Triethylamine → 3-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazide

HRID 2204807Notes

Reaction equation

HRID 2204807 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[NH2:30][C:31]1[C:32]([C:38]([OH:40])=O)=[N:33][C:34]([Br:37])=[CH:35][N:36]=1.[C:41]([NH:49][NH2:50])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C.O>[NH2:30][C:31]1[C:32]([C:38]([NH:50][NH:49][C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:48])=[O:40])=[N:33][C:34]([Br:37])=[CH:35][N:36]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 594723553-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazideYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBTU (22.09 g, 68.80 mmol) and triethylamine (4.642 g, 6.394 mL, 45.87 mmol) were added to a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol) and benzohydrazide (7.494 g, 55.04 mmol) in DMF (100.0 mL) and the resulting solution stirred at ambient temperature for 48 hours and then poured into water (400 mL) with vigorous stirring. This was allowed to stir for 30 minutes, filtered and washed with water. The moist solid was dissolved in hot EtOAc, dried (MgSO4), filtered and concentrated in vacuo and the resultant solid dried under vacuum to give the desired product (11.34 g, 73% Yield). 1H NMR (400.0 MHz, DMSO) d 7.51 (2H, m), 7.61 (1H, m), 7.69 (2H, br s), 7.92 (2H, m), 8.44 (1H, s), 10.48 (1H, br s), 10.54 (1H, br s) ppm; MS (ES+) 338.01

Workup

  1. stirringto stir for 30 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe moist solid was dissolved in hot EtOAc
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resultant solid dried under vacuum

Sources & evidence

ORD record
ord-6cbac2f16b0d47fe9ae4b517ebef44f1
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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