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

HRID 980638Notes

Reaction equation

HRID 980638 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-94b135930e574e8681e27ccb0b155867
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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