Potassium Carbonate → 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester

HRID 2381399Notes

Reaction equation

HRID 2381399 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:27]1[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:27]2[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 668754303-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester

Product 1

HCID 668752343-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (3.0 g, 11.3 mmol) in N,N-dimethylformamide was treated with potassium carbonate (2.33 g, 16.9 mmol) and 2-chloro-4-trifluoromethyl-pyrimidine (3.1 g, 16.9 mmol). The reaction mixture was stirred at 110° C. for 1 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The combined organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography afforded 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester as a light oil (4.0 g, 86%).

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. washThe combined organics were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e897f851babf4fc49a689b6fd5aaf853
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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