Water → Isopropyl 6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylate

HRID 1169144Notes

Reaction equation

HRID 1169144 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=2)[N:7]=1.C(N(C(C)C)[CH:17]([CH3:19])[CH3:18])C.C(I)(C)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([O:13][CH:17]([CH3:19])[CH3:18])=[O:12])[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 81531DiisopropylethylamineHCID 229892926-Chloro-[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylic acid

Product 1

HCID 22989245Isopropyl 6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2.14 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylic acid and 5.57 ml of N-ethyldiisopropylamine were dissolved in 30 ml of N,N-dimethylformamide; 3.23 ml of isopropyl iodide was added, followed by stirring at room temperature for 10 hours and at 50° C. for 3 hours. After cooling, water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate. The desired fraction was collected and concentrated under reduced pressure to yield 2.21 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate
  7. customThe desired fraction was collected
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-131f586a4f3c49bda5e03417908d6d78
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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