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【结 构 式】

【分子编号】36300

【品名】1-cyclopropyl-3-[[(difluoroboryl)oxy]carbonyl]-6,7-difluoro-8-methoxy-4(1H)-quinolinone

【CA登记号】

【 分 子 式 】C14H10BF4NO4

【 分 子 量 】343.0423528

【元素组成】C 49.02% H 2.94% B 3.15% F 22.15% N 4.08% O 18.66%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIVa)

Condensation of the protected pyrrolidine (XII) with either the BF2-chelate (XVIa) or the B(OAc)2-chelate (XIVb) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid provided the 7-(pyrrolidinyl)quinoline (XV). The boron chelate of (XV) was then removed upon refluxing with Et3N in aqueous EtOH to give the quinolinecarboxylic acid (XVI). Finally, treatment of (XVI) with concentrated HCl cleaved the Boc protecting group.

1 Takahaski, H.; et al.; DC-756: A new methoxyquinolone: Synthesis and in vitro activity of 7-(3-amino-4-substituted-pyrrolidin-1-yl) derivatives. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-73.
2 Takeda, T.; Kimura, K.; Ohki, H.; Takahashi, H.; Miyauchi, R.; Takemura, M. (Daiichi Pharmaceutical Co., Ltd.); Cis-substd. fluoromethylpyrrolidine derivs.. EP 0995744; WO 9858923 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIVa) 36300 1-cyclopropyl-3-[[(difluoroboryl)oxy]carbonyl]-6,7-difluoro-8-methoxy-4(1H)-quinolinone C14H10BF4NO4 详情 详情
(XIVb) 36301 diacetyl (1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinyl)carbonyl borate C18H16BF2NO8 详情 详情
(XVa) 36302 tert-butyl (3S,4S)-1-(1-cyclopropyl-3-[[(difluoroboryl)oxy]carbonyl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-7-quinolinyl)-4-(fluoromethyl)pyrrolidinylcarbamate C24H28BF4N3O6 详情 详情
(XVb) 36303 tert-butyl (3S,4S)-1-[3-([[bis(acetoxy)boryl]oxy]carbonyl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-7-quinolinyl]-4-(fluoromethyl)pyrrolidinylcarbamate C28H34BF2N3O10 详情 详情
(XII) 36298 tert-butyl (3S,4S)-4-(fluoromethyl)pyrrolidinylcarbamate C10H19FN2O2 详情 详情
(XVI) 36304 7-[(3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-(fluoromethyl)pyrrolidinyl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C24H29F2N3O6 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XIVa)

In a further procedure, the deprotected pyrrolidine (XIII) was condensed with the fluoroquinoline (XIV) to give (XVII). The boron chelate of (XVII) was then deprotected with Et3N in EtOH-H2O at 50 C.

1 Takeda, T.; Kimura, K.; Ohki, H.; Takahashi, H.; Miyauchi, R.; Takemura, M. (Daiichi Pharmaceutical Co., Ltd.); Cis-substd. fluoromethylpyrrolidine derivs.. EP 0995744; WO 9858923 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIVa) 36300 1-cyclopropyl-3-[[(difluoroboryl)oxy]carbonyl]-6,7-difluoro-8-methoxy-4(1H)-quinolinone C14H10BF4NO4 详情 详情
(XIVb) 36301 diacetyl (1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinyl)carbonyl borate C18H16BF2NO8 详情 详情
(XVIIa) 36305 7-[(3S,4S)-3-amino-4-(fluoromethyl)pyrrolidinyl]-1-cyclopropyl-3-[[(difluoroboryl)oxy]carbonyl]-6-fluoro-8-methoxy-4(1H)-quinolinone C19H20BF4N3O4 详情 详情
(XVIIb) 36306 diacetyl [7-[(3S,4S)-3-amino-4-(fluoromethyl)pyrrolidinyl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinyl]carbonyl borate C23H26BF2N3O8 详情 详情
(XIII) 36299 (3S,4S)-4-(fluoromethyl)-3-pyrrolidinamine; (3S,4S)-4-(fluoromethyl)pyrrolidinylamine C5H11FN2 详情 详情
Extended Information