Acryloyl chloride → HCID 67194447, compound

HRID 1841950Notes

Reaction equation

HRID 1841950 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:36](Cl)(=[O:39])[CH:37]=[CH2:38]>CN(C=O)C>[CH2:1]([NH:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:36](=[O:39])[CH:37]=[CH2:38])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 67195790HCID 67195790, compound

Product 1

HCID 67194447HCID 67194447, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Amino-benzenesulfonyl)-piperazine-1-carboxylic acid benzylamide (0.47 g, 1.25 mmol) was dissolved in DMF (10 ml). To this was added diisopropylethylamine (0.33 ml, 1.9 mmol) in one portion followed by the drop wise addition of acryloyl chloride (0.12 ml, 1.5 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. The THF was removed under vacuum and the resulting crude material was purified by column chromatography (elution: 50% heptane, 50% ethyl acetate to 100% ethyl acetate) to give the title compound (54 mg, 10% yield) as a white solid.

Workup

  1. customThe THF was removed under vacuum
  2. customthe resulting crude material was purified by column chromatography (elution: 50% heptane, 50% ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-ae5fdb350817450ca07ba9b583955f40
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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