Diisopropylethylamine → 5-(3-Thienyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 2382762Notes

Reaction equation

HRID 2382762 reaction equation
C(OC(=O)[NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[N:10]=1)=S)C.Cl.NO.CC[N:26](C(C)C)C(C)C>CO.CCO>[S:17]1[CH:18]=[CH:19][C:15]([C:11]2[N:10]3[N:26]=[C:6]([NH2:5])[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=2)=[CH:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59437441Ethyl({[6-(3-thienyl)pyridin-2-yl]amino}carbonothioyl)carbamate

Product 1

HCID 252159375-(3-Thienyl)[1,2,4]triazolo[1,5-a]pyridin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A suspension of ethyl({[6-(3-thienyl)pyridin-2-yl]amino}carbonothioyl)carbamate (4.0 g; 13.01 mmol; 1.0 eq.), hydroxylamine hydrochloride (4.52 g; 65.1 mmol; 5.0 eq.) and DIEA (6.55 mL) in MeOH/EtOH (1:1, 120 mL) was stirred at rt for 2 hours and then at 70° C. for 3 hours. Solvents were removed under reduced pressure, the residue was taken up in dioxane/water (1:1) and filtered to give the title compound as a white powder (2.3 g; 82%). HPLC, Rt: 1.75 min. (purity 94.8%). LC/MS, M+(ESI): 217.3.

Workup

  1. waitat 70° C. for 3 hours
  2. customSolvents were removed under reduced pressure
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8ec9b7699b45403698cc4fd20c9d1ce5
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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