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【结 构 式】

【分子编号】41465

【品名】ethyl (E)-3-(4-chlorophenyl)-2-cyano-2-butenoate

【CA登记号】

【 分 子 式 】C13H12ClNO2

【 分 子 量 】249.69652

【元素组成】C 62.53% H 4.84% Cl 14.2% N 5.61% O 12.82%

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:(IIb)

Knoevenagel condensation of ketone (I) with ethyl cyanoacetate followed by Michael addition of cyanoacetamide to the resulting alpha-cyanocinnamate (IIa-b) yields cyclic imide (III). Hydrolysis and decarboxylation of (III) with H2SO4 gives diacid (IV), which is cyclized by means of hot H2SO4 to provide indanone (V). Treatment of (V) with oxalyl chloride in CH2Cl2 and catalytic DMF followed by addition of EtOH affords ethyl ester (VI), which is then converted into oxime (VII) by means of t-BuONO in Et2O and HCl. Hydrogenolysis of (VII) with H2 over Pd/C in HOAc/HCl provides alpha-amino derivative (VIII). By reacting (VIII) with ethyl oxalyl chloride (A), in CH2Cl2 in presence of Et3N, (IX) was obtained and then cyclized in presence of NH4OAc in refluxing HOAc to yield pyrazino derivative (X). Finally (X) is hydrolyzed with HCl in dioxane.

1 Jimonet, P.; Ribeill, Y.; Bohme, A.; et al.; Indeno[1,2-b]pyrazin-2,3-diones: A new class of antagonists at the glycine site of the NMDA receptor with potent in vivo activity. J Med Chem 2000, 43, 12, 2371.
2 Jimonet, P.; Ribeill, Y.; Audiau, F.; Aloup, J.-C.; Barreau, M.; Mignani, S.; Genevois-Borella, A.; Damour, D. (Aventis Pharma SA); 5H-Indeno[1,2-b]pyrazine-2,3-dione derivs., their preparation and medicinal products containing them. US 5922716; WO 9526342 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
12122 Cyanoacetamide; 2-Cyanoacetamide 107-91-5 C3H4N2O 详情 详情
(A) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(IIa) 41464 ethyl (Z)-3-(4-chlorophenyl)-2-cyano-2-butenoate C13H12ClNO2 详情 详情
(IIb) 41465 ethyl (E)-3-(4-chlorophenyl)-2-cyano-2-butenoate C13H12ClNO2 详情 详情
(I) 12685 4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone 99-91-2 C8H7ClO 详情 详情
(III) 41466 4-(4-chlorophenyl)-4-methyl-2,6-dioxo-3,5-piperidinedicarbonitrile C14H10ClN3O2 详情 详情
(IV) 41467 3-(4-chlorophenyl)-3-methylpentanedioic acid C12H13ClO4 详情 详情
(V) 41468 2-(5-chloro-1-methyl-3-oxo-2,3-dihydro-1H-inden-1-yl)acetic acid C12H11ClO3 详情 详情
(VI) 41469 ethyl 2-(5-chloro-1-methyl-3-oxo-2,3-dihydro-1H-inden-1-yl)acetate C14H15ClO3 详情 详情
(VII) 41470 ethyl 2-[5-chloro-2-(hydroxyimino)-1-methyl-3-oxo-1,3-dihydro-2H-inden-1-yl]acetate C14H14ClNO4 详情 详情
(VIII) 41471 ethyl 2-(2-amino-5-chloro-1-methyl-3-oxo-2,3-dihydro-1H-inden-1-yl)acetate C14H16ClNO3 详情 详情
(IX) 41472 ethyl 2-[[5-chloro-1-(2-ethoxy-2-oxoethyl)-1-methyl-3-oxo-2,3-dihydro-1H-inden-2-yl]amino]-2-oxoacetate C18H20ClNO6 详情 详情
(X) 41473 ethyl 2-(6-chloro-9-methyl-2,3-dioxo-2,3,4,9-tetrahydro-1H-indeno[1,2-b]pyrazin-9-yl)acetate C16H15ClN2O4 详情 详情
Extended Information