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【结 构 式】 
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【分子编号】48160 【品名】ethyl 5-[5-(4-formylphenyl)-2H-1,2,3,4-tetraazol-2-yl]pentanoate 【CA登记号】 |
【 分 子 式 】C15H18N4O3 【 分 子 量 】302.33308 【元素组成】C 59.59% H 6% N 18.53% O 15.88% |
合成路线1
该中间体在本合成路线中的序号：(VII)4-Formylbenzonitrile (IV) was converted to the aryl tetrazole (V) upon treatment with trimethylsilyl azide and dibutyltin oxide. Regioselective alkylation of tetrazole (V) with ethyl 5-bromovalerate (VI) afforded the (2-tetrazolyl)pentanoate (VII).
| 【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 |
|---|---|---|---|---|---|---|
| (IV) | 17552 | 4-formylbenzonitrile; 4-Cyanobenzaldehyde | 105-07-7 | C8H5NO | 详情 | 详情 |
| (V) | 48159 | 4-(1H-1,2,3,4-tetraazol-5-yl)benzaldehyde | C8H6N4O | 详情 | 详情 | |
| (VI) | 37151 | ethyl 5-bromopentanoate | 14660-52-7 | C7H13BrO2 | 详情 | 详情 |
| (VII) | 48160 | ethyl 5-[5-(4-formylphenyl)-2H-1,2,3,4-tetraazol-2-yl]pentanoate | C15H18N4O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)The condensation between aldehyde (VII), piperazine (III) and benzotriazole furnished adduct (VIII). The Grignard reagent (X), prepared by silylation of 3-bromophenol (IX) followed by reaction with Mg, was then condensed with the benzotriazolyl adduct (VIII) to give the (diarylmethyl)piperazine (XI). Finally, basic hydrolysis of the ethyl ester of (XI) yielded the title compound.
| 【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 | |
| (VII) | 48160 | ethyl 5-[5-(4-formylphenyl)-2H-1,2,3,4-tetraazol-2-yl]pentanoate | C15H18N4O3 | 详情 | 详情 | |
| (VIII) | 48161 | ethyl 5-(5-[4-[[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](1H-1,2,3-benzotriazol-1-yl)methyl]phenyl]-2H-1,2,3,4-tetraazol-2-yl)pentanoate | C30H39N9O2 | 详情 | 详情 | |
| (IX) | 20704 | 3-bromophenol | 591-20-8 | C6H5BrO | 详情 | 详情 |
| (X) | 48162 | bromo[3-[(trimethylsilyl)oxy]phenyl]magnesium | C9H13BrMgOSi | 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 |