p-Toluenesulfonic acid → HCID 178485564, compound

HRID 923322Notes

Reaction equation

HRID 923322 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([NH:9][CH3:10])=[O:8])[N:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:31](=O)[CH2:32][C:33](OCC)=[O:34])=[CH:30][C:25]=2[N:24]=[N:23]1>CCCCO>[NH:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:31]3[NH:1][C:2]4[N:6]([N:5]=[C:4]([C:7]([NH:9][CH3:10])=[O:8])[N:3]=4)[C:33](=[O:34])[CH:32]=3)=[CH:30][C:25]=2[N:24]=[N:23]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178472159HCID 178472159, compoundHCID 178485598HCID 178485598, compound

Product 1

HCID 178485564HCID 178485564, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 5-amino-N-methyl-1H-1,2,4-triazole-3-carboxamide (100 mg, 0.71 mmol) in n-BuOH (3 ml) was added TsOH (4.8 mg, 0.03 mmol), ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (230 mg, 0.88 mmol). The resulting solution was stirred for 12 h at reflux. The solids were collected by filtration to afford 5-(1H-benzo[d][1,2,3]triazol-5-yl)-N-methyl-7-oxo-4,7-dihydro-[1,2,4]triazolo[1,5-α]pyrimidine-2-carboxamide as a white solid (39.8 mg, 18%).

Workup

  1. temperatureat reflux
  2. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-3510d2c98ca448539b0d70391f399fc7
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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