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Sodium Bicarbonate → 5-Bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-ylamine

HRID 78597
Notes
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Reaction equation

HRID 78597 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.C([O-])(O)=O.[Na+]>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

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 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 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3-amino-N′-(benzoyloxy)-6-bromopyrazine-2-carboximidamide (890 mg, 2.648 mmol) and polyphosphonic acid (3.560 mL) were mixed and the reaction heated to 70° C. Further polyphosphonic acid (8.900 mL) was added and the reaction allowed to stir for a further 3 hours at 70° C. The mixture was then allowed to cool to RT, diluted with water and neutralised by the portionwise addition of solid NaHCO3. The resulting precipitate was isolated by filtration and dried (643 mg, 76% Yield). 1H NMR (400.0 MHz, DMSO) d 7.49 (2H, br s), 7.69 (2H, m), 7.77 (1H, m), 8.28 (2H, m), 8.43 (1H, s); MS (ES+) 319.89

Workup

  1. temperatureto cool to RT
  2. customThe resulting precipitate was isolated by filtration
  3. customdried (643 mg, 76% Yield)

Sources & evidence

ORD record
ord-65c4e01a32674b43ab061bd854dc6ad0
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