2-methoxy-6-methyl-4-[(3-pyridinylimino)methyl]phenol -Drug Synthesis Database

【结构式】

【分子编号】58411

【品名】2-methoxy-6-methyl-4-[(3-pyridinylimino)methyl]phenol

【CA登记号】

【分子式】C₁₄H₁₄N₂O₂

【分子量】242.27744

【元素组成】C 69.41% H 5.82% N 11.56% O 13.21%

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)

The condensation between 4-hydroxy-3-methoxy-5-methylbenzaldehyde (I) and 3-aminopyridine (II) yields the corresponding benzalimine (III). The phenolic hydroxyl group of (III) is then protected as the silyl ether (IV) by using t-butyldimethylsilyl chloride and imidazole. Condensation of imine (IV) with the lithium derivative of diethyl methylphosphonate (V) affords the beta-amino phosphonate (VI). Finally, desilylation of (VI) with tetrabutylammonium fluoride and acetic acid provides the target phenol.

参考文献中间体

合成目标

【1】 Phan, H.T.; et al.; Synthesis of a new series of compounds with lipoprotein(a)-lowering activity, Part 3: beta-Substituted-beta-amino-ethylphosphonates. Drugs Fut 2002, 27, Suppl. A.
【2】 Ife, R.J.; Nguyen, L.M.; Bentzen, C.L.; Diep, V.V.; Azoulay, R.; Phan, H.T.; Niesor, E.J. (Ilex Oncology Research-Europe SA); beta-Substd. beta-aminoethyl phosphonates. US 2002111488; WO 0234756 .

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)	43812	1-(6-methoxy-2-naphthyl)-1-ethanone	3900-45-6	C₁₃H₁₂O₂	详情	详情
(II)	33327	3-Pyridinylamine; 3-Aminopyridine; 3-Pyridinamine	462-08-8	C₅H₆N₂	详情	详情
(III)	58411	2-methoxy-6-methyl-4-[(3-pyridinylimino)methyl]phenol		C₁₄H₁₄N₂O₂	详情	详情
(IV)	58412	N-[(E)-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)methylidene]-N-(3-pyridinyl)amine; N-[(E)-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)methylidene]-3-pyridinamine		C₂₀H₂₈N₂O₂Si	详情	详情
(V)	38496	diethyl methylphosphonate	683-08-9	C₅H₁₃O₃P	详情	详情
(VI)	58413	diethyl 2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)-2-(3-pyridinylamino)ethylphosphonate		C₂₅H₄₁N₂O₅PSi	详情	详情

Extended Information