Pyrrolidine → 4-(5-Fluoro-pyridin-2-ylmethoxy)-1-[2-(2-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

HRID 1425765Notes

Reaction equation

HRID 1425765 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]([F:25])=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:26])=[C:5]([CH3:28])[CH:4]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C>[F: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:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:4][C:5]=3[CH3:28])=[O:27])[C:12](=[O:26])[CH:13]=2)=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 866955401-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-fluoro-pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 866955654-(5-Fluoro-pyridin-2-ylmethoxy)-1-[2-(2-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-fluoro-pyridin-2-ylmethoxy)-1H-pyridin-2-one (preparation 2b, 111 mg, 0.25 mmol) in DMF (2 mL) is added pyrrolidine (63 μL, 0.75 mmol). The reaction mixture is stirred for 60 min 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-1be50fb110c740e4a662413c8d29b94f
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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