Acetic Acid → 6-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 873970

Reaction equation

HRID 873970 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[CH:3]=1.[CH3:11][C:12](O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[N:6]([C:11]([CH3:12])=[N:9][N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 114464906-Chloro-3-hydrazinyl-4-methylpyridazine

Product 1

HCID 155038066-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazineYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

6-chloro-3-hydrazinyl-4-methylpyridazine (Step 111.1) (721 mg, 4.55 mmol) was dissolved in AcOH (15 mL, 262 mmol) and the resulting mixture was heated up and stirred at 115° C. for 1 hr. The reaction was cooled down to RT, diluted with CH2Cl2 and poured into a saturated aq. NaHCO3 solution. The aq. layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title product (752 mg, 3.91 mmol, 84% yield) as grey solid. tR: 0.59 min (LC-MS 2); ESI-MS: 183 [M+H]+ (LC-MS 2).

Workup

  1. temperaturethe resulting mixture was heated up
  2. temperatureThe reaction was cooled down to RT
  3. extractionThe aq. layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-106a0be2b2bf43a3ab0a6fdcc0b1ced0
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Linked notes

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