Potassium Iodide → HCID 76283391, compound

HRID 1482596Notes

Reaction equation

HRID 1482596 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.[F:14][C:15]1[CH:29]=[CH:28][C:18]2[C:19]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[N:20][O:21][C:17]=2[CH:16]=1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[F:14][C:15]1[CH:29]=[CH:28][C:18]2[C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][N:5]4[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[N:7]=[N:6]4)[CH2:24][CH2:23]3)=[N:20][O:21][C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 52439381-(3-chloropropyl)-1H-1,2,3-benzotriazoleHCID 19805377HCID 19805377, compound

Product 1

HCID 76283391HCID 76283391, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-chloropropyl)-1H-benzotriazole (7.02 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 6-fluoro-3-(piperazine-1-yl)benzisoxazole (6.6 g, 0.03 mol), diisopropylethylamine (15.5 g, 0.12 mol) and potassium iodide (5.0 g, 0.03 mol) were respectively added. The mixture was stirred and mixed, then heated and refluxed to react for 15 hours. The mixture was cooled down to ambient temperature and filtered. The filtrate was concentrated to produce oily products, and treated by chromatography with neutral Al2O3 and purified, eluted with dichloromethane to produce 7.9 g compound (I-37) with a yield of 69.3%. ESI-MS [M+H]+: m/z 380.2.

Workup

  1. additionwere respectively added
  2. additionmixed
  3. temperatureheated
  4. temperaturerefluxed
  5. customto react for 15 hours
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto produce oily products
  9. additiontreated by chromatography with neutral Al2O3
  10. custompurified
  11. washeluted with dichloromethane

Sources & evidence

ORD record
ord-e3eca9ec50df4b53865731af8135c6c2
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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