반응 #41755

반응 방정식

sodium thiocyanate

4-(chloromethyl)benzoylchloride

4-(4-(3-pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine

1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride

→

[4-(chloromethyl)phenyl]-N-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide

용매

acetone

acetone

acetone

반응 조건

후처리

1. 1
   농축The mixture was concentrated
2. 2
   농축The mixture was concentrated
3. 3
   기타partitioned between ethyl acetate and water
4. 4
   기타The organic layer was then dried
5. 5
   농축concentrated

실험 절차

A solution of sodium thiocyanate (1 eq) in acetone was added slowly in to a solution of 4-(chloromethyl)benzoylchloride (1 eq) in acetone at 0° C. The mixture was then filtered in to a solution of 4-(4-(3-pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine (1 eq) in acetone. Formation of N-acylthiourea was followed by LC/MS. The mixture was concentrated and taken in tetrahydrofuran and to it was added 1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride (2 eq) and stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was then dried and concentrated to yield [4-(chloromethyl)phenyl]-N-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide. It was taken in tetrahydrofuran and added methylpiperazine (4 eq) and stirred at ambient temperature for 16 h. The reaction mixture was concentrated and purified on preparative chromatography to yield {4-[(4-methylpiperazinyl)methyl]phenyl}-N-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide. MS: MH30 =520.

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