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【结 构 式】 
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【药物名称】Linogliride, McN-3935 【化学名称】N-(1-Methyl-2-pyrrolidinylidene)-N'-phenyl-4-morpholinecarboxamidine 【CA登记号】75358-37-1, 78782-47-5 (fumarate) 【 分 子 式 】C16H22N4O 【 分 子 量 】286.37994 |
【开发单位】Ortho-McNeil (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS |
合成路线1
The reaction of phenyl isothiocyanate (I) with 2-imino-1-methyl pyrrolidine (II) in benzene gives N-(1-methyl-2-pyrrolidinylidene)-N'-phenylthiourea (III), which is treated with iodomethane in refluxing acetone to afford methyl N-1-methyl-2-pyrrolidinylidene)-N'-phenylcarbamidothioate (IV). Finally, this compound is treated with morpholine in refluxing isopropanol.
| 【1】 Rasmussen, C.R. (Ortho-McNeil Pharmaceutical, Inc.); Nitrogen heterocyclic carboximidamide compounds. US 4211867 . |
| 【2】 Castaner, J.; Serradell, M.N.; Linogliride. Drugs Fut 1986, 11, 4, 265. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 22146 | 1-isothiocyanatobenzene; phenyl isothiocyanate | 103-72-0 | C7H5NS | 详情 | 详情 |
| (II) | 27770 | 1-methyl-2-pyrrolidinimine | C5H10N2 | 详情 | 详情 | |
| (III) | 27771 | N-(1-methyl-2-pyrrolidinylidene)-N'-phenylthiourea | C12H15N3S | 详情 | 详情 | |
| (IV) | 27772 | 1-methyl-2-[[(methylsulfanyl)(phenylimino)methyl]imino]pyrrolidine | C13H17N3S | 详情 | 详情 | |
| (V) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
Extended Information