1,1'-Carbonyldiimidazole → 3-[2-(Dimethylamino)ethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1822105Notes

Reaction equation

HRID 1822105 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>CN(C=O)C>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[NH:12][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14174125N~2~-[2-(Dimethylamino)ethyl]pyridine-2,3-diamine

Product 1

HCID 589976113-[2-(Dimethylamino)ethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
77.5 °C

Procedure

A solution of N-[2-(dimethylamino)ethyl]pyridine-2,3-diamine (1.49 g, 8.3 mmol) in DMF is treated with carbonyldiimidazole (CDI) (2.01 g, 12.4 g) under nitrogen, stirred at 75-80° C. for 24 h, cooled to room temperature and concentrated in vacuo. The resultant residue is chromatographed, eluting with 10:90 conc. NH4OH:ethanol to afford a solid which is triturated with ethanol:ethyl acetate to afford the title compound as a tan solid, 0.387 g, mp 141-142° C., identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is chromatographed
  4. washeluting with 10:90 conc. NH4OH
  5. customethanol to afford a solid which
  6. customis triturated with ethanol

Sources & evidence

ORD record
ord-5d9c684637d34df99245410d83928fd1
Source dataset
uspto-grants-2009_10
Patent number
US07608717B2

Reaction notes

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