p-Toluenesulfonic acid → HCID 178437552, compound

HRID 923317Notes

Reaction equation

HRID 923317 reaction equation
[CH2:1]([C:3]1[N:7]=[C:6]([NH2:8])[NH:5][N:4]=1)[CH3:2].[NH:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18](=O)[CH2:19][C:20](OCC)=[O:21])=[CH:17][C:12]=2[N:11]=[N:10]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3[NH:8][C:6]4[N:5]([N:4]=[C:3]([CH2:1][CH3:2])[N:7]=4)[C:20](=[O:21])[CH:19]=3)=[CH:17][C:12]=2[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 17142045-ethyl-1H-1,2,4-triazol-3-amineHCID 178472159HCID 178472159, compound

Product 1

HCID 178437552HCID 178437552, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-ethyl-1H-1,2,4-triazol-5-amine (150 mg, 0.89 mmol) in diphenyl ether (2 ml) was added ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (500 mg, 2.15 mmol) and TsOH (8 mg, 0.04 mmol), and the reaction mixture was stirred overnight at 130° C. The solids were collected by filtration and washed with methanol (20 ml) to afford 5-(1H-benzo[d][1,2,3]triazol-5-yl)-2-ethyl-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (66.4 mg, 18%).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with methanol (20 ml)

Sources & evidence

ORD record
ord-56a6e11602de425e8a63ca80c12efbf2
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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