• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】28377

【品名】[3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl]sodium

【CA登记号】

【 分 子 式 】C6H4N3NaO

【 分 子 量 】157.107148

【元素组成】C 45.87% H 2.57% N 26.75% Na 14.63% O 10.18%

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:(X)

The reaction of 3-chloroaniline (I) with ethanolamine (II) by means of 47% HBr by heating at 170 C gives N-(3-chlorophenyl)ethylenediamine (III), which is condensed with ethyl 2-bromopropionate (IV) by means of triethylamine in refluxing toluene yielding the alanine derivative (V). The cyclization of (V) with refluxing 2N HCl affords the piperazinone (VI), which is reduced with LiAlH4 in ethyl ether providing 1-(3-chlorophenyl)-3-methylpiperazine (VII). The alkylation of (VII) with 1-bromo-3-chloropropane (VIII) by means of NaOH in acetone/water gives 4-(3-chlorophenyl)-1-(3-chloropropyl)-2-methylpiperazine (IX), which is condensed with the sodium salt of 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one (X) in refluxing xylene/isobutanol yielding the target compound as a racemic mixture (XI). Finally, this compound is submitted to optical resolution with L-(+)-tartaric acid (XII).

1 Giannangeli, M.; Gazzolla, N.; Luparini, M.R.; Magnani, M.; Mabilia, M.; Picconi, G.; Tomaselli, M.; Baiocchi, L.; Effect of modifications of the alkylpiperazine moiety of trazodone on 5HT2A and alpha1 receptor binding affinity. J Med Chem 1999, 42, 3, 336.
2 Baiocchi, L.; Cioli, V. (Angelini Group); Pharmacologically active enantiomers. EP 0707587; JP 1996512036; WO 9501354 .
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) 25239 3-chloroaniline; 3-chlorophenylamine 108-42-9 C6H6ClN 详情 详情
(II) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(III) 34091 N(1)-(3-chlorophenyl)-1,2-ethanediamine; N-(2-aminoethyl)-N-(3-chlorophenyl)amine C8H11ClN2 详情 详情
(IV) 19460 ethyl 2-bromopropanoate; 2-Bromopropionic acid ethyl ester 535-11-5 C5H9BrO2 详情 详情
(V) 28373 ethyl 2-[[2-(3-chloroanilino)ethyl]amino]propanoate C13H19ClN2O2 详情 详情
(VI) 28374 1-(3-chlorophenyl)-3-methyl-2-piperazinone C11H13ClN2O 详情 详情
(VII) 28375 1-(3-chlorophenyl)-3-methylpiperazine C11H15ClN2 详情 详情
(VIII) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(IX) 28376 4-(3-chlorophenyl)-1-(3-chloropropyl)-2-methylpiperazine C14H20Cl2N2 详情 详情
(X) 28377 [3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl]sodium C6H4N3NaO 详情 详情
(XI) 28378 2-[3-[4-(3-chlorophenyl)-2-methyl-1-piperazinyl]propyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one C20H24ClN5O 详情 详情
(XII) 28379 (2R,3R)-2,3-dihydroxybutanedioic acid; L-Tartaric acid; (2R,3R)-2,3-dihydroxysuccinic acid 87-69-4 C4H6O6 详情 详情
Extended Information