Reacción #1100118

Ecuación de reacción

NaBH4

trans-4-(4-methoxy-benzothiazol-2-yloxy)-cyclohexylamine

intermediate 25.b

trans-4-(4-methoxy-benzothiazol-2-yloxy)-cyclohexylamine

3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde

→

title compound

Rendimiento 16.4%

6-{[trans-4-(4-methoxy-benzothiazol-2-yloxy)-cyclohexylamino]-methyl}-4H-benzo[1,4]oxazin-3-one

Rendimiento 16.4%

Disolventes

MeOH

DCE

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 1 h
3. 3
   OtroThe reaction mixture was partitioned between DCM and NH4OH
4. 4
   SecadoThe organic layer was dried over MgSO4
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroPurification
7. 7
   Otroby chromatography (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether

Procedimiento

trans-4-(4-methoxy-benzothiazol-2-yloxy)-cyclohexylamine (0.5 mmol, intermediate 25.b) and 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.5 mmol) were dissolved in DCE (4 ml) and MeOH (4 ml). The mixture was stirred at RT overnight, NaBH4 (1 eq) was added and stirring continued for 1 h. The reaction mixture was partitioned between DCM and NH4OH. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Purification by chromatography (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether gave 36 mg (16%) of the title compound as a colourless solid.

Fuente