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【结 构 式】 
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【分子编号】58502 【品名】tert-butyl 2-{[7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinyl]carbonyl}-2-(1-methyl-2-propynyl)-1-hydrazinecarboxylate 【CA登记号】 |
【 分 子 式 】C24H27ClN4O5 【 分 子 量 】486.95504 【元素组成】C 59.2% H 5.59% Cl 7.28% N 11.51% O 16.43% |
合成路线1
该中间体在本合成路线中的序号：(XI)Treatment of 3-butyn-2-ol (VIII) with methanesulfonyl chloride and triethylamine produces the propargyl chloride (IX). This is then condensed with tert-butyl carbazate to yield the Boc-protected propargylhydrazine (X). Acylation of (X) with the quinolonecarboxylic acid (VII) affords hydrazide (XI). Palladium-catalyzed coupling between acetylene (XI) and the aryl halide (XII) produces the arylpropinyl compound (XIII). This is finally cyclized in the presence of methanesulfonic acid to the target pyridazinoquinoline.
| 【1】 Horchler, C.L.; et al.; Synthesis of 7-chloro-4-hydroxy-2-(3-(aryl/heteroaryl)prop-2-ynyl)1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-diones (PQD I); potent oral glycine antagonists. 28th Natl Med Chem Symp (June 8 2002, San Diego) 2002, Abst 19. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 58498 | 7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinecarboxylic acid | C15H13ClN2O4 | 详情 | 详情 | |
| (VIII) | 58499 | 3-butyn-2-ol; Ethynylmethylcarbinol | 65337-13-5 | C4H6O | 详情 | 详情 |
| (IX) | 58500 | 3-chloro-1-butyne | 21020-24-6 | C4H5Cl | 详情 | 详情 |
| (X) | 58501 | tert-butyl 2-(1-methyl-2-propynyl)-1-hydrazinecarboxylate | C9H16N2O2 | 详情 | 详情 | |
| (XI) | 58502 | tert-butyl 2-{[7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinyl]carbonyl}-2-(1-methyl-2-propynyl)-1-hydrazinecarboxylate | C24H27ClN4O5 | 详情 | 详情 | |
| (XII) | 58503 | 3-iodophenol; m-iodophenol | 626-02-8 | C6H5IO | 详情 | 详情 |
| (XIII) | 58504 | tert-butyl 2-{[7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinyl]carbonyl}-2-[3-(3-hydroxyphenyl)-1-methyl-2-propynyl]-1-hydrazinecarboxylate | C30H31ClN4O6 | 详情 | 详情 |