Chloroform → 3-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide

HRID 6928

Reaktionsgleichung

Reaktionsgleichung von HRID 6928
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1O[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[N:8][N:7]=1.[NH2:23][C:24]1[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH2:29])=[O:28].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C(Cl)(Cl)Cl>CN1CCN(C)C1=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:23]([C:24]2[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27]([NH2:29])=[O:28])[C:9]([C:11]2[CH:16]=[N:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:8][N:7]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 164957733-Amino-2-methylbenzamideHCID 220192365-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine

Produkt 1

HCID 220192513-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamideAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66611,3-Dimethyl-2-imidazolidinoneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine (1.0 g) prepared in the Reference Example 7 was dissolved in 1,3-dimethyl-2-imidazolidinone (10 ml), followed by addition of 3-amino-2-methylbenzamide (1.53 g) prepared in the Reference Example 6 and D-10-camphorsulfonic acid (290 mg), and stirred at 200° C. for 16 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, which was then washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1), to afford the entitled compound (812 mg, 56%). The physico-chemical values are as follows.

Aufarbeitung

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. washwas then washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-1220b742e04a4582a13bd0b0471941a4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084164B2

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