HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-[4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]naphthalene-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Naphthoyl chloride | HCID 75246 | — |
| Reactant | 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride | HCID 86587768 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]naphthalene-2-carboxamide | HCID 10145908 | 73.4% |
Reaction Steps
A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.32 ml), 2-naphthoyl chloride (153 mg), 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) and anhydrous N,N-dimethylformamide (8 ml). The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate and water. The precipitate was isolated by filtration to afford the title compound (337 mg, white powder, mp 221-223° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06562849B1 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-30fc791967ed4708876ca7c2b0f5afde |
| Source note | uspto-grants-2003_05 |