Potassium Iodide → HCID 21973233, compound

HRID 350698Notes

Reaction equation

HRID 350698 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[N:10][NH:9][C:8](=[O:12])[CH:7]=1.CN(C)C=O.[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:24][O:25][C:21]=2[CH:20]=1.[I-].[K+]>C(N(CC)CC)C>[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:27][CH2:28][N:29]([CH2:3][CH2:4][NH:5][C:6]4[CH:11]=[N:10][NH:9][C:8](=[O:12])[CH:7]=4)[CH2:30][CH2:31]3)=[N:24][O:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 21973225HCID 21973225, compound

Product 1

HCID 21973233HCID 21973233, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.72 g (12.9 millimoles) of 5-(2-chloroethylamino)-2H-pyridazine-3-one-hydrochloride, 11 ml of anhydrous dimethyl formamide, 5.0 g (22.7 millimoles) of 6-fluoro-3-piperidine-4-yl-1,2-benzisoxazole, 6.3 ml of triethyl amine and 0.21 g of potassium iodide are admixed. The reaction mixture is heated to boiling under stirring for 8 hours, cooled to room temperature and filtered. To the mother lye a solution of 2.6 g of sodium hydrogen carbonate and 40 ml of water is added dropwise. The precipitate is filtered, suspended in 100 ml of dichloro methane, stirred for 30 minutes and filtered. The crude product is recrystallized from a 4:1 mixture of water and acetonitrile. The crystals are filtered off. Thus 2.98 g of the desired compound are obtained. Yield 64.6%. M.p.: 97–99° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. filtrationfiltered
  3. additionis added dropwise
  4. filtrationThe precipitate is filtered
  5. stirringstirred for 30 minutes
  6. filtrationfiltered
  7. customThe crude product is recrystallized from a 4:1 mixture of water and acetonitrile
  8. filtrationThe crystals are filtered off

Sources & evidence

ORD record
ord-19b60e59a3c74c97be9c67db80b7aa84
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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