Formaldehyde → HCID 58438409, Verbindung

HRID 1971945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971945
[Cl-].[Cl-].[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH2:27][CH:28]2[C:33]([F:35])([F:34])[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH3:6].C=O.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH2:27][CH:28]2[C:33]([F:35])([F:34])[CH2:32][CH2:31][N:30]([CH3:38])[CH2:29]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86657794HCID 86657794, Verbindung

Produkt 1

HCID 58438409HCID 58438409, VerbindungAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(4,4-difluoro-piperidin-3-ylmethoxy)-pyridazine dichloride (0.17 mmol, 90 mg), 37% paraformaldehyde (0.4 mmol, 32 mg), and 1 drop of acetic acid in 5 mL of DCM was stirred for 5 min then added sodium triacetoxyborohydride (0.4 mmol, 85 mg) and continued stirring for 0.5 h at room temperature. Quenched with water, solvent was evaporated; the residue was diluted with ethyl acetate, and then washed with saturated NaHCO3 solution, brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to get 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(4,4-difluoro-1-methyl-piperidin-3-ylmethoxy)-pyridazine (52 mg).

Aufarbeitung

  1. customQuenched with water, solvent
  2. customwas evaporated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75fe293bbdb94a1ea34333009afebb68
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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