Reacción #48806

Ecuación de reacción

3-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

triethylamine

→

product

Rendimiento 73.0%

3-{[4-(Azetidin-1-ylcarbonyl)phenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

Rendimiento 73.0%

Disolventes

THF

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurged with argon (×3)
2. 2
   workup.ADDITIONPalladium on carbon (10% w/w, 52 mg) was added
3. 3
   Otroreaction mixture
4. 4
   Otrowas evacuated
5. 5
   workup.ADDITIONfinally filled with hydrogen gas
6. 6
   workup.WAITThe reaction mixture was left
7. 7
   FiltraciónThe Pd/C was filtered off
8. 8
   Otromixture partitioned between ethyl acetate and 1M hydrochloric acid solution
9. 9
   SecadoThe organic phase was dried (MgSO4)
10. 10
    Concentraciónthe filtrate concentrated in vacuo

Procedimiento

A solution of 3-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide (246 mg, 0.504 mmol) and triethylamine (0.42 mL, 3.02 mmol) in THF (6 mL) and methanol (6 mL) was evacuated and purged with argon (×3). Palladium on carbon (10% w/w, 52 mg) was added and reaction mixture was evacuated and finally filled with hydrogen gas. The reaction mixture was left to stir at ambient temperature under hydrogen for 2 hours. The Pd/C was filtered off and mixture partitioned between ethyl acetate and 1M hydrochloric acid solution. The organic phase was dried (MgSO4) and the filtrate concentrated in vacuo to give the product (170 mg, 73%).

Fuente