1,1'-Carbonyldiimidazole → 8-methoxy-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

HRID 1037307

Reaction equation

HRID 1037307 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:9][NH2:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]2[N:5]([C:11](=[O:12])[NH:10][N:9]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 185454042-Hydrazinyl-3-methoxypyridine

Product 1

HCID 670677818-methoxy-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-oneYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3-methoxypyridin-2-yl)hydrazine (2.7 g, 19.4 mmol) in THF (70 mL) was added 1,1′-carbonyldiimidazole (15.75 g, 90.1 mmol) at RT. After 16 hours, the resultant solid was collected by filtration and washed with THF. The solid was dissolved in a mixture of MeOH (120 mL) and water (20 mL) and stirred at RT for 10 minutes before evaporating to dryness. The resultant residue was subjected to flash chromatography (SiO2, gradient 3 to 5% MeOH in CHCl3) to afford the title compound (2.81 g, 88%) as a white solid. LCMS (Method A): RT=2.08 min, [M+H]+=166.

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. washwashed with THF
  3. dissolutionThe solid was dissolved in a mixture of MeOH (120 mL) and water (20 mL)
  4. custombefore evaporating to dryness

Sources & evidence

ORD record
ord-16cd5dc4c0484c3fb1ee5adaf2ca57e5
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Linked notes

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