Acetic Acid → 1-Cyclopropyl-6-fluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651396Notes

Reaction equation

HRID 1651396 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](Cl)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[OH:21][CH:22]1[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C.C(O)(=O)C>CS(C)=O.O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:24]4[CH2:25][CH:22]([OH:21])[CH2:23]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

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 483180Fluoroquinolonic acidHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 98834721-Cyclopropyl-6-fluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g (3.5 mmoles) of 1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 0.77 g (7.9 mmoles) of 3-hydroxyazetidine hydrochloride, 2.15 g (21.3 mmoles) of triethylamine is heated to 160° C. in 10 ml of dimethyl sulphoxide for 6 hours. The mixture is cooled, diluted with water and acidified with acetic acid. After filtering and recrystallising from dimethylformamide 0.3 g (27%) of 1-cyclopropyl-6-fluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 296°-8° C.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationAfter filtering
  3. customrecrystallising from dimethylformamide 0.3 g (27%) of 1-cyclopropyl-6-fluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  4. customare obtained

Sources & evidence

ORD record
ord-f54f4e9971e04f298d79ccd5db90a452
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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