참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Potassium Iodide | HCID 4875 | — |
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | Dofetilide | HCID 71329 | — |
| 반응물 | 1-(2-Chloroethoxy)-4-nitrobenzene | HCID 2764587 | — |
| 반응물 | Selenium | HCID 6326970 | — |
| 반응물 | N-methyl-4-nitrophenethylamine hydrochloride | HCID 16218354 | — |
| 촉매 | Tetrabutylammonium Iodide | HCID 67553 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine | HCID 14645090 | — |
반응 단계
In another embodiment, the competitive inhibitor is a selenium analog of dofetilide (N-[4-(2-[2-[4-(methanesulphonamido)phenoxy]-N-methylethylamino]ethyl)phenyl]methane-sulfphonamide). In one aspect of this embodiment, the selenium analog is di-seleno-dofetilide(n-[4-(2-[2-[4-(methaneselenodoioxamido)phenoxyl]-N-methylethylamino)ethyl)phenyl]-methane-selenodioxamide). Di-seleno-dofetilide may be synthesized according to the scheme shown in FIG. 3, which is based on the synthesis of dofetilide described in U.S. Pat. No. 6,124,363. First, N-methyl-2-(4-nitrophenyl)ethylamine hydrochloride (compound 310) is mixed with 4-(2-chloroethoxy)nitrobenzene (compound 320), anhydrous potassium carbonate, potassium iodide, tetra-n-butylammonium iodide and deionized water and heated under reflux for 3 hours. Next, the mixture is cooled to about 40° C., ethyl acetate is added, and the mixture is extracted with ethyl acetate and concentrated. Ethanol is then added to the extract to precipitate the product and the product is filtered to give N-Methyl-N-[2-(4-nitrophenoxy)ethyl]-4-nitrophenethylamine (compound 330). In the next step, compound 330 and 5% w/v palladium-on-carbon are added to methanol, stirred and hydrogenated at 60 p.s.i. to give N-Methyl-N-[2-(4-aminophenoxy)ethyl]-4-aminophethylamine (compound 340). Compound 340 is then added to acetonitrile, followed by triethylamine and methaneselenodioxy chloride. Sodium carbonate is then added to the reaction mixture and distilled. Next, sodium hydroxide is added to the mixture, followed by concentrated hydrochloric acid. The solid is the collected by filtration, washed with water, and dried to obtain di-seleno-dofetilide (compound 350).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US07326772B2 |
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| 출처 데이터셋 | uspto-grants-2008_02 |
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| ORD ID | ord-9bde05bad10a448691af53a030af1ca0 |
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| 출처 메모 | uspto-grants-2008_02 |
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