Tetrahydrofuran → HCID 66636916, compound

HRID 1094191Notes

Reaction equation

HRID 1094191 reaction equation
C1COCC1.[CH:6]1([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:35])[C:18]([CH2:28][CH2:29][C:30](OCC)=[O:31])=[CH:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:36])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH:6]1([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:35])[C:18]([CH2:28][CH2:29][CH2:30][OH:31])=[CH:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:36])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 66637033HCID 66637033, compound

Product 1

HCID 66636916HCID 66636916, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 8 ml THF solution of 400 mg of ethyl 3-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]propanoate was added 40 mg of lithium aluminum hydride at 0° C., followed by stirring for 2 hours. Water was added to the reaction mixture, followed by and filteraion through celite. After evaporation under a reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain 288 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(3-hydroxypropyl)quinolin-4(1H)-one.

Workup

  1. customAfter evaporation under a reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b14c121e4c1d4d9ca3ae9fbf994151f4
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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