tert-butyl [1-(5-[[(1-methyl-1H-indol-3-yl)carbonyl]amino]pentyl)-4-piperidinyl]methylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】37907

【品名】tert-butyl [1-(5-[[(1-methyl-1H-indol-3-yl)carbonyl]amino]pentyl)-4-piperidinyl]methylcarbamate

【CA登记号】

【分子式】C₂₆H₄₀N₄O₃

【分子量】456.62876

【元素组成】C 68.39% H 8.83% N 12.27% O 10.51%

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：(VIII)

1-Benzyl-4-(aminomethyl)piperidine (I) was protected at the primary amino group as the Boc derivative (II) and the N-benzyl group was subsequently removed by transfer hydrogenolysis with hydrazine and Pd/C to give piperidine (III). Alkylation of (III) with N-(5-bromopentyl)phthalimide (IV) afforded (V), which was subjected to hydrazinolysis of the phthalimido group, yielding primary amine (VI). Coupling of (VI) with 1-methylindole-3-carboxylic acid (VII) by means of EDC and HOBt gave rise to amide (VIII). The Boc protecting group of (VIII) was then cleaved by acidic treatment to furnish amine (IX). Finally, coupling of (IX) with 4-amino-5-chloro-2-methoxybenzoic acid (X) provided the title benzamide.

参考文献中间体

合成目标

【1】 Haga, K.; Tomozane, H.; Sato, N.; Kawakita, T.; Itoh, K.; Sonda, S.; Asano, K.; Fujimura, M.; Hakira, H.; Synthesis and pharmacological properties of novel benzamide derivatives acting as ligands to the 5-hydroxytryptamine 4 (5-HT4) receptor. Eur J Med Chem 1999, 34, 12, 1101.
【2】 Kawakita, T.; Hakira, H.; Haga, K.; Murozono, T.; Kuroita, T. (Welfide Corporation); Benzoic acid cpd. and use thereof as medicine. EP 0774460; WO 9526953 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	37901	(1-benzyl-4-piperidinyl)methylamine; (1-benzyl-4-piperidinyl)methanamine		C₁₃H₂₀N₂	详情	详情
(II)	37902	tert-butyl (1-benzyl-4-piperidinyl)methylcarbamate		C₁₈H₂₈N₂O₂	详情	详情
(III)	37903	tert-butyl 4-piperidinylmethylcarbamate		C₁₁H₂₂N₂O₂	详情	详情
(IV)	37904	2-(5-bromopentyl)-1H-isoindole-1,3(2H)-dione	954-81-4	C₁₃H₁₄BrNO₂	详情	详情
(V)	37905	tert-butyl [1-[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentyl]-4-piperidinyl]methylcarbamate		C₂₄H₃₅N₃O₄	详情	详情
(VI)	37906	tert-butyl [1-(5-aminopentyl)-4-piperidinyl]methylcarbamate		C₁₆H₃₃N₃O₂	详情	详情
(VII)	15067	1-methyl-1H-indole-3-carboxylic acid; N-Methylindole-3-carboxylic acid	32387-21-6	C₁₀H₉NO₂	详情	详情
(VIII)	37907	tert-butyl [1-(5-[[(1-methyl-1H-indol-3-yl)carbonyl]amino]pentyl)-4-piperidinyl]methylcarbamate		C₂₆H₄₀N₄O₃	详情	详情
(IX)	37908	N-[5-[4-(aminomethyl)-1-piperidinyl]pentyl]-1-methyl-1H-indole-3-carboxamide		C₂₁H₃₂N₄O	详情	详情
(X)	12419	4-Amino-5-chloro-2-methoxybenzoic acid	7206-70-4	C₈H₈ClNO₃	详情	详情

Extended Information