p-Toluenesulfonic acid → HCID 178487578, compound

HRID 923324Notes

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.CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33][C:34](OCC)=[O:35])=[CH:28][C:27]=1[O:40][CH3:41]>CCCCO>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[NH:13][C:11]3[N:10]([N:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:12]=3)[C:34](=[O:35])[CH:33]=2)=[CH:28][C:27]=1[O:40][CH3:41]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-(4-fluorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.56 mmol) in n-BuOH (3 ml) was added TsOH (5 mg, 0.03 mmol), and ethyl 3-(4-chloro-3-methoxyphenyl)-3-oxopropanoate (200 mg, 0.78 mmol), and the resulting mixture was stirred for 36 hours at 130° C. in an oil bath. The solids were collected by filtration to give a crude product, which was purified by Flash-Prep-HPLC to afford 5-(4-chloro-3-methoxyphenyl)-2-(4-fluorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a white solid (33.5 mg, 16%).

Workup

filtrationThe solids were collected by filtration
customto give a crude product, which
customwas purified by Flash-Prep-HPLC

Sources & evidence

ORD record: ord-1e43ab7c4daa4a3b99d787d0083614ea
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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