【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% |
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 |