Pyridinium chloride → 8-[(4-Chloro-5-methoxy-2-methylphenyl)amino]thiazolo[4,5-g]quinoline-7-carbonitrile

HRID 989318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989318
O[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][S:14][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[C:24]([O:25][CH3:26])=[CH:23][C:21]([NH2:22])=[C:20]([CH3:27])[CH:19]=1.Cl.N1C=CC=CC=1>P(Cl)(Cl)(Cl)=O.CN(C)C=O>[Cl:17][C:18]1[C:24]([O:25][CH3:26])=[CH:23][C:21]([NH:22][C:2]2[C:11]3[CH:10]=[C:9]4[N:12]=[CH:13][S:14][C:8]4=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:15]#[N:16])=[C:20]([CH3:27])[CH:19]=1

Komponenten

6

Edukt 3

HCID 10176127Pyridinium chlorideHCID 123258794-Chloro-5-methoxy-2-methylanilineHCID 178510287HCID 178510287, Verbindung

Produkt 1

HCID 101778338-[(4-Chloro-5-methoxy-2-methylphenyl)amino]thiazolo[4,5-g]quinoline-7-carbonitrileAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

To a mixture of 100 mg (0.44 mmol) of 8-hydroxy[1,3]thiazolo[4,5-g]quinoline-7-carbonitrile in 5 mL of phosphoryl chloride is added five drops of N,N-dimethylformamide. The mixture is heated at reflux temperature for 30 minutes and then concentrated in vacuo. To the residue at 0° C. is added 50 mL of water. The solids are collected, washed with water, and dried in vacuo. To a mixture of this compound in 2 mL of 2-ethoxyethanol are added 76 mg (0.44 mmol) of 4-chloro-5-methoxy-2-methylaniline and 20 mg of pyridine hydrochloride. The mixture is refluxed for one hour and concentrated. The residue is chromatographed by silica gel chromatography, eluting with 9:1 methylene chloride/methanol to yield 26 mg (16%) of product as a dark oil.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 30 minutes
  3. concentrationconcentrated in vacuo
  4. additionTo the residue at 0° C. is added 50 mL of water
  5. customThe solids are collected
  6. washwashed with water
  7. customdried in vacuo
  8. additionTo a mixture of this compound in 2 mL of 2-ethoxyethanol
  9. temperatureThe mixture is refluxed for one hour
  10. concentrationconcentrated
  11. customThe residue is chromatographed by silica gel chromatography
  12. washeluting with 9:1 methylene chloride/methanol

Quellen und Nachweise

ORD-Eintrag
ord-6b522b5f0c2446869ebd722df2622806
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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