Potassium Carbonate → 5-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-(1-{[3-(2,2,2-trifluoroethoxy)phenyl]-carbonyl}piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one

HRID 524224Notes

Reaction equation

HRID 524224 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]=[C:26]([OH:30])[CH:25]=4)=[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+].[F:40][C:41]([F:45])([F:44])[CH2:42]I>CN(C=O)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]=[C:26]([O:30][CH2:42][C:41]([F:45])([F:44])[F:40])[CH:25]=4)=[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 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 462066295-(3,4-Dimethoxyphenyl)-2-{1-[(3-hydroxyphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 462027285-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-(1-{[3-(2,2,2-trifluoroethoxy)phenyl]-carbonyl}piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.8 g of 5-(3,4-dimethoxyphenyl)-2-{1-[(3-hydroxyphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 76) and 0.75 g potassium carbonate are suspended in 10 ml of DMF. 0.4 g of 1,1,1-trifluoro-2-iodoethane are added and the reaction mixture is heated to 100° C. for 8 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 column chromatography (silica gel and EA/PE/TEA=10:10:1) and by crystallization from diethyl ether yields the title compound.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. customthe solvent is removed under reduced pressure
  5. customPurification of the resulting crude product by column chromatography (silica gel and EA/PE/TEA=10:10:1)
  6. customby crystallization from diethyl ether

Sources & evidence

ORD record
ord-88bf133e6fef4de795f436db6ddd6ae9
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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