Triethylamine → 1-(4-Fluorophenyl)-6-fluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651409Notes

Reaction equation

HRID 1651409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:19])=[C:15](F)[CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([OH:23])=[O:22])=[CH:9]2)=[CH:4][CH:3]=1.Cl.[CH3:25][C:26]1([NH:30]C(=O)C(F)(F)F)[CH2:29][NH:28][CH2:27]1.C(N(CC)CC)C>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:19])=[C:15]([N:28]4[CH2:29][C:26]([NH2:30])([CH3:25])[CH2:27]4)[CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([OH:23])=[O:22])=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104486226,7-Difluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 200879193-Methyl-3-trifluoroacetamidoazetidine hydrochloride

Product 1

HCID 104301641-(4-Fluorophenyl)-6-fluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.8 g (2.5 mmoles) of 1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.3 g (6 mmoles) of 3-methyl-3-trifluoroacetamidoazetidine hydrochloride and 1 g of triethylamine is heated under reflux in 20 ml of pyridine for 3 hours. The mixture is evaporated, and extracted with methylene chloride. Filtration and evaporation yield 1.1 g of 1-(4-fluorophenyl)-6-fluoro-7-(3-trifluoroacetamido-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting at 146°-151° C., which is subsequently hydrolysed in a manner similar to that in example 41, to obtain 0.5 g (56%) of 1-(4-fluorophenyl)-6-fluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting at 270°-6° C.

Workup

  1. temperatureis heated
  2. customThe mixture is evaporated
  3. extractionextracted with methylene chloride
  4. filtrationFiltration and evaporation yield 1.1 g of 1-(4-fluorophenyl)-6-fluoro-7-(3-trifluoroacetamido-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting at 146°-151° C., which

Sources & evidence

ORD record
ord-935c909ff03f40a088166da546a032d1
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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