Cyanogen Bromide → HCID 58136948, compound

HRID 217683Notes

Reaction equation

HRID 217683 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:13][NH2:14])[N:7]=[N:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[N:15]#[C:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:11]([O:10][C:9]1[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]2[N:7]([C:16]([NH2:15])=[N:14][N:13]=2)[N:8]=1)[CH3:12]

Participants

6

Reactant 3

HCID 10476Cyanogen Bromide2×HCID 11430Potassium CarbonateHCID 55279276HCID 55279276, compound

Product 1

HCID 58136948HCID 58136948, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

(5,6-Diethoxy-pyridazin-3-yl)hydrazine (W3.120; 50 mg) was initially charged in a mixture of ethanol (3.5 ml) and water (0.75 ml) at RT while stirring. Thereafter, cyanogen bromide (55 mg, dissolved in 0.75 ml of ethanol and 0.15 ml of water) was cautiously added dropwise. After stirring for 7 h, the mixture was left to stand overnight. Thereafter, a further 2 equivalents of cyanogen bromide, dissolved in 0.75 ml of ethanol and 0.15 ml of water, were added and the mixture was stirred further at RT for 2 h and then at 55° C. for 8 h. After cooling, the solvent was drawn off and the residue was admixed with water. After it had been alkalized with saturated potassium carbonate solution, it was extracted four times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The residue was purified by means of preparative HPLC (met. A). The clean product fractions were combined, freed of the acetonitrile under reduced pressure, alkalized with saturated potassium carbonate solution and extracted four times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 36 mg of the title compound were obtained. LC-MS rt: 0.54 min [M+H]+: 224.2 (met. b)

Workup

  1. stirringAfter stirring for 7 h
  2. waitthe mixture was left
  3. stirringthe mixture was stirred further at RT for 2 h
  4. waitat 55° C. for 8 h
  5. temperatureAfter cooling
  6. extractionwas extracted four times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationafter the desiccant had been filtered off
  9. customdried under reduced pressure
  10. customThe residue was purified by means of preparative HPLC (
  11. extractionextracted four times with dichloromethane
  12. dry with materialThe combined organic phases were dried over sodium sulfate
  13. filtrationafter the desiccant had been filtered off
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-1a4059adada14d5286b16009bf0296a9
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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