Reacción #41767

Ecuación de reacción

4-bromophenyl acetic acid

oxalyl chloride

[4-(3,4-diaminophenoxy)(2-pyridyl)]-N-methylcarboxamide

triethyl amine

→

(4-{2-[(4-bromophenyl)methyl]-1-methylbenzimidazol-5-yloxy)-(2-pyridyl))-N-methylcarboxamide

Disolventes

dichoromethane

N,N-dimethyl formamide

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas then brought to ambient temperature
2. 2
   ConcentraciónThe mixture was concentrated and to it
3. 3
   workup.STIRRINGstirred for 2 h
4. 4
   ConcentraciónThe mixture was concentrated
5. 5
   Otropartitioned between ethyl acetate and water
6. 6
   SecadoThe organic layer was dried with sodium sulfate
7. 7
   Concentraciónconcentrated

Procedimiento

To 4-bromophenyl acetic acid (1 eq) in dichoromethane containing a drop of N,N-dimethyl formamide at 0° C. was added oxalyl chloride (1.2 eq). The resulting mixture was then brought to ambient temperature and stirred for 2 h. The mixture was concentrated and to it was added tetrahydrofuran and [4-(3,4-diaminophenoxy)(2-pyridyl)]-N-methylcarboxamide (1 eq) and triethyl amine (1 eq) and stirred for 2 h. Formation of the N-acylated product was followed by LC/MS. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated and taken in acetic acid and heated to 60° C. for 2 h. Preparative chromatography yielded (4-{2-[(4-bromophenyl)methyl]-1-methylbenzimidazol-5-yloxy)-(2-pyridyl))-N-methylcarboxamide. MS: MH+=451.

Fuente