Pyridine → [(4E)-2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-4-(pyridine-3-carbonyloxyimino)-3H-chromen-6-yl] pyridine-3-carboxylate

HRID 1030365Notes

Reaction equation

HRID 1030365 reaction equation
[OH:1][C:2]1[C:3]([CH3:33])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6]/[C:5]/2=[N:31]\[OH:32].Cl.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[C:50](=O)([O-])[O-:51].[K+].[K+]>C(OCC)(=O)C.CN(C)C=O>[CH3:14][C:7]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=2)[CH2:6]/[C:5](=[N:31]\[O:32][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=2)/[C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([O:1][C:50](=[O:51])[C:46]3[CH:47]=[CH:48][CH:49]=[N:44][CH:45]=3)[C:3]=2[CH3:33])[O:8]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 883935005-[[4-[[(4E)-6-hydroxy-4-hydroxyimino-2,5,7,8-tetramethyl-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Product 1

HCID 19822281[(4E)-2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-4-(pyridine-3-carbonyloxyimino)-3H-chromen-6-yl] pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g of 5-{4-[6-hydroxy-4-(E)-hydroxyimino-2,5,7,8-tetramethylchroman-2-ylmethoxy ]benzyl}thiazolidine-2,4-dione (prepared as described in Example 13), 1.1 g of nicotinoyl chloride hydrochloride, 12 ml of pyridine and 12 ml of dimethylformamide was allowed to stand for 6 days at room temperature, after which it was heated for 8 hours at 60°-80° C. An aqueous solution of potassium carbonate and ethyl acetate were added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography eluted with a 2:3 by volume mixture of hexane and ethyl acetate, followed by preparative thin layer silica gel chromatography (developing solvent, hexane:ethyl acetate=1.10 by volume), to give the title compound, softening at 123°-130° C.

Workup

  1. temperatureafter which it was heated for 8 hours at 60°-80° C
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography
  6. washeluted with a 2:3 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-0fa1cc02f0c2470d9d60a330f0e18b8d
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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