p-Toluenesulfonic acid → HCID 178499053, compound

HRID 923356Notes

Reaction equation

HRID 923356 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10](=O)[CH2:11][C:12]([O:14]CC)=O)[CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:29][C:30]1[NH:34][N:33]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[N:31]=1>CCCCO>[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]3[NH:29][C:30]4[N:34]([N:33]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[N:31]=4)[C:12](=[O:14])[CH:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178472160HCID 178472160, compoundHCID 178499187HCID 178499187, compound

Product 1

HCID 178499053HCID 178499053, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 3-(1H-benzo[d][1,2,3]triazol-6-yl)-3-oxopropanoate (246 mg, 1.5eq) in n-BuOH (5 ml) was added TsOH (10 mg, 0.1eq) and methyl 5-amino-1H-1,2,4-triazole-3-carboxylate (100 mg, 1.0 eq), and the reaction mixture was stirred for 20 h at 130° C. The solids were collected by filtration and washed with methanol (10 ml) to afford methyl 5-(1H-benzo[d][1,2,3]triazol-6-yl)-7-oxo-4,7-dihydro-[1,2,4]triazolo[1,5-α]pyrimidine-2-carboxylate (80 mg, 60%).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with methanol (10 ml)

Sources & evidence

ORD record
ord-ba98366117054fdd9d1dfe8135b9c56a
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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