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Sodium hydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-one

HRID 2203107
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2203107
[H-].[Na+].[F:3][C:4]([F:16])([C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)[C:5]([F:8])([F:7])[F:6].Br[C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:31]=[C:30]([CH:32]4[CH2:34][CH2:33]4)[N:29]([CH3:35])[C:28]=3[CH:36]=2)[C:20](=[O:37])[CH:19]=1>CC(N(C)C)=O>[CH:32]1([C:30]2[N:29]([CH3:35])[C:28]3[CH:36]=[C:24]([N:21]4[CH:22]=[CH:23][C:18]([O:15][CH2:14][C:12]5[N:13]=[C:9]([C:4]([F:3])([F:16])[C:5]([F:8])([F:7])[F:6])[S:10][CH:11]=5)=[CH:19][C:20]4=[O:37])[CH:25]=[CH:26][C:27]=3[N:31]=2)[CH2:33][CH2:34]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 54209966(2-(Perfluoroethyl)thiazol-4-yl)methanolHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Produkt 1

HCID 896912031-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-oneAusbeute 5,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374
Dimethylacetamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (60% in oil, 51.5 mg) was added to a solution of (2-(perfluoroethyl)thiazol-4-yl)methanol (300 mg) in DMA (5 ml) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (295 mg) was added to the reaction mixture. The mixture was stirred at 120° C. under N2 atmosphere for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc), followed by crystallization from EtOH-water to give the title compound (25 mg) as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at 120° C. under N2 atmosphere for 1 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  9. customfollowed by crystallization from EtOH-water

Quellen und Nachweise

ORD-Eintrag
ord-3378319c6142478eb3ad1d89d892dbdd
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09365540B2

Notizen zur Reaktion

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