(2-amino-5-bromo-3-pyridinyl)methanol -Drug Synthesis Database

【结构式】

【分子编号】56113

【品名】(2-amino-5-bromo-3-pyridinyl)methanol

【CA登记号】

【分子式】C₆H₇BrN₂O

【分子量】203.03846

【元素组成】C 35.49% H 3.47% Br 39.35% N 13.8% O 7.88%

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：(VII)

Reduction of 2-aminonicotinic acid (V) by means of LiAlH4 afforded amino alcohol (VI). Subsequent bromination of (VI) with N-bromosuccinimide gave 2-amino-5-bromo-3-(hydroxymethyl)pyridine (VII). Alcohol (VII) was then converted to the bromomethyl pyridine derivative (VIII) by treatment with concentrated hydrobromic acid. Condensation of bromo amine (VIII) with dimethyl malonate led to the naphthyridine carboxylate (IX). Basic hydrolysis of the methyl ester of (IX), followed by decarboxylation under acidic conditions, gave rise to naphthyridinone (X).

参考文献中间体

合成目标

【1】 Seefeled, M.A.; et al.; Discovery and characterization of highly potent naphthyridine-based FabI inhibitors with in vivo activity. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-1690.
【2】 Uzinskas, I.N.; Miller, W.H.; Newlander, K.A.; Jakas, D.R.; Seefeld, M.A.; DeWolf, W.E. Jr. (GlaxoSmithKline Inc.); Fab I inhibitors. EP 1226138; WO 0127103 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	55933	2-Aminonicotinic acid; 2-Aminopyridine-3-carboxylic acid	5345-47-1	C₆H₆N₂O₂	详情	详情
(VI)	56112	(2-amino-3-pyridinyl)methanol	23612-57-9	C₆H₈N₂O	详情	详情
(VII)	56113	(2-amino-5-bromo-3-pyridinyl)methanol		C₆H₇BrN₂O	详情	详情
(VIII)	56114	5-bromo-3-(bromomethyl)-2-pyridinamine; 5-bromo-3-(bromomethyl)-2-pyridinylamine	335033-38-0	C₆H₆Br₂N₂.HBr	详情	详情
(IX)	56115	methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro[1,8]naphthyridine-3-carboxylate	335031-10-2	C₁₀H₉BrN₂O₃	详情	详情
(X)	56116	6-bromo-3,4-dihydro[1,8]naphthyridin-2(1H)-one		C₈H₇BrN₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

2-Aminonicotinic acid (I) is reduced to alcohol (II) employing LiAlH4 in refluxing THF. Subsequent bromination of (II) with N-bromosuccinimide affords 2-amino-5-bromo-3-(hydroxymethyl)pyridine (III). Heating of alcohol (III) with concentrated HBr leads to the bromomethyl pyridine (IV). This is further condensed with dimethyl malonate in the presence of NaOMe to produce the naphthyridinecarboxylate (V). Then, alkaline hydrolysis of ester (V), followed by acidic decarboxylation gives rise to 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (VI)

参考文献中间体

合成目标

【1】 Uzinskas, I.N.; Miller, W.H.; Newlander, K.A.; Jakas, D.R.; Seefeld, M.A.; DeWolf, W.E. Jr. (GlaxoSmithKline Inc.); Fab I inhibitors. EP 1226138; WO 0127103 .

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)	55933	2-Aminonicotinic acid; 2-Aminopyridine-3-carboxylic acid	5345-47-1	C₆H₆N₂O₂	详情	详情
(II)	56112	(2-amino-3-pyridinyl)methanol	23612-57-9	C₆H₈N₂O	详情	详情
(III)	56113	(2-amino-5-bromo-3-pyridinyl)methanol		C₆H₇BrN₂O	详情	详情
(IV)	56114	5-bromo-3-(bromomethyl)-2-pyridinamine; 5-bromo-3-(bromomethyl)-2-pyridinylamine	335033-38-0	C₆H₆Br₂N₂.HBr	详情	详情
(V)	56115	methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro[1,8]naphthyridine-3-carboxylate	335031-10-2	C₁₀H₉BrN₂O₃	详情	详情
(VI)	56116	6-bromo-3,4-dihydro[1,8]naphthyridin-2(1H)-one		C₈H₇BrN₂O	详情	详情

Extended Information