反応 #7689

ord-e9942dd2878d4dca917c28cc1fed1a55

反応方程式

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
収率 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
収率 60.4%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07087609B2uspto-grants-2006_08