1,1'-Carbonyldiimidazole → ethyl 2-(2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)acetate

HRID 587593Notes

Reaction equation

HRID 587593 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1>[O:21]=[C:20]1[N:8]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]2=[N:4][CH:5]=[CH:6][CH:7]=[C:2]2[NH:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14390203Ethyl 2-(3-aminopyridin-2-ylamino)acetate

Product 1

HCID 67335103ethyl 2-(2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)acetateYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl N-(3-aminopyridin-2-yl)glycinate (18 g) in THF (200 mL) was added CDI (15 g) at room temperature, and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure. The residual crystals were washed with AcOEt to give the title compound (5.5 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washThe residual crystals were washed with AcOEt

Sources & evidence

ORD record
ord-9528c9440c29475991617bc731da2453
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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