Réaction #41755

Équation de réaction

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

Solvants

acetone

acetone

acetone

Conditions de réaction

Traitement

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   ConcentrationThe mixture was concentrated
3. 3
   Autrepartitioned between ethyl acetate and water
4. 4
   AutreThe organic layer was then dried
5. 5
   Concentrationconcentrated

Mode opératoire

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.

Source