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【结 构 式】 
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【分子编号】27532 【品名】4-[(3-bromopropyl)amino]-5-chloro-3(2H)-pyridazinone 【CA登记号】 |
【 分 子 式 】C7H9BrClN3O 【 分 子 量 】266.52478 【元素组成】C 31.55% H 3.4% Br 29.98% Cl 13.3% N 15.77% O 6% |
合成路线1
该中间体在本合成路线中的序号：(VI)Pyridazinone (I) was converted to 3,4,5-trichloropyridazine (VIII) on treatment with POCl3. Nucleophylic substitution in (II) with 3-aminopropanol (III) gave, after crystallization, the desired isomer (IV). Hydrolysis of the 3-chloro group of (IV) was carried out with AcOH and AcONa, resulting in the N,O-diacetyl derivative (V). Subsequent reaction of (V) with aqueous HBr provided bromide (VI), which was then treated with N-methyl homoveratrylamine (VII) to furnish the target compound (VIII). This compound was finally isolated as the fumarate salt on treatment with fumaric acid in EtOH (1).
| 【1】 Kotay-Nagy, P.; et al.; A new synthesis of EGIS-7229, a potent antiarrhythmic drug-candidate. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.151. |
| 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) | 24570 | 4,5-dichloro-3(2H)-pyridazinone | C4H2Cl2N2O | 详情 | 详情 | |
| (II) | 27529 | 3,4,5-trichloropyridazine | 14161-11-6 | C4HCl3N2 | 详情 | 详情 |
| (III) | 18522 | 3-amino-1-propanol | 156-87-6 | C3H9NO | 详情 | 详情 |
| (IV) | 27530 | 3-[(3,5-dichloro-4-pyridazinyl)amino]-1-propanol | C7H9Cl2N3O | 详情 | 详情 | |
| (V) | 27531 | 3-[acetyl(5-chloro-3-oxo-2,3-dihydro-4-pyridazinyl)amino]propyl acetate | C11H14ClN3O4 | 详情 | 详情 | |
| (VI) | 27532 | 4-[(3-bromopropyl)amino]-5-chloro-3(2H)-pyridazinone | C7H9BrClN3O | 详情 | 详情 | |
| (VII) | 18938 | 2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine | 3490-06-0 | C11H17NO2 | 详情 | 详情 |
| (VIII) | 27533 | 5-chloro-4-([3-[(3,4-dimethoxyphenethyl)(methyl)amino]propyl]amino)-3(2H)-pyridazinone | C18H25ClN4O3 | 详情 | 详情 | |
| (IX) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |