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Butyric Acid → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-propyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202900
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2202900
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:10][C:9]2=[O:23])=[CH:4][C:3]=1[NH:24][CH3:25].CN(C(ON1N=N[C:36]2[CH:37]=CC=N[C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:50](O)(=O)CCC.C(N(CC)C(C)C)(C)C.[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:25]([CH2:35][CH2:36][CH3:37])[N:24]([CH3:50])[C:3]=4[CH:4]=3)[C:9](=[O:23])[CH:10]=2)=[CH:17][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 5284359Calcium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896902791-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

Produkt 1

HCID 89691535
4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-propyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (90 mg), HATU (106 mg), n-butyric acid (0.024 ml), N,N-diisopropylethylamine (0.136 ml) and DMF (2 ml) was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2.0 ml) and stirred at 90° C. for 1 h. After evaporation, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOAc/MeOH to give the title compound (48.7 mg) as an off-white solid.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting residue was dissolved in AcOH (2.0 ml)
  8. customAfter evaporation
  9. customthe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  10. customThe resulting solid was recrystallized from EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-36249f2799a049f4b3c3cf3a3ebed522
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09365540B2

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