ChemicalBook CAS DataBase List Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate synthesis

8synthesis methods

Product Name:Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
CAS Number:113028-17-4
Molecular formula:C18H20FN3O3S
Molecular Weight:377.43

110-85-0

Ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

113046-72-3

Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

113028-17-4

The general procedure for the synthesis of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazepine[3,2-a]quinoline-3-carboxylate from ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazepine[3,2-a]quinoline-3-carboxylate and piperazine was carried out as follows: 50 g of ethyl 6,7-difluoro-1-methyl-4 -oxo-4H-[1,3]thiazino[3,2-a]quinoline-3-carboxylic acid ethyl ester was dissolved in 5 volumes of DMSO and heated to 60 °C. Subsequently, 40 g of piperazine was added and the reaction was kept stirred at 60°C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, 5 volumes of acetonitrile was added and stirring was continued at room temperature for 4 hours. The precipitate was collected by filtration and dried to give 52.8 g of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-[1,3]thiazolocyclo[3,2-a]quinoline-3-carboxylate in 87% yield. After further purification, the yield of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-[1,3]thiazolocyclo[3,2-a]quinoline-3-carboxylate was up to 99%.

110-85-0 Synthesis

110-85-0
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113046-72-3
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113028-17-4
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$83.00/100mg

Yield: 87%

Reaction Conditions:

in dimethyl sulfoxide at 60; for 4 h;

Steps:

1 Preparation of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazacyclo [3,2-a] quinoline-3-carboxylate
50 g of ethyl 6,7-difluoro-1-methyl-4-oxo-4H- [1,3] thiazine [3,2-a] Dissolve in 5 volumes of DMSO at 60°C, add 40 g of piperazine, and stir at 60°C for 4 hours. The mixture was cooled to room temperature, then 5 volumes of acetonitrile were added and stirring was continued for 4 hours at room temperature. The precipitate was collected by filtration and dried to give 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazacyclo [3,2-a] Ethyl acid 52.8g, yield 87%. The yield of 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazacyclo [3,2-a] quinoline-3-carboxylic acid B Ester purity 99%.

References:

Zhaoke Pharmaceutical (Hefei) Co., Ltd.;Li Xiaoyi;Dai Xiangrong;Zhou Guanqun CN107383069, 2017, A Location in patent:Paragraph 0061; 0062