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【结 构 式】

【分子编号】45197

【品名】 

【CA登记号】

【 分 子 式 】C8H4ClNO2

【 分 子 量 】181.578

【元素组成】C 52.92% H 2.22% Cl 19.52% N 7.71% O 17.62%

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:(II)

The synthesis of [14C]-labeled tenidap sodium has been reported: The chlorination of [14C]-2,3-dihydro-1H-indole-2,3-dione (I) with sulfuryl chloride and triethylamine in hot acetonitrile gives the 5-chloro derivative (II), which is partially reduced by treatment with hydrazine hydrate in refluxing ethanol, followed by a treatment with KOH in the same refluxing solvent, to yield 5-chloro-2,3-dihydro-1H-indol-2-one (III). The reaction of (III) with chlorosulfonyl isocyanate (IV) in refluxing dichloromethane affords 5-chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide (V), which is condensed with 2-thienylcarbonyl chloride (VI) by means of dimethylaminopyridine (DMAP) and triethylamine (TEA) in DMF, giving tenidap (VII). Finally, this compound is treated with NaHCO3 in hot acetone.

1 Hale, K.J.; Lennon, J.A.; Hobbs, C.J.; Javaid, M.H.; Manaviazar, S.; Asymmetric synthesis of the C17-C27 segment of the antineoplasticmacrolide bryostatin 1. J Label Compd Radiopharm 1995, 36, 8, 1359.
2 Johnson, D.L.; Melvin, L.S.; Falkner, F.C.; Rusek, F.W.; Robinson, R.P.; Synthesis of C-14 isotopic isomers of tenidap - A novel antiinflammatory agent. J Label Compd Radiopharm 1996, 38, 3, 207.
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) 14098 2,3-Indolinedione; 1H-Indole-2,3-dione; Isatin 91-56-5 C8H5NO2 详情 详情
(I) 45196   C8H5NO2 详情 详情
(II) 14099 5-Chloro-1H-indole-2,3-dione; 5-Chloroisatin 17630-76-1 C8H4ClNO2 详情 详情
(II) 45197   C8H4ClNO2 详情 详情
(III) 14100 5-Chlorooxindole; 5-Chloro-1,3-dihydro-2H-indol-2-one 17630-75-0 C8H6ClNO 详情 详情
(III) 45198   C8H6ClNO 详情 详情
(IV) 14101 Chlorosulfonyl isocyanate 1189-71-5 CClNO3S 详情 详情
(V) 14096 5-Chloro-2-oxo-1-indolinecarboxamide C9H7ClN2O2 详情 详情
(V) 45199   C9H7ClN2O2 详情 详情
(VI) 14103 2-Thiophenecarbonyl chloride 5271-67-0 C5H3ClOS 详情 详情
(VII) 14104 5-Chloro-3-[(Z)-hydroxy(2-thienyl)methylidene]-2-oxo-1H-indole-1(2H)-carboxamide C14H9ClN2O3S 详情 详情
(VII) 45200   C14H9ClN2O3S 详情 详情
Extended Information