Reacción #86178

Ecuación de reacción

tert-butyl 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate

2,2,2-trifluoroethyl trifluoromethanesulfonate

K2CO3

→

tert-butyl(±)-6-hydroxy-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Rendimiento 46.5%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of the reaction
2. 2
   Otrothe reaction mixture was quenched with EtOAc (100 mL)
3. 3
   Lavadowashed with brine (50 mL)
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel chromatography
7. 7
   Lavadoas eluting solvents

Procedimiento

A suspension of tert-butyl 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (150 mg, 0.32 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.48 mmol), and K2CO3 (87 mg, 0.64 mmol) in DMF (10 mL) was stirred at room temperature for 18 hours, which was monitored by LCMS. After completion of the reaction, the reaction mixture was quenched with EtOAc (100 mL), washed with brine (50 mL), dried over MgSO4, concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/EtOAc (1/1) as eluting solvents to afford tert-butyl(±)-6-hydroxy-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a white solid (82 mg, 46.5%). MS (ESI) m/z: 559 [M+H]+.

Fuente