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【结 构 式】 
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【分子编号】43678 【品名】methyl 3-methoxy-4,7-dihydroisoxazolo[5,4-c]pyridine-6(5H)-carboxylate 【CA登记号】 |
【 分 子 式 】C9H12N2O4 【 分 子 量 】212.20536 【元素组成】C 50.94% H 5.7% N 13.2% O 30.16% |
合成路线1
该中间体在本合成路线中的序号：(II)The methylation of intermediate 3-hydroxy-4,5,6,7-tetrahydropyrido[4,3-d]oxazole-6-carboxylic acid methyl ester (I) (see intermediate (XI) in the synthesis of scheme 28607501a) with diazomethane gives the methoxy compound (II), which is decarboxylated with KOH to yield 3-methoxy-4,5,6,7-tetrahydropyrido[4,3-d]oxazole (III). The nitrosation of (III) with HNO2 affords 3-methoxy-6-nitroso-4,5,6,7-tetrahydropyrido[4,3-d]oxazole (IV), which is tritiated with 3H2O and TEA to afford the tritiated intermediate (V). Finally, this compound is desmethylated with HBr to provide the target compound.
| 【1】 Johansen, J.S.; Falch, E.; Krogsgaard-Larsen, P.; Deuterium labelling of the GABA agonists THIP, piperidine-4-sulphonic acid and the GABA uptake inhibitor THPO. J Label Compd Radiopharm 1982, 19, 689-702. |
| 【2】 Christensen, V.; Krogsgaard-Larsen, P.; Falch, E.; Chemistry and pharmacology of the GABA agonists THIP (Gabodaxol) and isoguvacine. Drugs Fut 1984, 9, 8, 597. |
| 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) | 43677 | methyl 3-hydroxy-4,7-dihydroisoxazolo[5,4-c]pyridine-6(5H)-carboxylate | C8H10N2O4 | 详情 | 详情 | |
| (II) | 43678 | methyl 3-methoxy-4,7-dihydroisoxazolo[5,4-c]pyridine-6(5H)-carboxylate | C9H12N2O4 | 详情 | 详情 | |
| (III) | 43679 | 3-methoxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine; methyl 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-yl ether | C7H10N2O2 | 详情 | 详情 | |
| (IV) | 43680 | methyl 6-nitroso-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-yl ether; 3-methoxy-6-nitroso-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine | C7H9N3O3 | 详情 | 详情 | |
| (V) | 43681 | C7H9N3O3 | 详情 | 详情 |