3-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazide → 5-Bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959362Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:9]([NH:11][NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1>O>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:20][C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:12][N:11]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Polyphosphonic acid (25 mL of 84% w/v, 256.1 mmol) was heated to 100° C. and treated with 3-amino-N′-benzoyl-6-bromo-pyrazine-2-carbohydrazide (6.82 g, 20.29 mmol) in portions. Analysis after 1 hour showed SM remaining therefore further polyphosphonic acid was added (25 mL of 84% w/v, 256.1 mmol). The reaction was heated for a total of 3 hours and then allowed to cool. Water was added and the mixture allowed to stir to obtain a precipitate which was filtered and dried under vacuum (5.02 g, 78% Yield). MS (ES+) 317.86

Workup

additionfurther polyphosphonic acid was added (25 mL of 84% w/v, 256.1 mmol)
temperatureThe reaction was heated for a total of 3 hours
temperatureto cool
customto obtain a precipitate which
filtrationwas filtered
customdried under vacuum (5.02 g, 78% Yield)

Sources & evidence

ORD record: ord-f48e6c0a7d8b4a758f58055e2eb1f729
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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