Reacción #7689

ord-e9942dd2878d4dca917c28cc1fed1a55

Ecuación de reacción

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
Rendimiento 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
Rendimiento 60.4%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07087609B2uspto-grants-2006_08