2-chloro-N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3-pyridinamine -Drug Synthesis Database

【结构式】

【分子编号】26502

【品名】2-chloro-N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3-pyridinamine

【CA登记号】

【分子式】C₁₇H₁₉ClN₂O

【分子量】302.80344

【元素组成】C 67.43% H 6.32% Cl 11.71% N 9.25% O 5.28%

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)

Reductive condensation of 3-amino-2-chloropyridine (I) with 5-isopropylbenzofuran-7-carbaldehyde (II) in the presence of sodium triacetoxyborohydride provided secondary amine (III). Displacement of the chlorine atom of (III) with phenylmagnesium bromide (IV) using NiCl2 produced phenylpyridine (V), which was hydrogenated with hydrogen over PtO2 in acetic acid to give racemic piperidine (VI). Resolution of (VI) with (R)-(-)-mandelic acid yielded the (2S,3S)-isomer, which was finally isolated as the dihydrochloride salt.

参考文献中间体

合成目标

【1】 Tanaoue, Y.; Beppu, K.; Okayama, A.; Sakamoto, O. (Hisamitsu Pharmaceutical Co., Ltd.); Piperidine derivs.. EP 0826684; US 5886011; WO 9630367 .

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)	11160	2-Chloro-3-pyridinamine; 2-Chloro-3-pyridinylamine; 3-Amino-2-chloropyridine; 2-Chloro-3-aminopyridine	6298-19-7	C₅H₅ClN₂	详情	详情
(II)	26501	5-isopropyl-2,3-dihydro-1-benzofuran-7-carbaldehyde		C₁₂H₁₄O₂	详情	详情
(III)	26502	2-chloro-N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3-pyridinamine		C₁₇H₁₉ClN₂O	详情	详情
(IV)	17616	bromo(phenyl)magnesium; Phenyl Magnesium Bromide	100-58-3	C₆H₅BrMg	详情	详情
(V)	26503	N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-phenyl-3-pyridinamine		C₂₃H₂₄N₂O	详情	详情
(VI)	26504	N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-phenyl-3-piperidinamine		C₂₃H₃₀N₂O	详情	详情

Extended Information