Triethylamine → Methyl cis(+/-)-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-2-carboxylate

tert-Butyl cis(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1g) (25 mg, 0.06 mmol) was dissolved in methanol (3 mL). A 4 N hydrochloric acid/ethyl acetate solution (2 mL) was added, and the mixture was stirred at room temperature for one hour. Following concentration under reduced pressure, the residue was dissolved in NMP (0.5 mL). Triethylamine (9.81 mg, 0.1 mmol) and methyl 6-bromo-pyridine-2-carboxylate (13.96 mg, 0.06 mmol) were added, and the mixture was stirred using a microwave irradiation reactor at 150° C. for 10 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. Sodium chloride was added to the aqueous layer, followed by reextraction with ethyl acetate four times. The organic layers were combined and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol 40/1, 20/1, 10/1) to obtain 30.6 mg of the title compound.

1. concentrationconcentration under reduced pressure
2. dissolutionthe residue was dissolved in NMP (0.5 mL)
3. stirringthe mixture was stirred
4. customa microwave irradiation reactor at 150° C. for 10 minutes
5. extractionfollowed by extraction with ethyl acetate
6. additionSodium chloride was added to the aqueous layer
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentration under reduced pressure
9. customthe residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol 40/1, 20/1, 10/1)

ORD record

ord-1abb6b0e88224daeb0e86d6152010c8b

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927588B2