4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene → 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773870
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][CH:12]=[C:13]3C#CC2C=CC=CC=2)[CH2:4][CH2:3]1>CO.O=[Pt]=O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13]3)[CH2:6][CH2:7]1

Komponenten

4

Edukt 1

HCID 867039564-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Produkt 1

HCID 867039574-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 34) (50 mg, 0.126 mmole) in MeOH (1.3 mL) is added PtO2 (1.4 mg). The flask is evacuated and filled with hydrogen (balloon). The reaction mixture is stirred at room temperature overnight, then filtered on celite and cake washed with MeOH. Solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (95:5:0.5) and the residue is submitted to a preparative thin-layer chromatography eluting with (CH2Cl2:MeOH:NH4OH) (9:1:1) to afford 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Aufarbeitung

  1. customThe flask is evacuated
  2. additionfilled with hydrogen (balloon)
  3. filtrationfiltered on celite and cake
  4. washwashed with MeOH
  5. customSolvent is removed under reduced pressure
  6. customThe residue is pre-purified by silica gel chromatography
  7. washeluting with (CH2Cl2:MeOH:NH4OH) (9:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2b8cb98e5078401a91a8c9a60ed51827
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255101B2

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