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【结 构 式】 
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【分子编号】14627 【品名】N-ethyl-N-heptyl-4-[4-[(methylsulfonyl)amino]phenyl]-4-oxobutanamide 【CA登记号】 |
【 分 子 式 】C20H32N2O4S 【 分 子 量 】396.55116 【元素组成】C 60.58% H 8.13% N 7.06% O 16.14% S 8.09% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VII)The acylation of aniline (I) with methanesulfonyl chloride (II) in pyridine gives the corresponding sulfonamide (III), which is submitted to a Friedel-Crafts condensation with succinic anhydride (IV) and AlCl3 in hot carbon disulfide to afford 4-[4-(methanesulfonyl)phenyl]-4-oxobutyric acid (V). The amidation of (V) with N-ethylheptylamine (VI) yields the corresponding amide (VII), which is finally reduced with LiAlH4 in THF and treated with an ethanolic solution of fumaric acid in order to precipitate the corresponding salt.
| 【1】 Stolle, W.T.; Stelzer, L.S.; Hester, J.B.; Perricone, S.C.; Hsi, R.S.P.; Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents. J Label Compd Radiopharm 1994, 34, 10, 929. |
| 【2】 Robinson, C.; Robinson, K.; Castaner, J.; Ibutilide Fumarate. Drugs Fut 1996, 21, 9, 894. |
| 【3】 Hester, J.B. Jr. (Pharmacia Corp.); N-(Aminoalkylphenyl)sulfonamides their preparation and therapeutic use. EP 0164865; JP 1985239458; US 5155268 . |
| 【4】 Hester, J.B.; Gibson, J.K.; Cimini, M.G.; Emmert, D.E.; Locker, P.K.; Perricone, S.C.; Skaletzky, L.L.; Sykes, J.K.; West, B.E.; N-[(omega-Amino-1-hydroxyalkyl)phenyl]methanesulfonamide derivatives with Class III antiarrhythmic activity. J Med Chem 1991, 34, 1, 308-15. |
| 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) | 12294 | Aniline; Phenylamine | 62-53-3 | C6H7N | 详情 | 详情 |
| (II) | 13467 | Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride | 124-63-0 | CH3ClO2S | 详情 | 详情 |
| (III) | 13699 | N-Phenylmethanesulfonamide; N-Phenyl methanesulfonamide | 1197-22-4 | C7H9NO2S | 详情 | 详情 |
| (IV) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |
| (V) | 14625 | 4-[4-[(methylsulfonyl)amino]phenyl]-4-oxobutyric acid | C11H13NO5S | 详情 | 详情 | |
| (VI) | 14626 | N-ethyl-1-heptanamine; N-ethyl-N-heptylamine | C9H21N | 详情 | 详情 | |
| (VII) | 14627 | N-ethyl-N-heptyl-4-[4-[(methylsulfonyl)amino]phenyl]-4-oxobutanamide | C20H32N2O4S | 详情 | 详情 |
Extended Information