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【结 构 式】 
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【分子编号】42317 【品名】N-(2-aminoethyl)-N-[2-(dimethylamino)ethyl]-N-methylamine; N(1)-(2-aminoethyl)-N(1),N(2),N(2)-trimethyl-1,2-ethanediamine 【CA登记号】 |
【 分 子 式 】C7H19N3 【 分 子 量 】145.24808 【元素组成】C 57.89% H 13.18% N 28.93% |
合成路线1
该中间体在本合成路线中的序号：(VI)Ethanolamine (I) was protected as the N-benzyloxycarbonyl derivative (II) and subsequently converted to tosylate (III). Alkylation of N,N,N'-trimethylethylenediamine (IV) with tosylate (III) produced triamine (V). The benzyloxycarbonyl protecting group was then removed by transfer hydrogenolysis with ammonium formate and Pd/C to yield triamine (VI).
| 【1】 Ritchie, T.J.; Hallett, A.; Dziadulewicz, E.K.; et al.; 1-(2-Nitrophenyl)thiosemicarbazides: A novel class of potent, orally active non-peptide antagonist for the bradykinin B2 receptor. J Med Chem 2000, 43, 5, 769. |
| 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) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (II) | 32497 | benzyl 2-hydroxyethylcarbamate | 77987-49-6 | C10H13NO3 | 详情 | 详情 |
| (III) | 42170 | 2-[[(benzyloxy)carbonyl]amino]ethyl 4-methylbenzenesulfonate | C17H19NO5S | 详情 | 详情 | |
| (IV) | 15778 | N-[2-(dimethylamino)ethyl]-N-methylamine; N,N,N'-trimethyl-1,2-ethanediamine; N(1),N(1),N(2)-trimethyl-1,2-ethanediamine | 142-25-6 | C5H14N2 | 详情 | 详情 |
| (V) | 42316 | benzyl 2-[[2-(dimethylamino)ethyl](methyl)amino]ethylcarbamate | C15H25N3O2 | 详情 | 详情 | |
| (VI) | 42317 | N-(2-aminoethyl)-N-[2-(dimethylamino)ethyl]-N-methylamine; N(1)-(2-aminoethyl)-N(1),N(2),N(2)-trimethyl-1,2-ethanediamine | C7H19N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)Condensation of 4-chloro-3-nitrobenzenesulfonyl chloride (VII) with L-proline tert-butyl ester (VIII) yielded sulfonamide (IX). Displacement of the chloro group of (IX) with hydrazine hydrate furnished the aryl hydrazine (X), which was reacted with benzhydryl isothiocyanate (XI) to produce the thiosemicarbazide (XII). After acid cleavage of the tert-butyl ester of (XII), the resulting carboxylic acid (XIII) was activated with isobutyl chloroformate and then coupled with triamine (VI) to furnish the title amide.
| 【1】 Ritchie, T.J.; Hallett, A.; Dziadulewicz, E.K.; et al.; 1-(2-Nitrophenyl)thiosemicarbazides: A novel class of potent, orally active non-peptide antagonist for the bradykinin B2 receptor. J Med Chem 2000, 43, 5, 769. |
| 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) | 42318 | 4-chloro-3-nitrobenzenesulfonyl chloride | 97-08-5 | C6H3Cl2NO4S | 详情 | 详情 |
| (II) | 19832 | tert-butyl (2S)-2-pyrrolidinecarboxylate | C9H17NO2 | 详情 | 详情 | |
| (III) | 42319 | tert-butyl (2S)-1-[(4-chloro-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate | C15H19ClN2O6S | 详情 | 详情 | |
| (IV) | 42320 | tert-butyl (2S)-1-[(4-hydrazino-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate | C15H22N4O6S | 详情 | 详情 | |
| (V) | 42321 | 1-[isothiocyanato(phenyl)methyl]benzene; benzhydryl isothiocyanate | 3550-21-8 | C14H11NS | 详情 | 详情 |
| (VI) | 42322 | tert-butyl (2S)-1-[(4-[2-[(benzhydrylamino)carbothioyl]hydrazino]-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate | C29H33N5O6S2 | 详情 | 详情 | |
| (VII) | 42323 | (2S)-1-[(4-[2-[(benzhydrylamino)carbothioyl]hydrazino]-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylic acid | C25H25N5O6S2 | 详情 | 详情 | |
| (VIII) | 42317 | N-(2-aminoethyl)-N-[2-(dimethylamino)ethyl]-N-methylamine; N(1)-(2-aminoethyl)-N(1),N(2),N(2)-trimethyl-1,2-ethanediamine | C7H19N3 | 详情 | 详情 |