【结 构 式】 |
【分子编号】51583 【品名】4-(2-ethyl-5-nitro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole 【CA登记号】 |
【 分 子 式 】C14H15N3O2 【 分 子 量 】257.29212 【元素组成】C 65.36% H 5.88% N 16.33% O 12.44% |
合成路线1
该中间体在本合成路线中的序号:(II)The previously reported indanyl imidazole (I) was nitrated by means of urea nitrate in sulfuric acid to afford (II). Reduction of the nitro group of (II) to the corresponding aniline (III) was carried out by catalytic hydrogenation over PtO2. Diazotization of (III) with sodium nitrite and fluoroboric acid gave rise to the diazonium fluoroborate (IV), which was then subjected to thermal decomposition to generate the title fluoro derivative.
【1】 Sorbera, L.A.; Castaner, J.; Bayes, M.; Fipamezole Hydrochloride. Drugs Fut 2003, 28, 1, 14. |
【2】 Karjalainen, A.J.; Virtanen, R.E.; Karjalainen, A.L.; Eloranta, M.M.; Salonen, J.S.; Sipilä, H.T.; Haapalinna, A.S. (Orion Corporation); Substd. imidazole derivs. and their preparation and use. EP 0618906; JP 1995506087; US 5498623; WO 9313074 . |
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) | 51582 | 4-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H16N2 | 详情 | 详情 | |
(II) | 51583 | 4-(2-ethyl-5-nitro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H15N3O2 | 详情 | 详情 | |
(III) | 51584 | 2-ethyl-2-(1H-imidazol-4-yl)-2,3-dihydro-1H-inden-5-ylamine; 2-ethyl-2-(1H-imidazol-4-yl)-5-indanamine | C14H17N3 | 详情 | 详情 | |
(IV) | 51585 | C14H15BF4N4 | 详情 | 详情 | ||
(V) | 51586 | 4-Methylimidazole; 4-Methyl-1H-imidazole; 4-Methyl Imidazole | 822-36-6 | C4H6N2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(XVIII)Coupling/deprotection cycles with N-Boc-D-(3-pyridyl)alanine (XV), N-Boc-D-4-chlorophenylalanine (XVII) and N-Boc-D-(2-naphthyl)alanine (XIX) furnished the peptide resins (XVI), (XVIII) and (XX).
【1】 Rivier, J.E.; et al.; Gonadotropin-releasing hormone antagonists: Novel members of the azaline B family. J Med Chem 1995, 38, 14, 2649. |
【2】 Rivier, J.E.F.; Porter, J.S.; Hoeger, C.A.; Jiang, G.; Rivier, C.L. (The Salk Institute for Biological Studies); GnRH antagonists. EP 0804471; JP 1998500397; US 5506207; WO 9525741 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(XIV) | 51381 | benzyl (5S,8S,11R,14S,17S)-17-amino-5-[[(2S)-2-([[(1R)-2-amino-1-methyl-2-oxoethyl]amino]carbonyl)pyrrolidinyl]carbonyl]-11,14-bis(4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]benzyl)-8-isobutyl-7,10,13,16-tetraoxo-20-phenyl-19-oxa-6,9,12,15-tetraazaicos-1-yl(isopropyl)carbamate | C89H101N11O14 | 详情 | 详情 | |
(XV) | 23494 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-pyridinyl)propionic acid | C13H18N2O4 | 详情 | 详情 | |
(XVI) | 51382 | benzyl (5S,8S,11R,14S,17S,20R)-20-amino-5-[[(2S)-2-([[(1R)-2-amino-1-methyl-2-oxoethyl]amino]carbonyl)pyrrolidinyl]carbonyl]-17-[(benzyloxy)methyl]-11,14-bis(4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]benzyl)-8-isobutyl-7,10,13,16,19-pentaoxo-21-(3-pyridinyl)-6,9,12,15,18-pentaazahenicos-1-yl(isopropyl)carbamate | C97H109N13O15 | 详情 | 详情 | |
(XVII) | 23496 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propionic acid | C14H18ClNO4 | 详情 | 详情 | |
(XVIII) | 51583 | 4-(2-ethyl-5-nitro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H15N3O2 | 详情 | 详情 | |
(XIX) | 23498 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionic acid | C18H21NO4 | 详情 | 详情 | |
(XX) | 51384 | benzyl (5S,8S,11R,14S,17S,20R,23R,26R)-26-amino-5-[[(2S)-2-([[(1R)-2-amino-1-methyl-2-oxoethyl]amino]carbonyl)pyrrolidinyl]carbonyl]-17-[(benzyloxy)methyl]-23-(4-chlorobenzyl)-11,14-bis(4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]benzyl)-8-isobutyl-27-(2-naphthyl)-7,10,13,16,19,22,25-heptaoxo-20-(3-pyridinylmethyl)-6,9,12,15,18,21,24-heptaazaheptacos-1-yl(isopropyl)carbamate | C119H128ClN15O17 | 详情 | 详情 |