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【结 构 式】

【分子编号】46377

【品名】ethyl 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[3-(ethoxycarbonyl)benzyl]-4-oxo-1,4-dihydro-2-quinolinecarboxylate

【CA登记号】

【 分 子 式 】C30H26BrNO7

【 分 子 量 】592.44298

【元素组成】C 60.82% H 4.42% Br 13.49% N 2.36% O 18.9%

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:(X)

Condensation of o-nitroacetophenone (I) with aldehyde (II) in the presence of piperidine acetate afforded the chalcone (III). Both the double bond and the nitro group of (III) were reduced by catalytic hydrogenation over PtO2 to give (IV). 5-Bromopiperonal (VI) was prepared by treatment of 5-bromo-3,4-dihydroxybenzaldehyde (V) with dibromomethane. Reductive condensation of aldehyde (V) with amine (IV) by means of sodium cyanoborohydride produced the secondary amine (VII), which was condensed with ethyl oxalyl chloride (VIII) to produce amide (IX). Cyclization of (IX) to the corresponding quinolone (X) was achieved by treatment with K2CO3 in EtOH. The ethyl group of the target compound was introduced by Stille coupling of bromide (X) with vinyl tributyltin, followed by catalytic hydrogenation of the resulting ethylene derivative (XI) to give (XII). Finally, saponification of diester (XII) with KOH furnished the title dipotassium salt.

1 Haesslein, J.-L. (Aventis Pharma SA); Quinoline derivs., process for their preparation, the resultant intermediates, their use as medicaments and the pharmaceutical compsns. containing them. FR 2733233; WO 9633190 .
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) 46369 1-(2-nitrophenyl)-1-ethanone C8H7NO3 详情 详情
(II) 46370 ethyl 3-formylbenzoate C10H10O3 详情 详情
(III) 46371 ethyl 3-[(E)-3-(2-nitrophenyl)-3-oxo-1-propenyl]benzoate C18H15NO5 详情 详情
(IV) 46372 ethyl 3-[3-(2-aminophenyl)-3-oxopropyl]benzoate C18H19NO3 详情 详情
(V) 46374 2-bromo-4,5-dihydroxybenzaldehyde C7H5BrO3 详情 详情
(VI) 46373 6-bromo-1,3-benzodioxole-5-carbaldehyde C8H5BrO3 详情 详情
(VII) 46375 ethyl 3-[3-(2-[[(6-bromo-1,3-benzodioxol-5-yl)methyl]amino]phenyl)-3-oxopropyl]benzoate C26H24BrNO5 详情 详情
(VIII) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(IX) 46376 ethyl 3-(3-[2-[[(6-bromo-1,3-benzodioxol-5-yl)methyl](2-ethoxy-2-oxoacetyl)amino]phenyl]-3-oxopropyl)benzoate C30H28BrNO8 详情 详情
(X) 46377 ethyl 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[3-(ethoxycarbonyl)benzyl]-4-oxo-1,4-dihydro-2-quinolinecarboxylate C30H26BrNO7 详情 详情
(XI) 46378 ethyl 3-[3-(ethoxycarbonyl)benzyl]-4-oxo-1-[(6-vinyl-1,3-benzodioxol-5-yl)methyl]-1,4-dihydro-2-quinolinecarboxylate C32H29NO7 详情 详情
(XII) 46379 ethyl 3-[3-(ethoxycarbonyl)benzyl]-1-[(6-ethyl-1,3-benzodioxol-5-yl)methyl]-4-oxo-1,4-dihydro-2-quinolinecarboxylate C32H31NO7 详情 详情
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