Triethylamine → (4-Benzyl-4-hydroxypiperidin-1-yl)(3-methyl-5-(pyridin-4-yl)-1,2-oxazol-4-yl)methanone

HRID 717268

Reaktionsgleichung

Reaktionsgleichung von HRID 717268
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=O)=[C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[O:4][N:3]=1.[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][N:26]([C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 981524-Benzyl-4-piperidinolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 282757673-Methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid

Produkt 1

HCID 86680845(4-Benzyl-4-hydroxypiperidin-1-yl)(3-methyl-5-(pyridin-4-yl)-1,2-oxazol-4-yl)methanoneAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 3-methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid (0.25 g), 4-benzyl-4-hydroxypiperidine (0.35 g), HATU (0.70 g) and triethylamine (0.85 mL) in DMF (5.0 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and then purified by preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)), and the obtained fraction was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.29 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. custompurified by preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA))
  7. concentrationthe obtained fraction was concentrated under reduced pressure
  8. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe extract was dried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2fd43b6e3cd74b42ba7a9d235a8e14d6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193709B2

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