t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxyphenoxy)phenyl}-N-methylcarbamate → 5-{4-[6-(4-Hydroxyphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

HRID 2303758Notes

Reaction equation

HRID 2303758 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:42]=[CH:41][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]([OH:31])=[CH:27][CH:26]=4)=[CH:20][C:19]=3[N:32]([CH3:40])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.Cl.O1CCOCC1>>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([O:24][C:21]2[CH:22]=[CH:23][C:18]3[N:17]=[C:15]([CH2:14][O:13][C:12]4[CH:41]=[CH:42][C:9]([CH2:8][CH:4]5[S:3][C:2](=[O:1])[NH:6][C:5]5=[O:7])=[CH:10][CH:11]=4)[N:32]([CH3:40])[C:19]=3[CH:20]=2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 18461324t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxyphenoxy)phenyl}-N-methylcarbamateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 99128145-{4-[6-(4-Hydroxyphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dioneYield 21.8%

Procedure

Using 1.49 g of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxyphenoxy)phenyl}-N-methylcarbamate and 10 ml of a 4N hydrochloric acid/dioxane solution, reaction and purification were carried out in a similar manner to that described in Example (2-2a), whereby 0.26 g of the title compound were obtained.

Sources & evidence

ORD record
ord-54fbc21c4039474488fc3ab0b8f3e254
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…