Iodoethane → N-[4-(4-Ethyl-piperazine-1-sulfonyl)-phenyl]-acrylamide

HRID 1841929Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.I[CH2:28][CH3:29]>CN(C=O)C>[CH2:28]([N:10]1[CH2:9][CH2:8][N:7]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:20][CH:21]=2)(=[O:14])=[O:15])[CH2:12][CH2:11]1)[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (0.2 g, 1.36 mmol) was added in one portion to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.1 g, 0.34 mmol) in DMF (5 ml). The mixture was stirred at room temperature for 5 minutes before iodoethane (0.03 ml, 0.44 mmol) was added drop wise and the resulting mixture heated to 60° C. and stirred under a nitrogen atmosphere for 18 hours. The crude reaction mixture was concentrated under vacuum and the residue was purified by Prep HPLC to give the title compound (0.015 g, 11% yield) as a white powder.

Workup

additionwas added drop wise
customThe crude reaction mixture
concentrationwas concentrated under vacuum
customthe residue was purified by Prep HPLC

Sources & evidence

ORD record: ord-5c7053487c934176b0019300b617b0d1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946197B2

Reaction notes

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