Water → tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate

온도

80 °C

To a solution of tert-butyl (1-{4-[(6-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate (5.4 g, 8.9 mmol) in THF/MeOH (150 mL, 1:1), was added Pd on carbone (5% wet, 1 g). The mixture was stirred under hydrogen gas (1 atm) for 2 h. The mixture was filtered through celite and evaporated. The residue was dissolved in acetic acid (30 mL) and 2-aminonicotinaldehyde (1.1 g, 9.3 mmol) was added then the mixture was stirred at rt for 1 h. The mixture was heated at 80° C. for 1 h and the mixture was poured into water and neutralized with sodium hydroxide (20 g). The solid was collected by filtration and purified with silica gel column chromatography (hexane/ethyl acetate/methanol, 10:0:0 to 0:10:1) to give a pale orange solid. The solid was slurried in diethyl ether (200 mL) and collected to give the titled compound as a pale yellow solid (3.4 g, 62%).

1. filtrationThe mixture was filtered through celite
2. customevaporated
3. dissolutionThe residue was dissolved in acetic acid (30 mL)
4. stirringthe mixture was stirred at rt for 1 h
5. filtrationThe solid was collected by filtration
6. custompurified with silica gel column chromatography (hexane/ethyl acetate/methanol, 10:0:0 to 0:10:1)
7. customto give a pale orange solid
8. customcollected

ORD 기록

ord-63dbc8fddb0440409809109367003a16

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609688B2