【结 构 式】 |
【分子编号】11284 【品名】(6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid 【CA登记号】 |
【 分 子 式 】C18H20N2O2 【 分 子 量 】296.36908 【元素组成】C 72.95% H 6.8% N 9.45% O 10.8% |
合成路线1
该中间体在本合成路线中的序号:(VI)The synthesis of [14C]-cabergoline has also been described: The reaction of 6-allylergoline-8beta-carboxylic acid methyl ester (I) with hydrazine in refluxing methanol gives the hydrazide (II), which by reaction with NaNO2-HCl in water is converted to the amine (III). The reaction of (III) again with NaNO2-HCl in water, followed by reaction with SnCl2, affords the chloro derivative (IV), which is condensed with [14C]-CNK in refluxing ethanol-water yielding the nitrile (V). Hydrolysis of (V) with NaOH in refluxing ethanol affords the acid (VI), which is finally condensed with N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide in DMF.
【1】 Mantegani, S.; Brambilla, E.; Ermoli, A.; Fontana, E.; Angiuli, P.; Vicario, G.P.; Syntheses of tritium and carbon-14 labelled N-(3-dimethyl aminopropyl)-N-(ethylaminocarbonyl)-6-(2-propenyl)ergoline-8beta-carboxamide (cabergoline), a potent long lasting prolactin lowering agent. J Label Compd Radiopharm 1991, 29, 5, 519. |
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) | 11279 | methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate | C19H22N2O2 | 详情 | 详情 | |
(II) | 11280 | (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbohydrazide | C18H22N4O | 详情 | 详情 | |
(III) | 11281 | (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-amine; (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-ylamine | C17H21N3 | 详情 | 详情 | |
(IV) | 11282 | (6aR,9R,10aR)-7-Allyl-9-chloro-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | C17H19ClN2 | 详情 | 详情 | |
(V) | 11283 | (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbonitrile | C18H19N3 | 详情 | 详情 | |
(V) | 63078 | (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbonitrile | C18H19N3 | 详情 | 详情 | |
(VI) | 11284 | (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid | C18H20N2O2 | 详情 | 详情 | |
(VI) | 28739 | (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid | C18H20N2O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(III)Reaction of glycine (II) with phthalic anhydride (I) in a microwave oven gave phthaloylglycine (III). Subsequent condensation with phenylamidoxime (IV) in the presence of DCC in dimethoxyethane afforded the O-acyl intermediate (V), which on heating cyclized to the title oxadiazole.
【1】 Antunes, R.; Batista, H.; Srivastava, R.M.; Thomas, G.; Araujo, C.C.; New phthalimide derivatives with potent analgesic activity: II. Bioorg Med Chem Lett 1998, 8, 21, 3071. |
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) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
(II) | 20436 | glycine | 56-40-6 | C2H5NO2 | 详情 | 详情 |
(III) | 11284 | (6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid | C18H20N2O2 | 详情 | 详情 | |
(IV) | 20438 | N'-hydroxybenzenecarboximidamide | 613-92-3 | C7H8N2O | 详情 | 详情 |
(V) | 20439 | 2-[2-([[(Z)-amino(phenyl)methylidene]amino]oxy)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione | C17H13N3O4 | 详情 | 详情 |