Potassium Carbonate → HCID 71599174, compound

HRID 1428951Notes

Reaction equation

HRID 1428951 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH3:15])[CH:9]=2)[N:5]=[C:4]1[CH2:16][C:17]([OH:19])=O)[CH3:2].CCN(C(C)C)C(C)C.[N:29]1([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH3:15])[CH:9]=2)[N:5]=[C:4]1[CH2:16][C:17]([N:32]1[CH2:33][CH2:34][N:29]([C:35]2[N:36]=[CH:37][CH:38]=[CH:39][N:40]=2)[CH2:30][CH2:31]1)=[O:19])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 86688152HCID 86688152, compound

Product 1

HCID 71599174HCID 71599174, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

50 mg (1-ethyl-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl)-acetic acid was dissolved in 2 mL DMF. 100 mg PFTU and 60 μL DIPEA were added to this solution and the mixture was stirred for 10 min at RT. 160 mg 2-piperazin-1-yl-pyrimidine was added and the reaction was stirred over night. Then, potassium carbonate solution (5%) and dichlormethane were added, the organic layer was separated and the solvent was removed. The residue was purified by HPLC and crystallized with diisopropylether to give 55 mg of the desired compound.

Workup

  1. stirringthe reaction was stirred over night
  2. customthe organic layer was separated
  3. customthe solvent was removed
  4. customThe residue was purified by HPLC
  5. customcrystallized with diisopropylether

Sources & evidence

ORD record
ord-5ceb2e7350eb41cfb5dcb9d9a9e42b03
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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