methyl 6-[(E)-2-(4-pyridinyl)ethenyl]nicotinate -Drug Synthesis Database

【结构式】

【分子编号】18603

【品名】methyl 6-[(E)-2-(4-pyridinyl)ethenyl]nicotinate

【CA登记号】

【分子式】C₁₄H₁₂N₂O₂

【分子量】240.26156

【元素组成】C 69.99% H 5.03% N 11.66% O 13.32%

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：(XIV)

Methyl 6-methylnicotinate (XII) was condensed with 4-pyridinecarboxaldehyde (XIII) in AcOH-Ac2O at 120 C to produce (XIV). Then, ester group was reduced with LiAlH4 to alcohol (XV), and this was subsequently oxidized with DMSO and SO3-pyridine complex to give aldehyde (XVI). Wittig reaction with phosphorane (XVII) afforded ester (XVIII), which was saponified to yield acid (XIX). Finally, coupling of acid (XIX) with amine (XI) in the presence of EDC and HOBt provided the title amide.

参考文献中间体

合成目标

【1】 Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Inamura, N.; Asano, M.; Aramori, I.; Hatori, C.; Sawai, H.; Oku, T.; Tanaka, H.; A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 3. Discovering bioisosteres of the imidazo[1,2-a]pyridine moiety. J Med Chem 1998, 41, 21, 4062.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	18600	2-amino-N-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-N-methylacetamide		C₂₀H₁₉Cl₂N₃O₂	详情	详情
(XII)	14160	methyl 6-methylnicotinate	5470-70-2	C₈H₉NO₂	详情	详情
(XIII)	17203	4-Pyridinecarboxaldehyde; isonicotinaldehyde	872-85-5	C₆H₅NO	详情	详情
(XIV)	18603	methyl 6-[(E)-2-(4-pyridinyl)ethenyl]nicotinate		C₁₄H₁₂N₂O₂	详情	详情
(XV)	18604	[6-[(E)-2-(4-pyridinyl)ethenyl]-3-pyridinyl]methanol		C₁₃H₁₂N₂O	详情	详情
(XVI)	18605	6-[(E)-2-(4-pyridinyl)ethenyl]nicotinaldehyde		C₁₃H₁₀N₂O	详情	详情
(XVII)	14689	Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate	2605-67-6	C₂₁H₁₉O₂P	详情	详情
(XVIII)	18607	methyl (E)-3-[6-[(E)-2-(4-pyridinyl)ethenyl]-3-pyridinyl]-2-propenoate		C₁₆H₁₄N₂O₂	详情	详情
(XIX)	18608	(E)-3-[6-[(E)-2-(4-pyridinyl)ethenyl]-3-pyridinyl]-2-propenoic acid		C₁₅H₁₂N₂O₂	详情	详情

Extended Information