1,1'-Carbonyldiimidazole → 3-[4-(benzyloxy)phenyl]-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82619Notes

Reaction equation

HRID 82619 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:16]3=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=[C:21]3[NH:22][C:29]2=[O:30])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58577457N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine

Product 1

HCID 585775733-[4-(benzyloxy)phenyl]-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine (0.63 g) and CDI (0.67 g) in THF (20 mL) was refluxed overnight. The mixture was concentrated in vacuo. The residual solid was washed with AcOEt to give 3-[4-(benzyloxy)phenyl]-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.64 g) as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washThe residual solid was washed with AcOEt

Sources & evidence

ORD record
ord-9cf964908ba44a8c8914133d226444ee
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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