Triethylamine → HCID 86662070, compound

HRID 1959361Notes

Reaction equation

HRID 1959361 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC.[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]([N:49]([C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:48])[NH2:50])=[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 86662070HCID 86662070, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBTU (22.09 g, 68.80 mmol) and Et3N (4.642 g, 6.394 mL, 45.87 mmol) were added to a solution 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 overnight. The reaction mixture was poured into water and the resultant precipitate was filtered and dried under vacuum. This was triturated with hot EtOAc and the resulting precipitate filtered and dried to give the desired product (13.11 g, 85% Yield).

Workup

  1. filtrationthe resultant precipitate was filtered
  2. customdried under vacuum
  3. customThis was triturated with hot EtOAc
  4. filtrationthe resulting precipitate filtered
  5. customdried

Sources & evidence

ORD record
ord-3c9cd2582d2349538128ca73a10053e7
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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