Tetrahydrofuran → 3-acetyl-7-(cyclohexylamino)-1-cyclopentyl-6-fluoroquinolin-4(1H)-one

HRID 469241Notes

Reaction equation

HRID 469241 reaction equation
[CH2:1]1COCC1.[CH:6]1([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:34])[C:18]([C:28](N(OC)C)=[O:29])=[CH:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:35])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>O>[C:28]([C:18]1[C:17](=[O:34])[C:16]2[C:21](=[CH:22][C:13]([NH:12][CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)=[C:14]([F:35])[CH:15]=2)[N:20]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:19]=1)(=[O:29])[CH3:1]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 866330497-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 666370703-acetyl-7-(cyclohexylamino)-1-cyclopentyl-6-fluoroquinolin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 10 ml THF solution of 500 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide was added 1.2 ml of a 1 M methyl lithium THF solution, followed by stirring at room temperature for 3 days. Water was added to the reaction mixture to carry out celite filtration. After evaporation under a reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain 150 mg of 3-acetyl-7-(cyclohexylamino)-1-cyclopentyl-6-fluoroquinolin-4(1H)-one.

Workup

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

Sources & evidence

ORD record
ord-a5f5277eaae94b10afd0a736011c789e
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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