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

HRID 923311Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([NH2:12])[NH:9][N:8]=1.[C:13]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)(=[O:15])[CH3:14].CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[C:13]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]3[NH:12][C:10]4[N:9]([N:8]=[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[N:11]=4)[C:27](=[O:28])[CH:26]=3)=[CH:22][CH:23]=2)[CH:18]=[N:17]1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 3-(pyridin-2-yl)-1H-1,2,4-triazol-5-amine (150 mg, 0.93 mmol) in diphenyl ether (3 mL) was added ethyl 3-(1-acetyl-1H-indazol-5-yl)-3-oxopropanoate (510 mg, 1.86 mmol) and TsOH (8 mg, 0.05 mmol), and the mixture was stirred for 1 h at 170° C. The resulting solution was diluted with n-hexane (8 ml), and the product was collected by filtration and washed with methanol (2 ml) to afford 5-(1-acetyl-1H-indazol-5-yl)-2-(pyridin-2-yl)-4H,7H-[1,2,4]triazolo[1,5-α]pyrimidin-7-one as a brown crude solid (120 mg, crude).

Workup

filtrationthe product was collected by filtration
washwashed with methanol (2 ml)

Sources & evidence

ORD record: ord-964d569483ac4f928a68e598c9624546
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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