Triethylamine → 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-3-quinolinecarboxylic acid

HRID 1651399Notes

Reaction equation

HRID 1651399 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].Cl.[CH3:21][C:22]1([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:24]3[CH2:25][C:22]([CH3:21])([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:23]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 200879193-Methyl-3-trifluoroacetamidoazetidine hydrochloride

Product 1

HCID 117435771-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-3-quinolinecarboxylic acidYield 37.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.1 g (4 mmoles) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.32 g (6 mmoles) of 3-methyl-3-trifluoroacetamidoazetidine hydrochloride and 0.8 g (8 mmoles) of triethylamine in 10 ml of pyridine is heated under reflux for 3 hours. Cooling, filtering and washing with water acidified with a little acetic acid yields 0.65 g (37%) of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-3-quinolinecarboxylic acid, melting at 196°-210° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureCooling
  3. filtrationfiltering
  4. washwashing with water

Sources & evidence

ORD record
ord-fbbbe28f3ea94a9eb0e5eba6e0e220e1
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

Loading…