Sodium hydride → HCID 58577627, compound

HRID 1044145Notes

Reaction equation

HRID 1044145 reaction equation
Cl[CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:27]3[NH:26][C:25]2=[O:33])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:27]3[N:26]([CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[C:25]2=[O:33])=[CH:22][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 5284359Calcium ChlorideHCID 585776613-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577627HCID 58577627, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

[2-(Chloromethoxy)ethyl](trimethyl)silane (1.673 mL) was added to a solution of 3-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2.0 g) and sodium hydride (0.504 g) (60% in mineral oil) in DMF (5.0 ml) at 0° C. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After the reaction, the reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give 3-[4-(benzyloxy)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2.75 g) as a white solid.

Workup

  1. customAfter the reaction
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-fe0c8eb4dee841c5b780b982d1c28f9e
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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