N-(2,6-Dichlorophenyl)thiourea → 8-[2-(2,6-dichlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970077

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH2:12])=[S:11].Br[CH2:14][C:15]([C:17]1[CH:26]=[CH:25][C:24]2[NH:23][C:22](=[O:27])[C:21]3[NH:28][CH:29]=[CH:30][C:20]=3[C:19]=2[CH:18]=1)=O.[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[S:11][CH:14]=[C:15]([C:17]2[CH:26]=[CH:25][C:24]3[NH:23][C:22](=[O:27])[C:21]4[NH:28][CH:29]=[CH:30][C:20]=4[C:19]=3[CH:18]=2)[N:12]=1.[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

87 mg (1.2 mmol) of (2,6-dichlorophenyl)-thiourea 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, 43 mg (26%) of 8-[2-(2,6-dichlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

Aufarbeitung

temperaturethe mixture is cooled to room temperature
customThe solvent is evaporated
customthe product is purified by preparative LCMS
customAfter drying

Quellen und Nachweise

ORD-Eintrag: ord-20ced089a63341a9b5b3cb03e85ad8fa
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08426437B2

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