Triphenylphosphine → 3,7-Di(pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-one

HRID 920899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920899
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:14](=[O:16])[NH:13][N:12]=[C:11]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:10]=3[S:9][CH:8]=2)=[CH:3][CH:2]=1.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:34][CH2:33][C:24]4[CH:25]=[CH:26][C:27]5[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:23]=4)[N:12]=[C:11]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:10]=3[S:9][CH:8]=2)=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866831153,7-di(pyridin-4-yl)thieno[2,3-d]pyridazin-4(5H)-one

Produkt 1

HCID 715508883,7-Di(pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-oneAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3,7-di(pyridin-4-yl)thieno[2,3-d]pyridazin-4(5H)-one from example 1.5 (100 mg, 0.32 mmol), 2-quinolin-2-yl-ethanol from example a1 (58 mg, 0.33 mmol) and PPh3 (256 mg, 0.98 mmol) in DCM (10 mL), DIAD (198 mg, 0.98 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, concentrated and the residue was purified by Prep-HPLC to give the title compound as white solid (26 mg, 17.6% yield).

Aufarbeitung

  1. concentrationconcentrated
  2. customthe residue was purified by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bfbcbf93d4984f28bf34fd1f1c416329
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273068B2

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