Hydrochloric Acid → N-(2-(4-chlorophenyl)ethyl)-3-hydroxypyridine-2-Carboxamide

HRID 584723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584723
F[C:2](F)(F)[C:3]1[CH:16]=[CH:15][C:6](OC2C=CC(N)=CC=2)=[CH:5][CH:4]=1.Br[C:20]1[N:25]=[C:24]([C:26](Cl)=[O:27])[C:23]([O:29]CC2C=CC=CC=2)=[C:22](OC)[CH:21]=1.[ClH:39].C([N:42]([CH2:45]C)CC)C.[H][H]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O.[Pd]>[Cl:39][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][CH2:45][NH:42][C:26]([C:24]2[C:23]([OH:29])=[CH:22][CH:21]=[CH:20][N:25]=2)=[O:27])=[CH:16][CH:15]=1

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27607514-(4-(Trifluoromethyl)phenoxy)anilineHCID 221750736-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl ChlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22175087N-(2-(4-chlorophenyl)ethyl)-3-hydroxypyridine-2-Carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(4-trifluoromethylphenoxy)aniline (0.20 g, 0.8 mmol) and DMAP (0.10 g, 0.085 mmol) in CH2Cl2 (10 mL) was added all at once a solution of 3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride (3) (0.29 g, 0.8 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred overnight at room temperature then poured into 2N HCl (10 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a gummy solid. This solid was taken up in EtOAc (20 mL), and triethylamine (0.80 g, 0.8 mmol) and 5% Pd on carbon (0.10 g) were added. The resulting mixture was subjected to a hydrogen atmosphere (initial pressure=50 psi) on a Parr shaker for 30 minutes. The mixture was filtered, washed with 0.1N HCl (20 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (0.14 g), m.p.=122-129° C. Coupling Procedure C: Preparation of N-(4-Cyclohexylphenyl)-3-hydroxypyridine-2-carboxamide.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a gummy solid
  6. customfor 30 minutes
  7. filtrationThe mixture was filtered
  8. washwashed with 0.1N HCl (20 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-26989112bbae4c98a2b758c4ef471153
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927225B2

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