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【结 构 式】

【分子编号】34491

【品名】5-amino-3-(5-chloro-3-thienyl)indeno[1,2-c]pyrazol-4(2H)-one

【CA登记号】

【 分 子 式 】C14H8ClN3OS

【 分 子 量 】301.75584

【元素组成】C 55.73% H 2.67% Cl 11.75% N 13.93% O 5.3% S 10.63%

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:(VII)

Dimethyl 3-nitrophthalate (I) was hydrogenated in the presence of Pd/C to give aminophthalate (II), which was acylated with Ac2O in pyridine, yielding acetamidophthalate (III). Condensation of phthalate ester (III) with 4-acetyl-2-chlorothiophene (IV) using NaH in DMF produced triketone (V). After acid hydrolysis of the amide function of (V), the resulting aminoindenetrione (VI) was cyclized with hydrazine hydrate to generate the indenopyrazolone system (VII). Condensation of (VII) with phenyl chloroformate afforded the phenyl carbamate (VIII). This was finally treated with concentrated ammonia to furnish the target urea derivative.

1 Yue, E.W.; Carini, D.J.; Nugiel, D.A.; Dimeo, S.V. (DuPont Pharmaceuticals Co.); 5-Aminoindeno(1,2-c)pyrazol-4-ones as anti-cancer and anti-proliferative agents. WO 9954308 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
13580 1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate 1885-14-9 C7H5ClO2 详情 详情
(I) 34481 dimethyl 3-nitrophthalate 13365-26-9 C10H9NO6 详情 详情
(II) 34482 dimethyl 3-aminophthalate C10H11NO4 详情 详情
(III) 34483 dimethyl 3-(acetamido)phthalate C12H13NO5 详情 详情
(IV) 34488 1-(5-chloro-3-thienyl)-1-ethanone C6H5ClOS 详情 详情
(V) 34489 N-[2-[(5-chloro-3-thienyl)carbonyl]-1,3-dioxo-2,3-dihydro-1H-inden-4-yl]acetamide C16H10ClNO4S 详情 详情
(VI) 34490 4-amino-2-[(5-chloro-3-thienyl)carbonyl]-1H-indene-1,3(2H)-dione C14H8ClNO3S 详情 详情
(VII) 34491 5-amino-3-(5-chloro-3-thienyl)indeno[1,2-c]pyrazol-4(2H)-one C14H8ClN3OS 详情 详情
(VIII) 34492 phenyl 3-(5-chloro-3-thienyl)-4-oxo-2,4-dihydroindeno[1,2-c]pyrazol-5-ylcarbamate C21H12ClN3O3S 详情 详情
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