Thiobenzamide → HCID 86627596, Verbindung

HRID 1970080

Reaktionsgleichung

Reaktionsgleichung von HRID 1970080
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12]([C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[C:18]3[NH:25][CH:26]=[CH:27][C:17]=3[C:16]=2[CH:15]=1)=O.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]>C(O)C>[O:24]=[C:19]1[C:18]2[NH:25][CH:26]=[CH:27][C:17]=2[C:16]2[CH:15]=[C:14]([C:12]3[N:9]=[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[S:8][CH:11]=3)[CH:23]=[CH:22][C:21]=2[NH:20]1.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]

Komponenten

4

Edukt 2

HCID 683563ThiobenzamideHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Produkt 1

HCID 86627596HCID 86627596, VerbindungAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

54 mg (1.2 mmol) of thiobenzamide 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, 29 mg (21%) of 4-oxo-8-(2-phenyl-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-74dbf60bb4d24f90b9aacf5cadb06b38
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426437B2

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