7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → HCID 13772737, compound

HRID 1198574Notes

Reaction equation

HRID 1198574 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].[CH:19]1([N:22]2[CH2:26][CH2:25][CH:24]([CH2:27][NH2:28])[CH2:23]2)[CH2:21][CH2:20]1>C(#N)C>[CH:19]1([NH:22][CH2:23][CH:24]2[CH2:25][CH2:26][N:28]([C:2]3[N:11]=[C:10]4[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]4[CH2:12][CH3:13])=[CH:4][C:3]=3[F:18])[CH2:27]2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 191027441-(1-Cyclopropylpyrrolidin-3-yl)methanamine

Product 1

HCID 13772737HCID 13772737, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 cyclopropyl-3-pyrrolidinemethanamine in 50 mL of acetonitrile was heated at reflux for two hours. 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 6M hydrochloric acid. The resulting clear solution was lyophilized and the residue recrystallized from ethanol to give 600 mg of 7-[3-[(cyclopropylamino)methyl]-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -naphthyridine-3-carboxylic acid, mp 271°-274° C. as the hydrochloride.

Workup

  1. temperatureat reflux for two hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in water
  4. filtrationfiltered through a fiber glass pad
  5. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-96a42f45592245cfb8b665c9b8f725f0
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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