7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → 1-Ethyl-6-fluoro-7-[3-[(isopropylamino)methyl]pyrrolidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
Reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[CH3:19][CH:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:21]>C(#N)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:26]3[CH2:27][CH2:28][CH:24]([CH2:23][NH:22][CH:20]([CH3:21])[CH3:19])[CH2:25]3)[N:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A near solution of 0.82 g (3.0 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and 1.4 g (10 mmole) of N-(2-propyl)-3-pyrrolidinemethanamine in 50 ml of acetonitrile was heated at reflux for one hour. The solvent was removed in vacuo, the residue dissolved in water, filtered through a fiber glass pad to clarify and the filtrate adjusted to pH 2.0 with 6 M hydrochloric acid. The resulting clear solution was lyophilized and the residue recrystallized from ethanol to give 200 mg of 1-ethyl-6-fluoro-1,4-dihydro-7-[3-[[(1-methylethyl)amino]methyl]-1-pyrrolidinyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid, mp 302°-304° C. as the hydrochloride.
Workup
- temperatureat reflux for one hour
- customThe solvent was removed in vacuo
- dissolutionthe residue dissolved in water
- filtrationfiltered through a fiber glass pad
- customthe residue recrystallized from ethanol
Sources & evidence
- ORD record
- ord-71cbc4b03ed945b88e5a1eb38319f317
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04665079
Reaction notes
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