4-chloropyrrolo[1,2-a]quinoxalin-7-yl methyl ether; 4-chloro-7-methoxypyrrolo[1,2-a]quinoxaline -Drug Synthesis Database

【结构式】

【分子编号】23597

【品名】4-chloropyrrolo[1,2-a]quinoxalin-7-yl methyl ether; 4-chloro-7-methoxypyrrolo[1,2-a]quinoxaline

【CA登记号】

【分子式】C₁₂H₉ClN₂O

【分子量】232.66904

【元素组成】C 61.95% H 3.9% Cl 15.24% N 12.04% O 6.88%

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)

Phenyl pyrrole (III) was prepared by Clauson-Kaas reaction of 4-methoxy-2-nitroaniline (I) with 2,5-dimethoxytetrahydrofuran (II). Subsequent reduction of the nitro group of (III) using hydrazine and Raney Nickel provided aniline (IV), which was cyclized with phosgene in refluxing toluene to furnish the pyrroloquinoxaline (V). This was chlorinated with POCl3 to obtain the chloroquinoxaline (VI). Finally, nucleophilic substitution in (VI) with N-(4-fluorobenzyl)piperazine (VII) yielded the title compound.

参考文献中间体

合成目标

【1】 Katounina, T.; et al.; Synthesis of [18F]MR 18445 and its in vivo evaluat. J Label Compd Radiopharm 1997, 40, 542.
【2】 Lancelot, J.-C.; Prunier, H.; Rault, S.; et al.; Novel and selective partial agonists of 5-HT3 rece. J Med Chem 1997, 40, 12, 1808.
【3】 Katounina, T.; et al.; Synthesis and biological investigations of [18F]MR. Bioorg Med Chem 1998, 6, 6, 789.
【4】 Rault, S.; Lancelot, J.-C.; Prunier, H.; Robba, M.; Delagrange, P.; Renard, P.; Adam, G. (ADIR et Cie.); Pyrrolopyrazine derivs. with 5-HT3 activity. CA 2122890; EP 0623620; FR 2704547; JP 1994340666; US 5599812 .

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)	23592	4-methoxy-2-nitrophenylamine; 4-methoxy-2-nitroaniline	96-96-8	C₇H₈N₂O₃	详情	详情
(II)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(III)	23594	1-(4-methoxy-2-nitrophenyl)-1H-pyrrole; methyl 3-nitro-4-(1H-pyrrol-1-yl)phenyl ether		C₁₁H₁₀N₂O₃	详情	详情
(IV)	23595	5-methoxy-2-(1H-pyrrol-1-yl)phenylamine; 5-methoxy-2-(1H-pyrrol-1-yl)aniline		C₁₁H₁₂N₂O	详情	详情
(V)	23596	7-methoxypyrrolo[1,2-a]quinoxalin-4(5H)-one		C₁₂H₁₀N₂O₂	详情	详情
(VI)	23597	4-chloropyrrolo[1,2-a]quinoxalin-7-yl methyl ether; 4-chloro-7-methoxypyrrolo[1,2-a]quinoxaline		C₁₂H₉ClN₂O	详情	详情
(VII)	23598	1-(4-fluorobenzyl)piperazine		C₁₁H₁₅FN₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

A synthesis for the 18F-labeled compound has also been reported. The piperazinylquinoxaline (IX) was obtained from chloroquinoxaline (VI) and excess piperazine (VIII) at 160 C. This was then alkylated with 4-[18F]fluorobenzyl iodide (X) in refluxing CH2Cl2 to provide the labeled product.

参考文献中间体

合成目标

【1】 Katounina, T.; et al.; Synthesis and biological investigations of [18F]MR. Bioorg Med Chem 1998, 6, 6, 789.
【2】 Lancelot, J.-C.; Prunier, H.; Rault, S.; et al.; Novel and selective partial agonists of 5-HT3 rece. J Med Chem 1997, 40, 12, 1808.
【3】 Katounina, T.; et al.; Synthesis of [18F]MR 18445 and its in vivo evaluat. J Label Compd Radiopharm 1997, 40, 542.
【4】 Rault, S.; Lancelot, J.-C.; Prunier, H.; Robba, M.; Delagrange, P.; Renard, P.; Adam, G. (ADIR et Cie.); Pyrrolopyrazine derivs. with 5-HT3 activity. CA 2122890; EP 0623620; FR 2704547; JP 1994340666; US 5599812 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	23597	4-chloropyrrolo[1,2-a]quinoxalin-7-yl methyl ether; 4-chloro-7-methoxypyrrolo[1,2-a]quinoxaline		C₁₂H₉ClN₂O	详情	详情
(VIII)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(IX)	23600	7-methoxy-4-(1-piperazinyl)pyrrolo[1,2-a]quinoxaline; methyl 4-(1-piperazinyl)pyrrolo[1,2-a]quinoxalin-7-yl ether		C₁₆H₁₈N₄O	详情	详情
(X)	23601	1-fluoro-4-(iodomethyl)benzene		C₇H₆FI	详情	详情
(X)	45316	1-fluoro-4-(iodomethyl)benzene		C₇H₆FI	详情	详情

Extended Information