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【结 构 式】

【分子编号】56585

【品名】10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinoline-8-carbaldehyde

【CA登记号】

【 分 子 式 】C25H15F2NO2

【 分 子 量 】399.3964464

【元素组成】C 75.18% H 3.79% F 9.51% N 3.51% O 8.01%

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:(XVII)

In a different strategy for protecting the quinoline carboxyl group, acid (VI) was reduced to alcohol (XI) via chlorination with SOCl2, followed by treatment with NaBH4. Alcohol (XI) was then converted to the alkyl chloride (XII) with SOCl2 in dichloroethane. Subsequent ester group hydrolysis in (XII) under acidic conditions furnished the carboxylic acid (XIII). The tetracyclic compound (XIV) was obtained by cyclization of acid (XIII) in hot triflic acid. Displacement of the chloride group of (XIV) with sodium acetate in HOAc yielded acetate ester (XV), which was subsequently hydrolyzed to alcohol (XVI). Oxidation of (XVI) with DMSO and Ac2O provided aldehyde (XVII).

1 Chujo, I.; et al.; Synthetic study on novel immunosuppressant KF20444. Bioorg Med Chem 2001, 9, 12, 3273.
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) 56574 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-(3-methoxy-3-oxopropyl)-4-quinolinecarboxylic acid C26H19F2NO4 详情 详情
(XI) 56579 methyl 3-[6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-4-(hydroxymethyl)-3-quinolinyl]propanoate C26H21F2NO3 详情 详情
(XII) 56580 methyl 3-[4-(chloromethyl)-6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-quinolinyl]propanoate C26H20ClF2NO2 详情 详情
(XIII) 56581 3-[4-(chloromethyl)-6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-quinolinyl]propanoic acid C25H18ClF2NO2 详情 详情
(XIV) 56582 8-(chloromethyl)-10-fluoro-3-(2-fluorophenyl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinolin-5-one C25H16ClF2NO 详情 详情
(XV) 56583 [10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinolin-8-yl]methyl acetate C27H19F2NO3 详情 详情
(XVI) 56584 10-fluoro-3-(2-fluorophenyl)-8-(hydroxymethyl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinolin-5-one C25H17F2NO2 详情 详情
(XVII) 56585 10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinoline-8-carbaldehyde C25H15F2NO2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XVII)

Aldehyde (XVII) was further oxidized to carboxylic acid (XVIII) using sodium chlorite. Conversion of acid (XVIII) into the methyl ester (XIX) was effected by treatment with iodomethane and K2CO3. Finally, the two-step reduction of the carbonyl group of (XIX) with NaBH4 followed by HI/Ac2O, proceeded with concomitant ester hydrolysis, yielding the title compound.

1 Chujo, I.; et al.; Synthetic study on novel immunosuppressant KF20444. Bioorg Med Chem 2001, 9, 12, 3273.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVII) 56585 10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinoline-8-carbaldehyde C25H15F2NO2 详情 详情
(XVIII) 56586 10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinoline-8-carboxylic acid C25H15F2NO3 详情 详情
(XIX) 56587 methyl 10-fluoro-3-(2-fluorophenyl)-5-oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]quinoline-8-carboxylate C26H17F2NO3 详情 详情
Extended Information