Ethanol → N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide

HRID 907573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907573
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:28]#CC4C=CN=CC=4)=N[CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:38]([OH:40])[CH3:39]>[Pd]>[F:1][C:2]([F:36])([F:37])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([O:40][CH2:38][C:39]4[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=4)=[CH:28][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 590139503'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

Produkt 1

HCID 10436864N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

3′-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide (˜0.4 mmol) was dissolved in 5 mL ethanol. Then, 50 mg of 10% palladium on carbon was added. The reaction flask was flushed with hydrogen and the reaction was stirred at room temperature for 5 hr under 1 atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated under vacuum. The residue was purified by reverse phase HPLC to give N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide (80 mg) as a yellow solid. 1H NMR (DMSO-d6) δ 9.34 (s, 1H), 8.48 (d, 2H), 8.23 (s, 1H), 8.20 (d, 1H), 8.14 (d, 2H), 7.58 (s, 1H), 7.39 (d, 2H), 3.66 (m, 4H), 3.13-3.43 (m, 8H) ppm.

Aufarbeitung

  1. customThe reaction flask was flushed with hydrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fd875057d89b4ba0a405e5f7874fde0b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013156B2

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