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

HRID 923315Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 3-ethyl-1H-1,2,4-triazol-5-amine (150 mg, 1.34 mmol) in diphenyl ether (2 ml) was added ethyl 3-(1-acetyl-1H-indazol-5-yl)-3-oxopropanoate (550 mg, 2.00 mmol) and TsOH (8 mg, 0.04 mmol), and the reaction mixture was stirred for 1 h at 170° C. The solids were collected by filtration and washed with hexane (10 ml) and ethanol (3 ml) to afford 5-(1-acetyl-1H-indazol-5-yl)-2-ethyl-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a yellow solid (130 mg, crude).

Workup

filtrationThe solids were collected by filtration
washwashed with hexane (10 ml) and ethanol (3 ml)

Sources & evidence

ORD record: ord-fee0d481fea54c31a928f991a4af739b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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