Pyrazole → HCID 25216189, compound

HRID 2382769Notes

Reaction equation

HRID 2382769 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.[OH-].[K+]>O>[N:12]1([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 14797Potassium HydroxideHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25216189HCID 25216189, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A3); 1.06 g; 5.0 mmol; 1.0 eq.), pyrazole (3.40 g; 50.0 mmol; 10 eq.) and potassium hydroxide (842 mg; 15.0 mmol; 3.0 eq.) were melted and stirred overnight at 110° C. After this time, reaction mixture was cooled to rt poured into water and extracted with Et2O. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the title compound as a white solid (650 mg, 65%). HPLC, Rt: 1.22 min. (purity 96.6%). LC/MS, M+(ESI): 201.0.

Workup

  1. customAfter this time, reaction mixture
  2. temperaturewas cooled to rt
  3. extractionextracted with Et2O
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a225a5a202794a0cab262fa6e56436da
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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