Triethylamine → HCID 67479813, compound

HRID 509527Notes

Reaction equation

HRID 509527 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:36]([C:37]([OH:39])=O)=[CH:35][C:34]([Br:40])=[CH:33][N:32]=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.CCOC(C)=O>[NH2:30][C:31]1[C:36]([C:37]([NH:50][NH:49][C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:48])=[O:39])=[CH:35][C:34]([Br:40])=[CH:33][N:32]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 7374452-Amino-5-bromonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 67479813HCID 67479813, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

TBTU (2.219 g, 6.912 mmol) and triethylamine (466.3 mg, 642.3 μL, 4.608 mmol) were added to a solution of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g, 4.608 mmol) and benzohydrazide (752.9 mg, 5.530 mmol) in DMF (40.00 mL) and the resulting solution stirred at ambient temperature over the weekend. The reaction was treated with water/EtOAc and the organics separated. The organic layer was washed with water (3×), dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil which was triturated with ether and dried under high vacuum to give the product as an off-white solid that was used directly in the next step without further purification (1.177 g, 62% Yield). MS (ES+) 336.86.

Workup

  1. washThe organic layer was washed with water (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil which
  6. customwas triturated with ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-ff703aa33b0940cd84970ff935f9ed56
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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