5-nitro-1-benzofuran-2-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】42310

【品名】5-nitro-1-benzofuran-2-carbonitrile

【CA登记号】

【分子式】C₉H₄N₂O₃

【分子量】188.14244

【元素组成】C 57.46% H 2.14% N 14.89% O 25.51%

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：(V)

5-Nitrosalicylaldehyde (I) was condensed with diethyl bromomalonate (II) to give ethyl 5-nitrobenzofuran-2-carboxylate (III), which was converted into the corresponding primary amide (IV) by reaction with ethanolic ammonia. Dehydration of amide (IV) to the nitrile (V) was effected by treatment with POCl3. After formation of imidate (VI) with HCl/MeOH, cyclization with ethylenediamine produced the imidazoline (VII). The nitro group of (VII) was then reduced to amine (VIII) using Fe and HCl. This was finally converted to the title isothiocyanate by reaction with thiophosgene.

参考文献中间体

合成目标

【1】 Hudson, A.L.; Nutt, D.J.; Grundt, P.; Coates, P.A.; Husbands, S.M.; Tyacke, R.; Robinson, E.S.J.; Lewis, J.W.; Probes for imidazole binding sites: Synthesis and evaluation of a selective, irreversible I2 ligand. Bioorg Med Chem Lett 2000, 10, 6, 605.

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)	42307	2-hydroxy-5-nitrobenzaldehyde；5-nitrosalicylaldehyde	97-51-8	C₇H₅NO₄	详情	详情
(II)	35647	diethyl 2-bromomalonate	685-87-0	C₇H₁₁BrO₄	详情	详情
(III)	42308	ethyl 5-nitro-1-benzofuran-2-carboxylate	69404-00-8	C₁₁H₉NO₅	详情	详情
(IV)	42309	5-nitro-1-benzofuran-2-carboxamide		C₉H₆N₂O₄	详情	详情
(V)	42310	5-nitro-1-benzofuran-2-carbonitrile		C₉H₄N₂O₃	详情	详情
(VI)	42311	methyl 5-nitro-1-benzofuran-2-carboximidoate		C₁₀H₈N₂O₄	详情	详情
(VII)	42312	2-(5-nitro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole		C₁₁H₉N₃O₃	详情	详情
(VIII)	42313	2-(4,5-dihydro-1H-imidazol-2-yl)-1-benzofuran-5-amine; 2-(4,5-dihydro-1H-imidazol-2-yl)-1-benzofuran-5-ylamine		C₁₁H₁₁N₃O	详情	详情

Extended Information