1-Phenylthiosemicarbazide → HCID 86627597, Verbindung

HRID 1970081

Reaktionsgleichung

Reaktionsgleichung von HRID 1970081
[C:1]1([NH:7][NH:8][C:9]([NH2:11])=[S:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:13][C:14]([C:16]1[CH:25]=[CH:24][C:23]2[NH:22][C:21](=[O:26])[C:20]3[NH:27][CH:28]=[CH:29][C:19]=3[C:18]=2[CH:17]=1)=O.[CH2:30]([C:32]([O-:34])=[O:33])[CH3:31]>C(O)C>[O:26]=[C:21]1[C:20]2[NH:27][CH:28]=[CH:29][C:19]=2[C:18]2[CH:17]=[C:16]([C:14]3[N:11]=[C:9]([NH:8][NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:10][CH:13]=3)[CH:25]=[CH:24][C:23]=2[NH:22]1.[CH2:30]([C:32]([O-:34])=[O:33])[CH3:31]

Komponenten

4

Edukt 2

HCID 27810941-PhenylthiosemicarbazideHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Produkt 1

HCID 86627597HCID 86627597, VerbindungAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

66 mg (1.2 mmol) of 1-phenylthiosemicarbazide is added to a suspension of 124 mg (0.33 mmol) of 8-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3.5 mL of ethanol. The mixture is stirred at 90° C. for 6 hours then the mixture is cooled to room temperature. The solvent is evaporated, then the product is purified by preparative LCMS. After drying, 62 mg (42%) of 4-oxo-8-[2-(N′-phenyl-hydrazino)-thiazol-4-yl]-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

Aufarbeitung

  1. temperaturethe mixture is cooled to room temperature
  2. customThe solvent is evaporated
  3. customthe product is purified by preparative LCMS
  4. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-4d7f1c760d5b41cf994c4a0946a57eca
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426437B2

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