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【结 构 式】 
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【分子编号】24750 【品名】Bis(isopropylamine)dichloro platinum complex 【CA登记号】 |
【 分 子 式 】C6H18Cl2N2Pt 【 分 子 量 】384.2078 【元素组成】C 18.76% H 4.72% Cl 18.45% N 7.29% Pt 50.77% |
合成路线1
该中间体在本合成路线中的序号：(I)Iproplatin is prepared by treating cis-dichlorobis(isopropylamine)platinum (I) with hydrogen peroxide, mixing the product by N,N-dimetylacetamide at 5 C to give iproplatin-dimethylacetamide 1:1 addiction product (II). After elimination of N,N-dimethylacetamide by heating (II) at 50 C / 0.1 torr iproplatin is obtained.
| 【1】 Hepburn, D.R.; Hydes, P.C. (Johnson Matthey plc); cis-Dichloro-trans-dihydroxy-bis(isopropylamine)platinum(IV), preparation and intermediate. BE 890209; JP 1982077694 . |
| 【2】 Chang, P.; Iroplatin. Drugs Fut 1985, 10, 7, 561. |
合成路线2
该中间体在本合成路线中的序号：(XI)The reaction of isovanillin with hydroxylamine sulfate and NaOH in refluxing ethanol/water gives the corresponding oxime (II), which is reduced with Raney-Ni and NaOH in the same solvent yielding the benzylamine (III). The protection of the amino group of (III) with benzyloxycarbonyl chloride affords the carbamate (IV), which is condensed with ethyl bromoacetate (IV) by means of K2CO3 in refluxing 2-butanone to give the ester (VI). The hydrolysis of (VI) with NaOH in hot methanol/water yields the corresponding acid (VII), which is condensed with 1-benzylpiperazine (VIII) by means of ethyl chloroformate in THF to afford the piperazide (IX). The deprotection of the amino group of (IX) with H2 over Pd/C in hot ethanol gives the benzylamine (X), which is finally condensed with 4,5-dichloropyridazin-3(2H)-one (XI) by means of triethylamine in refluxing ethanol/water.
| 【1】 Tanikawa, K.; Saito, A.; Hirotsuka, M.; Shikada, K. (Nissan Chemical Industry, Ltd.); Pyridazinone derivs. with pharmaceutical activity. EP 0706517; JP 1996041033; US 5728702; US 5929074; WO 9501343 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10101 | Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene | 501-53-1 | C8H7ClO2 | 详情 | 详情 | |
| (I) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (II) | 30957 | 2-methoxy-5-[(methylimino)methyl]phenol | C9H11NO2 | 详情 | 详情 | |
| (III) | 30958 | 5-(aminomethyl)-2-methoxyphenol | C8H11NO2 | 详情 | 详情 | |
| (IV) | 30959 | benzyl 3-hydroxy-4-methoxybenzylcarbamate | C16H17NO4 | 详情 | 详情 | |
| (V) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (VI) | 30960 | ethyl 2-[5-([[(benzyloxy)carbonyl]amino]methyl)-2-methoxyphenoxy]acetate | C20H23NO6 | 详情 | 详情 | |
| (VII) | 30961 | 2-[5-([[(benzyloxy)carbonyl]amino]methyl)-2-methoxyphenoxy]acetic acid | C18H19NO6 | 详情 | 详情 | |
| (VIII) | 28542 | N-Benzylpiperazine; 1-Benzylpiperazine | 2759-28-6 | C11H16N2 | 详情 | 详情 |
| (IX) | 30962 | benzyl 3-[2-(4-benzyl-1-piperazinyl)-2-oxoethoxy]-4-methoxybenzylcarbamate | C29H33N3O5 | 详情 | 详情 | |
| (X) | 30963 | 2-[5-(aminomethyl)-2-methoxyphenoxy]-1-(4-benzyl-1-piperazinyl)-1-ethanone | C21H27N3O3 | 详情 | 详情 | |
| (XI) | 24750 | Bis(isopropylamine)dichloro platinum complex | C6H18Cl2N2Pt | 详情 | 详情 |