Ethyl Acetate → 2-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one

HRID 8248

Reaction equation

HRID 8248 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].BrCCO.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:9]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:6]2[C:4](=[O:5])[O:3][CH2:1][CH2:2][N:7]2[N:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 178418693HCID 178418693, compound

Product 1

HCID 99241292-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-ethoxycarbonyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole (0.35 g, 1.00 mmol), 2-bromoethanol (0.15 g, 1.12 mmol), and cesium carbonate (0.50 g, 1.5 mmol) in N,N-dimethylformamide (20 mL) is heated at 60° C. for 2 h. The mixture is cooled to room temperature and poured into ethyl acetate (60 mL). The organic portion is washed with water, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (ethyl acetate/hexane) to yield the title compound, 110 mg (32%).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. washThe organic portion is washed with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c379553fdac94f1c90f2ccafb8db9214
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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