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-3f84aaa80efa41e0b15a4df8dae3af7a

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000026B2