Pyridinium chloride → (4-Chloro-5-methoxy-2-methylphenylamino]thiazolo[4,5-g]quinoline-7-carbonitrile

HRID 2213754Notes

Reaction equation

HRID 2213754 reaction equation
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:13]2[S:14][C:8]3[C:9]([N:12]=2)=[CH:10][C:11]2[CH:2]=[C:3]([C:15]#[N:16])[CH:4]=[N:5][C:6]=2[CH:7]=3)=[C:20]([CH3:27])[CH:19]=1

Participants

6

Reactant 3

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

Product 1

HCID 86592755(4-Chloro-5-methoxy-2-methylphenylamino]thiazolo[4,5-g]quinoline-7-carbonitrileYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24813Phosphorus oxychlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0ffd05b107fc42699a4c7ba62c77b87d
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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