Triethylamine → 1-cyclopropyl-6,8-difluoro-7-{3-methyl-3-[N-(methyl)trifluoroacetamido]-1-azetidinyl}-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 275348Notes

Reaction equation

HRID 275348 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.[CH3:22][C:23]1([NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH2:26][NH:25][CH2:24]1.[CH2:34](N(CC)CC)C>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:25]4[CH2:24][C:23]([CH3:22])([N:27]([CH3:34])[C:28](=[O:33])[C:29]([F:32])([F:30])[F:31])[CH2:26]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 200879193-Methyl-3-trifluoroacetamidoazetidine hydrochloride

Product 1

HCID 100043701-cyclopropyl-6,8-difluoro-7-{3-methyl-3-[N-(methyl)trifluoroacetamido]-1-azetidinyl}-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.35 g (4.8 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.45 g (6.2 mmol) of 3-methyl-3-trifluoroacetamido-azetidine hydrochloride and 1 ml of triethylamine in 15 ml of pyridine is heated to reflux for 2 hours. The mixture is evaporated under vacuum, the residue is diluted with ice-cold water and filtered and the product is washed with water. 2.2 g of 1-cyclopropyl-6,8-difluoro-7-{3-methyl-3-[N-(methyl)trifluoroacetamido]-1-azetidinyl}-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting point 291°-4° C., are thereby obtained, which product is then hydrolysed by heating it in a mixture of 4 ml of 10% sodium hydroxide and 20 ml of water with 1 ml of ethanol for 1 hour. The mixture is filtered while hot, the filtrate is acidified with acetic acid, the resulting mixture is filtered and the product is washed with water. 1.57 g of 1-cyclopropyl- 6,8-difluoro-7-(3-methyl-3-methylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylic acid, melting point >300° C., are thereby obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2 hours
  3. customThe mixture is evaporated under vacuum
  4. additionthe residue is diluted with ice-cold water
  5. filtrationfiltered
  6. washthe product is washed with water

Sources & evidence

ORD record
ord-4cb724bbc7fd4d9b89a8fa53aeea0bfa
Source dataset
uspto-grants-1995_02
Patent number
US05393758

Reaction notes

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