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

HRID 923328Notes

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].C([N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27](=O)[CH2:28][C:29](OCC)=[O:30])=[CH:24][CH:25]=2)[CH:20]=[N:19]1)(=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]=[C:12]3[NH:14][C:27]([C:23]4[CH:22]=[C:21]5[C:26](=[CH:25][CH:24]=4)[NH:18][N:19]=[CH:20]5)=[CH:28][C:29](=[O:30])[N:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

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-(1-acetyl-1H-indazol-5-yl)-3-oxopropanoate (300 mg, 1.00 mmol) and TsOH (5 mg, 0.03 mmol), and the resulting mixture was stirred for 36 h at 130° C. The solids were collected by filtration and washed with methanol (10 ml) to afford 2-(3,4-dichlorophenyl)-5-(1H-indazol-5-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (29 mg, 17%).

Workup

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

Sources & evidence

ORD record: ord-41950b73a40c4ce68e8b5ce8b15a466c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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