t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-phenoxyphenoxy)phenyl}-N-methylcarbamate → 5-{4-[1-Methyl-6-(4-phenoxyphenoxy)-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

HRID 2303788Notes

Reaction equation

HRID 2303788 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:48]=[CH:47][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]=[CH:29][C:28]([O:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:27][CH:26]=4)=[CH:20][C:19]=3[N:38](C)[C:39](=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:49].O1CCOCC1>>[ClH:49].[CH3:39][N:38]1[C:19]2[CH:20]=[C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)[CH:22]=[CH:23][C:18]=2[N:17]=[C:15]1[CH2:14][O:13][C:12]1[CH:47]=[CH:48][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 18461372t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-phenoxyphenoxy)phenyl}-N-methylcarbamateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 867584365-{4-[1-Methyl-6-(4-phenoxyphenoxy)-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

Procedure

A mixture of t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-phenoxyphenoxy)phenyl}-N-methylcarbamate (1.99 g) and 4N hydrogen chloride/dioxane (20 ml) was stirred at ambient temperature for 22 hours. The solvent of the reaction mixture was evaporated to dryness. To the residue was added ethyl acetate and insoluble product was collected by filtration and washed with ethyl acetate to give the title compound (1.57 g).

Workup

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

Sources & evidence

ORD record
ord-be94cd0cc6084ee2b2723e1561ded072
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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