3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide → ethyl 8-(3,4-difluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398172
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[C:6]([NH:8][NH2:9])=O.[F:19][C:20]1[CH:21]=[C:22]([C:27]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:32][CH2:31][CH2:30][N:29]=[C:28]2SC)[CH:23]=[CH:24][C:25]=1[F:26]>C(O)C.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[C:22]([C:27]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:32][CH2:31][CH2:30][N:29]3[C:6]([C:5]4[CH:10]=[CH:11][C:12]([N:13]5[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]5)=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:8][N:9]=[C:28]23)[CH:23]=[CH:24][C:25]=1[F:26]

Komponenten

5

Edukt 2

HCID 666078503-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazideHCID 66608443Ethyl 3-(3,4-difluorophenyl)-2-(methylsulfanyl)-3,4,5,6-tetrahydropyridine-3-carboxylate

Produkt 1

HCID 66608479ethyl 8-(3,4-difluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide (236 mg) was added to a mixture of ethyl 3-(3,4-difluorophenyl)-2-(methylsulfanyl)-3,4,5,6-tetrahydropyridine-3-carboxylate (300 mg) in ethanol (3 mL) at room temperature, and the mixture was stirred at 90° C. for 2 days. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (217 mg).

Aufarbeitung

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0835a7a82d6442fea10806d37bb56315
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901309B2

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