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【结 构 式】

【分子编号】53129

【品名】N-(4-formylphenyl)-2-thiophenecarboxamide

【CA登记号】n/a

【 分 子 式 】C12H9NO2S

【 分 子 量 】231.275

【元素组成】C 62.32% H 3.92% N 6.06% O 13.84% S 13.86%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The precursor aldehyde (VI) was prepared as follows. 4-Nitrobenzaldehyde (I) was protected as the ethylene acetal (II) and subsequently reduced by catalytic hydrogenation in the presence of PtO2 to furnish aniline (III). Acylation of (III) with 2-thiophenecarbonyl chloride (IV) provided amide (V). The ethylene acetal group of (V) was then hydrolyzed to the target aldehyde (VI) under acidic conditions.

1 Folkes, A.; et al.; Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. Bioorg Med Chem Lett 2001, 11, 19, 2589.
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) 18184 4-Nitrobenzaldehyde 555-16-8 C7H5NO3 详情 详情
(II) 53126 2-(4-nitrophenyl)-1,3-dioxolane n/a C9H9NO4 详情 详情
(III) 53127 4-(1,3-dioxolan-2-yl)aniline; 4-(1,3-dioxolan-2-yl)phenylamine n/a C9H11NO2 详情 详情
(IV) 14103 2-Thiophenecarbonyl chloride 5271-67-0 C5H3ClOS 详情 详情
(V) 53128 N-[4-(1,3-dioxolan-2-yl)phenyl]-2-thiophenecarboxamide n/a C14H13NO3S 详情 详情
(VI) 53129 N-(4-formylphenyl)-2-thiophenecarboxamide n/a C12H9NO2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VI)

Dioxopiperazine (X) was diacetylated in refluxing acetic anhydride to yield (XI). Aldol condensation of (XI) with the precursor aldehyde (VI) using potassium tert-butoxide in THF gave the mono-arylidene piperazine (XII). Further condensation of (XII) with the intermediate aldehyde (IX) in the presence of Cs2CO3 in DMF furnished the deacetylated bis-arylidene piperazine (XIII). The methyl ester group of (XIII) was finally hydrolyzed to the title carboxylic acid using NaOH in H2O/MeOH/THF.

1 Folkes, A.; et al.; Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. Bioorg Med Chem Lett 2001, 11, 19, 2589.
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) 53129 N-(4-formylphenyl)-2-thiophenecarboxamide n/a C12H9NO2S 详情 详情
(IX) 53131 methyl 8-(4-formylphenoxy)octanoate n/a C16H22O4 详情 详情
(X) 29800 2,5-piperazinedione;2,5-diketopiperazine;cycloglycylglycine;2,5-dioxopiperazine;cyclodiglycine;cyclo(glycylglycyl) 106-57-0 C4H6N2O2 详情 详情
(XI) 19188 1,4-diacetyl-2,5-piperazinedione;N,N'-DIACETYLGLYCINE ANHYDRIDE;1,4-DIACETYL-PIPERAZINE-2,5-DIONE;1,4-DIACETYLTETRAHYDRO-2,5-PYRAZINEDIONE;1,4-DIACETYL-2,5-DIKETOPIPERAZINE;1,4-DIACETYL-2,5-DIOXOPIPERAZINE 3027-05-2 C8H10N2O4 详情 详情
(XII) 53132 N-{4-[(4-acetyl-3,6-dioxo-2-piperazinylidene)methyl]phenyl}-2-thiophenecarboxamide n/a C18H15N3O4S 详情 详情
(XIII) 53133 methyl 8-(4-{[3,6-dioxo-5-((Z)-{4-[(2-thienylcarbonyl)amino]phenyl}methylidene)-2-piperazinylidene]methyl}phenoxy)octanoate n/a C32H33N3O6S 详情 详情
Extended Information