Triethylamine → (4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(1,3-oxazol-5-yl)phenyl)methanone

HRID 240413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240413
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)=[CH:4][N:3]=[CH:2]1.Cl.[F:16][C:17]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:18]=1[CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]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>[F:16][C:17]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:18]=1[CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][N:23]([C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5]2[O:1][CH:2]=[N:3][CH:4]=2)=[O:10])[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 533937912-(5-Oxazolyl)benzoic AcidHCID 866808664-(2,4-Difluorobenzyl)-4-hydroxypiperidine hydrochloride

Produkt 1

HCID 86680870(4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(1,3-oxazol-5-yl)phenyl)methanoneAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 2-(1,3-oxazol-5-yl)benzoic acid (0.15 g), 4-(2,4-difluorobenzyl)-4-hydroxypiperidine hydrochloride (0.16 g), HATU (0.36 g) and triethylamine (1.1 mL) in DMF (5.0 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.26 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and 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)

Quellen und Nachweise

ORD-Eintrag
ord-1acae0d66d7c4fe880bef670b81ab21b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648079B2

Notizen zur Reaktion

Wird geladen…