p-Toluenesulfonic acid → HCID 178487577, compound

HRID 923323Notes

Reaction equation

HRID 923323 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][C:23](OCC)=[O:24])=[CH:17][C:16]=1[O:29][CH3:30].CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:13][C:11]3[N:10]([N:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[N:12]=3)[C:23](=[O:24])[CH:22]=2)=[CH:17][C:16]=1[O:29][CH3:30]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90109524Ethyl 3-(4-chloro-3-methoxyphenyl)-3-oxopropanoateHCID 178508293HCID 178508293, compound

Product 1

HCID 178487577HCID 178487577, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-(4-chlorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.51 mmol) in n-BuOH (1 ml) was added ethyl 3-(4-chloro-3-methoxyphenyl)-3-oxopropanoate (200 mg, 0.78 mmol) and TsOH (5 mg, 0.02 mmol), and the resulting mixture was stirred overnight at 130° C. The solids were collected by filtration and washed with methanol (2×5 ml) to afford 5-(4-chloro-3-methoxyphenyl)-2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (56.6 mg, 28%).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with methanol (2×5 ml)

Sources & evidence

ORD record
ord-b1cc6793f427467e9373f7c4e6645ec3
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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