Hydrochloric Acid → HCID 67374073, Verbindung

HRID 1972001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972001
[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:13]([N+:24]([O-])=O)[CH:12]=1)[CH2:2][CH2:3][CH3:4].[ClH:35]>C(O)(=O)C.O.CCOC(C)=O.C([O-])(O)=O.[Na+].C(Cl)Cl.CCOCC.[Fe]>[ClH:35].[ClH:35].[ClH:35].[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:13]([NH2:24])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

9

Edukt 2

HCID 313Hydrochloric AcidHCID 67371453HCID 67371453, Verbindung

Produkt 1

HCID 67374073HCID 67374073, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-butyl-4-(4-cyclohexyloxy-3-nitro-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine (5 mmol, 2.34 g) in acetic acid (10 mL) was added iron powder (˜325 mesh, 50 mmol, 2.80 g). And the mixture was stirred at 100° C. for 0.5 hour. It was then diluted with water/EtOAc and neutralized slowly with NaHCO3 powder. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (10 mL), 2N HCl in ether (10 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenylamine trihydrochloride (2.06 g).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH)
  3. customto give a colorless sticky solid, which
  4. waitkept at room temperature for 10 min
  5. customcondensed
  6. customtriturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8572489f319e45b999c23af1d94fd73d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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