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【结 构 式】

【分子编号】17465

【品名】2-aminobenzoyl chloride

【CA登记号】

【 分 子 式 】C7H6ClNO

【 分 子 量 】155.58348

【元素组成】C 54.04% H 3.89% Cl 22.79% N 9% O 10.28%

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:(LII)

6) Synthesis of the quinoline (XXI): Anthranilic acid (LI) is tolylated with tosyl chloride and treated with PCl5 in 1,2-dichloroethane to give the corresponding acyl chloride (LII), which is submitted to a Friedel Crafts condensation with fluorobenzene (LIII)/AlCl3 yielding 2-amino-4'-fluorobenzophenone (LIV). The cyclization of (LIV) with ethyl 2-(cyclopropylcarbonyl)acetate (LV) [obtained by condensation of cyclopropyl methyl ketone (LVI) and diethyl carbonate (LVII) with H2SO4] by means of p-toluenesulfonic acid yields 2-cyclopropyl-4-(4-fluorophenyl)-quinoline-3-carboxylic acid ethyl ester (LVIII), which is submitted to a decarboxylative iodination with I2 and acetyl peroxide to afford 2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline (XXI). 7) Synthesis of the quinoline (XXXVII): The reduction of the quinolinecarboxylate (LVIII) with LiAlH4 in THF gives the corresponding methanol derivative (LIX), which is then treated with diphenyl disulfide (LX) and tri-butylphosphine in pyridine to afford 2-cyclopropyl-4-(4-fluorophenyl)-3-(phenylsulfanylmethyl)quinoline (XXXVII).

1 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; NK-104. Drugs Fut 1998, 23, 8, 847-859.
2 Kamikubo, T.; Takano, S.; Sugihara, T.; Suzuki, M.; Ogasawara, K.; Enantioconvergent synthesis of a promising HMG-CoA reductase inhibitor NK-104 from both enantiomers of epichlorohydrin. Tetrahedron Asymmetry 1993, 4, 2, 201-4.
3 Iwasaki, H.; Miyachi, N.; Yanagawa, Y.; Ohara, Y.; Hiyama, T.; A novel synthetic method of HMG-CoA reductase inhibitor NK-104 via a hydroboration-cross-coupling sequence. Tetrahedron Lett 1993, 34, 51, 8267-70.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXI) 17435 2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline C18H13FIN 详情 详情
(XXXVII) 17451 [2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]methyl phenyl sulfide; 2-cyclopropyl-4-(4-fluorophenyl)-3-[(phenylsulfanyl)methyl]quinoline C25H20FNS 详情 详情
(LI) 11661 2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid 118-92-3 C7H7NO2 详情 详情
(LII) 17465 2-aminobenzoyl chloride C7H6ClNO 详情 详情
(LIII) 17466 Fluorobenzene 462-06-6 C6H5F 详情 详情
(LIV) 17467 (2-aminophenyl)(4-fluorophenyl)methanone C13H10FNO 详情 详情
(LV) 15949 3-Cyclopropyl-3-oxo-propionic acid ethyl ester; ethyl 3-cyclopropyl-3-oxopropanoate 24922-02-9 C8H12O3 详情 详情
(LVI) 12435 Acetylcyclopropane; 1-Cyclopropyl-1-ethanone; Cyclopropylmethylketone 765-43-5 C5H8O 详情 详情
(LVII) 17470 diethyl carbonate; diethylcarbonate 105-58-8 C5H10O3 详情 详情
(LVIII) 17471 ethyl 2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxylate C21H18FNO2 详情 详情
(LIX) 17472 [2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]methanol C19H16FNO 详情 详情
(LX) 17473 diphenyl disulfide; 1-(phenyldisulfanyl)benzene; diphenyldisulfide 882-33-7 C12H10S2 详情 详情
Extended Information