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【结 构 式】 
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【分子编号】59912 【品名】4-(8-bromo[1,7]naphthyridin-6-yl)benzoic acid 【CA登记号】 |
【 分 子 式 】C15H9BrN2O2 【 分 子 量 】329.15274 【元素组成】C 54.74% H 2.76% Br 24.28% N 8.51% O 9.72% |
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：(XV)In an alternative synthetic procedure, dinitrile (VII) was cyclized in the presence of sodium methoxide to produce 6-amino-8-methoxy-1,7-naphthyridine (XII). This was converted to triflate (XIII) by diazotization in the presence of trifluoromethanesulfonic acid. Suzuki coupling of triflate (XIII) with 4 carboxyphenylboronic acid (XI) yielded adduct (XIV). The 8-methoxy group of (XIV) was then displaced with PBr3 to produce bromide (XV), which was subjected to further Suzuki coupling with the benzofurazan boronic acid (V) to provide the title compound.
| 【1】 Hersperger, R.; Dawson, J.; Mueller, T.; Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic acid: A potent and selective phosphodiesterase type 4D inhibitor. Bioorg Med Chem Lett 2002, 12, 2, 233. |
| 【2】 Hersperger, R. (Novartis AG); Naphtyridine derivs.. EP 0934320; US 6136821; WO 9818796 . |
| 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) | 59799 | 2,1,3-benzoxadiazol-5-ylboronic acid | C6H5BN2O3 | 详情 | 详情 | |
| (VII) | 40932 | 3-(cyanomethyl)-2-pyridinecarbonitrile | C8H5N3 | 详情 | 详情 | |
| (XI) | 32841 | 4-(dihydroxyboryl)benzoic acid；4-Boronobenzoic acid；4-carboxyphenylboronic acid;4-(Dihydroxyboryl)benzoic acid | 14047-29-1 | C7H7BO4 | 详情 | 详情 |
| (XII) | 59909 | 8-methoxy[1,7]naphthyridin-6-amine; 8-methoxy[1,7]naphthyridin-6-ylamine | C9H9N3O | 详情 | 详情 | |
| (XIII) | 59910 | 8-methoxy[1,7]naphthyridin-6-yl trifluoromethanesulfonate | C10H7F3N2O4S | 详情 | 详情 | |
| (XIV) | 59911 | 4-(8-methoxy[1,7]naphthyridin-6-yl)benzoic acid | C16H12N2O3 | 详情 | 详情 | |
| (XV) | 59912 | 4-(8-bromo[1,7]naphthyridin-6-yl)benzoic acid | C15H9BrN2O2 | 详情 | 详情 |
Extended Information