Hydrochloric Acid → 2-(Pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridin-6-amine

HRID 1844439Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:23]=[C:10]3[CH:11]=[CH:12][C:13]([NH:15]C(=O)OC(C)(C)C)=[CH:14][N:9]3[N:8]=2)[CH:2]=1.Cl.C(OCC)C>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:23]=[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][N:9]3[N:8]=2)[CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate (1.34 g, 4.3 mmol), dichloromethane (10 ml) and hydrochloric acid (5 molar in diethyl ether (36.0 g, 30 ml, 987 mmol) was stirred for 18 hours at 25° C. The solvents were evaporated under reduced pressure and the residue treated with sodium hydroxide solution (2 molar in water). The mixture was extracted with ethyl acetate, the organic layers were washed with water and brine, dried over magnesium sulfate, filtrated and evaporated to dryness, affording 2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylamine (482 mg, 53%) as light brown solid. Mp.: 230° C. MS: m/z=212.1 (M+H+).

Workup

customThe solvents were evaporated under reduced pressure
additionthe residue treated with sodium hydroxide solution (2 molar in water)
extractionThe mixture was extracted with ethyl acetate
washthe organic layers were washed with water and brine
dry with materialdried over magnesium sulfate
filtrationfiltrated
customevaporated to dryness

Sources & evidence

ORD record: ord-d94319b28d9645a1828dbda7cef786ca
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946427B2

Reaction notes

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