Ammonium Chloride → 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 469202Notes

Reaction equation

HRID 469202 reaction equation
ClC(OCC(C)C)=O.[CH:9]1([NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[C:21]([C:31]([OH:33])=O)=[CH:22][N:23]3[CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][C:17]=2[F:35])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl.[CH3:37][NH:38][O:39][CH3:40].[Cl-].[NH4+]>C(Cl)(Cl)Cl.ClCCl.C(N(CC)CC)C>[CH:9]1([NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[C:21]([C:31]([N:38]([O:39][CH3:40])[CH3:37])=[O:33])=[CH:22][N:23]3[CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][C:17]=2[F:35])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 666369197-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 866330497-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamideYield 85.2%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

0.87 ml of triethylamine and 0.4 ml of isobutyl chloroformate were added to a 20 ml of dichloromethane solution of 1.0 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid at 0° C., followed by stirring at 0° C. for 30 minutes. Then, 315 mg of N,O-dimethylhydroxylamine hydrochloride was added thereto, followed by stirring at room temperature for 1 hour. Chloroform and aqueous saturated ammonium chloride were added to the reaction mixture, the layers were separated, and the organic layer was washed with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate and subsequent filtration, the solvent was evaporated under a reduced pressure. By purifying the resulting residue by silica gel column chromatography, 950 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide was obtained.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customthe layers were separated
  3. washthe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate and subsequent filtration
  5. customthe solvent was evaporated under a reduced pressure
  6. customBy purifying the resulting residue by silica gel column chromatography

Sources & evidence

ORD record
ord-3d982abd6b94485f8182223e98d5e486
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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