Water → 6-[(2-Aminoethyl)amino]-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Temperature

115 °C

7-Chloro-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-quinoline-3-carboxylic acid (56.3 g) and ethylenediamine (36 g) were dissolved in N,N-dimethylacetamide (650 mL) at 100° C. and stirred for 8.5 h at 115° C. Water (700 mL) was added to the reaction mixture cooled at room temperature. The reaction mixture was stirred at room temperature for 2 h, cooled at 0-5° C. and stirred for 1 h. The precipitate obtained was filtered, washed with cold water, cold EtOH, and dried at 110° C. under reduced pressure for 1 h. The crude product was treated with HCl (6% aqueous solution) heating for 1 h in the presence of charcoal. After filtration, the solution was cooled to 35-40° C. and a first precipitation happened. The precipitate was filtered, washed with water and dried at 110° C. for 1 h. The title compound (6.4 g) was obtained as the hydrochloride salt. The hydrochloride salt was then converted to the free base using standard conditions; ESMS m/z 320 [M−H]−.

1. temperaturecooled at room temperature
2. stirringThe reaction mixture was stirred at room temperature for 2 h
3. temperaturecooled at 0-5° C.
4. stirringstirred for 1 h
5. customThe precipitate obtained
6. filtrationwas filtered
7. washwashed with cold water, cold EtOH
8. customdried at 110° C. under reduced pressure for 1 h
9. additionThe crude product was treated with HCl (6% aqueous solution)
10. temperatureheating for 1 h in the presence of charcoal
11. filtrationAfter filtration
12. temperaturethe solution was cooled to 35-40° C.
13. customa first precipitation
14. filtrationThe precipitate was filtered
15. washwashed with water
16. customdried at 110° C. for 1 h

ORD record

ord-79cc89808a514931b9266ca40aaf51c1

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569550B2