Pyridine → HCID 19978206, compound

HRID 1449516Notes

Reaction equation

HRID 1449516 reaction equation
N1C=CC=CC=1.Cl.[CH2:8]([C:11]1[N:15]2[CH2:16][CH2:17][CH2:18][N:19]=[C:14]2[S:13][C:12]=1[C:20]([Cl:22])=[O:21])[CH2:9][CH3:10].[CH3:23][NH:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=1.CN(C1C=CC=CN=1)C>O.CN(C)C=O>[ClH:22].[Cl:31][C:29]1[CH:30]=[C:25]([N:24]([CH3:23])[C:20]([C:12]2[S:13][C:14]3=[N:19][CH2:18][CH2:17][CH2:16][N:15]3[C:11]=2[CH2:8][CH2:9][CH3:10])=[O:21])[CH:26]=[C:27]([Cl:32])[CH:28]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 123777573,5-Dichloro-N-methylanilineHCID 19978122HCID 19978122, compound

Product 1

HCID 19978206HCID 19978206, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In the mixture of 30 ml of pyridine and 3 ml of dimethylformamide was suspended 938 mg of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride (described in Example 13). To the suspension was added 587 mg of N-methyl-3,5-dichloroaniline, and 40 mg of dimethylaminopyridine, followed by stirring at 70° C. for 18 hours. The reaction mixture was cocentrated and to the mixture was added water. The organic layer was extracted with chloroform. The extact was washed with 5% sodium hydrogencarbonate aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the solution was added saturated hydrogenchloride diethylether solution. The mixture was stirred at room temperature, followed by removing the solvent under reduced pressure. The residue was purified by column chromatography (silica gel: 45 g) using a mixed solvent of chloroform and methanol (20:1 by volume) as an eluent. The resulting substance was treated with saturated hydrogenchloride diethylether solution and recrystallized from a mixed solvent of ethanol and diethylether to obtain 461 mg of the titled compound.

Workup

  1. extractionThe organic layer was extracted with chloroform
  2. washThe extact was washed with 5% sodium hydrogencarbonate aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol
  6. additionTo the solution was added saturated hydrogenchloride diethylether solution
  7. stirringThe mixture was stirred at room temperature
  8. customby removing the solvent under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel: 45 g)
  10. additionThe resulting substance was treated with saturated hydrogenchloride diethylether solution
  11. customrecrystallized from a mixed solvent of ethanol and diethylether

Sources & evidence

ORD record
ord-2032b3c9ff04465b98fbf951b8e2e322
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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