Chloroacetamide → HCID 46202730, compound

HRID 1914154Notes

Reaction equation

HRID 1914154 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+].Cl[CH2:41][C:42]([NH2:44])=[O:43]>C(#N)C>[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[O:30][CH2:41][C:42]([NH2:44])=[O:43])=[O:23])[CH2:18][CH2:17]3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 46202727HCID 46202727, compound

Product 1

HCID 46202730HCID 46202730, 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. 0.3 g of 2-chloroacetamide 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 DCM. 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 EA 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 EA

Sources & evidence

ORD record
ord-d6bb22e2be524dd595b395c7ed4141af
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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