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【结 构 式】 
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【分子编号】60164 【品名】4-{2-[methyl(2-pyridinyl)amino]ethoxy}benzaldehyde 【CA登记号】 |
【 分 子 式 】C15H16N2O2 【 分 子 量 】256.30432 【元素组成】C 70.29% H 6.29% N 10.93% O 12.48% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of 4-fluoroiodobenzene (I) with 14C-KCN and CuI in refluxing DMF gives 4-fluorobenzonitrile (II), which is reduced with HCO2H and RaNi in DMF to yield 4-fluorobenzaldehyde (III). The condensation of (III) with the substituted ethanolamine (IV) by means of tBu-OK in DMF affords 4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzaldehyde (V), which is condensed with thiazolidine-2,4-dione (VI) by means of piperidine acetate in refluxing toluene to provide the benzylidene-thiazolidinedione (VII). Finally this compound is hydrogenated with H2 over Pd/C in DMF to furnish the target labeled compound.
| 【1】 Kirefu, T.; Landwater, S.W.; Latter, A.J.; Lawrie, K.W.M.; Morecombe, D.J.; Willcocks, K.; Rosiglitazone maleate (BRL 49653-C); the preparation of [14C] and [3H] isotopomers. J Label Compd Radiopharm 2001, 44, 5, 329. |
| 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) | 54686 | 1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene | 352-34-1 | C6H4FI | 详情 | 详情 |
| (II) | 60162 | 4-fluorobenzonitrile | C7H4FN | 详情 | 详情 | |
| (III) | 60163 | 4-fluorobenzaldehyde | C7H5FO | 详情 | 详情 | |
| (IV) | 17505 | 2-[methyl(2-pyridinyl)amino]-1-ethanol | C8H12N2O | 详情 | 详情 | |
| (V) | 60164 | 4-{2-[methyl(2-pyridinyl)amino]ethoxy}benzaldehyde | C15H16N2O2 | 详情 | 详情 | |
| (VI) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (VII) | 59997 | C18H17N3O3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)
| 【1】 Giles RG. Lewis NJ, Quick JK, et aL. 2000. Regiospecific reduction of 5-benzylidene-2,4-thiuolidoines and 4-oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran. Tetnhedron, 56: 4531～4537(本论文作者来自于SmithKline Beecham Pharmaceuticals．Old Powder Mills, Kent, UK) |
| 【2】 Li X, Abell C, Warrington BH．et aL. 2003. Polymer-assisted solution phase synthesis of the antihyperglycemic agent Rosiglitazone (Avandia). Org Biomol Chem. 1: 4392～4395(本论文作者来自于Department of Chemistry, University Chemical Laboratories, Cambridge,UK) |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 66657 | (4-(2-(methylamino)ethoxy)phenyl)methanol | C10H15NO2 | 详情 | 详情 | |
| (I) | 29474 | 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol | 623-05-2 | C7H8O2 | 详情 | 详情 |
| (II) | 66655 | ethyl 2-iodoacetate | 623-48-3 | C4H7IO2 | 详情 | 详情 |
| (III) | 51988 | ethyl 2-[4-(hydroxymethyl)phenoxy]acetate | C11H14O4 | 详情 | 详情 | |
| (IV) | 66656 | 2-(4-(hydroxymethyl)phenoxy)-N-methylacetamide | C10H13NO3 | 详情 | 详情 | |
| (VI) | 34512 | 2-fluoropyridine | 372-48-5 | C5H4FN | 详情 | 详情 |
| (VII) | 66658 | (4-(2-(methyl(pyridin-2-yl)amino)ethoxy)phenyl)methanol | C15H18N2O2 | 详情 | 详情 | |
| (VIII) | 60164 | 4-{2-[methyl(2-pyridinyl)amino]ethoxy}benzaldehyde | C15H16N2O2 | 详情 | 详情 | |
| (IX) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (X) | 59997 | C18H17N3O3S | 详情 | 详情 |