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【结 构 式】 
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【分子编号】48168 【品名】ethyl 5-(5-[4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)methyl]phenyl]-1H-1,2,3,4-tetraazol-1-yl)pentanoate 【CA登记号】 |
【 分 子 式 】C36H54N6O3Si 【 分 子 量 】646.9489 【元素组成】C 66.84% H 8.41% N 12.99% O 7.42% Si 4.34% |
合成路线1
该中间体在本合成路线中的序号：(XVI)A related procedure for the synthesis of the precursor ethyl ester (XI) was also reported. The condensation between 4-formylbenzonitrile (IV), piperazine (III) and benzotriazole furnished the benzotriazolyl adduct (XII). Subsequent reaction of (XII) with the Grignard reagent (XIII) yielded the (diarylmethyl)piperazine (XIV). The cyano group of (XIV) was then converted to the tetrazole (XV) by treatment with trimethylsilyl azide and dibutyltin oxide. Alkylation of tetrazole (XV) with ethyl 5-bromovalerate (VI) gave rise to a mixture of 1-triazolyl (XVII) and 2-triazolylpentanoate (XVI). After desilylation of this mixture with tetraethylammonium fluoride, the desired 2-triazolyl derivative (XI) was isolated by column chromatography.
| 【1】 Maw, G.N. (Pfizer Inc.); Anti-inflammatory piperazinyl-benzyl-tetrazole derivs. and intermediates thereof. EP 0983251; JP 2000513024; WO 9852929 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 20690 | (2R,5S)-1-allyl-2,5-dimethylpiperazine | C9H18N2 | 详情 | 详情 | |
| (IV) | 17552 | 4-formylbenzonitrile; 4-Cyanobenzaldehyde | 105-07-7 | C8H5NO | 详情 | 详情 |
| (VI) | 37151 | ethyl 5-bromopentanoate | 14660-52-7 | C7H13BrO2 | 详情 | 详情 |
| (XI) | 48163 | ethyl 5-(5-[4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-hydroxyphenyl)methyl]phenyl]-2H-1,2,3,4-tetraazol-2-yl)pentanoate | C30H40N6O3 | 详情 | 详情 | |
| (XII) | 48164 | 4-[[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](1H-1,2,3-benzotriazol-1-yl)methyl]benzonitrile | C23H26N6 | 详情 | 详情 | |
| (XIII) | 20706 | bromo(3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)magnesium | C12H19BrMgOSi | 详情 | 详情 | |
| (XIV) | 48165 | 4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)methyl]benzonitrile | C29H41N3OSi | 详情 | 详情 | |
| (XV) | 48166 | (2R,5S)-1-allyl-4-[(R)-(3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)[4-(1H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]-2,5-dimethylpiperazine; 3-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl][4-(1H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]phenyl tert-butyl(dimethyl)silyl ether | C29H42N6OSi | 详情 | 详情 | |
| (XVI) | 48168 | ethyl 5-(5-[4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)methyl]phenyl]-1H-1,2,3,4-tetraazol-1-yl)pentanoate | C36H54N6O3Si | 详情 | 详情 | |
| (XVII) | 48167 | ethyl 5-(5-[4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-[[tert-butyl(dimethyl)silyl]oxy]phenyl)methyl]phenyl]-2H-1,2,3,4-tetraazol-2-yl)pentanoate | C36H54N6O3Si | 详情 | 详情 |