Reacción #72886

Ecuación de reacción

N-methylhydroxylamine hydrochloride

triethylamine

potassium 8-(cyclopentylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

oxalyl chloride

→

title compound

Rendimiento 199.8%

8-(cyclopentylamino)-N-hydroxy-N,1-dimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Rendimiento 199.8%

Disolventes

—

same solvent

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added at 0° C
2. 2
   Otroevaporated
3. 3
   workup.DISSOLUTIONredissolved in anhydrous dichloromethane
4. 4
   Temperaturacooled to 0° C
5. 5
   LavadoAfter 4 hours the mixture was washed with a saturated solution of sodium hydrogenocarbonate
6. 6
   Secadodried over sodium sulfate
7. 7
   Otroevaporated to dryness
8. 8
   OtroThe residue was triturated with diethylether
9. 9
   Filtraciónfiltered

Procedimiento

To a suspension of 400 mg (1.14 mmol) of potassium 8-(cyclopentylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in 80 mL of dichloromethane and a few drops of dimethylformamide 0.11 mL (0.13 mmol) of oxalyl chloride were added at 0° C. The mixture was stirred at room temperature for 6 hours and then evaporated, redissolved in anhydrous dichloromethane and dropped into a solution of 344 mg (2.28 mmol) of N-methylhydroxylamine hydrochloride and 0.33 mL of triethylamine in 20 mL of the same solvent, cooled to 0° C. After 4 hours the mixture was washed with a saturated solution of sodium hydrogenocarbonate, dried over sodium sulfate and evaporated to dryness. The residue was triturated with diethylether and filtered to give 780 mg (60% yield) of the title compound.

Fuente