Reacción #48844

Ecuación de reacción

DIPEA

4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

HATU

piperidine

→

desired compound

Rendimiento 71.2%

3-[(1S)-2-Hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(piperidin-1-ylcarbonyl)phenoxy]benzamide

Rendimiento 71.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated
2. 2
   workup.ADDITIONWater (30 mL) was added
3. 3
   Extracciónthe mixture extracted with ethyl acetate (3×15 mL)
4. 4
   LavadoThe combined organic extracts were washed with brine (30 mL)
5. 5
   Secadodried, (MgSO4),
6. 6
   Otroevaporated to a residue which
7. 7
   Otrowas chromatographed on silica
8. 8
   Lavadoeluting with a gradient of 0-20% methanol in ethyl acetate

Procedimiento

DIPEA (0.36 mL, 1.95 mmol) was added to a suspension of 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid (200 mg, 0.49 mmol), HATU (390 mg, 1.02 mmol) and piperidine (0.19 mL, 1.95 mmol) in DMF (3 mL) and the mixture stirred at, ambient temperature for 24 hours. The solvent was evaporated. Water (30 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with brine (30 mL), dried, (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-20% methanol in ethyl acetate, to give the desired compound (167 mg).

Fuente