p-Toluenesulfonic acid → HCID 178515488, compound

HRID 923306Notes

Reaction equation

HRID 923306 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([NH2:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O: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[O:16][CH2:15]1.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[O: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]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[N:12]=4)[C:25](=[O:26])[CH:24]=3)=[CH:22][C:17]=2[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11166975-benzyl-1H-1,2,4-triazol-3-amineHCID 2756586Ethyl 3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanoate

Product 1

HCID 178515488HCID 178515488, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 3-benzyl-1H-1,2,4-triazol-5-amine (100 mg, 0.57 mmol) in n-BuOH (3 ml) was added ethyl 3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanoate (200 mg, 0.85 mmol) and 4-methylbenzene-1-sulfonic acid (4 mg, 0.02 mmol). After stirring overnight at reflux, the solids were collected by filtration and washed with ethyl acetate (3×10 mL), methanol (3×10 ml) and dried to give 5-(benzo[d][1,3]dioxol-5-yl)-2-benzyl-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a white solid (50.2 mg, 25%).

Workup

  1. temperatureat reflux
  2. filtrationthe solids were collected by filtration
  3. washwashed with ethyl acetate (3×10 mL), methanol (3×10 ml)
  4. customdried

Sources & evidence

ORD record
ord-daf29a290e864ec389263aeb67d0a58a
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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