Cesium carbonate → 4-(5-Chloro-pyridin-2-ylmethoxy)-1-{2-[4-(4-ethyl-piperazin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-1H-pyridin-2-one

HRID 1425766Notes

Reaction equation

HRID 1425766 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:27])[CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:26])=[C:5]([CH3:28])[CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH3:36]>CN(C)C(=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][N:11]([CH2:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:40]4[CH2:41][CH2:42][N:37]([CH2:35][CH3:36])[CH2:38][CH2:39]4)=[CH:4][C:5]=3[CH3:28])=[O:27])[C:12](=[O:26])[CH:13]=2)=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 791961-EthylpiperazineHCID 866955421-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-chloro-pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 866955664-(5-Chloro-pyridin-2-ylmethoxy)-1-{2-[4-(4-ethyl-piperazin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-chloro-pyridin-2-ylmethoxy)-1H-pyridin-2-one (preparation 3b, 110 mg, 0.23 mmol) in N,N-dimethylacetamide (2 mL) is added Cs2CO3 (184 mg, 0.57 mmol) and N-ethylpiperazine (63 μL, 0.75 mmol). The reaction mixture is stirred overnight at room temperature. The mixture is purified via reverse phase HPLC chromatography (Gilson Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min).

Workup

  1. customThe mixture is purified via reverse phase HPLC chromatography (Gilson Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-4d43be4dbeb94ebfaf452f76eec531e4
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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