Trifluoroacetic acid → 6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine

HRID 515782Notes

Reaction equation

HRID 515782 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:8][NH2:9])=[CH:6][CH:7]=1.[C:10](O)([C:12]([F:15])([F:14])[F:13])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:10]([C:12]([F:15])([F:14])[F:13])=[N:9][N:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine

Conditions

Temperature
85 °C

Procedure

A mixture of 3-chloro-6-hydrazinylpyridazine (3.3 g, 22.8 mmol) in TFA (60 mL) was heated to 85° C. for 18 h. The reaction mixture was cooled to room temperature and TFA was removed in vacuo. The residue was partitioned between DCM and saturated aqueous sodium bicarbonate and the organic layer was washed with a saturated solution of sodium bicarbonate (3×), dried over sodium sulfate, and evaporated to dryness to afford 2.8 g of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine as a beige solid. 1H NMR (300 MHz, DMSO-d6) δ 8.72 (d, 1H), 7.78 (d, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customTFA was removed in vacuo
  3. customThe residue was partitioned between DCM and saturated aqueous sodium bicarbonate
  4. washthe organic layer was washed with a saturated solution of sodium bicarbonate (3×)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7ac6f6645a824e74bf03e3b8124da660
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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