4-(4-quinolinyl)butylamine; 4-(4-quinolinyl)-1-butanamine -Drug Synthesis Database

【结构式】

【分子编号】45920

【品名】4-(4-quinolinyl)butylamine; 4-(4-quinolinyl)-1-butanamine

【CA登记号】

【分子式】C₁₃H₁₆N₂

【分子量】200.28352

【元素组成】C 77.96% H 8.05% N 13.99%

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：(XIV)

Acidolysis of (VII) with HCl furnishes des(hexopyranosyloxy) derivative (VIII), which is then acetylated with acetic anhydride in ethyl acetate to give protected derivative (IX). Compound (IX) is then oxidized by treatment with 3-ethylcarbodiimide (EDCI) and pyridinium trifluoroacetate in DMSO/CH2Cl2 to afford ketone (X). Mesylation of (X) with methanesulfonyl chloride (MsCl) in pyridine yields mesylated derivative (XI), which is then converted into the 10,11-anhydro form (XII) by reaction with 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) in acetone. Activation of compound (XII) by means of NaH and carbonyl diimidazole (CDI) in THF/DMF provides derivative (XIII), which is coupled with amine (XIV). Finally, treatment with refluxing MeOH furnishes the desired compound.

参考文献中间体

合成目标

【1】 Chu, D.; Grant, E.; Hlasta, D.; Henninger, T.; Khosla, C. (Kosan Biosciences, Inc.; Ortho-McNeil Pharmaceutical, Inc.); Ketolide antibacterials. WO 0062783 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIIII)	45919	(2R,3S,7R,9R,10R,11R,13R)-10-[[(2S,3R,4S,6R)-3-(acetoxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy]-9-methoxy-2,3,5,7,9,11,13-heptamethyl-6,12,14-trioxooxa-4-cyclotetradecen-3-yl 1H-imidazole-1-carboxylate	C₃₅H₅₃N₃O₁₁	详情	详情
(VII)	45913	(3R,4S,5R,6R,7R,9R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-12,13-dihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-oxacyclotetradecanedione	C₃₇H₆₇NO₁₃	详情	详情
(VIII)	45914	(3R,4S,5S,6R,7R,9R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-oxacyclotetradecanedione	C₂₉H₅₃NO₁₀	详情	详情
(IX)	45915	(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-2-[[(3R,4S,5S,6R,7R,9R,12R,13S,14R)-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-dioxooxacyclotetradecanyl]oxy]tetrahydro-2H-pyran-3-yl acetate	C₃₁H₅₅NO₁₁	详情	详情
(X)	45916	(2S,3R,4S,6R)-2-[[(3R,5R,6R,7R,9R,12R,13S,14R)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,4,10-trioxooxacyclotetradecanyl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate	C₃₁H₅₃NO₁₁	详情	详情
(XI)	45917	(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7R,9R,12R,13R,14R)-13-hydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-12-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2,4,10-trioxooxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate	C₃₄H₅₉NO₁₁S	详情	详情
(XII)	45918	(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,13S,14R)-13-hydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,4,10-trioxooxa-11-cyclotetradecen-6-yl]oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate	C₃₁H₅₁NO₁₀	详情	详情
(XIV)	45920	4-(4-quinolinyl)butylamine; 4-(4-quinolinyl)-1-butanamine	C₁₃H₁₆N₂	详情	详情

Extended Information