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

【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 合成路线2

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).

参考文献中间体

合成目标

【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	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.

参考文献中间体

合成目标

【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	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