Sodium hydride → HCID 20636593, compound

HRID 49268Notes

Reaction equation

HRID 49268 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=1.[H-].[Na+]>CN(C=O)C>[Cl:27][C:25]1[CH:26]=[C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:9]2[CH2:10][CH2:11][N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[C:8]2=[O:12])[CH:22]=[N:23][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 37468181-Pyridin-4-yl-imidazolidin-2-oneHCID 20636600HCID 20636600, compound

Product 1

HCID 20636593HCID 20636593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-pyridyl)-2-imidazolidinone (100 mg, 0.61 mmol) and 3-[(6-bromohexyl)oxy]-5-chloropyridine (269 mg, 0.92 mmol) in DMF (5 mL) was added sodium hydride (39 mg, 1.23 mmol, 75% in mineral oil) in an ice bath. The mixture was stirred at room temperature overnight. After removing the solvent under reduced pressure, the crude residue was purified by column chromatography eluted with 15% methanol in ethyl acetate to afford the product (i.e., Compound 11) as a light yellow solid (0.17 g, 75%).

Workup

  1. customAfter removing the solvent under reduced pressure
  2. customthe crude residue was purified by column chromatography
  3. washeluted with 15% methanol in ethyl acetate

Sources & evidence

ORD record
ord-26b351bf5b3d4518bd96e1dbba4035f7
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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