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

HRID 1386926

Reaktionsgleichung

Reaktionsgleichung von HRID 1386926
[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

Komponenten

6

Edukt 4

HCID 2723922Sodium ethoxideHCID 10953452Ether hydrochlorideHCID 123262194-Methoxybenzamidine HydrochlorideHCID 635713743-Dimethylaminomethyl-benzoic acid hydrazide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5141d93998634d50aca842132148e1d3
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265426B1

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