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【结 构 式】 
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【分子编号】38946 【品名】6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one 【CA登记号】 |
【 分 子 式 】C12H9N3O 【 分 子 量 】211.22308 【元素组成】C 68.24% H 4.29% N 19.89% O 7.57% |
合成路线1
该中间体在本合成路线中的序号：(III)Condensation between 1,2-phenylenediamine (I) and 2-chloronicotinic acid (II) in refluxing cyclohexanol generated the tricyclic system (III). Reduction of keto group of (III) with borane-dimethyl sulfide complex afforded 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (IV). Acid chloride (VI), prepared from 4-fluoro-2-(trifluoromethyl)benzoic acid (V), was then condensed with tricyclic amine (IV) to produce amide (VII). Finally, displamecement of the 4-fluoro group of (VII) by the sodium salt of 3-methylpyrazole (VIII) in hot DMF yielded a 5:1 mixture of the title 3-methylpyrazole derivative and its 5-methyl regioisomer (IX), which were separated by column chromatography.
| 【1】 Failli, A.A.; Steffan, R.J.; Sumsky, J.S.; et al.; Pyridobenzodiazepines: Synthesis and structure-activity relationship of a novel class of orally active vasopressin V2 receptor agonists. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 201. |
| 【2】 Failli, A.A.; Shumsky, J.S.; Steffan, R.J. (American Home Products Corp.); Tricyclic vasopressin agonists. EP 1000059; WO 9906403 . |
| 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) | 12824 | 2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine | 95-54-5 | C6H8N2 | 详情 | 详情 |
| (II) | 28824 | 2-Chloropyridine-3-carboxylic acid; 2-Chloronicotinic acid | 2942-59-8 | C6H4ClNO2 | 详情 | 详情 |
| (III) | 38946 | 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one | C12H9N3O | 详情 | 详情 | |
| (IV) | 38947 | 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine | C12H11N3 | 详情 | 详情 | |
| (V) | 38951 | 4-fluoro-2-(trifluoromethyl)benzoic acid | 141179-72-8 | C8H4F4O2 | 详情 | 详情 |
| (VI) | 38948 | 4-fluoro-2-(trifluoromethyl)benzoyl chloride | C8H3ClF4O | 详情 | 详情 | |
| (VII) | 38949 | 5,11-dihydro-6H-pyrido[2,3-b][1,5]benzodiazepin-6-yl[4-fluoro-2-(trifluoromethyl)phenyl]methanone | C20H13F4N3O | 详情 | 详情 | |
| (VIII) | 37998 | 3-methyl-1H-pyrazole | 1453-58-3 | C4H6N2 | 详情 | 详情 |
| (IX) | 38950 | 5,11-dihydro-6H-pyrido[2,3-b][1,5]benzodiazepin-6-yl[4-(5-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)phenyl]methanone | C24H18F3N5O | 详情 | 详情 |