HCID 18461418, compound → 5-{4-[6-(3,5-Di-t-butyl-4-hydroxyphenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

HRID 2303802Notes

Reaction equation

HRID 2303802 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:50]=[CH:49][C:12]([O:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:28]([OH:35])=[C:27]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:26]=4)=[CH:20][C:19]=3[N:40]([CH3:48])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:51].O1CCOCC1>>[ClH:51].[C:36]([C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([C:31]([CH3:32])([CH3:34])[CH3:33])[C:28]=1[OH:35])[O:24][C:21]1[CH:22]=[CH:23][C:18]2[N:17]=[C:15]([CH2:14][O:13][C:12]3[CH:11]=[CH:10][C:9]([CH2:8][CH:4]4[S:3][C:2](=[O:1])[NH:6][C:5]4=[O:7])=[CH:50][CH:49]=3)[N:40]([CH3:48])[C:19]=2[CH:20]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

3

Reactant 2

HCID 18461418HCID 18461418, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 867584465-{4-[6-(3,5-Di-t-butyl-4-hydroxyphenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

Procedure

A mixture of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(3,5-di-t-butyl-4-hydroxyphenoxy)phenyl}-N-methylcarbamate (0.72 g) and 4N hydrogen chloride/dioxane (20 ml) was stirred at room temperature for 17 hours. The solvent of the reaction mixture was evaporated to dryness. To the residue was added ethyl acetate and insoluble product was isolated by filtration and washed with ethyl acetate to give the title compound (0.41 g).

Workup

  1. customThe solvent of the reaction mixture was evaporated to dryness
  2. additionTo the residue was added ethyl acetate
  3. custominsoluble product was isolated by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-175f68421dd7418787cc934b4fdeeeda
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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