Pentylamine → HCID 178446446, Verbindung

HRID 1071784

Reaktionsgleichung

Reaktionsgleichung von HRID 1071784
[NH2:1][NH:2][C:3]([NH2:5])=S.I(OC)(=O)=O.CS/C(/N)=N/N.I.[CH2:18]([NH2:23])[CH2:19][CH2:20][CH2:21][CH3:22].I.CCCC(NNC(N)=N)C.[C:35]([C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]([S:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)(=[O:49])=[O:48])[CH:39]=1)(=O)[CH3:36]>C(O)C.CO.C(O)(C)C.Cl>[CH2:18]([NH:23][C:3]([NH:2][N:1]=[C:35]([C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]([S:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)(=[O:48])=[O:49])[CH:39]=1)[CH3:36])=[NH:5])[CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

11

Edukt 6

HCID 8060PentylamineHCID 8485351H-Indole, 3-acetyl-1-(phenylsulfonyl)-HCID 2723789ThiosemicarbazideHCID 6508896Methyl hydrazinecarbimidothioate hydroiodideHCID 13203471Methyl iodateHCID 178446846HCID 178446846, Verbindung

Produkt 1

HCID 178446446HCID 178446446, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of thiosemicarbazide (2.73 g, 30 mmol) in ethanol is treated with methyl iodate (1.96 mL, 31.5 mmol), heated at 60° C. for 1 h, cooled to room temperature, stored at −20° C. for 18 h and filtered. The filtercake is washed with cold ethanol and dried in vacuo. The thus-obtained S-methylisothiosemicarbazide hydrogen iodide (46.6 mg, 0.2 mmol) is dissolved in methanol, treated with pentylamine (24 μL, 0.22 mmol), heated at 60° C. for 2 h, cooled to room temperature and concentrated in vacuo. The resultant residue, 4-pentylaminoguanidine hydrogen iodide (0.2 mmol), is suspended in isopropanol, added to a suspension of 3-acetyl-N-(phenylsulfonyl) indole (59 mg, 0.2 mmol) in isopropanol and concentrated HCl (50 μL), heated at 80° C. for 4 h, cooled to room temperature and concentrated in vacuo to give a residue. This residue is purified by HPLC to give the title product, 17.9 mg (21% yield), identified by HPLC and mass spectral analyses, (M+H) 426; retention time 4.75 min.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filtercake is washed with cold ethanol
  4. customdried in vacuo
  5. temperatureheated at 60° C. for 2 h
  6. temperaturecooled to room temperature
  7. concentrationconcentrated in vacuo
  8. temperatureheated at 80° C. for 4 h
  9. temperaturecooled to room temperature
  10. concentrationconcentrated in vacuo
  11. customto give a residue
  12. customThis residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a4cbb51dc60f458c8fe0f1f39db9aaea
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906095B2

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