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【结 构 式】 
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【分子编号】51493 【品名】3-Amino-5-bromobenzotrifluoride 【CA登记号】54962-75-3 |
【 分 子 式 】C7H5BrF3N 【 分 子 量 】240.0226496 【元素组成】C 35.03% H 2.1% Br 33.29% F 23.75% N 5.84% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III), which rearranges in the reaction medium to yield indenone (IV). The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V), which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
| 【1】 Manley, P.W.; Martiny-Baron, G.; Brüggen, J.; Mestan, J.; Meyer T.; Wood, J.M.; Ferrari, S.; Hofmann, F.; Bold, G.; Frei, J.; Furet, P.; Cozens, R.M.; CGP 79787D (PTK787/ZK222584), CGP 84738, NVP-AAC789, NVP-AAD777 and related 1-anilino-(4-pyridylmethyl)phthalazines as inhibitors of VEGF- and bFGF-induced angiogenesis. Drugs Fut 2002, 27, 1, 43. |
| 【2】 Letourneux, Y.; Floc'h, R.; Le Baut, G.; Ploquin, J.; Sparfel, L.; beta-Dicéto énamines hétérocycliques: 1. Indanediones-1,3-disubstitutées en 2 par un hétérocycle azoté. J Heterocycl Chem 1980, 17, 961-73. |
| 【3】 Manly, D.G.; Tilford, C.H.; Richardson, A.; Stock, A.M.; Amstutz, E.D.; A Study of the chemistry of pyrophthalone and related compounds. J Org Chem 1958, 23, 373-80. |
| 【4】 Frei, J.; Bold, G.; Altmann, K.-H.; et al.; New anilinophthalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis. J Med Chem 2000, 43, 12, 2310. |
| 【5】 Wietfeld, B.; Wood, J.M.; Manley, P.W.; Heng, R.; Frei, J.; Bold, G.; Dawson King, J. (Novartis AG); Phthalazine derivs. for treating inflammatory diseases. WO 0059509 . |
| 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) | 12576 | 2-Benzofuran-1(3H)-one; Phthalide; Benzo[b]furan-1(3H)-one; 1(3H)-Isobenzofuranoneisobenzofuran-1-one | 87-41-2 | C8H6O2 | 详情 | 详情 |
| (II) | 17203 | 4-Pyridinecarboxaldehyde; isonicotinaldehyde | 872-85-5 | C6H5NO | 详情 | 详情 |
| (III) | 49917 | 3-[(Z)-4-pyridinylmethylidene]-2-benzofuran-1-one | C14H9NO2 | 详情 | 详情 | |
| (IV) | 49918 | 3-hydroxy-2-(4-pyridinyl)-1H-inden-1-one | C14H9NO2 | 详情 | 详情 | |
| (V) | 49919 | 4-(4-pyridinylmethyl)-1(2H)-phthalazinone | C14H11N3O | 详情 | 详情 | |
| (VI) | 41367 | 1-chloro-4-(4-pyridinylmethyl)phthalazine | C14H10ClN3 | 详情 | 详情 | |
| (VII) | 51493 | 3-Amino-5-bromobenzotrifluoride | 54962-75-3 | C7H5BrF3N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)
| 【1】 Wang YL. Li J, Kansal VK, et al. 2010. Nilotinib intermediates and preparation thereof. WO 2010009402A9. |
| 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) | 38737 | ethyl 4-amino-3-methylbenzoate | 40800-65-5 | C10H13NO2 | 详情 | 详情 |
| (II) | 67345 | ethyl 3-guanidino-4-methylbenzoate | C11H15N3O2 | 详情 | 详情 | |
| (III) | 12027 | 1-(3-Pyridinyl)-1-ethanone; 1-(3-Pyridinyl)ethanone | 350-03-8 | C7H7NO | 详情 | 详情 |
| (IV) | 67346 | (Z)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one | C10H12N2O | 详情 | 详情 | |
| (V) | 67347 | ethyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate | 641569-97-3 | C19H18N4O2 | 详情 | 详情 |
| (VI) | 67348 | 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid | 641569-94-0 | C17H14N4O2 | 详情 | 详情 |
| (VII) | 51493 | 3-Amino-5-bromobenzotrifluoride | 54962-75-3 | C7H5BrF3N | 详情 | 详情 |
| (VIII) | 67349 | N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide | C24H17BrF3N5O | 详情 | 详情 | |
| (IX) | 34070 | 5-methyl-1H-imidazole | 822-36-6 | C4H6N2 | 详情 | 详情 |
Extended Information