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【结 构 式】 
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【分子编号】44039 【品名】tert-butyl (1S,9S)-9-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6,10-dioxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate 【CA登记号】 |
【 分 子 式 】C22H25N3O6 【 分 子 量 】427.45712 【元素组成】C 61.82% H 5.89% N 9.83% O 22.46% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of acyl chloride (I) with hexahydropyridazine (II) gives the corresponding amide (III), which is debenzylated with H2 over Pd/C and cyclized by means of SOCl2 to yield the pyridazinodiazepinedione (IV). Selective reduction of (IV) with borane in THF affords the pyridazinodiazepinone (V), which is treated with hydrazine to provide (1S,9S)-9-amino-10-oxoperhydropyridazino[1,2-a]azepine-1-carboxylic acid tert-butyl ester (VI). Finally, this compound is condensed with 4-phenyl-2(R)-(trifluoromethanesulfonyloxy)butyric acid ethyl ester (VII) and selectively hydrolyzed to afford the target carboxylic acid.
| 【1】 Natoff, I.L.; Redshaw, S.; Angiotensin-converting enzyme inhibitors - Cilazapril and other bicyclic hexahydropyridazines. Drugs Fut 1987, 12, 5, 475. |
| 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) | 44036 | phenyl (6S)-7-chloro-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-7-oxoheptanoate | C21H18ClNO5 | 详情 | 详情 | |
| (II) | 44037 | di(tert-butyl) (3S)tetrahydro-1,3(2H)-pyridazinedicarboxylate | C14H26N2O4 | 详情 | 详情 | |
| (III) | 44038 | di(tert-butyl) (3S)-2-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-oxo-6-phenoxyhexanoyl]tetrahydro-1,3(2H)-pyridazinedicarboxylate | C34H41N3O9 | 详情 | 详情 | |
| (IV) | 44039 | tert-butyl (1S,9S)-9-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6,10-dioxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate | C22H25N3O6 | 详情 | 详情 | |
| (V) | 44040 | tert-butyl (1S,9S)-9-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate | C22H27N3O5 | 详情 | 详情 | |
| (VI) | 44041 | tert-butyl (1S,9S)-9-amino-10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate | C14H25N3O3 | 详情 | 详情 | |
| (VII) | 20818 | ethyl (2R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butanoate | C13H15F3O5S | 详情 | 详情 |