Cyanogen Bromide → HCID 58136866, compound

HRID 532326Notes

Reaction equation

HRID 532326 reaction equation
Cl.[CH2:2]([C:4]1[N:9]=[N:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)[CH3:3].[N:12]#[C:13]Br>C(O)C.O>[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:13]([NH2:12])=[N:11][N:10]=2)[N:9]=1)[CH3:3]

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 53434476HCID 53434476, compound

Product 1

HCID 58136866HCID 58136866, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

(6-Ethylpyridazin-3-yl)hydrazine hydrochloride (2 g) was initially charged in a mixture of ethanol (30 ml) and water (6 ml) while stirring at RT. Thereafter, cyanogen bromide was cautiously added dropwise (2.4 g dissolved in 7.5 ml of ethanol and 1.5 ml of water). After stirring at RT for one hour, the mixture was left to stand overnight and, the next day, stirred for 4 further hours. The solvent was then drawn off and the residue was purified by means of preparative HPLC (met. C). The clean product fractions were combined, freed of the acetonitrile under reduced pressure, alkalized with saturated potassium carbonate solution and extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 830 mg of the title compound were obtained. The aqueous potassium carbonate phase was likewise freeze-dried, then taken up with a little water and extracted five times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. A further 180 mg of the title compound were obtained.

Workup

  1. stirringAfter stirring at RT for one hour
  2. waitthe mixture was left
  3. stirringthe next day, stirred for 4 further hours
  4. customthe residue was purified by means of preparative HPLC (met. C)
  5. extractionextracted repeatedly with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8ef5f2d7954a4af699871cf14a98cc24
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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