Hydrochloric Acid → 2-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione

HRID 469256Notes

Reaction equation

HRID 469256 reaction equation
[C:1](=[O:6])=[N:2][C:3](Cl)=[O:4].[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([CH2:29][NH:30][OH:31])=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:33])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1>[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([CH2:29][N:30]4[C:3](=[O:4])[NH:2][C:1](=[O:6])[O:31]4)=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:33])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 119708Isocyanatocarbonyl chlorideHCID 866330717-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one

Product 1

HCID 666369432-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.14 ml of N-(chlorocarbonyl) isocyanate was added dropwise at −50° C. to a 4 ml THF solution of 110 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one, followed by stirring at room temperature for 1 hour. 1 M hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 45 mg of 2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washwashing with aqueous saturated sodium chloride
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d82decd8c2ff4e959d88356f5f5d8121
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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