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【结 构 式】

【分子编号】13062

【品名】[2-thioxo-3-(2,3,4-trifluorophenyl)-2,3-dihydro-1,3-thiazol-4-yl]methyl acetate

【CA登记号】

【 分 子 式 】C12H8F3NO2S2

【 分 子 量 】319.3282696

【元素组成】C 45.14% H 2.53% F 17.85% N 4.39% O 10.02% S 20.08%

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:(V)

A new synthesis for KB-5246 has been described: The reaction of 2,3,4-trifluoroaniline (I) with carbon disulfide (II) and triethylamine gives the corresponding dithiocarbamate (III), which by cyclization with 1-acetoxy-3-chloro-2-propanone (IV) in ethyl acetate yields 4-(acetoxymethyl)-3-(2,3,4-trifluorophenyl)thiazole-2(3H)-thione (V). The cyclization of (V) with potassium hydroxide in refluxing ethanol-water affords 6,7-difluoro-1H,4H-thiazolo[4,3-c][1,4]benzoxazine-1-thione (VI), which is treated with trichloromethyl chloroformate in hot toluene to give the thiazolium chloride (VII), which is not isolated. The in situ reaction of (VII) with diethyl malonate by means of triethylamine in toluene gives (6,7-difluoro-1H,4H-thiazolo[4,3-c][1,4]benzoxazin-1-ylidene)malonic acid diethyl ester (IX), which is cyclized again with polyphosphoric acid (PPA) at 115 C to afford 7,8-difluoro-5-oxo-9,1-(epoxymethano)-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid ethyl ester (X). The hydrolysis of (X) with oleum gives the corresponding acid (XI), which is finally condensed with N-methylpiperazine (XII) in hot DMSO.

1 Kondo, H.; Tsukamoto, G.; Taguchi, M.; Jinbo, Y.; Kawahata, Y.; Sakamoto, F.; Inoue, Y.; Synthesis and antibacterial activity of new tetracyclic quinolone antibacterials. J Med Chem 1992, 35, 1, 94.
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) 13059 2,3,4-Trifluorophenylamine; 2,3,4-Trifluoroaniline 3862-73-5 C6H4F3N 详情 详情
(III) 13060 2,3,4-trifluorophenylcarbamodithioate C7H3F3NS2 详情 详情
(IV) 13061 2-(chlorooxy)-2-oxoethyl acetate C4H5ClO4 详情 详情
(V) 13062 [2-thioxo-3-(2,3,4-trifluorophenyl)-2,3-dihydro-1,3-thiazol-4-yl]methyl acetate C12H8F3NO2S2 详情 详情
(VI) 13063 6,7-Difluoro-4H-[1,3]thiazolo[4,3-c][1,4]benzoxazine-1-thione C10H5F2NOS2 详情 详情
(VII) 13064 1-Chloro-6,7-difluoro-4H-[1,3]thiazolo[4,3-c][1,4]benzoxazin-10-ium chloride C10H5Cl2F2NOS 详情 详情
(VIII) 16829 Diethyl malonate 105-53-3 C7H12O4 详情 详情
(IX) 13066 diethyl 2-(6,7-difluoro-4H-[1,3]thiazolo[4,3-c][1,4]benzoxazin-1-ylidene)malonate C17H15F2NO5S 详情 详情
(X) 13067 ethyl 5,6-difluoro-8-oxo-3H,8H-4-oxa-1-thia-9b-azacyclopenta[cd]phenalene-9-carboxylate C15H9F2NO4S 详情 详情
(XI) 13068 5,6-Difluoro-8-oxo-3H,8H-4-oxa-1-thia-9b-azacyclopenta[cd]phenalene-9-carboxylic acid C13H5F2NO4S 详情 详情
(XII) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
Extended Information