1H-Imidazole-1-propanamine → 6-[3-(3-imidazol-1-yl-propylamino)propoxy]-1-methyl-1H-quinolin-2-one

3-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propionaldehyde (127.5 mg) prepared from 6-hydroxy-1-methylquinolin-2(1H)-one and N-(3-aminopropyl)imidazole (82.9 mg) were added to methanol (10 ml). The mixture was stirred at room temperature for 7 hours. The mixture was cooled to 0° C., and sodium borohydride(31.4 mg) was added thereto. The mixture was further stirred at room temperature overnight. Water was added to the reaction mixture and methanol was distilled off under reduced pressure. The residue was subjected to extraction using dichloromethane. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, and was condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound(21 mg) as a yellow oil.

1. temperatureThe mixture was cooled to 0° C.
2. stirringThe mixture was further stirred at room temperature overnight
3. distillationwas distilled off under reduced pressure
4. extractionThe residue was subjected to extraction
5. washThe organic layer was washed with saturated saline
6. dry with materialdried with anhydrous sodium sulfate
7. customcondensed under reduced pressure
8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=10:0→4:1)
9. customcondensed under reduced pressure

ORD record

ord-3cc86bdf62204fbebaf26adb61884ce3

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212187B2