Reacción #1929075

Ecuación de reacción

triethylamine

methyl 1-aminocyclohexanecarboxylate hydrochloride

(5-bromo-2-methylphenyl)acetic acid

thionyl chloride

→

Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}cyclohexanecarboxylate

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in 20 ml of dichloromethane
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 0.5 h
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 36 h
5. 5
   workup.ADDITIONThe mixture was then diluted
6. 6
   Lavadowashed with water, 1N aqueous hydrogen chloride solution and saturated aqueous sodium bicarbonate solution
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

2.06 g (9.00 mmol) of (5-bromo-2-methylphenyl)acetic acid (described in EP 1791816 and WO 2006/29799) were dissolved in 3.7 ml (51.3 mmol) of thionyl chloride. The reaction mixture was stirred at 80° C. for 2 h and then concentrated. The residue was dissolved in 20 ml of dichloromethane. 2.09 g (10.8 mmol) of methyl 1-aminocyclohexanecarboxylate hydrochloride were dissolved in 25 ml of dichloromethane, 55 mg (0.45 mmol) of 4-dimethylaminopyridine and 3.1 ml (22.5 mmol) of triethylamine were added and the mixture was stirred at room temperature for 0.5 h. The solution of the acid chloride was added dropwise, and the mixture was stirred at room temperature for 36 h. The mixture was then diluted with diluted with dichloromethane, washed with water, 1N aqueous hydrogen chloride solution and saturated aqueous sodium bicarbonate solution, dried, filtered and concentrated. This gave 2.80 g (84% of theory) of the title compound.

Fuente