2-nitro-1-(2-oxiranylmethyl)-1H-imidazole -Drug Synthesis Database

【结构式】

【分子编号】44589

【品名】2-nitro-1-(2-oxiranylmethyl)-1H-imidazole

【CA登记号】

【分子式】C₆H₇N₃O₃

【分子量】169.14

【元素组成】C 42.61% H 4.17% N 24.84% O 28.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

[2H]-Labeled RSU-1069 is synthesized as follows: The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III), which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV). The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V), which is cyclized with NaOH to the corresponding labeled epoxide (VI). Finally, this compound is condensed with aziridine (VII) by means of triethylamine in refluxing ethanol.

参考文献中间体

合成目标

【1】 Webb, P.; Threadgill, M.D.; Labelled compounds of interest as antitumour agents. Part II (1). Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03-8799 (pimonidazole). J Label Compd Radiopharm 1990, 28, 3, 257.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III),(V)	10147	1-Chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol		C₆H₈ClN₃O₃	详情	详情
(I)	10145	2-Nitro-1H-imidazole; 2-Nitroimidazole	527-73-1	C₃H₃N₃O₂	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(IV)	10148	1-Chloro-3-(2-nitro-1H-imidazol-1-yl)acetone		C₆H₆ClN₃O₃	详情	详情
(V)	44588	1-chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol		C₆H₈ClN₃O₃	详情	详情
(VI)	10150	2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole		C₆H₇N₃O₃	详情	详情
(VI)	44589	2-nitro-1-(2-oxiranylmethyl)-1H-imidazole		C₆H₇N₃O₃	详情	详情
(VII)	10151	Ethyleneimine; Aziridine; Azirane	151-56-4	C₂H₅N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

[2H]-Labeled pimonidazole is synthesized as follows: The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III), which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV). The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V), which is cyclized with NaOH to the corresponding labeled epoxide (VI). Finally, this compound is condensed with piperidine (VII) in refluxing ethanol.

参考文献中间体

合成目标

【1】 Webb, P.; Threadgill, M.D.; Labelled compounds of interest as antitumour agents. Part II (1). Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03-8799 (pimonidazole). J Label Compd Radiopharm 1990, 28, 3, 257.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III),(V)	10147	1-Chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol		C₆H₈ClN₃O₃	详情	详情
(I)	10145	2-Nitro-1H-imidazole; 2-Nitroimidazole	527-73-1	C₃H₃N₃O₂	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(IV)	10148	1-Chloro-3-(2-nitro-1H-imidazol-1-yl)acetone		C₆H₆ClN₃O₃	详情	详情
(V)	44588	1-chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol		C₆H₈ClN₃O₃	详情	详情
(VI)	10150	2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole		C₆H₇N₃O₃	详情	详情
(VI)	44589	2-nitro-1-(2-oxiranylmethyl)-1H-imidazole		C₆H₇N₃O₃	详情	详情
(VII)	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情

Extended Information