3,4-Diaminopyridine; 3,4-pyridinediamine -Drug Synthesis Database

【结构式】

【分子编号】29128

【品名】3,4-Diaminopyridine; 3,4-pyridinediamine

【CA登记号】54-96-6

【分子式】C₅H₇N₃

【分子量】109.1308

【元素组成】C 55.03% H 6.47% N 38.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

3,4-Diaminopyridine (I) is condensed with 2-methoxy-4-methylthiobenzoic acid (II) in the presence of phosphorus oxychloride (with or without pyridine cosolvent) to provide the sulfide LY-137150 (III), which is selectively oxidized to LY-175326 by low-temperature reaction with 3-chloroperoxybenzoic acid. The sulfone LY-16325 (IV) is obtained by oxidation of (III) with 40% peracetic acid in methanol.

参考文献中间体

合成目标

【1】 Robertson, D.W.; Beedle E.E.; Pollock G.D.; Hayes J.S.; Wilson H.; Krushinski J.H.; Wyss V.L.; Structure-activity relationship of arylimidazopyridine cradiotonics: Discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine. J Med Chem 1985, 28, 6, 717-27.
【2】 Robertson, D.W.; Hayes, J.S. (Eli Lilly and Company); Pyridine compounds. DD 210273; EP 0093593; GB 2119377; JP 58203991 .
【3】 Hayes, J.S.; Robertson, D.W.; LY-175326. Drugs Fut 1985, 10, 4, 295.

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)	29128	3,4-Diaminopyridine; 3,4-pyridinediamine	54-96-6	C₅H₇N₃	详情	详情
(II)	29129	2-methoxy-4-(methylsulfanyl)benzoic acid	72856-73-6	C₉H₁₀O₃S	详情	详情
(III)	29130	2-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(methylsulfanyl)phenyl methyl ether		C₁₄H₁₃N₃OS	详情	详情
(IV)	29131	2-[2-methoxy-4-(methylsulfonyl)phenyl]-3H-imidazo[4,5-c]pyridine		C₁₄H₁₃N₃O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Reaction of 3,4-diaminopyridine (I) with potassium O-ethyl dithiocarbonate produced 2-mercaptoimidazo[4,5-c]pyridine (II), which was susequently alkylated with 3-methoxybenzyl bromide (III) and KOH, yielding sulfide (IV). Selective oxidation of (IV) to the target sulfoxide was then achieved by treatment with N-chlorosuccinimide in the presence of NaHCO3 at 0 C.

参考文献中间体

合成目标

【1】 Jiang, B.; et al.; Preparation of 3-[(aryl)methyl ]sulfinyl-1H-imidazo[4,5-c]pyridine, useful as an antiosteoporotic agent. Org Process Res Dev 1998, 2, 6, 425.

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)	29128	3,4-Diaminopyridine; 3,4-pyridinediamine	54-96-6	C₅H₇N₃	详情	详情
(II)	36733	3H-imidazo[4,5-c]pyridin-2-ylhydrosulfide; 3H-imidazo[4,5-c]pyridine-2-thiol		C₆H₅N₃S	详情	详情
(III)	34403	1-(bromomethyl)-3-methoxybenzene; 3-(bromomethyl)phenyl methyl ether		C₈H₉BrO	详情	详情
(IV)	36734	2-[(3-methoxybenzyl)sulfanyl]-3H-imidazo[4,5-c]pyridine; 3-[(3H-imidazo[4,5-c]pyridin-2-ylsulfanyl)methyl]phenyl methyl ether		C₁₄H₁₃N₃OS	详情	详情

Extended Information