4-Amino-1,2,2,6,6-pentamethylpiperidine → 4-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamide

A solution of 5,6-dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazole (0.8 g, 2,36 mmol), prepared as described in Preparation 6,1-hydroxybenzotriazole (0.32 g, 2.36 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.56 g, 2.9 mmol) in 80 ml of DMF/THF (50:50) was refluxed for 5 h. A solution of 1,2,2,6,6-pentamethyl-4-aminopiperidine (0.5 g, 2.9 mmol) in THF (5 ml) was added dropwise and the reaction was refluxed for additional 3 h. After cooling, solvent was removed under reduced pressure and the residue was treated with 1N NaOH (10 ml) and extracted with dichloromethane (50 ml). The organic layer was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated with diisopropyl ether (150 ml), stirred for 1 h, filtered to give 0.55 g of the title compound (yield 47.6%), mp=285–286° C.

1. temperaturewas refluxed for 5 h
2. temperaturethe reaction was refluxed for additional 3 h
3. temperatureAfter cooling
4. customsolvent was removed under reduced pressure
5. additionthe residue was treated with 1N NaOH (10 ml)
6. extractionextracted with dichloromethane (50 ml)
7. washThe organic layer was washed with water
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customThe residue was triturated with diisopropyl ether (150 ml)
12. filtrationfiltered

ORDレコード

ord-af7ad8f0a1dc42b390a8d59218c54b8b

出典データセット

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07220769B2