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【结 构 式】

【分子编号】15102

【品名】1-cyclopropyl-7-[(2-ethoxy-2-oxoethyl)amino]-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

【CA登记号】

【 分 子 式 】C18H19FN2O5

【 分 子 量 】362.3577432

【元素组成】C 59.66% H 5.29% F 5.24% N 7.73% O 22.08%

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)

The syntheses of the metabolites of grepafloxacin, 7-(2-aminoethylamino)-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro quinoline-3-carboxylic acid (III), 7-(2-aminopropylamino)-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydr oquinoline-3-carboxylic acid (V), 7-amino-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-ca rboxylic acid (VIII), 7-(carboxymethylamino)-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydr oquinoline-3-carboxylic acid (XI), 1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-7-(3-methylpiperazin-1-yl)-4-o xo-1,4-dihydroquinoline-3-carboxylic acid (XVIII) and 7-amino-1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-4-oxo-1,4-dihydroquino line-3-carboxylic acid (XX) have been reported: 1) Compound (III): By condensation of 7-bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-ca rboxylic acid diacetoxyborane ester (I) with 2-(tert-butoxycarbonylamino)ethylamine (II) by heating at 110 C followed by a treatment with HCl in ethanol/water. 2) Compound (V): By condensation of quinolone (I) with 2-(tert-butoxycarbonylamino)ethylamine (IV) by heating at 110 C, followed by hydrolysis with HCl as before. 3) Compound (VIII): The condensation of quinolone (I) with 4-methoxybenzylamine (VII) by heating at 110 C gives 1-cyclopropyl-6-fluoro-7-(4-methoxybenzylamino)-5-methyl-4-oxo-1,4-dihy droquinoline-3-carboxylic acid (VII), which is then debenzylated by treatment with a mixture of trifluoroacetic acid and concentrated sulfuric acid. 4) Compound (XI): The condensation of quinolone (I) with glycine ethyl ester (IX) by heating at 110 C gives 1-cyclopropyl-7-(ethoxycarbonylmethylamino)-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (X), which is then saponified with NaOH in refluxing ethanol.

1 Otsubo, K.; Kawano, Y.; Ohguro, K.; Uchida, M.; Ohtani, T.; Ohmori, K.; Matsubara, J.; Morita, S.; Synthesis of possible metabolites of 1-cyclopropyl-1,4-dihydro-6-fluoro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (grepafloxacin, OPC-17116). Chem Pharm Bull 1995, 43, 12, 2246.
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) 15093 diacetyl (7-bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinyl)carbonyl borate C18H16BBrFNO7 详情 详情
(II) 13241 N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate;tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate 57260-73-8 C7H16N2O2 详情 详情
(III) 15095 7-[(2-aminoethyl)amino]-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C16H18FN3O3 详情 详情
(IV) 15096 tert-butyl N-(2-amino-1-methylethyl)carbamate C8H18N2O2 详情 详情
(V) 15097 7-[(2-aminopropyl)amino]-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C17H20FN3O3 详情 详情
(VI) 15098 4-Methoxybenzylamine; (4-Methoxyphenyl)methanamine 2393-23-9 C8H11NO 详情 详情
(VII) 15099 1-cyclopropyl-6-fluoro-7-[(4-methoxybenzyl)amino]-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C22H21FN2O4 详情 详情
(VIII) 15100 7-amino-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C14H13FN2O3 详情 详情
(IX) 10309 ethyl 2-aminoacetate; Glycine ethyl ester 459-73-4 C4H9NO2 详情 详情
(X) 15102 1-cyclopropyl-7-[(2-ethoxy-2-oxoethyl)amino]-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C18H19FN2O5 详情 详情
(XI) 15103 7-[(carboxymethyl)amino]-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C16H15FN2O5 详情 详情
Extended Information