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 83559ノート

反応式

HRID 83559 の反応式
[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

参加物

6

反応物 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

生成物 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}amide収率 44.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-936fbc13486245b59caa4e4e06fcff00
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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