Potassium Fluoride → 1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(Pyrimidin-4-yl)urea

HRID 1807755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807755
[Si]([O:8][C:9]([C:18]1[CH:49]=[CH:48][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][C:41]4[CH:46]=[CH:45][N:44]=[CH:43][N:42]=4)=[O:39])=[C:33]([F:47])[CH:32]=3)=[O:30])[CH2:25][CH2:24]2)=[CH:20][CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])(C(C)(C)C)(C)C.[F-].[K+]>O1CCCC1>[F:47][C:33]1[CH:32]=[C:31]([C:29]([N:26]2[CH2:27][CH2:28][N:23]([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([C:9]([OH:8])([C:10]([F:13])([F:11])[F:12])[C:14]([F:15])([F:17])[F:16])=[CH:49][CH:48]=3)[CH2:24][CH2:25]2)=[O:30])[CH:36]=[CH:35][C:34]=1[NH:37][C:38]([NH:40][C:41]1[CH:46]=[CH:45][N:44]=[CH:43][N:42]=1)=[O:39]

Komponenten

4

Edukt 2

HCID 522689Potassium FluorideHCID 866385631-(4-(4-(4-(2-(Tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)-piperazine-1-carbonyl)-2-fluorophenyl)-3-(pyrimidin-4-yl)urea

Produkt 1

HCID 445123941-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(Pyrimidin-4-yl)ureaAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(4-(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)-piperazine-1-carbonyl)-2-fluorophenyl)-3-(pyrimidin-4-yl)urea (0.088 mmol, 0.0627 g) and potassium fluoride (50% on celite) (0.877 mmol, 0.102 g) were combined and heated to reflux in tetrahydrofuran (5 mL) overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%) to afford the title compound (8 mg). MS (ESI) m/z 601.3 [M+H]+

Aufarbeitung

  1. temperatureheated
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-e789497be40c4fd983a34b845bcb9d8f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357679B2

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