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

HRID 923345Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([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:16])[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:14]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[N:12]=4)[C:28](=[O:29])[CH:27]=3)=[CH:23][CH:24]=2)[CH:19]=[N:18]1)(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 3-(4-fluorophenyl)-1H-1,2,4-triazol-5-amine (120 mg, 0.67 mmol) in diphenyl ether (2 ml) was added ethyl 3-(1-acetyl-1H-indazol-5-yl)-3-oxopropanoate (650 mg, 2.36 mmol) and TsOH (5.76 mg, 0.03 mmol), and the resulting mixture was stirred for 5 h at 170° C. The reaction was then quenched by the addition of ethyl ether (8 ml). The solids were collected by filtration to afford 5-(1-acetyl-1H-indazol-5-yl)-2-(4-fluorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow crude solid (100 mg, crude).

Workup

customThe reaction was then quenched by the addition of ethyl ether (8 ml)
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-40a884b74972493a94910249bcd1c796
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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