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

HRID 1524444Notes

Reaction equation

HRID 1524444 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.

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-785ce937593b43cd85f43a140be65b9f
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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