【结 构 式】 |
【分子编号】52949 【品名】9-acridinyl methyl ether; 9-methoxyacridine 【CA登记号】n/a |
【 分 子 式 】C14H11NO 【 分 子 量 】209.24748 【元素组成】C 80.36% H 5.3% N 6.69% O 7.65% |
合成路线1
该中间体在本合成路线中的序号:(VII)Activation of N-Boc-beta-alanine (I) as the mixed anhydride (II) with isobutyl chloroformate, followed by condensation with triethanolamine (III), furnished the [bis(2-hydroxyethyl)amino]ethyl ester (IV). Silylation of the free hydroxyl groups of (IV) by means of tert-butyldimethylsilyl chloride and imidazole afforded the bis-silylether (V). The N-Boc protecting group of (V) was then selectively removed upon treatment with trifluoroacetic acid to give amino ester (VI). This was subsequently coupled with 9-methoxyacridine (VII), yielding adduct (VIII), which was further desilylated with HF/pyridine. The resultant bis(hydroxyethyl) derivative (IX) was finally converted to the target dichloro compound by treatment with thionyl chloride.
【1】 Wollowitz, S.; Rapoport, H.; Cook, D.; Merritt, J.; Neiro, A.; Stassinopoulos, A.; Matejovic, J. (Cerus Corp.); Frangible cpds. for pathogen inactivation. WO 9830545 . |
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) | 26616 | N-(tert-butoxycarbonyl)-beta-alanine | 3303-84-2 | C8H15NO4 | 详情 | 详情 |
(II) | 52945 | n/a | C13H23NO6 | 详情 | 详情 | |
(III) | 28168 | 2-[bis(2-hydroxyethyl)amino]-1-ethanol | 102-71-6 | C6H15NO3 | 详情 | 详情 |
(IV) | 52946 | 2-[bis(2-hydroxyethyl)amino]ethyl 3-[(tert-butoxycarbonyl)amino]propanoate | n/a | C14H28N2O6 | 详情 | 详情 |
(V) | 52947 | 2-[bis(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]ethyl 3-[(tert-butoxycarbonyl)amino]propanoate | n/a | C26H56N2O6Si2 | 详情 | 详情 |
(VI) | 52948 | 2-[bis(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]ethyl 3-aminopropanoate | n/a | C21H48N2O4Si2 | 详情 | 详情 |
(VII) | 52949 | 9-acridinyl methyl ether; 9-methoxyacridine | n/a | C14H11NO | 详情 | 详情 |
(VIII) | 52950 | 2-[bis(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]ethyl 3-(9-acridinylamino)propanoate | n/a | C34H55N3O4Si2 | 详情 | 详情 |
(IX) | 52951 | 2-[bis(2-hydroxyethyl)amino]ethyl 3-(9-acridinylamino)propanoate | n/a | C22H27N3O4 | 详情 | 详情 |