Tetrabutylammonium Fluoride → HCID 15079108, compound

HRID 1111141Notes

Reaction equation

HRID 1111141 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:12](=[O:13])[C:11]([Cl:14])=[C:10]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=2)[C:9]([O:28][CH:29]([CH2:31][CH3:32])[CH3:30])=[N:8]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>COCCOC>[Cl:14][C:11]1[C:12](=[O:13])[NH:7][N:8]=[C:9]([O:28][CH:29]([CH2:31][CH3:32])[CH3:30])[C:10]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15079019HCID 15079019, compound

Product 1

HCID 15079108HCID 15079108, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture comprising 150 mg of 2-(2-trimethylsilylethoxymethyl)-4-chloro-5-(3-ethoxy-4-methoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone prepared in Reference Example 4, 1.46 ml of tetra-n-butylammonium fluoride (1M tetrahydrofuran solution) and 5 ml of 1,2-dimethoxyethane, was refluxed under stirring for 3 hours. The solvent was distilled off under reduced pressure, and the residue thereby obtained was extracted with chloroform. The extract was washed twice with 1N hydrochloric acid and once with water in this order and dried over sodium sulfate. Then, the solvent was distilled off to obtain a dark brown oily substance. The oily substance was purified by silica gel preparative thin layer chromatography by using ethyl acetate as the developer, to obtain a light yellow solid substance. The product was crystallized from chloroform-diethyl ether, to obtain 50 mg of the above identified compound having a melting point of from 130.5° to 132° C. as slightly yellow crystals.

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue thereby obtained
  4. extractionwas extracted with chloroform
  5. washThe extract was washed twice with 1N hydrochloric acid and once with water in this order
  6. dry with materialdried over sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customto obtain a dark brown oily substance
  9. customThe oily substance was purified by silica gel preparative thin layer chromatography
  10. customto obtain a light yellow solid substance
  11. customThe product was crystallized from chloroform-diethyl ether
  12. customto obtain 50 mg of the
  13. customof from 130.5° to 132° C.

Sources & evidence

ORD record
ord-f8c781ec5a1d4b769a97815b25671dd2
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

Loading…