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

HRID 2204820
Notes
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Reaction equation

HRID 2204820 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-2efc5244bd094de385e137af75bd2e84
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365557B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes