Thiophenol → 1-(1-Methylethyl)-N-[6-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide

HRID 244718ノート

反応式

HRID 244718 の反応式
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC=CC=3)(=O)=O)[N:9]=[CH:10][C:3]=12.C[N:21]1[CH:25]=[C:24](C)[C:23]([C:27]([NH:29][C:30]2[CH:38]=[C:37]([Sn](C)(C)C)[CH:36]=[C:35]3[C:31]=2[CH:32]=[N:33][N:34]3S(C2C=CC=CC=2)(=O)=O)=[O:28])=[N:22]1.[C:52]1(S)[CH:57]=CC=C[CH:53]=1>CN(C=O)C>[CH3:53][CH:52]([N:22]1[C:23]([C:27]([NH:29][C:30]2[CH:38]=[C:37]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[NH:8][N:9]=[CH:10][C:3]=34)[CH:36]=[C:35]3[C:31]=2[CH:32]=[N:33][NH:34]3)=[O:28])=[CH:24][CH:25]=[N:21]1)[CH3:57]

参加物

5

反応物 3

HCID 7969ThiophenolHCID 583564471,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamideHCID 673189474-Iodo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 583563451-(1-Methylethyl)-N-[6-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indazol-4-yl]-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-Iodo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine (69 mg) in DMF (0.4 ml) was added to 1,4-dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-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. 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, 9 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. customThe solvent was removed under a stream of nitrogen
  12. dissolutionthe residue was dissolved in DMSO (0.5 ml)
  13. custompurified by MDAP (method C)
  14. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-424c5cf71c5f41c3948d6ef67aa0d923
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

反応ノート

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