Sodium Hydroxide → (3,5-Bis-(4-methoxy-phenyl)-pyrazol-1-yl)-acetic acid

HRID 68561Notes

Reaction equation

HRID 68561 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]([CH2:19][C:20]([OH:22])=[O:21])[N:9]=2)=[CH:4][C:3]=1C.CN([C:27]([O:31]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:46]CN(C(C)C)C(C)C.ClC1C=C(N2CCNCC2)N=CN=1.[OH-:68].[Na+]>CN(C=O)C.C(Cl)Cl>[CH3:46][O:68][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:31][CH3:27])=[CH:17][CH:18]=3)[N:10]([CH2:19][C:20]([OH:22])=[O:21])[N:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 160922664-Chloro-6-(piperazin-1-yl)pyrimidineHCID 867626713-(4-Fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl acetic acid

Product 1

HCID 86762670(3,5-Bis-(4-methoxy-phenyl)-pyrazol-1-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

700 mg (3-(4-fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl)-acetic acid was dissolved in 10 mL DMF. 869 mg TBTU and 465 μL DIPEA were added to this solution and the mixture was stirred 1 min at RT. 448 mg 4-chloro-6-piperazine-1-yl-pyrimidine was added and stirring was continued for 2 h. Then 10 mL of a 1M NaOH solution and 50 mL CH2Cl2 were added, the organic phase was separated. The solvent was removed. The residue was dissolved in dichlormethane, water was added and the layers were separated. The organic layer was evaporated and the residue was purified by flash chromatography (silica gel, DCM/MeOH 0-30 to yield 500 mg of the desired compound.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customthe organic phase was separated
  4. customThe solvent was removed
  5. dissolutionThe residue was dissolved in dichlormethane
  6. additionwater was added
  7. customthe layers were separated
  8. customThe organic layer was evaporated
  9. customthe residue was purified by flash chromatography (silica gel, DCM/MeOH 0-30

Sources & evidence

ORD record
ord-9dd0692f9e734fd5ba2174a7f14de08b
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

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