Hydrochloric Acid → HCID 15079112, compound

HRID 1111142Notes

Reaction equation

HRID 1111142 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][CH3:26])[CH:18]=2)[C:9]([S:27][CH2:28][CH2:29][CH3:30])=[N:8]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>CN(C)C=O>[Cl:14][C:11]1[C:12](=[O:13])[NH:7][N:8]=[C:9]([S:27][CH2:28][CH2:29][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][CH3:26])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 15079021HCID 15079021, compound

Product 1

HCID 15079112HCID 15079112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture comprising 256 mg of 2-(2-trimethylsilylethoxymethyl)-4-chloro-5-(3,4-dimethoxybenzylamino)-6-n-propylmercapto-3(2H)pyridazinone prepared in Reference Example 5, 3 ml of tetra-n-butylammonium fluoride (1M tetrahydrofuran solution) and 1.5 ml of N,N-dimethylformamide, was stirred at a temperature of 150° C. for 3 hours. A 1N hydrochloric acid aqueous solution was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with water and a sodium hydrogencarbonate aqueous solution in this order, and dried over sodium sulfate. The solvent was distilled off and the residue thereby obtained was purified by silica gel thin layer chromatography by using benzene-ethyl acetate (1:1 v/v) as the developer, to obtain 39 mg of the above identified compound as a light yellow solid substance. The product was changed into slightly yellow crystals having a melting point of from 129° to 130° C. by the recrystallization thereof from a solvent mixture of ethyl acetate-diethyl ether-n-hexane.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materiala sodium hydrogencarbonate aqueous solution in this order, and dried over sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue thereby obtained
  6. customwas purified by silica gel thin layer chromatography
  7. customto obtain 39 mg of the
  8. customof from 129° to 130° C.
  9. customby the recrystallization
  10. additionfrom a solvent mixture of ethyl acetate-diethyl ether-n-hexane

Sources & evidence

ORD record
ord-01edc2d540e94020a335fd9306add003
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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