Triethylamine → HCID 461441, compound

HRID 1632713Notes

Reaction equation

HRID 1632713 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].C(N(CC)CC)C.[S:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>CN(C)C=O>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:28]3[CH2:29][CH2:30][S:26][CH2:27]3)[N:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10444ThiazolidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 461441HCID 461441, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g (3.7 mmol) of 7-chloro-1,4-dihydro-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.8 g (8.0 mmol) of triethylamine, 1.1 g (12.0 mmol) of 97% thiazolidine in 30 ml of N,N-dimethylformamide was stirred at room temperature for 18 hours. The solvent was removed at reduced pressure and the residue dissolved in water using 1.0N sodium hydroxide to adjust to pH 12.0. The solution was filtered to remove a trace of insoluble material and the filtrate was acidified to pH=3.0 with 6.0N hydrochloric acid. The precipitate was removed by filtration, washed with water and the wet filter cake recrystallized from ethanol clarifying with charcoal to give 0.6 g of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(3-thiazolidinyl)-1,8-naphthyridine-3-carboxylic acid; mp 288°-289° C.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in water using 1.0N sodium hydroxide
  3. filtrationThe solution was filtered
  4. customto remove a trace of insoluble material
  5. customThe precipitate was removed by filtration
  6. washwashed with water
  7. customthe wet filter cake recrystallized from ethanol clarifying with charcoal

Sources & evidence

ORD record
ord-2ef090f4e8724337a5613c9ca90332b2
Source dataset
uspto-grants-1984_10
Patent number
US04477449

Reaction notes

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