p-Toluenesulfonic acid → HCID 178463002, compound

HRID 923358Notes

Reaction equation

HRID 923358 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([NH2:13])[NH:10][N:9]=1.[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]2[NH:13][C:25]([C:21]3[CH:20]=[C:19]4[C:24](=[CH:23][CH:22]=3)[N:16]([CH2:14][CH3:15])[N:17]=[CH:18]4)=[CH:26][C:27](=[O:28])[N:10]2[N:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90109086ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoateHCID 178508279HCID 178508279, compound

Product 1

HCID 178463002HCID 178463002, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 3-(2-chlorophenyl)-1H-1,2,4-triazol-5-amine (50 mg, 0.25 mmol) in n-BuOH (0.2 mL) was added ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoate (100 mg, 0.37 mmol) and p-TsOH (10 mg) at room temperature. After refluxing overnight, the solids were collected by filtration and washed with methanol (3×2 mL) to afford 2-(2-chlorophenyl)-5-(1-ethyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a yellow solid (39.5 mg, 40%).

Workup

  1. temperatureAfter refluxing overnight
  2. filtrationthe solids were collected by filtration
  3. washwashed with methanol (3×2 mL)

Sources & evidence

ORD record
ord-35fab2cbde8748ae98f15fff89a1c9f3
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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