乙醇钠 → {3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-dimethylamine hydrochloride

HRID 1386926

反应方程式

HRID 1386926 反应方程式
[ClH:1].[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.CC[O-].[Na+].[CH3:17][N:18]([CH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26]N)=O)[CH3:19].Cl.CCOCC>C(O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[NH:10][N:26]=[C:24]([C:23]3[CH:22]=[C:21]([CH:30]=[CH:29][CH:28]=3)[CH2:20][N:18]([CH3:19])[CH3:17])[N:9]=2)=[CH:6][CH:5]=1

参与物

6

反应物 4

HCID 2723922乙醇钠HCID 10953452Ether hydrochlorideHCID 123262194-甲氧基苯甲脒盐酸盐HCID 635713743-Dimethylaminomethyl-benzoic acid hydrazide

产物 1

HCID 21180376{3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-dimethylamine hydrochloride收率 25%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂2 次

实验过程

To a stirred ethanolic suspension of 4-methoxybenzamidine hydrochloride salt (280 mg, 1.5 mmol, 1.5 eq.) was added over 3 minutes 1.2N NaOEt in ethanol (1.7 ml, 2 eq.) and stirring was continued for 30 min. at r.t. 3-Dimethylaminomethyl-benzoic acid hydrazide (193 mg, 1 mmol) in ethanol was then added at 20° C. and the mixture heated at reflux for 24 hrs. Upon cooling the product mixture was filtered, the solvent was evaporated and the residue subjected to preparative reversed phase-HPLC purification using a YMC ODS-AQ column (20×50 mm) and a (0.1% trifluoroacetic acid) water-acetonitrile gradient (25 ml/min.). The pure fractions were concentrated and the product obtained was converted to the hydrochloride salt by addition of excess 2N HCl/ether solution. Solvent evaporation and high vacuum drying afforded the title compound (86 mg, 0.25 mmol, 25% yield) as a white foam. MS: m/e=309.4 (M+H+).

后处理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hrs
  3. temperatureUpon cooling the product mixture
  4. filtrationwas filtered
  5. customthe solvent was evaporated
  6. custompurification
  7. concentrationThe pure fractions were concentrated
  8. customthe product obtained
  9. customSolvent evaporation and high vacuum
  10. customdrying

来源与证据

ORD记录
ord-5141d93998634d50aca842132148e1d3
来源数据集
uspto-grants-2001_07
专利号
US06265426B1

关联笔记

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