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【结 构 式】

【分子编号】14944

【品名】ethyl 4-(3-formyl-4-nitrophenoxy)butanoate

【CA登记号】

【 分 子 式 】C13H15NO6

【 分 子 量 】281.26524

【元素组成】C 55.51% H 5.38% N 4.98% O 34.13%

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)

Alkylation of 5-hydroxy-2-nitrobenzaldehyde (I) with ethyl 4-bromobutyrate (II) in the presence of potassium carbonate at 110 C in DMF provided the aldehyde (III). Coupling of (III) with the phosphonate (IV) using triethylamine as the base afforded the unsaturated hydantoin derivative (V) as a mixture of geometrical isomers. Exhaustive catalytic hydrogenation of (V) over palladium on charcoal in DMF furnished the saturated aniline (VI), which underwent acid-catalyzed cyclization-dehydration in methanol at reflux, followed by oxidation upon addition of a molar equivalent of iodine to give the imidazo[4,5-b]quinoline derivative (VII). Alkaline hydrolysis of (VII) provided acid (VIII), which was coupled with N-cyclohexylmethylpiperazine, using diphenylphosphoryl azide in DMF at room temperature, to furnish BMY 43351 (IX). The dihydrochloride salt of (IX) was prepared by dissolution of the free base in a solution of 10% hydrogen chloride in methanol and subsequent precipitation with diethyl ether.

1 Wedding, D.L.; Meanwell, N.A.; Roth, H.R.; Wright, J.J.K.; Smith, E.C.R.; Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparations of C-5 unsaturated hydantoin derivatives. J Org Chem 1991, 56, 6897-904.
2 Russell, J.W.; Seiler, S.M.; Meanwell, N.A.; Fleming, J.S.; BMY 43351. Drugs Fut 1992, 17, 1, 15.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
63929 1-(cyclohexylmethyl)piperazine C11H22N2 详情 详情
(I) 14942 5-hydroxy-2-nitrobenzaldehyde 42454-06-8 C7H5NO4 详情 详情
(II) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(III) 14944 ethyl 4-(3-formyl-4-nitrophenoxy)butanoate C13H15NO6 详情 详情
(IV) 14945 Diethyl 5-hydantoylphosphonate; diethyl 2,5-dioxo-4-imidazolidinylphosphonate 95378-36-2 C7H13N2O5P 详情 详情
(V) 14946 ethyl 4-[3-[(2,5-dioxotetrahydro-4H-imidazol-4-ylidene)methyl]-4-nitrophenoxy]butanoate C16H17N3O7 详情 详情
(VI) 14947 ethyl 4-[4-amino-3-[(2,5-dioxo-4-imidazolidinyl)methyl]phenoxy]butanoate C16H21N3O5 详情 详情
(VII) 14948 methyl 4-[(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butanoate C15H15N3O4 详情 详情
(VIII) 14949 4-[(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butyric acid C14H13N3O4 详情 详情
(IX) 14950 7-[4-[4-(cyclohexylmethyl)piperazino]-4-oxobutoxy]-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one C25H33N5O3 详情 详情
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