Triethylamine → 7-(3-Amino-1-azetidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 868042Notes

Reaction equation

HRID 868042 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].CC([N:23]([CH:27]1[CH2:30][NH:29][CH2:28]1)C(=O)[O-])(C)C.C(N(CC)CC)C>C(#N)C>[NH2:23][CH:27]1[CH2:30][N:29]([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 86741236HCID 86741236, compound

Product 1

HCID 4614287-(3-Amino-1-azetidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 21.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.81 g (3.0 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 1.0 g (6.0 mmole) of 1,1-dimethylethyl-(3-azetidinyl)carbamate, 1.0 g (10 mmole) triethylamine and 50 ml of acetonitrile was heated at reflux 35 for four hours. The solvent was removed in vacuo and the residue was dissolved in 10 ml of trifluoroacetic acid. The solution was stirred at room temperature for one hour, the solvent was removed in vacuo and the residue dissolved in water. The turbid solution was clarified by filtration and the filtrate adjusted to pH 7.3 with 1.0N sodium hydroxide. The resulting precipitate was removed by filtration, washed successively with water, ethanol and ether. Drying in vacuo gave 0.2 g of 7-(3-amino-1-azetidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, mp 260°-262° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux 35 for four hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in 10 ml of trifluoroacetic acid
  5. customthe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. filtrationThe turbid solution was clarified by filtration
  8. customThe resulting precipitate was removed by filtration
  9. washwashed successively with water, ethanol and ether
  10. customDrying in vacuo

Sources & evidence

ORD record
ord-f02e995177f4440692c1edcf065998ec
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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