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

HRID 244729
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244729
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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 58356336HCID 58356336, VerbindungHCID 583564014-Bromo-1-(phenylsulfonyl)-1H-indazole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8450875b61214d61b4199e96d55d1f84
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658635B2

Notizen zur Reaktion

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