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Thiophenol → N-1H,1'H-4,6'-Biindazol-4'-yl-1-(1-methylethyl)-1H-pyrazole-5-carboxamide

HRID 244729
ノート
印刷プレビュー

反応式

HRID 244729 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2S(C1C=CC=CC=1)(=O)=O.[CH3:20][CH:21]([N:23]1[C:27]([C:28]([NH:30][C:31]2[CH:39]=[C:38]([Sn](C)(C)C)[CH:37]=[C:36]3[C:32]=2[CH:33]=[N:34][N:35]3S(C2C=CC=CC=2)(=O)=O)=[O:29])=[CH:26][CH:25]=[N:24]1)[CH3:22].C1(S)C=CC=CC=1>CN(C=O)C>[NH:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:38]3[CH:37]=[C:36]4[C:32]([CH:33]=[N:34][NH:35]4)=[C:31]([NH:30][C:28]([C:27]4[N:23]([CH:21]([CH3:20])[CH3:22])[N:24]=[CH:25][CH:26]=4)=[O:29])[CH:39]=3)[C:3]=2[CH:4]=[N:5]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7969ThiophenolHCID 58356336HCID 58356336、化合物HCID 583564014-Bromo-1-(phenylsulfonyl)-1H-indazole

生成物 1

HCID 44540058N-1H,1'H-4,6'-Biindazol-4'-yl-1-(1-methylethyl)-1H-pyrazole-5-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
135 °C

実験手順

4-Bromo-1-(phenylsulfonyl)-1H-indazole (61 mg) in DMF (0.4 ml) was added to 1-(1-Methylethyl)-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide (100 mg) in DMF (0.4 ml). Solvias catalyst (4 mg) was added and the sealed vessel was heated in the Anton Paar microwave at 135° C. for 20 min. PS-thiophenol resin was added and the reaction was stirred overnight before being filtered onto a C18SPE cartridge, pre-washed with 0.1% TFA, with acetonitrile. The cartridge was washed with 0.1% TFA in acetonitrile and the collected solvent was removed under a stream of nitrogen. The residue was dissolved in DMSO (1 ml) and purified by MDAP (method C). The solvent was evaporated in vacuo. The residue was dissolved in isopropanol (0.3 ml), 2M sodium hydroxide (aq) (0.3 ml) was added and the reaction was left at room temperature overnight, then heated to 60° C. for 2 h. The solvent was removed under a stream of nitrogen and the residue was dissolved in DMSO (0.5 ml) and purified by MDAP (method C). The solvent was evaporated in vacuo to give title compound, 15 mg.

後処理

  1. filtrationbefore being filtered onto a C18SPE cartridge
  2. washpre-washed with 0.1% TFA, with acetonitrile
  3. washThe cartridge was washed with 0.1% TFA in acetonitrile
  4. customthe collected solvent was removed under a stream of nitrogen
  5. dissolutionThe residue was dissolved in DMSO (1 ml)
  6. custompurified by MDAP (method C)
  7. customThe solvent was evaporated in vacuo
  8. dissolutionThe residue was dissolved in isopropanol (0.3 ml)
  9. addition2M sodium hydroxide (aq) (0.3 ml) was added
  10. waitthe reaction was left at room temperature overnight
  11. temperatureheated to 60° C. for 2 h
  12. customThe solvent was removed under a stream of nitrogen
  13. dissolutionthe residue was dissolved in DMSO (0.5 ml)
  14. custompurified by MDAP (method C)
  15. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-8450875b61214d61b4199e96d55d1f84
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658635B2

反応ノート

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