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【结 构 式】 
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【分子编号】54574 【品名】3-hydroxy-4-methoxybenzonitrile 【CA登记号】52805-46-6 |
【 分 子 式 】C8H7NO2 【 分 子 量 】149.14912 【元素组成】C 64.42% H 4.73% N 9.39% O 21.45% |
与该中间体有关的原料药合成路线共 3 条
合成路线1
该中间体在本合成路线中的序号：(VIII)ZK-807834 is obtained by condensation of the diaryl ether (I) with the phenol (II) by means of K2CO3 to afford the bisaryl ether (III). Reaction of the cyano group of (III), first with HCl in ethanol and then with ammonia, yields the corresponding amidino compound (IV), which is finally demethylated with HBr.
| 【2】 Discovery of N-[2-[5-[amino(imino)methyl]-2-hydroxyphenoxy]-3,5-difluoro-6-[3-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenoxy]pyridin-4-yl]-N-methylglycine (ZK-807834): A potent, selective, and orally active inhibitor of the blood coagulation enzyme factor. J Med Chem 1998, 41, 19, 3557. |
| 【1】 Ricart-Diaz, M.; Castaner, J.; ZK-807834. Drugs Fut 2002, 27, 8, 748. |
| 【3】 Buckman, B.O.; Davey, D.D.; Guilford, W.J.; Morrissey, M.M.; Ng, H.P.; Phillips, G.B.; Wu, S.C.; Xu, W. (Berlex Laboratories, Inc.); Benzamidine derivs. their preparation and their use as anti-coagulants. EP 0813525; US 5691364; WO 9628427 . |
| 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) | 54575 | 2-[[2-(5-cyano-2-methoxyphenoxy)-3,5,6-trifluoro-4-pyridinyl](methyl)amino]acetamide | C16H13F3N4O3 | 详情 | 详情 | |
| (II) | 54576 | 2-(3-methoxyphenyl)-1-methyl-4,5-dihydro-1H-imidazole; methyl 3-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl ether | C11H14N2O | 详情 | 详情 | |
| (III) | 54578 | 2-[{2-(5-cyano-2-methoxyphenoxy)-3,5-difluoro-6-[3-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenoxy]-4-pyridinyl}(methyl)amino]acetamide | C26H24F2N6O4 | 详情 | 详情 | |
| (IV) | 54579 | 2-[{2-{5-[amino(imino)methyl]-2-methoxyphenoxy}-3,5-difluoro-6-[3-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenoxy]-4-pyridinyl}(methyl)amino]acetamide | C26H27F2N7O4 | 详情 | 详情 | |
| (V) | 54571 | Pentafluoropyridine; Perfluoropyridine | 700-16-3 | C5F5N | 详情 | 详情 |
| (VI) | 54572 | 2-(methylamino)acetamide | C3H8N2O | 详情 | 详情 | |
| (VII) | 54573 | 2-[methyl(2,3,5,6-tetrafluoro-4-pyridinyl)amino]acetamide | C8H7F4N3O | 详情 | 详情 | |
| (VIII) | 54574 | 3-hydroxy-4-methoxybenzonitrile | 52805-46-6 | C8H7NO2 | 详情 | 详情 |
| (IX) | 36250 | 3-methoxybenzonitrile | 1527-89-5 | C8H7NO | 详情 | 详情 |
| (X) | 27777 | N-(2-aminoethyl)-N-methylamine | 109-81-9 | C3H10N2 | 详情 | 详情 |
| (XI) | 54575 | 2-[[2-(5-cyano-2-methoxyphenoxy)-3,5,6-trifluoro-4-pyridinyl](methyl)amino]acetamide | C16H13F3N4O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)
| 【1】 Welham MJ．2005．Process for the manufacture。gefitinib. W0 2005023783（本专利为AstraZeneca plc所有） |
| 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) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (II) | 54574 | 3-hydroxy-4-methoxybenzonitrile | 52805-46-6 | C8H7NO2 | 详情 | 详情 |
| (III) | 66433 | 4-methoxy-3-(3-morpholinopropoxy)benzonitrile | C15H20N2O3 | 详情 | 详情 | |
| (IV) | 66434 | 4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile | 675126-26-8 | C15H19N3O5 | 详情 | 详情 |
| (V) | 66435 | 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile | 675126-27-9 | C15H21N3O3 | 详情 | 详情 |
| (VI) | 66436 | (E)-N,N'-bis(3-chloro-4-fluorophenyl)formimidamide | C13H8Cl2F2N2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)
| 【1】 Wang JQ, Gao MZ, Miller KD, et al.2006. Synthesis of (11 C) iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase. Bioorg Med Chem Lett, 16 (15): 4102~4106 |
| 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) | 54574 | 3-hydroxy-4-methoxybenzonitrile | 52805-46-6 | C8H7NO2 | 详情 | 详情 |
| (II) | 18691 | 4-(3-chloropropyl)morpholine;N-(3-Chloropropyl)morpholine | 7357-67-7 | C7H14ClNO | 详情 | 详情 |
| (III) | 66433 | 4-methoxy-3-(3-morpholinopropoxy)benzonitrile | C15H20N2O3 | 详情 | 详情 | |
| (IV) | 66434 | 4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile | 675126-26-8 | C15H19N3O5 | 详情 | 详情 |
| (V) | 66435 | 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile | 675126-27-9 | C15H21N3O3 | 详情 | 详情 |
| (VI) | 66441 | 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzamide | C15H23N3O4 | 详情 | 详情 | |
| (VII) | 66445 | 7-methoxy-6-(3-morpholinopropoxy)quinazolin-4(1H)-one | C16H21N3O4 | 详情 | 详情 | |
| (VIII) | 66443 | 4-(3-((4-chloro-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine | C16H20ClN3O3 | 详情 | 详情 | |
| (IX) | 18688 | 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline | 367-21-5 | C6H5ClFN | 详情 | 详情 |
| (X) | 66448 | 4-((3-chloro-4-fluorophenyl)amino)-6-(3-morpholinopropoxy)quinazolin-7-ol | 847949-49-9 | C21H22ClFN4O3 | 详情 | 详情 |
Extended Information