p-Toluenesulfonic acid → HCID 178515497, compound

HRID 923307Notes

Reaction equation

HRID 923307 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([NH2:12])[NH:9][N:8]=1.[NH:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])=[CH:21][C:16]=2[N:15]=[N:14]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[NH:12][C:10]4[N:9]([N:8]=[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[N:11]=4)[C:24](=[O:25])[CH:23]=3)=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 120117925-(pyridin-2-yl)-4H-1,2,4-triazol-3-amineHCID 178472159HCID 178472159, compound

Product 1

HCID 178515497HCID 178515497, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 3-(pyridin-2-yl)-1H-1,2,4-triazol-5-amine (100 mg, 0.57 mmol) in diphenyl ether (3 ml) was added ethyl 3-(1H-1,2,3-benzotriazol-5-yl)-3-oxopropanoate (300 mg, 1.29 mmol) and 4-methylbenzene-1-sulfonic acid (5 mg, 0.02 mmol). After stirring 1 h at 170° C., the solids were collected by filtration, washed with ethyl acetate (2×10 ml), methanol (3×10 ml) and dried to give 5-(1H-benzo[d][1,2,3]triazol-5-yl)-2-(pyridin-2-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (36.7 mg, 18%).

Workup

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

Sources & evidence

ORD record
ord-3d4b687b320840868d29aa3fa1a7289f
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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