Acetic Anhydride → HCID 66636972, compound

HRID 469213Notes

Reaction equation

HRID 469213 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:33])[C:13]([CH2:23][NH:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:14][N:15]3[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=2[F:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:35]([N:24]([CH2:23][C:13]1[C:12](=[O:33])[C:11]2[C:16](=[CH:17][C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:9]([F:34])[CH:10]=2)[N:15]([CH:18]([CH2:19][CH3:20])[CH2:21][CH3:22])[CH:14]=1)[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 66637039HCID 66637039, compound

Product 1

HCID 66636972HCID 66636972, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

170 mg of ethyl 4-({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)butanoate was dissolved in 2.0 ml of pyridine, and 0.040 ml of acetic anhydride was added, followed by overnight stirring at room temperature. After concentrating the reaction mixture under a reduced pressure, water was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered and concentrated under a reduced pressure. By purifying the resulting residue by silica gel column chromatography, 165 mg of ethyl 4-(acetyl{[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)butanoate was obtained.

Workup

  1. concentrationAfter concentrating the reaction mixture under a reduced pressure, water
  2. additionwas added to the resulting residue
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under a reduced pressure
  7. customBy purifying the resulting residue by silica gel column chromatography

Sources & evidence

ORD record
ord-cf3281b9141f4c71a36caf93cfcf3c6f
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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