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N,N-Dimethylglycine → 1-[4-(4-morpholinylcarbonyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

HRID 1988672
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1988672
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[NH:20][N:19]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu-]=O>[N:10]1([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:20]3[C:21]4[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=4[C:18]([C:17]([F:16])([F:28])[F:27])=[N:19]3)=[CH:3][CH:4]=2)=[O:9])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 7726344-[(4-Iodophenyl)carbonyl]morpholineHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Produkt 1

HCID 13166291-[4-(4-morpholinylcarbonyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178419072HCID 178419072, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 4-[(4-iodophenyl)carbonyl]morpholine (1.90 g, 6.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (1.14 g, 6.0 mmol), copper (I) oxide (10 mol %, 0.6 mmol, 86 mg), N,N-dimethylglycine (20 mol %, 1.2 mmol, 124 mg), and cesium carbonate (12.0 mmol, 3.91 g) in dimethylsulfoxide (16 ml) was stirred in an oil bath heated at 130° C. for 24 h under argon and then allowed to cool to room temperature. The reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml). The organic layer was separated and dried over sodium sulphate. The solvent was removed by rotary evaporation to give a dark brown residue that was added to a 20 g isolute pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a brown gum (1.86 g, 82%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed by rotary evaporation
  6. customto give a dark brown residue that
  7. additionwas added to a 20 g isolute pre-packed silica column
  8. washeluted from 0-50% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-c678f62a1f984afa88226c7b7a1b9698
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07642256B2

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