Triethylamine → 1-Cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651411Notes

Reaction equation

HRID 1651411 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:22][N:23]([CH3:28])[CH:24]1[CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:26]4[CH2:27][CH:24]([N:23]([CH3:28])[CH3:22])[CH2:25]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 22121220N,N-dimethylazetidin-3-amine dihydrochloride

Product 1

HCID 100431761-Cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Procedure

A mixture of 0.25 g (1.32 mmoles) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.34 g (12 mmoles) of 3-dimethylaminoazetidine dihydrochloride and 3.3 g (33 mmoles) of triethylamine is heated under reflux in 10 ml of pryidine for 2 hours. The mixture is evaporated under vacuum, water is added and the resulting mixture made alkaline with 1N sodium hydroxide, heated, filtered while hot, acidified with acetic acid and filtered again. After washing with water, 0.4 g (88%) of 1-cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 255°-61° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux in 10 ml of pryidine for 2 hours
  3. customThe mixture is evaporated under vacuum, water
  4. additionis added
  5. temperatureheated
  6. filtrationfiltered while hot,
  7. filtrationfiltered again
  8. washAfter washing with water, 0.4 g (88%) of 1-cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  9. customare obtained

Sources & evidence

ORD record
ord-b155683b214249d5ac0aec0dd0b8c0d3
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

Loading…