Реакция #10909

Уравнение реакции

2-bromo-1-(3-methylsulfanyl-phenyl)ethanone

1-(4-isothiocyanatophenyl)-4-methylpiperazine

cyanamide

potassium tert-butoxide

→

[4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](3-methylsulfanyl-phenyl)methanone

Выход 50.0%

Растворители

ethyl acetate

acetonitrile

t-butanol

Условия реакции

Обработка

1. 1
   workup.ADDITION0.49 g, 2.0 mmol) was added
2. 2
   Температураrefluxed for 15 minutes
3. 3
   Промывкаwashed in turn with saturated aqueous sodium carbonate and brine
4. 4
   СушкаThe dried (sodium sulfate) solution
5. 5
   Другоеwas evaporated
6. 6
   Другоеthe residue chromatographed on silica gel
7. 7
   ПромывкаElution of the desired product
8. 8
   Другоеwith 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane

Методика

To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 0.466 g, 2.0 mmol) and cyanamide (0.088 g, 2.1 mmol) in acetonitrile (3 mL) and t-butanol (5 ml), a solution of potassium tert-butoxide (2.0 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(3-methylsulfanyl-phenyl)ethanone (which can be prepared by the procedure of Rogers, N. H. et. al. EP 87953; 0.49 g, 2.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 15 minutes. The cooled mixture was diluted with ethyl acetate and washed in turn with saturated aqueous sodium carbonate and brine. The dried (sodium sulfate) solution was evaporated and the residue chromatographed on silica gel. Elution of the desired product with 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane provided 0.439 g (50% yield) of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](3-methylsulfanyl-phenyl)methanone. Mass spectrum (ES) MH+=440.

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