Réaction #45007

Équation de réaction

NaHMDS

tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl) ethyl]pyrazole-1-carboxylate

methyl 4-[(4-fluoropiperidin-1-yl)methyl]benzoate

→

title compound

Rendement 16.4%

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-[(4-fluoropiperidin-1-yl)methyl]benzamide

Rendement 16.4%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   ConcentrationIt was then concentrated
2. 2
   Autrethe crude product was purified by reverse-phase prep
3. 3
   Autreevaporated

Mode opératoire

A solution of NaHMDS in THF (1 M, 0.65 ml, 0.65 mmol, 1.5 eq) was added dropwise at ambient temperature to a mixture of tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl) ethyl]pyrazole-1-carboxylate (150 mg, 0.43 mmol, 1 eq) and methyl 4-[(4-fluoropiperidin-1-yl)methyl]benzoate (131 mg, 0.52 mmol, 1.2 eq) in THF (0.5 ml). The reaction mixture was stirred at ambient temperature for 1 h. It was then concentrated and the crude product was purified by reverse-phase prep. HPLC (basic) using a 39-49% gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were taken and evaporated to afford the title compound as a colourless solid (33 mg, 16% yield).

Source