Potassium Iodide → HCID 21973237, compound

HRID 350694Notes

Reaction equation

HRID 350694 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[N:9][NH:8][C:7](=[O:11])[C:6]=1[Cl:12].[F:13][C:14]1[CH:28]=[CH:27][C:17]2[C:18]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:19][O:20][C:16]=2[CH:15]=1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C(N(CC)CC)C.CN(C)C=O>[F:13][C:14]1[CH:28]=[CH:27][C:17]2[C:18]([CH:21]3[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][NH:4][C:5]4[CH:10]=[N:9][NH:8][C:7](=[O:11])[C:6]=4[Cl:12])[CH2:25][CH2:26]3)=[N:19][O:20][C:16]=2[CH:15]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 22339775HCID 22339775, compound

Product 1

HCID 21973237HCID 21973237, compoundYield 77.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

5.6 g (22.2 millimoles) of 5-(2-bromoethylamino)-4-chloro-2H-pyridazine-3-one, 16 ml of anhydrous dimethyl formamide, 5.62 g (25.5 millimoles) of 6-fluoro-3-piperidine-4-yl-1,2-benzisoxazole, 8.85 ml of triethyl amine and 0.44 g of potassium iodide are admixed. The reaction mixture is heated at 60° C. for 2 hours, cooled to room temperature and a solution of 5.46 g of sodium carbonate and 50 ml of water is added dropwise. The mixture is stirred for half an hour, the suspension is filtered and the filtered product is washed three times with 20 ml of water each. The crude product thus obtained is dissolved in a 9:1 mixture of acetonitrile and water under heating to boiling, filtered warm and the mother lye is evaporated to one-third of its volume. The residual mother lye is stirred under cooling with icecold water for 2 hours. The precipitated crystals are filtered. Thus 6.75 g of the desired compound are obtained. Yield 77.6%. Mp.: 229–231° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe suspension is filtered
  3. washthe filtered product is washed three times with 20 ml of water each
  4. customThe crude product thus obtained
  5. temperatureunder heating
  6. filtrationfiltered
  7. temperaturewarm
  8. customthe mother lye is evaporated to one-third of its volume
  9. stirringThe residual mother lye is stirred
  10. temperatureunder cooling with icecold water for 2 hours
  11. filtrationThe precipitated crystals are filtered

Sources & evidence

ORD record
ord-25561ffd97c34b558477b851da585430
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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