1,2-Dichloroethane → N-{4-[4-(3-Pyridin-3-yl-propionyl)-piperazine-1-sulfonyl]-phenyl}-acrylamide

HRID 1841928Notes

Reaction equation

HRID 1841928 reaction equation
C(N(CC)CC)C.[N:8]1([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][C:36](O)=[O:37])[CH:29]=1.C(Cl)CCl>C1COCC1>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][C:36]([N:11]2[CH2:10][CH2:9][N:8]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])=[CH:21][CH:22]=3)(=[O:15])=[O:16])[CH2:13][CH2:12]2)=[O:37])[CH:29]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 2596243-(Pyridin-3-yl)propanoic acidHCID 56953730N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide

Product 1

HCID 52939044N-{4-[4-(3-Pyridin-3-yl-propionyl)-piperazine-1-sulfonyl]-phenyl}-acrylamideYield 15.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.28 ml, 2.04 mmol) was added in one portion to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.2 g, 0.68 mmol) and 3-pyridine propionic acid (0.1 g, 0.68 mmol) in THF (5 ml). The mixture was stirred at room temperature for 5 minutes before EDC (0.26 g, 1.36 mmol) was added in one portion and the resulting mixture and stirred at room temperature under a nitrogen atmosphere for 18 hours. The crude reaction mixture was concentrated under vacuum and the resulting residue dissolved in DCM (20 ml), washed with water (20 ml), dried (MgSO4), filtered and concentrated under vacuum. The crude product was purified by Prep HPLC to give the title compound (0.046 g, 15% yield) as a white powder.

Workup

  1. additionwas added in one portion
  2. customThe crude reaction mixture
  3. concentrationwas concentrated under vacuum
  4. dissolutionthe resulting residue dissolved in DCM (20 ml)
  5. washwashed with water (20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified by Prep HPLC

Sources & evidence

ORD record
ord-a3428c1c8c9a4cfb83781b8c2f74015a
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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