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

HRID 1386926

反応式

HRID 1386926 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-5141d93998634d50aca842132148e1d3
出典データセット
uspto-grants-2001_07
特許番号
US06265426B1

関連ノート

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