Sodium Hydroxide → 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one

HRID 469259Notes

Reaction equation

HRID 469259 reaction equation
C([BH3-])#N.[Na+].[CH:5]1([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:30])[C:17]([CH:27]=[N:28][OH:29])=[CH:18][N:19]3[CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:31])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O1CCOCC1.Cl.[OH-].[Na+]>C1COCC1.CO>[CH:5]1([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:30])[C:17]([CH2:27][NH:28][OH:29])=[CH:18][N:19]3[CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:31])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 204431481,4-Dioxane hydrochlorideHCID 86633070HCID 86633070, compound

Product 1

HCID 866330717-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-oneYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

15 ml of methanol, 15 ml of THF and 250 mg of sodium cyanoborohydride were added to 300 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde oxime. 2 ml of a 4 M hydrogen chloride dioxane solution was added thereto under ice-cooling, followed by stirring at room temperature for 3 hours. Under ice-cooling, aqueous 1 M sodium hydroxide solution was added thereto, followed by extraction with chloroform and subsequent 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 130 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one.

Workup

  1. temperatureunder ice-cooling
  2. temperatureUnder ice-cooling
  3. extractionfollowed by extraction with chloroform
  4. washsubsequent washing with aqueous saturated sodium chloride
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddc53bc1906f42cbb7affb84e77c30a7
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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