HCID 86758454, compound → HCID 77844649, compound

HRID 2303820Notes

Reaction equation

[C:1]([C:3]1[CH:54]=[CH:53][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH2:16][O:17][C:18]4[CH:50]=[CH:49][C:21]([CH2:22][CH:23]5[S:27][C:26](=[O:28])[N:25](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[C:24]5=[O:48])=[CH:20][CH:19]=4)[N:13]([CH3:51])[C:12]=3[CH:52]=2)=[CH:5][CH:4]=1)#[N:2]>C(O)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH2:16][O:17][C:18]4[CH:50]=[CH:49][C:21]([CH2:22][CH:23]5[S:27][C:26](=[O:28])[NH:25][C:24]5=[O:48])=[CH:20][CH:19]=4)[N:13]([CH3:51])[C:12]=3[CH:52]=2)=[CH:53][CH:54]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-{4-[6-(4-cyanophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione (0.69 g) and aqueous acetic acid solution (80%, 25 ml) was stirred at 70° C. for 3 hours. The reaction mixture was concentrated and an aqueous solution of sodium bicarbonate (10%, 250 ml) was added to the residue. The mixture was stirred at ambient temperature for several hours. The insoluble product was isolated by filtration and dried in the air to afford 5-{4-[6-(4-cyanophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione. A mixture of the product and 4N hydrogen chloride/dioxane was stirred at ambient temperature for 2 hours. Insoluble product was isolated by filtration and washed with ethyl acetate to give the title compound (0.41 g).

Workup

concentrationThe reaction mixture was concentrated
additionan aqueous solution of sodium bicarbonate (10%, 250 ml) was added to the residue
stirringThe mixture was stirred at ambient temperature for several hours
customThe insoluble product was isolated by filtration
customdried in the air

Sources & evidence

ORD record: ord-53b0779d94204e9caa3d66c90d9ee325
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06432993B1

Reaction notes

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