ethyl (2E)-4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}but-2-enoate → Ethyl 4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}butanoate

HRID 469246Notes

Reaction equation

HRID 469246 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:30])[C:13]([O:21][CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:14][N:15]3[CH:18]([CH3:20])[CH3:19])=[CH:10][C:9]=2[F:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[C].[Rh].C(O)C>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:30])[C:13]([O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:14][N:15]3[CH:18]([CH3:19])[CH3:20])=[CH:10][C:9]=2[F:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 66637058ethyl (2E)-4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}but-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 66637008Ethyl 4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}butanoateYield 71.8%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 702EthanolSolvent

Procedure

To an 8.0 ml ethanol solution of 280 mg of ethyl (2E)-4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}but-2-enoate was added 28 mg of rhodium-carbon (10%) at room temperature, followed by stirring for 2 hours in an atmosphere of hydrogen. After filtration using celite, the filtrate was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography to obtain 202 mg of ethyl 4-{[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}butanoate.

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated under a reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5a156ce251040d1a6d67bd769c5aecf
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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