4-[[(2S)-1-(2-pyridinyl)pyrrolidinyl]methoxy]benzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】34807

【品名】4-[[(2S)-1-(2-pyridinyl)pyrrolidinyl]methoxy]benzaldehyde

【CA登记号】

【分子式】C₁₇H₁₈N₂O₂

【分子量】282.3422

【元素组成】C 72.32% H 6.43% N 9.92% O 11.33%

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：(V)

2-Chloropyridine (I) was condensed with (S)-prolinol (II) to furnish the pyridinylpyrrolidine (III). Subsequent alkylation of the hydroxyl group of (III) with 4-fluorobenzaldehyde (IV) using NaH in hot DMF gave ether (V). Knoevenagel condensation of (V) with 2,4-thiazolidinedione (VI) in the presence of benzoic acid and piperidine afforded the required benzylidene thiazolidine, which was finally treated with maleic acid in acetone to yield the title maleate salt.

参考文献中间体

合成目标

【1】 Reddy, A.S.; Lohray, B.B.; Bhushan, V.; et al.; Novel euglycemic and hypolipidemic agents. 4. Pyridyl- and quinolinyl-containing thiazolidinediones. J Med Chem 1999, 42, 14, 2569.
【2】 Ramanujam, R.; Lohray, B.B.; Alla, S.R.; Chakrabarti, R.; Paraselli, R.B.; Lohray, V.B. (Dr. Reddy's Research Foundation); Thiazolidinedione cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. thereof. WO 9741120 .
【3】 Rao, P.B.; Ramanujam, R.; Alla, S.R.; Lohray, V.B.; Chakrabarti, R.; Lohray, B.B. (Dr. Reddy's Research Foundation); Heterocyclic cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5919782 .

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)	17503	2-chloropyridine	109-09-1	C₅H₄ClN	详情	详情
(II)	21347	(2S)pyrrolidinylmethanol	23356-96-9	C₅H₁₁NO	详情	详情
(III)	34806	[(2S)-1-(2-pyridinyl)pyrrolidinyl]methanol		C₁₀H₁₄N₂O	详情	详情
(IV)	12337	4-fluorobenzaldehyde	459-57-4	C₇H₅FO	详情	详情
(V)	34807	4-[[(2S)-1-(2-pyridinyl)pyrrolidinyl]methoxy]benzaldehyde		C₁₇H₁₈N₂O₂	详情	详情
(VI)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情

Extended Information