Triethylamine → HCID 86748485, compound

HRID 275350Notes

Reaction equation

HRID 275350 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][N:23]([CH:30]1[CH2:33][NH:32][CH:31]1[CH3:34])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26].C(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:32]4[CH2:33][C@@H:30]([N:23]([CH3:22])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[C@@H:31]4[CH3:34])[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 20087916HCID 20087916, compound

Product 1

HCID 86748485HCID 86748485, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.6 g (9.2 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 2.57 g (11 mmol) of 3-[N-(methyl)trifluoroacetamido]-2-methylazetidine hydrochloride and 3 g (30 mmol) of triethylamine in 30 ml of pyridine is heated to reflux for 2 hours. The mixture is evaporated under vacuum, the residue is diluted with ice-cold water, the resulting mixture is filtered and the product is washed with water. 2.5 g are obtained. The product is recrystallized from acetonitrile. 2.25 g of 1-cyclopropyl-6,8-difluoro-7-{trans-3-[N-(methyl)trifluoroacetamido]-2-methyl-1-azetidinyl}-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting point 246°-9° C., are obtained. 1H NMR, δ,J=Hz[DMSO]; 14.1, (s, 1H); 8.6 (s, 1H); 7.75 (d, 1H, J=13 Hz); 4.5 (m, 5H); 3.2 (s, 3H). IR(KBr).-1730, 1704, 1627, 1466 cm-1.

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. filtrationthe resulting mixture is filtered
  6. washthe product is washed with water
  7. custom2.5 g are obtained
  8. customThe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-aca6cfd54d9f46c7962e9b3ab256b230
Source dataset
uspto-grants-1995_02
Patent number
US05393758

Reaction notes

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