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【结 构 式】 
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【药物名称】 【化学名称】1-[4-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]cyclopropanol 【CA登记号】 【 分 子 式 】C20H17FN6O 【 分 子 量 】376.39649 |
【开发单位】Bayer (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Hypertension, Treatment of, Guanylate Cyclase Activators |
合成路线1
The cyclization of 1-(2-fluorobenzyl)pyrazolo[3,4-b]pyridine-3-carboxamidine (I) (see scheme no. 28591301a, intermediate (IX)) with ethyl 2-(ethoxymethylene)cyanacetate (II) in refluxing toluene gives the pyrimidine-5-carboxylate derivative (III), which is cyclized to the target 1-hydroxycyclopropyl derivation by reaction with CH2I2 and SmI2 in hot THF.
| 【1】 Straub, A.; Benet-Buckholz, J.; Fröde, R.; Kern, A.; Kohlsdorfer, C.; Schmitt, P.; Schwarz, T.; Siefert, H.-M.; Stasch, J.-P.; Metabolites of orally active NO-independent pyrazolopyridine stimulators of soluble guanylate cyclase. Bioorg Med Chem 2002, 10, 6, 1711. |
| 【2】 Perzborn, E.; Kern, A.; Stasch, J.-P.; Straub, A.; Feurer, A.; Dembowsky, K.; Alonso-Alija, C.; Stahl, E. (Bayer AG); Substd. pyrazole deriv.. DE 19920352; WO 0066582 . |
| 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) | 50477 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide | 256376-68-8 | C14H12FN5 | 详情 | 详情 |
| (II) | 43563 | ethyl (E)-2-cyano-3-ethoxy-2-propenoate；(E)-ethyl 2-cyano-3-ethoxyacrylate | 94-05-3 | C8H11NO3 | 详情 | 详情 |
| (III) | 63161 | ethyl 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinecarboxylate | C20H17FN6O2 | 详情 | 详情 |
Extended Information