Water → (S)-5-Oxopyrrolidine-3-carboxylic acid{5-[3-chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-yl}amide

HRID 83559Notes

Reaction equation

HRID 83559 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[C:19]([NH2:28])[CH:18]=2)[CH:5]=[C:6]([CH2:8][O:9][C:10]([CH3:16])([CH3:15])[C:11]([F:14])([F:13])[F:12])[CH:7]=1.[O:29]=[C:30]1[NH:34][CH2:33][C@@H:32]([C:35](O)=[O:36])[CH2:31]1.CCN=C=NCCCN(C)C.Cl.O>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[C:19]([NH:28][C:35]([C@H:32]3[CH2:31][C:30](=[O:29])[NH:34][CH2:33]3)=[O:36])[CH:18]=2)[CH:5]=[C:6]([CH2:8][O:9][C:10]([CH3:15])([CH3:16])[C:11]([F:14])([F:12])[F:13])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25100087(S)-5-oxopyrrolidine-3-carboxylic acidHCID 866803815-[3-Chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamine

Product 1

HCID 71510671(S)-5-Oxopyrrolidine-3-carboxylic acid{5-[3-chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-yl}amideYield 44.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under argon atmosphere, to a solution of 5-[3-chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamine (62 mg) in N,N-dimethylacetamide (1 ml) were sequentially added (S)-5-oxopyrrolidine-3-carboxylic acid (26 mg) prepared according to the same procedures as Preparation 14, WSC.HCl (40 mg) at room temperature, and the mixture was stirred for 1 hour. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1). To the resulting solid were added water and a small amount of methanol, and the mixture was stirred. A solid was collected from this suspension by filtration, and was dried under reduced pressure to give the titled compound (35 mg).

Workup

  1. customprepared
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1)
  7. additionTo the resulting solid were added water
  8. stirringa small amount of methanol, and the mixture was stirred
  9. filtrationA solid was collected from this suspension by filtration
  10. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-936fbc13486245b59caa4e4e06fcff00
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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