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【结 构 式】

【分子编号】15108

【品名】7-bromo-1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

【CA登记号】

【 分 子 式 】C14H11BrFNO4

【 分 子 量 】356.1480832

【元素组成】C 47.21% H 3.11% Br 22.44% F 5.33% N 3.93% O 17.97%

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:(XVI)

5) Compound (XVIII): The esterification of 7-bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-ca rboxylic acid (XII) with SOCl2/methanol gives the corresponding methyl ester (XIII), which is brominated with N-bromosuccinimide (NBS) and benzoyl peroxide (BPO) in refluxing CCl4 yielding the corresponding bromomethyl derivative (XIV). The reaction of (XIV) with sodium acetate in hot DMF affords the expected acetoxymethyl derivative (XV), which is saponified with K2CO3 in methanol/water to give 1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-4-oxo-1,4-dihydroquinoline-3-c arboxylic acid (XVI). Finally, this compound is condensed with 2-methylpiperazine (XVII) by heating at 110 C. 6) Compound (XX): The condensation of the hydroxymethylquinolone (XVI) with the benzylamine (VI) as before gives 6-fluoro-5-(hydroxymethyl)-4-(4-methoxybenzylamino)-4-oxo-1,4-dihydroqu inoline-3-carboxylic acid (XIX), which is then debenzylated with trifluoroacetic acid an H2SO4 as before.

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
(VI) 15098 4-Methoxybenzylamine; (4-Methoxyphenyl)methanamine 2393-23-9 C8H11NO 详情 详情
(XII) 15104 7-bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C14H11BrFNO3 详情 详情
(XIII) 15105 methyl 7-bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate C15H13BrFNO3 详情 详情
(XIV) 15106 methyl 7-bromo-5-(bromomethyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate C15H12Br2FNO3 详情 详情
(XV) 15107 methyl 5-[(acetoxy)methyl]-7-bromo-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate C17H15BrFNO5 详情 详情
(XVI) 15108 7-bromo-1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C14H11BrFNO4 详情 详情
(XVII) 12267 2-Methylpiperazine 109-07-9 C5H12N2 详情 详情
(XVIII) 15110 1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-7-(3-methylpiperazino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C19H22FN3O4 详情 详情
(XIX) 15111 1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-7-[(4-methoxybenzyl)amino]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C22H21FN2O5 详情 详情
(XX) 15112 7-amino-1-cyclopropyl-6-fluoro-5-(hydroxymethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C14H13FN2O4 详情 详情
Extended Information