7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → 7-[3-(N-acetyl-n-propylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
Reaction equation
[C:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2].Cl[C:14]1[N:23]=[C:22]2[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]2[CH2:24][CH3:25])=[CH:16][C:15]=1[F:30]>>[C:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH:5]1[CH2:9][CH2:8][N:7]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]3[CH2:24][CH3:25])=[CH:16][C:15]=2[F:30])[CH2:6]1)(=[O:3])[CH3:2]Participants
3
Procedure
3-(N-Acetyl-n-propylamino)pyrrolidine was allowed to react with 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid in the same manner as described above and yield 7-[3-(N-acetyl-n-propylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid. Subsequent hydrolysis of this compound with hydrochloric acid gave 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-N-propylamino-1-pyrrolidinyl)-1,8-naphthyridine-3-carboxylic acid hydrochloride, m.p. about 270° C. (decomp.).
Sources & evidence
- ORD record
- ord-2f199381f0e642d0b6e245e106b349ea
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04341784
Reaction notes
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