Reaktion #7689

ord-e9942dd2878d4dca917c28cc1fed1a55

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 60.4%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087609B2uspto-grants-2006_08