1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Cyclopropyl-6,8-difluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651410Notes

Reaction equation

HRID 1651410 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:23][N:24]([CH3:29])[CH:25]1[CH2:28][NH:27][CH2:26]1>C(N(CC)CC)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:27]4[CH2:28][CH:25]([N:24]([CH3:29])[CH3:23])[CH2:26]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 22121220N,N-dimethylazetidin-3-amine dihydrochloride

Product 1

HCID 103387331-Cyclopropyl-6,8-difluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.5 g (5.3 mmoles) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.4 g (8 mmoles) of 3-dimethylaminoazetidine dihydrochloride and 6.6 g of triethylamine is heated under reflux in 15 ml of pryidine for 3 hours. It is evaporated, water is added and the resulting mixture is made alkaline with 1N sodium hydroxide, heated, filtered while hot, acidified with acetic acid, and filtered. After washing with water, 1.7 g (88%) of 1-cyclopropyl-6,8-difluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 256°-60° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux in 15 ml of pryidine for 3 hours
  3. customIt is evaporated
  4. additionwater is added
  5. temperatureheated
  6. filtrationfiltered while hot,
  7. filtrationfiltered
  8. washAfter washing with water, 1.7 g (88%) of 1-cyclopropyl-6,8-difluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  9. customare obtained

Sources & evidence

ORD record
ord-a83293f3162d4da5b9201012a7945e43
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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