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3-amino-N'-(benzoyloxy)-6-bromopyrazine-2-carboximidamide → 5-Bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-ylamine

HRID 78570
Notes
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Reaction equation

HRID 78570 reaction equation
[NH2:1][C:2]1[C:3]([C:9](=[N:11][O:12][C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH2:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1>O>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[N:10]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:12][N:11]=2)[C:2]([NH2:1])=[N:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 722951133-amino-N'-(benzoyloxy)-6-bromopyrazine-2-carboximidamide

Product 1

HCID 594722055-Bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-ylamineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-N′-(benzoyloxy)-6-bromopyrazine-2-carboximidamide (575 mg, 1.711 mmol) and polyphosphonic acid (2.300 mL) was heated at 70° C. for 3.5 hours. The resultant solution was diluted with water (20 mL), quenched with NaHCO3 and the resultant product isolated by filtration (475 mg, 87% Yield) as a fawn solid.

Workup

  1. customquenched with NaHCO3

Sources & evidence

ORD record
ord-8edcdcba17ce4961bfffcc417cb57bed
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841308B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes