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【结 构 式】

【分子编号】43204

【品名】7-chloro-9-cyclopropyl-6,8-difluoroisothiazolo[5,4-b]quinoline-3,4(2H,9H)-dione

【CA登记号】

【 分 子 式 】C13H7ClF2N2O2S

【 分 子 量 】328.7263664

【元素组成】C 47.5% H 2.15% Cl 10.78% F 11.56% N 8.52% O 9.73% S 9.75%

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)

The cyclization of 2-(2,4-dichloro-3,5-difluorobenzoyl)acetic acid ethyl ester (I) with S-phenyl(cyclopropylimino)chlorothioformate (II) by means of NaH in DMF gives 7-chloro-1-cyclopropyl-6,8-difluoro-4-oxo-2-(phenylsulfanyl)-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (III), which is oxidized with MCPBA in dichloromethane, yielding the sulfinyl derivative (IV). The cyclization of (IV) with NaSH and hydroxylamine-O-sulfonic acid in THF affords the isothiazoloquinoline (V), which is finally condensed with piperazine in pyridine to furnish the target compound.

1 Aquilar-Bryan, L.; Bryan, J.; Boyd, A.E. III; et al.; Sulfonylurea signal transduction. Recent Prog Horm Res 1991, 47, 299-317.
2 Chu, D.T.W.; Isothiazoloquinolones: Antibacterial and antineoplastic agents. Drugs Fut 1992, 17, 12, 1101.
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) 43200 ethyl 3-(2,4-dichloro-3,5-difluorophenyl)-3-oxopropanoate C11H8Cl2F2O3 详情 详情
(II) 43201 1-[[chloro(cyclopropylimino)methyl]sulfanyl]benzene C10H10ClNS 详情 详情
(III) 43202 ethyl 7-chloro-1-cyclopropyl-6,8-difluoro-4-oxo-2-(phenylsulfanyl)-1,4-dihydro-3-quinolinecarboxylate C21H16ClF2NO3S 详情 详情
(IV) 43203 ethyl 7-chloro-1-cyclopropyl-6,8-difluoro-4-oxo-2-(phenylsulfinyl)-1,4-dihydro-3-quinolinecarboxylate C21H16ClF2NO4S 详情 详情
(V) 43204 7-chloro-9-cyclopropyl-6,8-difluoroisothiazolo[5,4-b]quinoline-3,4(2H,9H)-dione C13H7ClF2N2O2S 详情 详情
(VI) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
Extended Information