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【结 构 式】 
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【分子编号】29550 【品名】tert-butyl cyclohexylmethyl(2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl)carbamate 【CA登记号】 |
【 分 子 式 】C22H35N3O3 【 分 子 量 】389.53832 【元素组成】C 67.83% H 9.06% N 10.79% O 12.32% |
合成路线1
该中间体在本合成路线中的序号：(XXI)The intermediate amine (X) has been obtained as follows: The reaction of ethyl 2-bromoacetate (XV) with cyclohexylmethylamine (XVI) by means of Et3N in THF gives the N-(cyclohexylmethyl)glycine ethyl ester (XVII), which is protected with (Boc)2O in dichloromethane yielding (XVIII). The hydrolysis of (XVIII) with NaOH in water gives the corresponding free acid (XIX), which is condensed with 2-[2-(methylamino)ethyl]pyridine (XX) by means of BOP-PF6 and DIEA in DMF to provide the amide (XXI). Finally, this compound is deprotected with HCl in dioxane/water to obtain the ddesired intermediate (X).
| 【1】 Simoneau, B.; Lavallee, P.; Anderson, P.C.; et al.; Discovery of non-peptidic P2-P3 butanediamide renin inhibitors with high oral efficacy. Bioorg Med Chem 1999, 7, 3, 489. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 29540 | 2-[(cyclohexylmethyl)amino]-N-methyl-N-[2-(2-pyridinyl)ethyl]acetamide | C17H27N3O | 详情 | 详情 | |
| (XV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (XVI) | 29545 | cyclohexylmethanamine; cyclohexylmethylamine | 3218-02-8 | C7H15N | 详情 | 详情 |
| (XVII) | 29546 | ethyl 2-[(cyclohexylmethyl)amino]acetate | C11H21NO2 | 详情 | 详情 | |
| (XVIII) | 29547 | ethyl 2-[(tert-butoxycarbonyl)(cyclohexylmethyl)amino]acetate | C16H29NO4 | 详情 | 详情 | |
| (XIX) | 29548 | 2-[(tert-butoxycarbonyl)(cyclohexylmethyl)amino]acetic acid | C14H25NO4 | 详情 | 详情 | |
| (XX) | 29549 | N-methyl-2-(2-pyridinyl)-1-ethanamine; N-methyl-N-[2-(2-pyridinyl)ethyl]amine | 5579-84-0 | C8H12N2 | 详情 | 详情 |
| (XXI) | 29550 | tert-butyl cyclohexylmethyl(2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl)carbamate | C22H35N3O3 | 详情 | 详情 |