1,2-Dichloroethane → (S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide

HRID 7593

Reaction equation

HRID 7593 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[C:27]([C@@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1.C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH:33][C@H:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=4)[CH2:24][CH2:23]3)[CH:26]=2)[CH3:32])=[O:10])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 58680156(S)-1-[3-(4-Pyridin-2-ylpiperazin-1-yl)phenyl]ethylamine

Product 1

HCID 69591785(S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamideYield 60.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-e9942dd2878d4dca917c28cc1fed1a55
Source dataset
uspto-grants-2006_08
Patent number
US07087609B2

Linked notes

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