Reacción #2000303

Ecuación de reacción

6-cis-(4-amino-cyclohexyloxy)-7-chloro-2H-isoquinolin-1-one hydrochloride

6-(cis-4-amino-cyclohexyloxy)-7-chloro-isoquinolin-1-ol hydrochloride

sodium cyanoboro hydride

triethyl amine

acetic acid

→

cis-6-(4-Amino-cyclohexyloxy)-2H-isoquinolin-1-one

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato heat the mixture to 70° C.
2. 2
   FiltraciónFor the isolation of the products the solution was filtered
3. 3
   Otrothe solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   Lavadowashed with 1 N NaOH and sat. sodium chloride solution
6. 6
   Secadodried with magnesium sulfate
7. 7
   Otroevaporated
8. 8
   Otroif obtained
9. 9
   Otrowere purified by preparative HPLC
10. 10
    Otroprecipitated from methanolic HCl

Procedimiento

150 mg (0.46 mmol) of 6-cis-(4-amino-cyclohexyloxy)-7-chloro-2H-isoquinolin-1-one hydrochloride (10) were dissolved in 10 ml of methanol. After addition of molecular sieves 4 A, 92.3 mg (0.57 mmol) of triethyl amine, 273.8 mg (4.56 mmol) of acetic acid and 0.57 mmol of the corresponding aldehyde, a solution of 86.0 mg (1.37 mmol) of sodium cyanoboro hydride is added dropwise and the mixture is stirred at room temperature until complete conversion is achieved. In some cases it was necessary to heat the mixture to 70° C. to achieve complete conversion. For the isolation of the products the solution was filtered and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane, washed with 1 N NaOH and sat. sodium chloride solution, dried with magnesium sulfate and evaporated. The mono- or bis alkylated products, if obtained, were purified by preparative HPLC or precipitated from methanolic HCl

Fuente