Water → 4-(Furan-2-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564122Notes

Reaction equation

HRID 564122 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)=[CH:13][C:12]2=[O:24])=[CH:5][CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.O.C(#N)C>CN(C=O)C>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:4][CH:5]=2)[C:12](=[O:24])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 31268PyrrolidineHCID 670068811-[2-(4-Bromomethyl-phenyl)-ethyl]-4-(furan-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 580427464-(Furan-2-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 mg (0.13 mmol) 1-[2-(4-bromomethyl-phenyl)-ethyl]-4-(furan-2-ylmethoxy)-1H-pyridin-2-one in 1.5 mL DMF is added 42 μL (0.52 mmol) pyrrolidine at RT. The reaction mixture is stirred for 2 h at RT and is directly added to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Sources & evidence

ORD record
ord-bff6ab3f22cb4a0297baad971b89b34d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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