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【结 构 式】 
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【分子编号】18089 【品名】5-[(Z)-(4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]phenyl)methylidene]-1,3-thiazolidine-2,4-dione 【CA登记号】 |
【 分 子 式 】C34H38N2O5S 【 分 子 量 】586.7522 【元素组成】C 69.6% H 6.53% N 4.77% O 13.63% S 5.46% |
合成路线1
该中间体在本合成路线中的序号：(IX)Treatment of chromane (I) with metanesulfonyl chloride in pyridine at 0 C afforded mesylate (II), which was treated with 2-methylaminoethanol (III) to afford tertiary amine (IV). Reaction with SOCl2 gave chloride (V), and further reaction with p-hydroxybenzaldehyde (VI) provided (VII). Aldehyde (VII) was then condensed with 2,4-thiazolidinedione (VIII) in the presence of piperidine benzoate in toluene to furnish (IX). Finally, the benzyl protecting group was removed by treatment with acetic acid-hydrochloric acid at 60 C to give the title compound.
| 【1】 Reddy, K.A.; Lohray, B.B.; Bhushan, V.; Reddy, A.S.; Kishore, P.H.; Rao, VV.; Saibaba, V.; Bajji, A.C.; Rajesh, B.M.; Reddy, K.V.; Chakrabarti, R.; Rajagopalan, R.; Novel euglycemic and hypolipidemic agents: Part-2. Antioxidant moiety as structural motif. Bioorg Med Chem Lett 1998, 8, 9, 999-1002. |
| 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) | 18084 | [6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanol | C21H26O3 | 详情 | 详情 | |
| (II) | 18085 | [6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl methanesulfonate | C22H28O5S | 详情 | 详情 | |
| (III) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (IV) | 18086 | 2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]-1-ethanol | C24H33NO3 | 详情 | 详情 | |
| (V) | 18087 | N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-N-(2-chloroethyl)-N-methylamine; N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-2-chloro-N-methyl-1-ethanamine | C24H32ClNO2 | 详情 | 详情 | |
| (VI) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (VII) | 18088 | 4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]benzaldehyde | C31H37NO4 | 详情 | 详情 | |
| (VIII) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (IX) | 18089 | 5-[(Z)-(4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]phenyl)methylidene]-1,3-thiazolidine-2,4-dione | C34H38N2O5S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)A new synthesis of the title compound, very similar to that already published, is reported: The condensation of 6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethyl methanesulfonate (I) with 2-(methylamino)ethanol (II) by heating at 120 C gives the tertiary amine (III), which is condensed with 4-fluorobenzaldehyde (IV) by means of NaH in DMF yielding the 4-alkoxy benzaldehyde (V). A new condensation of (V) with thiazolidine-2,4-dione (VI) by means of piperidine in refluxing toluene affords the benzyloxy derivative of the target compound (VII). Finally, the target compound is obtained by treatment of (VII) with HCl in acetic acid.
| 【1】 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 . |
| 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) | 26454 | 6-(benzyloxy)-2,5,7,8-tetramethyl-2-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)chromane | C24H32O3S | 详情 | 详情 | |
| (II) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (III) | 18086 | 2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]-1-ethanol | C24H33NO3 | 详情 | 详情 | |
| (IV) | 12337 | 4-fluorobenzaldehyde | 459-57-4 | C7H5FO | 详情 | 详情 |
| (V) | 18088 | 4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]benzaldehyde | C31H37NO4 | 详情 | 详情 | |
| (VI) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (VII) | 18089 | 5-[(Z)-(4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]phenyl)methylidene]-1,3-thiazolidine-2,4-dione | C34H38N2O5S | 详情 | 详情 |