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Triethylamine → (4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(pyrimidin-4-yl)pyridin-3-yl)methanone

HRID 60615
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60615
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[N:5][CH:4]=1.Cl.[F:19][C:20]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:21]=1[CH2:22][C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]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:19][C:20]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:21]=1[CH2:22][C:23]1([OH:29])[CH2:28][CH2:27][N:26]([C:11]([C:10]2[C:9]([C:6]3[CH:7]=[CH:8][N:3]=[CH:4][N:5]=3)=[N:17][CH:16]=[CH:15][CH:14]=2)=[O:13])[CH2:25][CH2:24]1
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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 866808562-(Pyrimidin-4-yl)nicotinic acid dihydrochlorideHCID 866808664-(2,4-Difluorobenzyl)-4-hydroxypiperidine hydrochloride

Produkt 1

HCID 86680871
(4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(pyrimidin-4-yl)pyridin-3-yl)methanone
Ausbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 2-(pyrimidin-4-yl)nicotinic acid dihydrochloride (0.36 g), 4-(2,4-difluorobenzyl)-4-hydroxypiperidine hydrochloride (0.42 g), HATU (0.75 g) and triethylamine (1.1 mL) in DMF (5 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 saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and recrystallized from ethyl acetate/hexane to give the title compound (0.18 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 (NH, ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-78f1c83a45984f259543f7ec04bdb7dd
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440990B2

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