Water → 6-Chloro-3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1929979Notes

Reaction equation

HRID 1929979 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:8][NH2:9])=[CH:6][CH:7]=1.[C:10](Cl)(=O)[CH:11]([CH3:13])[CH3:12].O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:10]([CH:11]([CH3:13])[CH3:12])=[N:9][N:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 62325Isobutyryl chlorideHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 397324056-Chloro-3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazineYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-chloro-6-hydrazinylpyridazine (200 g, 1.38 mol) and isobutyryl chloride (175 mL, 1.66 mol) in 1,4-dioxane (2 L) was heated at about 90° C. overnight. The suspension was cooled to about 5° C. in an ice bath and then water (2 L) was added followed by slow addition of Na2CO3 (275 g, 2.59 mol). The resulting solution was extracted with DCM (3×1 L). The combined organic extracts were dried over MgSO4, concentrated under reduced pressure, and dried under vacuum overnight to give the title compound (255 g, 94%): LC/MS (Table 1, Method a) Rt=2.04 min; MS m/z: 197.1 (M+H)+.

Workup

  1. temperatureThe suspension was cooled to about 5° C. in an ice bath
  2. extractionThe resulting solution was extracted with DCM (3×1 L)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-5c4481e9323a444bbbf8452aedf8acc2
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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