Cesium carbonate → 3-(3-Chloro-2-methyl-phenyl)-1-(2-pyrazolo[3,4-b]pyridin-2-yl-acetyl)-imidazolidin-4-one

HRID 507389Notes

Reaction equation

HRID 507389 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[CH3:18])[CH2:6]1)=[O:4].[NH:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH:21]=[N:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:13]1[C:12]([CH3:18])=[C:11]([N:7]2[C:8](=[O:10])[CH2:9][N:5]([C:3](=[O:4])[CH2:2][N:20]3[CH:21]=[C:22]4[C:23]([N:24]=[CH:25][CH:26]=[CH:27]4)=[N:19]3)[CH2:6]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27558501H-pyrazolo(3,4-b)pyridineHCID 594340271-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one

Product 1

HCID 594340383-(3-Chloro-2-methyl-phenyl)-1-(2-pyrazolo[3,4-b]pyridin-2-yl-acetyl)-imidazolidin-4-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one (230 mg, 0.8 mmol, 1 eq), 1H-Pyrazolo[3,4-b]pyridine (96 mg, 0.8 mmol, 1 eq), Cesium carbonate (653 mg, 2.0 mmol, 2.5 eq) in DMF (6 ml) was stirred at room temperature overnight. It was diluted with ethyl acetate, washed with water and purified with HPLC to give the desired product. LCMS observed for (M+H)+: 370.1

Workup

  1. washwashed with water
  2. custompurified with HPLC

Sources & evidence

ORD record
ord-1cad5411547e4fdd82decc3140cf47e7
Source dataset
uspto-grants-2010_08
Patent number
US07786157B2

Reaction notes

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