Reaktion #609304

Reaktionsgleichung

Ethanolamine

TPTU

5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

N,N-diisopropylethylamine

→

title compound

Ausbeute 48.0%

5-{[2-chloro-4-fluoro-5-(pyridin-2-yl)benzoyl]amino}-N-(2-hydroxyethyl)-1-phenyl-1H-Pyrazole-3-carboxamide

Ausbeute 48.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 2 hours
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   Sonstigethe resulting brown solid triturated with dichloromethane/TBME/heptane (4:2:0.5, 5 mL)
4. 4
   Sonstigeto give a white solid, which
5. 5
   Sonstigewas further triturated with MeOH (5 mL)

Vorschrift

TPTU (510 mg, 1.72 mmol) and 5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 108, 500 mg, 1.14 mmol) were dissolved in DMF (2.5 mL) at 0° C. N,N-diisopropylethylamine (0.6 mL, 3.43 mmol) was then added and the mixture stirred at 0° C. for 15 minutes. Ethanolamine (99.5 mL, 1.65 mmol) was then added and the mixture stirred at room temperature for 2 hours. The solvent was removed in vacuo and the resulting brown solid triturated with dichloromethane/TBME/heptane (4:2:0.5, 5 mL) to give a white solid, which was further triturated with MeOH (5 mL) to afford the title compound as a white solid (262 mg, 48%).

Quelle