Succinic anhydride → HCID 58043262, compound

HRID 1618005Notes

Reaction equation

HRID 1618005 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[CH3:34])[CH2:15]/[C:16](/[C:19]3[CH:20]=[CH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=3)=[N:17]\[OH:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1.C(OCC)(=O)C>CN(C)C=O>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[CH2:15]/[C:16](=[N:17]\[OH:18])/[C:19]2[CH:20]=[CH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[C:28]([CH3:34])[CH:29]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8857Ethyl AcetateHCID 58043284HCID 58043284, compound

Product 1

HCID 58043262HCID 58043262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-5-(3-(4′-aminobiphenyl-4-yl)-3-(4-fluoro-2-methylphenyl)-1-(hydroxyimino)propyl)-1-methylpyridin-2(1H)-one (0.05 g, 110 μmol, example 259) in N,N-dimethylformamide was added at room temperature succinic anhydride (12.1 mg, 121 μmol) and the resulting solution was stirred at room temperature for 26 hours. The reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate and the organic layers were washed twice with water and once with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of dichloromethane:methanol (100:0 to 90:10). Light brown foam (0.043 g, 70%). MS (ESI+): m/z=556.2 ([M+H]+).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe organic layers were washed twice with water and once with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 10 g column
  9. washeluting with a gradient of dichloromethane:methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-c0c1abc9c92149e5af1347150735ae4b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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