p-Toluenesulfonic acid → 7-(Benzyloxy)-[1,2,4]triazolo[4,3-a]pyridine

HRID 240547Notes

Reaction equation

HRID 240547 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][NH2:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17]OC(OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]2[CH:17]=[N:16][N:15]=[C:11]2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 669373074-(Benzyloxy)-2-hydrazinylpyridine

Product 1

HCID 669370477-(Benzyloxy)-[1,2,4]triazolo[4,3-a]pyridineYield 63.3%

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(4-(benzyloxy)pyridin-2-yl)hydrazine (3.52 g, 16.35 mmol) in trimethoxymethane (20 mL, 16.35 mmol) was added 4-methylbenzenesulfonic acid (2.816 g, 16.35 mmol). After heating to 60° C. for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was chromatographed (ethyl acetate and 20:1 dichloromethane/methanol) to provide the product (2.33 g, 63%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was chromatographed (ethyl acetate and 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1c065284f5984b79948871f64bbcf31f
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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