2-[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]-2-hydroxyacetonitrile -Drug Synthesis Database

【结构式】

【分子编号】64960

【品名】2-[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]-2-hydroxyacetonitrile

【CA登记号】

【分子式】C₁₄H₁₃ClF₂N₂O₂

【分子量】314.7190064

【元素组成】C 53.43% H 4.16% Cl 11.26% F 12.07% N 8.9% O 10.17%

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：(III)

In an alternative, shorter route, 1-(3-chloro-4-fluorobenzoyl)-4-piperidinone (I) is subjected to Darzens condensation with chloroacetonitrile in the presence of NaOH and a phase-transfer catalyst to furnish the epoxy nitrile (II). Epoxide opening in (II) with HF-pyridine gives rise to the fluoro hydroxy nitrile (III). This is finally condensed with (5-methylpyridin-2-yl)methylamine (IV) under reductive amination conditions to produce the title compound.

参考文献中间体

合成目标

【1】 Bonnaud, B.; Maurel, J.-L.; Vacher, B.; Ribet, J.-P. (Pierre Fabre Medicament); Synthesis method and intermediates of pyridin-2-yl-methylamine. WO 0264585 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	24372	1-(3-chloro-4-fluorobenzoyl)-4-piperidinone	C₁₂H₁₁ClFNO₂	详情	详情
(II)	64959	6-(3-chloro-4-fluorobenzoyl)-1-oxa-6-azaspiro[2.5]octane-2-carbonitrile	C₁₄H₁₂ClFN₂O₂	详情	详情
(III)	64960	2-[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]-2-hydroxyacetonitrile	C₁₄H₁₃ClF₂N₂O₂	详情	详情
(IV)	64961	(5-methyl-2-pyridinyl)methanamine; (5-methyl-2-pyridinyl)methylamine	C₇H₁₀N₂	详情	详情

Extended Information