HCID 10044233, compound → HCID 10360184, compound

HRID 1651386Notes

Reaction equation

HRID 1651386 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:18][CH:17]([C:19](=O)[NH2:20])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1>C(OC(=O)C)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 10044233HCID 10044233, compound

Product 1

HCID 10360184HCID 10360184, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 0.57 g (1.5 mmoles) of 1-cyclopropyl-6,8-difluoro-7-(3-carbamoyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (example 6) in 12 ml of acetic anhydride is heated under reflux for 24 hours. Cooling, filtering and washing with water and ethanol yield 0.15 g (27%) of 1-cyclopropyl-6,8-difluoro-7-(3-cyano-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at >325° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureCooling
  3. filtrationfiltering
  4. washwashing with water and ethanol yield 0.15 g (27%) of 1-cyclopropyl-6,8-difluoro-7-(3-cyano-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at >325° C.

Sources & evidence

ORD record
ord-60c508058cc047e0afa4bb7a09cc3b85
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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