Thiomorpholine → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-1,8-naphthyridine-3-carboxylic acid

HRID 1632714Notes

Reaction equation

HRID 1632714 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].[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1>C(#N)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]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

HCID 67164ThiomorpholineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 133406311-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-1,8-naphthyridine-3-carboxylic acidYield 38.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.271 g (1.0 mmol) of 7-chloro-1,4-dihydro-1-ethyl-6-fluoro-4-oxo,1,8-naphthyridine-3-carboxylic acid, 0.316 g (3.0 mmol) of thiomorpholine and 30 ml of acetonitrile was heated at reflux for 18 hours. The solvent was removed in vacuo and the residue was recrystallized from aqueous ethanol to give 130 mg of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-1,8-naphthyridine-3-carboxylic acid; mp 241°-243° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-86e9f93439e447bd8ae34d7a79f29d26
Source dataset
uspto-grants-1984_10
Patent number
US04477449

Reaction notes

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