Potassium Carbonate → HCID 46202729, compound

HRID 524225Notes

Reaction equation

HRID 524225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]([CH3:33])([CH3:32])[C:13](=[O:31])[N:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[OH:30])=[O:23])[CH2:18][CH2:17]3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].I[CH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>C(#N)C>[CH:41]1([O:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:22]([N:19]2[CH2:20][CH2:21][CH:16]([N:14]3[C:13](=[O:31])[C:12]([CH3:33])([CH3:32])[C:11]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:15]3)[CH2:17][CH2:18]2)=[O:23])[CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 46202727HCID 46202727, compound

Product 1

HCID 46202729HCID 46202729, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.0 g of 5-(3,4-dimethoxyphenyl)-2-{1-[(2-hydroxyphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 94) and 1.0 g potassium carbonate are suspended in 20 ml of acetonitrile. 0.5 g of iodocyclopentane are added and the reaction mixture is heated to reflux for 5 h until the reaction is completed according to TLC analysis. The solvent is evaporated under reduced pressure, and the remaining residue is taken up in EA. The organic phase is washed with water, dried over MgSO4, and the solvent is removed under reduced pressure. Purification of the resulting crude product by crystallization from methanol yields the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 5 h until the reaction
  3. customThe solvent is evaporated under reduced pressure
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent is removed under reduced pressure
  7. customPurification of the resulting crude product
  8. customby crystallization from methanol

Sources & evidence

ORD record
ord-35d8dcd1173945f5985a369e96074d16
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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