p-Toluenesulfonic acid → HCID 178515495, compound

HRID 923334Notes

Reaction equation

HRID 923334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23](=O)[CH2:24][C:25](OCC)=[O:26])=[CH:22][C:17]=2[N:16]=[N:15]1.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[NH:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=5)[N:12]=4)[C:25](=[O:26])[CH:24]=3)=[CH:22][C:17]=2[N:16]=[N:15]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178472159HCID 178472159, compoundHCID 1785082905-(3-chlorophenyl)-4H-1,2,4-triazol-3-amine

Product 1

HCID 178515495HCID 178515495, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-(3-chlorophenyl)-1H-1,2,4-triazol-5-amine (120 mg, 0.62 mmol) in n-BuOH (1 mL) was added ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (214 mg, 0.92 mmol) and TsOH (5.3 mg, 0.03 mmol), and the resulting mixture was stirred for 5 h at 130° C. The solids were collected by filtration, washed with MeOH (3×1 mL) to afford 5-(1H-benzo[d][1,2,3]triazol-5-yl)-2-(3-chlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (73 mg, 33%).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with MeOH (3×1 mL)

Sources & evidence

ORD record
ord-62e0681289de4e9198c50853a32bb71a
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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