Hydrochloric Acid → 2-(Pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802218Notes

Reaction equation

HRID 1802218 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:23]=[C:10]3[CH:11]=[C:12]([NH:15]C(=O)OC(C)(C)C)[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=1.Cl>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:23]=[C:10]3[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67776082Carbamic acid, N-[2-(3-pyridinyl)[1,2,4]triazolo[1,5-a]pyridin-7-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 677758632-(Pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amineYield 92%

Procedure

A mixture of tert-butyl 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (755 mg, 2.43 mmol) in hydrochloric acid (5 N in ether, 15 ml, 75.0 mmol) is stirred for 7 hours at room temperature. The solvent is evaporated and the yellowish solid is dissolved in water and made basic with sodium hydroxide 32%; the precipitated solid is collected by filtration, washed with water and dried affording 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (471 mg, 92%) as a light brown solid. mp.: 228-233° C. MS: m/z=212.1 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe yellowish solid is dissolved in water
  3. filtrationthe precipitated solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-73d7c7c3223545d385b11baed998c04e
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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