Cyanogen Bromide → HCID 58136812, compound

HRID 532345Notes

Reaction equation

HRID 532345 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[N:13][C:12]([NH:15][NH2:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.[N:20]#[C:21]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.CCO.O>[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]([CH3:19])[CH3:18])[C:12]2[N:13]([C:21]([NH2:20])=[N:16][N:15]=2)[N:14]=1

Participants

7

Reactant 3

HCID 10476Cyanogen Bromide2×HCID 11430Potassium CarbonateHCID 86650805HCID 86650805, compound

Product 1

HCID 58136812HCID 58136812, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Procedure

(6-Chloro-4-isopropylpyridazin-3-yl)hydrazine trifluoroacetic acid salt (W3.009; 258 mg) was initially charged in ethanol/water (6/1 ml) at RT while stirring. Thereafter, cyanogen bromide (182 mg, dissolved in a mixture of 1.5 ml of EtOH and 0.5 ml of water) was cautiously added dropwise. After stirring for 5 hours, the mixture was left to stand overnight, another 1 eq. of the cyanogen bromide solution was added and the mixture was stirred all day. After standing overnight, the solvent was drawn off and the residue was admixed with water. Once the residue had been alkalized with saturated potassium carbonate solution, it was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after filtering off the desiccant, dried under reduced pressure. 180 mg of the title compound were obtained in sufficient purity. LC-MS rt: 0.65 min [M+H]+: 212.1 (met. b)

Workup

  1. additionwas cautiously added dropwise
  2. stirringAfter stirring for 5 hours
  3. waitthe mixture was left
  4. stirringthe mixture was stirred all day
  5. waitAfter standing overnight
  6. extractionwas extracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationafter filtering off the desiccant,
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e0e79c2f3edd4b268aa6142cba5cda2d
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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