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

Temperature

80 °C

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.

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in 20 ml of dichloromethane
3. stirringthe mixture was stirred at room temperature for 0.5 h
4. stirringthe mixture was stirred at room temperature for 36 h
5. additionThe mixture was then diluted
6. washwashed with water, 1N aqueous hydrogen chloride solution and saturated aqueous sodium bicarbonate solution
7. customdried
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-d7222d60a7b1471f8cbe6eb4fc08638e

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946124B2