Pyridine → HCID 19978206, Verbindung

HRID 1449516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449516
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 19978206HCID 19978206, VerbindungAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2032b3c9ff04465b98fbf951b8e2e322
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599813

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