Potassium Carbonate → 5-chloro-4-[4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

HRID 1692221ノート

反応式

HRID 1692221 の反応式
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:22])=[C:6]([S:8]([N:11](COCC)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.ClC1C(F)=CC(F)=C(S(/N=C2/N=CN(COCC)C=C/2)(=O)=O)C=1.[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([C:55]2[N:59]([CH3:60])[N:58]=[CH:57][CH:56]=2)[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([O:54][C:51]2[CH:52]=[CH:53][C:48]([Cl:47])=[CH:49][C:50]=2[C:55]2[N:59]([CH3:60])[N:58]=[CH:57][CH:56]=2)=[CH:4][C:5]([F:22])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:9])=[O:10])[CH:7]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 59436509(NE)-5-chloro-N-[1-(ethoxymethyl)pyrimidin-4-ylidene]-2,4-difluorobenzenesulfonamide2 回HCID 594366195-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamideHCID 1355532144-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol

生成物 1

HCID 468415015-chloro-4-[4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamide収率 27%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 5-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamide and 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide and 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide (Preparation 719) used as a mixture of three regioisomers, (64 mg, 0.18 mmol), 4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol (Preparation 89) (37 mg, 0.18 mmol) and potassium carbonate (37 mg, 0.26 mmol) in dimethyl sulfoxide (1 mL) was stirred at room temperature for 19 hours then diluted with ethyl acetate (30 mL), washed with 1M aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was taken up in trifluoroacetic acid (1 mL) and stirred for 3 hours then concentrated in vacuo. The residue was purified by reverse phase HPLC to give 29 mg (27%) of the desired product as a white solid.

後処理

  1. washwashed with 1M aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. stirringstirred for 3 hours
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-a23cbd6f46d149fd888e4be2bb09e1ff
出典データセット
uspto-grants-2012_04
特許番号
US08153814B2

反応ノート

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