ethyl 2-(5-fluoro-2-nitroanilino)-1-benzothiophene-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】46397

【品名】ethyl 2-(5-fluoro-2-nitroanilino)-1-benzothiophene-3-carboxylate

【CA登记号】

【分子式】C₁₇H₁₃FN₂O₄S

【分子量】360.3657032

【元素组成】C 56.66% H 3.64% F 5.27% N 7.77% O 17.76% S 8.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of ethyl 2-aminobenzo[b]thiophene-3-carboxylate (I) with 2,4-difluoronitrobenzene (II) afforded the diaryl amine (III). The nitro group of (III) was then reduced to amine (IV) by catalytic hydrogenation over Pd/C. Then, cyclization of amino ester (IV) with N-methylpiperazine (V) using TiCl4 in hot anisole produced the target benzothienobenzodiazepine, which was finally isolated as the corresponding maleate salt.

参考文献中间体

合成目标

【1】 Fujimura, M.; Horiuchi, H.; Tanaka, H.; Kohara, T.; Hashimoto, K.; Kimura, K.; Seio, K.; Yasumatsu, H. (Welfide Corporation); Fused thiophene cpds. and medicinal use thereof. EP 1016664; JP 2001072684; WO 9911647 .

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)	46396	ethyl 2-amino-1-benzothiophene-3-carboxylate		C₁₁H₁₁NO₂S	详情	详情
(II)	32036	2,4-difluoro-1-nitrobenzene	446-35-5	C₆H₃F₂NO₂	详情	详情
(III)	46397	ethyl 2-(5-fluoro-2-nitroanilino)-1-benzothiophene-3-carboxylate		C₁₇H₁₃FN₂O₄S	详情	详情
(IV)	46398	ethyl 2-(2-amino-5-fluoroanilino)-1-benzothiophene-3-carboxylate		C₁₇H₁₅FN₂O₂S	详情	详情
(V)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情

Extended Information