5-amino-1H-1,2,4-Triazole-3-methanol;3-amino-5-(hydroxymethyl)-1,2,4-triazole;5-amino-s-Triazole-3-methanol;(5-Amino-1H-[1,2,4]triazol-3-yl)methanol -Drug Synthesis Database

【结构式】

【分子编号】68356

【品名】5-amino-1H-1,2,4-Triazole-3-methanol;3-amino-5-(hydroxymethyl)-1,2,4-triazole;5-amino-s-Triazole-3-methanol;(5-Amino-1H-[1,2,4]triazol-3-yl)methanol

【CA登记号】27277-03-8

【分子式】C₃H₆N₄O

【分子量】114.107

【元素组成】C 31.58% H 5.3% N 49.1% O 14.02%

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：(XXXIV)

The triazolopyrimidine intermediate (IX) is prepared as follows. Cyclization of glycolic acid (XXXII) with aminoguanidine bicarbonate (XXXIII) in the presence of HNO3 at reflux yields 3-amino-5-(hydroxymethyl)-1,2,4-triazole (XXXIV) (1), optionally isolated as its glycolate salt , which then cyclizes with acetylacetone (XXXV) in refluxing AcOH/EtOH to afford the [1,2,4]triazolo[1,5-a]pyrimidine derivative (XXXVI) . Finally, alcohol (XXXVI) is oxidized by means of o-iodoxybenzoic acid (IBX) in DCE at 80 °C or with PhI(OAc)2 in the presence of TEMPO in CH2Cl2 .

参考文献中间体

合成目标

【1】 Gonzalez, J., Jewell, T.M., Li, H., Linton, A., Tatlock, J.H. (Pfizer, Inc.; Agouron Pharmaceuticals, Inc.). Inhibitors of hepatitis C virus RNAdependent RNA polymerase, and compositions and treatments using the same. EP 1781662, JP 2008509984, US 2006122399, US 7151105, US 8268835, WO 2006018725.
【2】 Matthews, C.F., Scott, R.W., Tucker, J.L. (Pfizer, Inc.). CN 102336758, EP 1928878, JP 2007056022, US 2009023921, US 7807838, WO 2007023381.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	68338	5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde		C₈H₈N₄O	详情	详情
(XXXII)	29856	2-hydroxyacetic acid;glycolic acid	79-14-1	C₂H₄O₃	详情	详情
(XXXIII)	68355	aminoguanidine bicarbonate;aminoguanidine carbonate;1-aminoguanidine bicarbonate;aminoguanidine hydrogen carbonate	2200-97-7	CH₆N₄.CH₂O₃	详情	详情
(XXXIV)	68356	5-amino-1H-1,2,4-Triazole-3-methanol;3-amino-5-(hydroxymethyl)-1,2,4-triazole;5-amino-s-Triazole-3-methanol;(5-Amino-1H-[1,2,4]triazol-3-yl)methanol	27277-03-8	C₃H₆N₄O	详情	详情
(XXXV)	11620	2,4-Pentanedione;acetylacetone	123-54-6	C₅H₈O₂	详情	详情
(XXXVI)	68357	(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol		C₈H₁₀N₄O	详情	详情

Extended Information