(3-chloro-4-fluorophenyl)[4-fluoro-4-({[(E)-(5-methyl-2-pyridinyl)methylidene]amino}methyl)-1-piperidinyl]methanone -Drug Synthesis Database

【结构式】

【分子编号】64958

【品名】(3-chloro-4-fluorophenyl)[4-fluoro-4-({[(E)-(5-methyl-2-pyridinyl)methylidene]amino}methyl)-1-piperidinyl]methanone

【CA登记号】

【分子式】C₂₀H₂₀ClF₂N₃O

【分子量】391.8479264

【元素组成】C 61.3% H 5.14% Cl 9.05% F 9.7% N 10.72% O 4.08%

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：(VII)

Ring opening of epoxide (I) with hydrogen fluoride-pyridine complex affords the fluorohydrin (II). After conversion of (II) to the corresponding tosylate (III), reaction with potassium phthalimide in boiling DMF furnishes the substituted phthalimide (IV). Hydrolysis of phthalimide (IV) in hot ethanolamine gives rise to the primary amine (V). Condensation of (V) with 5-methylpyridine-2-carbaldehyde (VI) leads to imine (VII). Finally, reduction of imine (VII) to the corresponding amine with methanolic KBH4, followed by conversion to the fumarate salt provides the title compound.

参考文献中间体

合成目标

【1】 Vacher, B.; Bonnaud, B.; Koek, W. (Pierre Fabre Medicament); Pyridin-2-yl-methylamine derivs., method of preparing and application as medicine. EP 0946546; JP 2001504129; US 6020345; WO 9822459 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	24373	(3-chloro-4-fluorophenyl)(1-oxa-6-azaspiro[2.5]oct-6-yl)methanone	C₁₃H₁₃ClFNO₂	详情	详情
(II)	24374	(3-chloro-4-fluorophenyl)[4-fluoro-4-(hydroxymethyl)-1-piperidinyl]methanone	C₁₃H₁₄ClF₂NO₂	详情	详情
(III)	24375	[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl 4-methylbenzenesulfonate	C₂₀H₂₀ClF₂NO₄S	详情	详情
(IV)	24376	2-[[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl]-1H-isoindole-1,3(2H)-dione	C₂₁H₁₇ClF₂N₂O₃	详情	详情
(V)	24377	[4-(aminomethyl)-4-fluoro-1-piperidinyl](3-chloro-4-fluorophenyl)methanone	C₁₃H₁₅ClF₂N₂O	详情	详情
(VI)	64957	5-methyl-2-pyridinecarbaldehyde	C₇H₇NO	详情	详情
(VII)	64958	(3-chloro-4-fluorophenyl)[4-fluoro-4-({[(E)-(5-methyl-2-pyridinyl)methylidene]amino}methyl)-1-piperidinyl]methanone	C₂₀H₂₀ClF₂N₃O	详情	详情

Extended Information