1-(4-pyridinyl)-4-piperidinyl hydroperoxide -Drug Synthesis Database

【结构式】

【分子编号】44839

【品名】1-(4-pyridinyl)-4-piperidinyl hydroperoxide

【CA登记号】

【分子式】C₁₀H₁₄N₂O₂

【分子量】194.23344

【元素组成】C 61.84% H 7.27% N 14.42% O 16.47%

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：(II)

Reduction of ethyl ester (I) with LiAlH4 provides primary carbinol (II), which is then converted into amine (III) by Mitsunobu reaction with phthalimide (A) in the presence of PPh3 and DEAD in THF, followed by an hydrazine mediated deprotection in EtOH. Reaction of amine (III) with 2-nitrophenyl isocyanate (IV) in CHCl3/THF or CH2Cl2, followed by reduction of the nitro group by hydrogenation over Pd/C in EtOH, affords aniline (V). Finally, aniline (V) is condensed with acid chloride (VI) in CHCl3 in the presence of pyridine to furnish the target compound.

参考文献中间体

合成目标

【1】 Tinsley, J.M.; Franciskoich, J.B.; Masters, J.J.; et al.; Non-amidine-containing 1,2-dibezamidobenzene inhibitors of human factor Xa with potent anticoagulant and antithrombotic activity. J Med Chem 2000, 43, 11, 2087.
【2】 Antithrombotic agents. WO 9900121 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	12376	Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione	85-41-6	C₈H₅NO₂	详情	详情
(I)	44838	ethyl 1-(4-pyridinyl)-4-piperidinecarboxylate		C₁₃H₁₈N₂O₂	详情	详情
(II)	44839	1-(4-pyridinyl)-4-piperidinyl hydroperoxide		C₁₀H₁₄N₂O₂	详情	详情
(III)	44840	O-[1-(4-pyridinyl)-4-piperidinyl]hydroxylamine; 4-(aminooxy)-1-(4-pyridinyl)piperidine		C₁₀H₁₅N₃O	详情	详情
(IV)	32771	1-isocyanato-2-nitrobenzene; 2-nitrophenyl isocyanate	3320-86-3	C₇H₄N₂O₃	详情	详情
(V)	44841	N-(2-aminophenyl)-N'-[[1-(4-pyridinyl)-4-piperidinyl]oxy]urea		C₁₇H₂₁N₅O₂	详情	详情
(VI)	10295	p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride	122-01-0	C₇H₄Cl₂O	详情	详情

Extended Information