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

HRID 1430050Notes

Reaction equation

HRID 1430050 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-19e09549ed0b4f5cba06a8b00f9fdcd8
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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