Acetone → HCID 9894488, compound

HRID 1837388Notes

Reaction equation

HRID 1837388 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]1(=[O:42])[O:41][C:39](=[O:40])[CH2:38][CH2:37]1.[CH3:43]C(C)=O>C(Cl)Cl>[CH3:9][CH:8]([CH3:43])[C@H:7]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[CH2:29][N:30]1[CH2:31][CH2:32][N:33]([C:36](=[O:42])[CH2:37][CH2:38][C:39]([OH:41])=[O:40])[CH2:34][CH2:35]1)=[O:12])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7922Succinic anhydrideHCID 10600223HCID 10600223, compound

Product 1

HCID 9894488HCID 9894488, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.42 mmol) of 2-phenyl-3-piperazin-1-ylmethylquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (compound of Description 13) were dissolved in 5 ml acetone and 42 mg of succinic anhydride were added. The mixture was then refluxed for 10 hours. After cooling the mixture was diluted with 50 ml of CH2Cl2, washed three times with 30 ml water, dried over MgSO4, concentrated to dryness. The residue was purified by flash chromatography on silicagel (CH2Cl2/MeOH: 90/10) to afford 130 mg of the title compound as white crystals (yield 54%).

Workup

  1. temperatureThe mixture was then refluxed for 10 hours
  2. temperatureAfter cooling the mixture
  3. washwashed three times with 30 ml water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by flash chromatography on silicagel (CH2Cl2/MeOH: 90/10)

Sources & evidence

ORD record
ord-b39e7398606944caa03f73f957ff14be
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

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