Hydrochloric Acid → 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt

HRID 386569

Reaktionsgleichung

Reaktionsgleichung von HRID 386569
[C:1]([C:4]1[C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:8][C:7](=[O:24])[N:6]([C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([F:33])[CH:26]=2)[N:5]=1)(=O)[NH2:2].[ClH:34].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:34].[C:31]([C:28]1[CH:29]=[CH:30][C:25]([N:6]2[C:7](=[O:24])[CH:8]=[C:9]([O:10][CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:4]([C:1]#[N:2])=[N:5]2)=[CH:26][C:27]=1[F:33])#[N:32]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 67445416tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Produkt 1

HCID 674470261-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl saltAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of tert-butyl 4-(3-cyano-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (example 34) (22 mg, 0.050 mmol) in DCM (3 mL) at room temperature under argon was added 4 M HCl in dioxane (0.375 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight. Et2O (10 mL) was added to the reaction mixture. The solid product was collected by filtration and further washed with ether (2 mL×2). After drying under vacuum for 2 hours, 19 mg (100%) of 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 340 (M+H).

Aufarbeitung

  1. filtrationThe solid product was collected by filtration
  2. washfurther washed with ether (2 mL×2)
  3. customAfter drying under vacuum for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-736e5b60b2b9431eb66248be4cd7047a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372837B2

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