Ethyl isothiocyanatoformate → 5-Methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine

HRID 2120759Notes

Reaction equation

HRID 2120759 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C(OC([N:21]=[C:22]=S)=O)C.Cl.[NH2:25]O>C(N(C(C)C)C(C)C)C>[CH3:1][O:2][C:3]1[N:8]2[N:25]=[C:22]([NH2:21])[N:9]=[C:7]2[C:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 85320Ethyl isothiocyanatoformateHCID 443297Hydroxyamine hydrochlorideHCID 234358856-Methoxy-3-phenyl-pyridin-2-yl-amine

Product 1

HCID 234358815-Methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amineYield 80%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of 230 mg (1.15 mmol) 6-methoxy-3-phenyl-pyridin-2-yl-amine and 142.8 μl ethoxycarbonyl isothiocyanate was stirred at room temperature for 2 h and afterwards evaporated to dryness. The residue was taken up in 20 ml MeOH/EtOH 1:1 and treated with a mixture of 399 mg (5.74 mmol) hydroxylamine hydrochloride and 590 μl N-ethyldiisopropylamine. The mixture was heated to 80° C. for 16 h, concentrated to dryness, taken up in 100 ml water and extracted with 3×150 ml diethyl ether. The combined organic phases were dried with MgSO4 and evaporated to yield 379 mg (80%) of the title compound. 1-H-NMR (300MHz, DMSO-d6): δ=8.05 (d, J=8.49 Hz, 2H, phenyl), 7.73 (d, J=8.31 Hz 1H, H-7), 7.45 (t, J=7.26 Hz, 2H, phenyl), 7.33 (d, t=7.26 Hz, 1H, phenyl), 6.52 (d, J=8.31 Hz, 1H, H-6), 6.08 (s, br, 2H, NH2), 4.09 (s, 3H, OCH3). MS m/e (%): 241.3 (M+H+, 100).

Workup

  1. customafterwards evaporated to dryness
  2. temperatureThe mixture was heated to 80° C. for 16 h
  3. concentrationconcentrated to dryness
  4. extractionextracted with 3×150 ml diethyl ether
  5. dry with materialThe combined organic phases were dried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-06ec50b180ce491bbe4c7b73480d0491
Source dataset
uspto-grants-2004_02
Patent number
US06693116B2

Reaction notes

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