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【结 构 式】 
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【分子编号】41452 【品名】3-[4-(3-chlorophenyl)-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-1H-pyrazol-4-yl]-1-propanone 【CA登记号】 |
【 分 子 式 】C21H23ClN6O 【 分 子 量 】410.90616 【元素组成】C 61.38% H 5.64% Cl 8.63% N 20.45% O 3.89% |
合成路线1
该中间体在本合成路线中的序号：(V)Pyrimidinyl pyrazole (III) was prepared by condensation of diketone (I) with 2-hydrazinopyrimidine (II). Subsequent Mannich reaction with N-(3-chlorophenyl)piperazine (IV) and paraformaldehyde furnished piperazinyl propanone (V). This was reduced to alcohol (VI) with NaBH4. Alcohol dehydration employing p-toluenesulfonic acid yielded the title compound, that was finally isolated as the hydrochloride salt. The intermediate N-(3-chlorophenyl)piperazine (IV) has been obtained by cyclization of bis(2-chloroethyl)amine (VII) with 3-chloroaniline (VIII) by means of Na2CO3 in refluxing butanol.
| 【1】 DE 2038503; US 3723433 . |
| 【2】 Ejima, A.; Sugimori, M.; Mitsui, I. (Daiichi Pharmaceutical Co., Ltd.); Pyrimidinylpyrazole deriv.. EP 0784055; JP 1997048776; US 5852019; WO 9610024 . |
| 【3】 Ishii, M.; Ejima, A.; Hirotani, K.; Iwahana, M.; Sugimori, M.; Mitsui, I.; Naito, H.; Nakamura, Y.; Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. Chem Pharm Bull 1999, 47, 12, 1679. |
| 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) | 41449 | 3-(ethoxymethylene)-2,4-pentanedione | C8H12O3 | 详情 | 详情 | |
| (II) | 41450 | 2-hydrazinopyrimidine | C4H6N4 | 详情 | 详情 | |
| (III) | 41451 | 1-[5-methyl-1-(2-pyrimidinyl)-1H-pyrazol-4-yl]-1-ethanone | C10H10N4O | 详情 | 详情 | |
| (IV) | 22114 | 1-(3-chlorophenyl)piperazine | 6640-24-0 | C10H13ClN2 | 详情 | 详情 |
| (V) | 41452 | 3-[4-(3-chlorophenyl)-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-1H-pyrazol-4-yl]-1-propanone | C21H23ClN6O | 详情 | 详情 | |
| (VI) | 41453 | 3-[4-(3-chlorophenyl)-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-1H-pyrazol-4-yl]-1-propanol | C21H25ClN6O | 详情 | 详情 | |
| (VII) | 21583 | 2-chloro-N-(2-chloroethyl)-1-ethanamine; Bis(2-chloroethyl)amine; 1,1'-iminobis(2-chloroethane); N,N-bis(2-chloroethyl)amine | 821-48-7 | C4H9Cl2N | 详情 | 详情 |
| (VIII) | 25239 | 3-chloroaniline; 3-chlorophenylamine | 108-42-9 | C6H6ClN | 详情 | 详情 |