Dimethylamine → 4-(5-Bromo-pyridin-2-ylmethoxy)-1-[2-(4-dimethylaminomethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

HRID 1425767Notes

Reaction equation

HRID 1425767 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]([Br:25])=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:26])=[C:5]([CH3:28])[CH:4]=1.[CH3:29][NH:30][CH3:31]>CN(C)C(=O)C>[Br: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:30]([CH3:31])[CH3:29])=[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 674DimethylamineHCID 866955441-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-bromo-pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 717320784-(5-Bromo-pyridin-2-ylmethoxy)-1-[2-(4-dimethylaminomethyl-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-bromo-pyridin-2-ylmethoxy)-1H-pyridin-2-one (preparation 4b, 1000 mg, 1.98 mmol) in N,N-dimethylacetamide (5 mL) is added dimethylamine (3.0 mL of 2M solution in THF, 6.0 mmol). The reaction mixture is stirred 2 h 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-c27de0ea3c904e0ead9943571b0c2fa0
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

Loading…