Potassium Carbonate → 2-(3-(4-Fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl)-1-(4-(2-pyrimidinyl)-1-piperazinyl)-ethanon

HRID 68562

Reaction equation

HRID 68562 reaction equation
[F:1][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](O)=[O:21])[N:9]=2)=[CH:4][C:3]=1[CH3:23].CCN(C(C)C)C(C)C.[N:33]1([C:39]2[N:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]([CH2:19][C:20]([N:36]3[CH2:37][CH2:38][N:33]([C:39]4[N:40]=[CH:41][CH:42]=[CH:43][N:44]=4)[CH2:34][CH2:35]3)=[O:21])[N:9]=2)=[CH:4][C:3]=1[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 867626713-(4-Fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl acetic acid

Product 1

HCID 715717422-(3-(4-Fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl)-1-(4-(2-pyrimidinyl)-1-piperazinyl)-ethanon

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

50 mg 3-(4-fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl acetic acid was dissolved in 2 mL DMF. 83 mg PFTU and 33 μL DIPEA were added to this solution and the mixture was stirred for 15 min at RT. Then, 25 μL 2-(1-piperazinyl)-pyrimidine was added and stirring was continued for 8 h. Then, 1 mL of a K2CO3 solution (5%) and 10 mL CH2Cl2 were added, the organic phase was separated and washed two times with water. The solvent was removed and the residue was crystallized from ACN to yield 46 mg of the desired compound.

Workup

  1. stirringstirring
  2. waitwas continued for 8 h
  3. customthe organic phase was separated
  4. washwashed two times with water
  5. customThe solvent was removed
  6. customthe residue was crystallized from ACN

Sources & evidence

ORD record
ord-8a49a257803b4b28833f6fe958b367d6
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Linked notes

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