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【结 构 式】 
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【分子编号】37973 【品名】tert-butyl 4-[[(2,7-dichloro-9H-xanthen-9-yl)carbonyl]amino]-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C24H26Cl2N2O4 【 分 子 量 】477.38692 【元素组成】C 60.38% H 5.49% Cl 14.85% N 5.87% O 13.41% |
合成路线1
该中间体在本合成路线中的序号：(III)Coupling between 2,7-dichloroxanthene-9-carboxylic acid (I) and 4-amino-1-tert-butoxycarbonylpiperidine (II) in the presence of EDC and HOBt afforded amide (III). After acidic cleavage of the Boc protecting group of (III), the resulting amine (IV) was reductively condensed with 1-cyclooctene carbaldehyde (V) by means of NaBH(OAc)3 to yield the cyclooctenylmethyl amine (VI). Subsequent alkylation of the tertiary amine (VI) with iodoethane gave rise to the target ammonium salt. Separation of the geometric isomers was carried out by column chromatography.
| 【1】 Naya, A.; et al.; Design, synthesis, and discovery of a novel CCR1 antagonist. J Med Chem 2001, 44, 9, 1429. |
| 【2】 Naya, A.; Owada, Y.; Saeki, T.; Ohwaki, K.; Iwasawa, Y. (Banyu Pharmaceutical Co., Ltd.); Chemokine receptor antagonists. EP 0916668; WO 9804554 . |
| 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) | 37972 | 2,7-dichloro-9H-xanthene-9-carboxylic acid | C14H8Cl2O3 | 详情 | 详情 | |
| (II) | 28414 | 4-Amino-1-N-Boc-piperidine; tert-butyl 4-amino-1-piperidinecarboxylate; N-Boc-4-aminopiperidine | 87120-72-7 | C10H20N2O2 | 详情 | 详情 |
| (III) | 37973 | tert-butyl 4-[[(2,7-dichloro-9H-xanthen-9-yl)carbonyl]amino]-1-piperidinecarboxylate | C24H26Cl2N2O4 | 详情 | 详情 | |
| (IV) | 37974 | 2,7-dichloro-N-(4-piperidinyl)-9H-xanthene-9-carboxamide | C19H18Cl2N2O2 | 详情 | 详情 | |
| (V) | 37975 | 1-cyclooctene-1-carbaldehyde | C9H14O | 详情 | 详情 | |
| (VI) | 37976 | 2,7-dichloro-N-[1-(1-cycloocten-1-ylmethyl)-4-piperidinyl]-9H-xanthene-9-carboxamide | C28H32Cl2N2O2 | 详情 | 详情 |