Dimethyl Sulfoxide → 7-Benzylthio-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile

HRID 1837361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837361
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH3:20])=[CH:14][C:13]=1[NH:21][C:22]1[C:31]2[C:26](=[CH:27][C:28](F)=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]=1[C:35]#[N:36].CS(C)=O>O1CCCC1>[CH2:3]([S:10][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([NH:21][C:13]3[CH:14]=[C:15]([O:19][CH3:20])[C:16]([Cl:18])=[CH:17][C:12]=3[Cl:11])=[C:23]([C:35]#[N:36])[CH:24]=[N:25]2)=[CH:30][C:29]=1[O:32][CH3:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 7509Benzyl mercaptan2×HCID 24758Sodium hydride2×HCID 114861534-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile

Produkt 1

HCID 104359117-Benzylthio-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrileAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of sodium hydride (169 mg, 4.2 mmol), benzyl mercaptan (145 mg, 1.2 mmol) and 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (250 mg, 0.64 mmol) in 1 mL of tetrahydrofuran is heated at 70° C. for 1 hour, then stirred at room temperature overnight. Upon addition of 1 mL of dimethyl sulfoxide a solution is obtained. Additional amounts of sodium hydride and benzyl mercaptan are added and the reaction mixture is heated at 100° C. The reaction mixture is partitioned between ethyl acetate and water. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by preparative thin layer chromatography, eluting with 1:2 ethyl acetate:hexane to provide 150 mg of 7-benzylthio-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile, mp 123-125° C.

Aufarbeitung

  1. customis obtained
  2. temperaturethe reaction mixture is heated at 100° C
  3. customThe reaction mixture is partitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by preparative thin layer chromatography
  8. washeluting with 1:2 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a307688d18ac46a8b7d0c05e6205d349
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780996B2

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