p-Toluenesulfonic acid → HCID 178515498, compound

HRID 923351Notes

Reaction equation

HRID 923351 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([NH2:13])[NH:10][N:9]=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>C(O)CCC>[NH:16]1[C:17]2[CH:22]=[C:21]([C:23]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[N:12]=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 178472159HCID 178472159, compoundHCID 178508279HCID 178508279, compound

Product 1

HCID 178515498HCID 178515498, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-(2-chlorophenyl)-1H-1,2,4-triazol-5-amine (50 mg, 0.26 mmol, 1.00 equiv), ethyl 3-(1H-1,2,3-benzotriazol-5-yl)-3-oxopropanoate (100 mg, 0.43 mmol, 1.67 equiv), butan-1-ol (1 mL), and p-TsOH (5 mg, 0.03 mmol, 0.11 equiv) was stirred for 1 h at 170° C. in an oil bath. After the reaction was completed, the solids were collected by filtration and washed with MeOH (3×1 ml). This resulted in 25.3 mg (27%) of 5-(1H-benzo[d][1,2,3]triazol-6-yl)-2-(2-chlorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7(4H)-one as a grey solid.

Workup

  1. filtrationthe solids were collected by filtration
  2. washwashed with MeOH (3×1 ml)
  3. customThis resulted in 25.3 mg (27%) of 5-(1H-benzo[d][1,2,3]triazol-6-yl)-2-(2-chlorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7(4H)-one as a grey solid

Sources & evidence

ORD record
ord-88ca8918442142fe91ce0e4c37db929f
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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