Water → 3-(3-but-3-enyl-2-oxo-pyrrolidin-1-yl)-N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-propanamide

HRID 929320Notes

Reaction equation

HRID 929320 reaction equation
[CH2:1]([CH:5]1[CH2:9][CH2:8][NH:7][C:6]1=[O:10])[CH2:2][CH:3]=[CH2:4].[H-].[Na+].[Cl:13][C:14]1[C:18]([N:19]([CH2:25][CH3:26])[C:20](=[O:24])[CH2:21][CH2:22]I)=[CH:17][N:16]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:15]=1.O>CN(C=O)C>[CH2:1]([CH:5]1[CH2:9][CH2:8][N:7]([CH2:22][CH2:21][C:20]([N:19]([C:18]2[C:14]([Cl:13])=[N:15][N:16]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:17]=2)[CH2:25][CH3:26])=[O:24])[C:6]1=[O:10])[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 149746223-(3-Buten-1-YL)-2-pyrrolidinoneHCID 118023001HCID 118023001, compound

Product 1

HCID 1180234813-(3-but-3-enyl-2-oxo-pyrrolidin-1-yl)-N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 3-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylpropan amide (0.500 g, 1.60 mmol) in acetone (8 mL) was added sodium iodide (0.359 g, 2.40 mmol). The reaction was heated to reflux for 24 hours. The reaction product was filtered and concentrated to provide N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-iodopropanamide (0.363 g, 0.898 mmol), which was used immediately without further purification. To 3-(but-3-en-1-yl)pyrrolidin-2-one (0.125 g, 0.898 mmol) dissolved in DMF (4.49 ml) was added sodium hydride (60% in mineral oil, 0.0360 g, 0.898 mmol). The reaction stirred for 45 minutes. Then, N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-iodopropanamide (0.363 g, 0.898 mmol) was added as a solution in DMF (2 mL). The reaction mixture was allowed to stir at room temperature overnight. The reaction product was poured into water, extracted with diethyl ether, and washed with brine. The organics were dried and concentrated to give an oil that was purified by flash column chromatography using 0-60% acetone/hexanes as eluent providing the title compound as a clear, colorless oil. (0.257 g, 69%).

Workup

  1. customwas used immediately without further purification
  2. stirringto stir at room temperature overnight
  3. extractionextracted with diethyl ether
  4. washwashed with brine
  5. customThe organics were dried
  6. concentrationconcentrated
  7. customto give an oil that
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-34f99688bdc6451f866432753aee1315
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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