tert-butyl 3-[(2-amino-3-pyridinyl)amino]propyl(methyl)carbamate -Drug Synthesis Database

【结构式】

【分子编号】54818

【品名】tert-butyl 3-[(2-amino-3-pyridinyl)amino]propyl(methyl)carbamate

【CA登记号】

【分子式】C₁₄H₂₄N₄O₂

【分子量】280.37032

【元素组成】C 59.98% H 8.63% N 19.98% O 11.41%

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：(VII)

In a different strategy, reductive alkylation of 2,3-diaminopyridine (V) with aldehyde (VI) using borane-pyridine complex yielded regioselectively the 3-alkylamino pyridine (VII). Subsequent cyclization of (VII) with triethyl orthoformate afforded the desired imidazopyridine (III). In an alternative, more direct procedure, the bicyclic compound (III) was obtained by reductive condensation of the 2-formamido derivative (VIII) with aldehyde (VI) in the presence of borane-pyridine complex.

参考文献中间体

合成目标

【1】 Itani, H.; et al.; S-3578, a new broad spectrum parenteral cephalosporin exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa synthesis and structure-activity relationships. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst 1P-16.
【2】 Miwa, H.; Yoshida, T.; Shimada, J.; Kuwahara, S.; Nishitani, Y.; S-3578, a new broad-spectrum cephalosporin: I. Synthesis and structure-activity relationships. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-370.
【3】 Itani, H.; Nishitani, Y.; Irie, T. (Shionogi & Co. Ltd.); Imidazo[4,5-b]pyridiniummethyl-containing cephem cpds. having broad antibacterial spectrum. EP 1134222; WO 0032606 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	54814	tert-butyl 3-(1H-imidazo[4,5-b]pyridin-1-yl)propyl(methyl)carbamate		C₁₅H₂₂N₄O₂	详情	详情
(V)	54816	2,3-Diaminopyridine	452-58-4	C₅H₇N₃	详情	详情
(VI)	54817	tert-butyl methyl(3-oxopropyl)carbamate		C₉H₁₇NO₃	详情	详情
(VII)	54818	tert-butyl 3-[(2-amino-3-pyridinyl)amino]propyl(methyl)carbamate		C₁₄H₂₄N₄O₂	详情	详情
(VIII)	54819	3-amino-2-pyridinylformamide		C₆H₇N₃O	详情	详情

Extended Information