Hydrochloric Acid → 4-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzoic acid

HRID 469220Notes

Reaction equation

HRID 469220 reaction equation
C(O)C.[OH-:4].[Na+].[CH:6]1([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:37])[C:18]([O:28][C:29]4[CH:36]=[CH:35][C:32]([C:33]#N)=[CH:31][CH:30]=4)=[CH:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:38])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.[OH2:40]>>[CH:6]1([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:37])[C:18]([O:28][C:29]4[CH:30]=[CH:31][C:32]([C:33]([OH:40])=[O:4])=[CH:35][CH:36]=4)=[CH:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:38])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 666368994-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzonitrile

Product 1

HCID 666370294-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzoic acid

Procedure

5.0 ml of ethanol and 1.5 ml of aqueous 6 M sodium hydroxide solution were added to 93 mg of 4-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzonitrile, followed by heating under reflux for 2 days. After cooling, the reaction system was neutralized with 1 M hydrochloric acid. Water was added and the solid precipitated was collected by filtration. By crystallizing the resulting solid from ethyl acetate-hexane, 65 mg of 4-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzoic acid was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 days
  3. temperatureAfter cooling
  4. customthe solid precipitated
  5. filtrationwas collected by filtration
  6. customBy crystallizing the resulting solid from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a5d1fc3eca9e46a9a0c46817001f9a43
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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