Pyrrolidine → 4-(Furan-3-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564118Notes

Reaction equation

HRID 564118 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[CH:23]=[CH:22][O:21][CH:20]=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>C(Cl)Cl>[O:21]1[CH:22]=[CH:23][C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:4][CH:5]=3)[C:12](=[O:24])[CH:13]=2)=[CH:20]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 670069631-[2-(4-bromomethylphenyl)-ethyl]-4-(furan-3-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 580428244-(Furan-3-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 mg (85% purity, 0.33 mmol) 1-[2-(4-bromomethyl-phenyl)-ethyl]-4-(furan-3-ylmethoxy)-1H-pyridin-2-one (example 5.1b) in 1.5 mL DCM is added 108 μL (1.31 mmol) pyrrolidine at RT. The reaction mixture is stirred for 2 h at RT and is directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. customis directly transferred 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-7aed629ff00b4902a103eefb0efa44e7
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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