N,N'-Dimethylethylenediamine → 1-(4-Fluoro-phenyl)-6-methanesulfonyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 1677709ノート

反応式

HRID 1677709 の反応式
[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21](Br)[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CNCCNC.[CH3:39][S:40]([O-:42])=[O:41].[Na+]>[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O.CS(C)=O>[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21]([S:40]([CH3:39])(=[O:42])=[O:41])[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

参加物

6

反応物 3

HCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

生成物 1

HCID 581387781-(4-Fluoro-phenyl)-6-methanesulfonyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

試薬・触媒・溶媒 2

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.07 g, 0.1 mmol), copper(II) triflate (0.05 g, 0.1 mmol), N,N′-dimethylethylenediamine (0.04 mL, 0.4 mmol), sodium methanesulfinate (0.02 g, 0.2 mmol) was charged in a sealed tube with DMSO (5 mL). The tube was capped and the solution was degassed with argon for 5 minutes. The mixture was heated in a microwave at 110° C. for 40 minutes and cooled to room temperature. The solution was diluted with ethyl acetate (30 mL) and washed with saturated aqueous ammonium chloride (10 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL) and dried over sodium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-50% ethyl acetate in hexanes to afford the title compound.

後処理

  1. customThe tube was capped
  2. customthe solution was degassed with argon for 5 minutes
  3. temperaturecooled to room temperature
  4. additionThe solution was diluted with ethyl acetate (30 mL)
  5. washwashed with saturated aqueous ammonium chloride (10 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 20-50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-bc423bf22d124f568d4bf104b1d01f83
出典データセット
uspto-grants-2011_08
特許番号
US08008327B2

反応ノート

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