p-Toluenesulfonic acid → HCID 178424200, compound

HRID 923355Notes

Reaction equation

HRID 923355 reaction equation
[C:1]1([CH3:13])[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: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:16]1[C:17]2[CH:22]=[C:21]([C:23]3[NH:12][C:10]4[N:9]([N:8]=[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=5[CH3:13])[N:11]=4)[C:25](=[O:26])[CH:24]=3)[CH:20]=[CH:19][C:18]=2[N:14]=[N:15]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178424211HCID 178424211, compoundHCID 178472159HCID 178472159, compound

Product 1

HCID 178424200HCID 178424200, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-o-tolyl-1H-1,2,4-triazol-5-amine (150 mg, 1.0 eq) in n-BuOH (2 ml) was added ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (240 mg, 1.2 eq) and TsOH (20 mg) and the reaction was stirred for 5 h at 120° C. in an oil bath. The product was collected by filtration and washed with MeOH (3×1 ml) to afford 5-(1H-benzo[d][1,2,3]triazol-6-yl)-2-o-tolyl-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one (117.6 mg, 40% yield) as a yellow solid.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with MeOH (3×1 ml)

Sources & evidence

ORD record
ord-ffe3d4b8f2c4436e96ef72dee505dd85
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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