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4-Methylmorpholine → 2-{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-1-morpholin-4-yl-ethanone

HRID 333821
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333821
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:27])[C:10]([C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23][C:24]([OH:26])=O)[CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:27])[C:10]([C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23][C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:26])[CH:17]=1)([OH:15])[C:11]([F:14])([F:12])[F:13]
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Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25254148HCID 25254148, Verbindung

Produkt 1

HCID 574212592-{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-1-morpholin-4-yl-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid (180 mg) and morpholin (0.04 mL) in DMF (6 mL), were treated with 4-methyl-morpholine (0.140 mL) and HBTU (241 mg). The reaction mixture was stirred at r.t. for 17 h. The reaction mixture was diluted with water (50 mL) and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 70:30) to give the title compound as white solid (134 mg). MS (m/e)=492.9 (MH+).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-4f54d03814334db6ad0ce450aefaff21
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883786B2

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