p-Toluenesulfonic acid → 2-(3-chlorophenyl)-5-(1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one

HRID 923333Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([N:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26](=O)[CH2:27][C:28](OCC)=[O:29])=[CH:23][CH:24]=2)[CH:19]=[N:18]1)(=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]3[NH:13][C:26]([C:22]4[CH:21]=[C:20]5[C:25](=[CH:24][CH:23]=4)[NH:17][N:18]=[CH:19]5)=[CH:27][C:28](=[O:29])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-(3-chlorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.52 mmol) in n-BuOH (1 ml) was added ethyl 3-(1-acetyl-1H-indazol-5-yl)-3-oxopropanoate (280 mg, 1.00 mmol) and TsOH (5 mg, 0.03 mmol), and the reaction mixture was stirred overnight at 130° C. The solids were collected by filtration and washed with methanol (10 ml) to afford 2-(3-chlorophenyl)-5-(1H-indazol-5-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (75 mg, 34%).

Workup

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

Sources & evidence

ORD record: ord-46753f942a264ef2a7fdca70b334d84e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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