Benzoylhydrazine → HCID 66831694, compound

HRID 570937Notes

Reaction equation

HRID 570937 reaction equation
[CH3:1][S:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]([OH:16])=O)=[C:7]2[N:6]=[N:5]1.C(N=C=NCCCN(C)C)C.[C:28]([NH:36][NH2:37])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[C:28]([NH:36][NH:37][C:14]([C:13]1[N:12]=[CH:11][N:8]2[C:9](=[O:10])[N:4]([CH2:3][S:2][CH3:1])[N:5]=[N:6][C:7]=12)=[O:16])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11955BenzoylhydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66831721HCID 66831721, compound

Product 1

HCID 66831694HCID 66831694, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Methylthiomethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (0.73 mmol, 175 mg, 1 eq.), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI) (0.76 mmol, 146 mg, 1.05 eq.) and benzohydrazide (0.76 mmol, 104 mg, 1.05 eq.) were placed in a round bottom flask and dissolved in acetonitrile (3 mL). A suspension developed 1 minute after starting room temperature stirring and it was stirred for further 90 minutes. The reaction mixture was filtered and the obtained solid washed with water, acetonitrile and ether, and dried under vacuum. The filtrate was poured into ice/water and the filtration, washing and drying steps were repeated. Yield 65%. δH (DMSO-d6) 10.35 (1H, bs), 10.28 (1H, bs), 8.75 (1H, bs), 7.74 (2H, m), 7.37 (3H, m), 5.25 (2H, bs), 2.07 (3H, bs).

Workup

  1. customafter starting room temperature
  2. stirringit was stirred for further 90 minutes
  3. filtrationThe reaction mixture was filtered
  4. washthe obtained solid washed with water, acetonitrile and ether
  5. customdried under vacuum
  6. additionThe filtrate was poured into ice/water
  7. filtrationthe filtration
  8. washwashing
  9. customdrying steps

Sources & evidence

ORD record
ord-10899fc87ef044a28bc1365c0f21073c
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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