Water → 6-Phenoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 217672Notes

Reaction equation

HRID 217672 reaction equation
Br.Cl[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1.[O-:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].O>CN1C(=O)CCC1>[O:13]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4445035Phenolate SodiumHCID 866507946-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

Product 1

HCID 581369666-Phenoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamineYield 20.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.001; 200 mg) were initially charged dissolved in NMP (4 ml). Thereafter, sodium phenoxide (185 mg) was introduced at RT. After stirring at RT for one hour, the reaction was completed by heating to 55° C. for 2 h. Subsequently, the mixture was admixed with water and extracted three 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 crude product was purified using silica gel with a dichloromethane/methanol gradient. 38 mg of the title compound were obtained in solid form. LC-MS rt: 0.80 min [M+H]+: 228.1 (met. a)

Workup

  1. temperatureby heating to 55° C. for 2 h
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationafter the desiccant had been filtered off
  5. customdried under reduced pressure
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-4c8652fcf6c440eda84b91f98c30781c
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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