p-Toluenesulfonic acid → HCID 178515496, compound

HRID 923329Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]=[C:12]([NH2:14])[NH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24](=O)[CH2:25][C:26](OCC)=[O:27])=[CH:23][C:18]=2[N:17]=[N:16]1.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[NH:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[NH:14][C:12]4[N:11]([N:10]=[C:9]([C:4]5[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=5)[N:13]=4)[C:26](=[O:27])[CH:25]=3)=[CH:23][C:18]=2[N:17]=[N:16]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-(3,4-dichlorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.44 mmol) in n-BuOH (1 ml) was added ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (300 mg, 1.28 mmol) and TsOH (5 mg, 0.03 mmol), and the resulting mixture was stirred for 24 h at 130° C. The solids were collected by filtration and washed with methanol (10 ml) to afford 5-(1H-benzo[d][1,2,3]triazol-5-yl)-2-(3,4-dichlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (70.2 mg, 40%).

Workup

filtrationThe solids were collected by filtration
washwashed with methanol (10 ml)

Sources & evidence

ORD record: ord-2fcafbeb3132450eb6bb89b1aeebb750
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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