N-(4-formylphenyl)-2-thiophenecarboxamide -Drug Synthesis Database

【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 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)

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.

参考文献中间体

合成目标

【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.

参考文献中间体

合成目标

【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