DZ-3358
Chemical Name: 1-(3-Chlorophenyl)-4-[3-[5-methyl-1-(2-pyrimidinyl)pyrazol-4-yl]-1(E)-propenyl]piperazine hydrochloride
CAS No. 178927-85-0, 258824-19-0 (undefined isomer)
项目整合开发状态: Preclinical
项目研究机构: Daiichi Pharmaceutical (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Pyrimidinylpyrazole deriv.
文献作者:Ejima,A.; Sugimori,M.; Mitsui,I.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:EP 0784055; JP 1997048776; US 5852019; WO 9610024
📄 详细内容
合成路线: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.
参考文献标题:Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives
文献作者:Naito,H.; Sugimori,M.; Mitsui,I.; Nakamura,Y.; Iwahana,M.; Ishii,M.; Hirotani,K.; Kumazawa,E.; Ejima,A.
参考来源:Chem Pharm Bull 1999,47(12),1679
合成路线: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.
参考文献标题:
文献作者:
参考来源:DE 2038503; US 3723433
产品链接: CAS No. 178927-85-0››