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

HRID 657849Notes

Reaction equation

HRID 657849 reaction equation
[H-].[Na+].Br.Cl[C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([NH2:14])=[N:12][N:13]=2)[N:10]=1.O.[CH:16]1([OH:20])[CH2:19][CH2:18][CH2:17]1>>[CH:16]1([O:20][C:5]2[CH:6]=[CH:7][C:8]3[N:9]([C:11]([NH2:14])=[N:12][N:13]=3)[N:10]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76218Cyclobutanol2×HCID 866507946-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

Product 1

HCID 581367906-Cyclobutoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Conditions

Temperature
0 °C

Procedure

Cyclobutanol (2.43 ml) was initially charged at RT with stirring and cooled almost to 0° C. with an ice bath. Subsequently, the mixture was admixed with portions of sodium hydride (146 mg). The suspension formed was heated to 55° C. for 30 min and admixed with portions of 6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.001, 200 mg), suspended in cyclobutanol (5 ml). After stirring at 55° C. for 1.5 h, the mixture was left to stand at RT overnight and then 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. 136 mg of the title compound were obtained in solid form. LC-MS rt: 0.82 min [M+H]+: 206.2 (met. a)

Workup

  1. customThe suspension formed
  2. temperaturewas heated to 55° C. for 30 min
  3. stirringAfter stirring at 55° C. for 1.5 h
  4. waitthe mixture was left
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationafter the desiccant had been filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2677fe37a5d24617be9c6cbe08cd4b4c
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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