Réaction #7689

ord-e9942dd2878d4dca917c28cc1fed1a55

Équation de réaction

O=C(O)C=Cc1ccc(F)cc1
4-fluorocinnamic acid
C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1
(S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine
ClCCCl
EDC
CCN(CC)CC
triethylamine
C[C@H](NC(=O)C=Cc1ccc(F)cc1)c1cccc(N2CCN(c3ccccn3)CC2)c1
title compound
Rendement 60.4%
C[C@H](NC(=O)C=Cc1ccc(F)cc1)c1cccc(N2CCN(c3ccccn3)CC2)c1
(S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide
Rendement 60.4%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1)

Mode opératoire

A solution of 4-fluorocinnamic acid (17 mg, 0.1 mmol), (S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine (24 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), DMAP (12 mg, 0.1 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (2 ml) was stirred at room temperature for 14 h. The reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1) to give the title compound as a solid (26 mg, 60% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07087609B2uspto-grants-2006_08