Реакция #499516

Уравнение реакции

5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

1-adamantyl isothiocyanate

triethylamine

N,N-dimethylformamide

→

title compound

1-(Adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)urea

Условия реакции

Обработка

1. 1
   workup.WAITat 80° C. for 4.5 hours
2. 2
   КонцентрированиеThe reaction mixture was concentrated
3. 3
   Другоеpartitioned between ethyl acetate and water
4. 4
   ПромывкаThe extract was washed with saturated aqueous sodium chloride solution
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was chromatographed on a silica gel column
8. 8
   Другоеn-hexane=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate

Методика

A mixture of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), 1-adamantyl isothiocyanate (284 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 4.5 hours, at 50° C. for 2.5 hours and then at 80° C. for 4.5 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate to afford the title compound (192 mg, mp 164.0-166.6° C.).

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