes

dichloromethane

ethanol

acetic acid

chloroform

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirred at the same temperature for 15 min
4. 4
   Otrothe organic layer was separated
5. 5
   Lavadowashed with aqueous saturated sodium chloride solution
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Otrothe solvent was removed under reduced pressure
8. 8
   OtroThe residue thus obtained
9. 9
   Otrowas purified by flash silica gel column chromatography [hexane:ethyl acetate=4:1]

Procedimiento

To a mixture of 3 mL of ethanol and 3 mL of dichloromethane solution containing 0.18 g of 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile, 1 mL of ethanol solution containing 0.13 g of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 0.30 g of molecular sieves 3A, and 45 μL of acetic acid were added at room temperature. After stirred at 40° C. for 1.5 hours, the mixture was cooled to the room temperature, 36 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 15 min. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, washed with 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 flash silica gel column chromatography [hexane:ethyl acetate=4:1], to give (A) 36 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a colorless oil and (B) 0.11 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a white foam.

Fuente